HRP20220329T1 - Novi derivati benzamida kao modulatori ppar-gama - Google Patents

Novi derivati benzamida kao modulatori ppar-gama Download PDF

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HRP20220329T1
HRP20220329T1 HRP20220329TT HRP20220329T HRP20220329T1 HR P20220329 T1 HRP20220329 T1 HR P20220329T1 HR P20220329T T HRP20220329T T HR P20220329TT HR P20220329 T HRP20220329 T HR P20220329T HR P20220329 T1 HRP20220329 T1 HR P20220329T1
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cyano
chloro
benzamide
substituted
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HRP20220329TT
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Julio Castro Palomino Laria
Juan CAMACHO GÓMEZ
Rodolfo RODRÍGUEZ IGLESIAS
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Medibiofarma, S.L.
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Publication of HRP20220329T1 publication Critical patent/HRP20220329T1/hr

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    • 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
    • C07D413/04—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 directly linked by a ring-member-to-ring-member bond
    • 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
    • A61K31/435—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
    • 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
    • A61K31/435—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
    • A61K31/444—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
    • 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
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
    • 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
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/50—Pyridazines; Hydrogenated pyridazines
    • 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
    • A61K31/535—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
    • A61K31/5375—1,4-Oxazines, e.g. morpholine
    • A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
    • 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
    • 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
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C255/57—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and carboxyl groups, other than cyano groups, bound to the carbon skeleton
    • 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
    • C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
    • C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
    • C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D237/20—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
    • C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
    • C07D295/182—Radicals derived from carboxylic acids
    • C07D295/192—Radicals derived from carboxylic acids from aromatic carboxylic acids
    • 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
    • C07D401/04—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 directly linked by a ring-member-to-ring-member bond

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  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pyridine Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Claims (12)

1. Spoj formule (I): [image] , naznačen time što: – R2 se bira između atoma Cl i F, – R1 predstavlja skupinu cijano, – G1 i G2 neovisno predstavljaju skupinu koju se bira između N atoma i -CR9, gdje G1 i G2 nisu istodobno CR9, – R9 se neovisno se bira iz skupine koju čine: a) petero- ili šesteročlani heteroarilni prsten, koji može biti supstituiran s jednim ili više supstituenata koje se bira iz skupine koju čine atom halogena, skupina cijano, skupina -COOH, nerazgranata ili razgranata C1-C3 alkilna skupina, nerazgranati ili razgranati C1-C3 alkoksi, nerazgranata ili razgranata C1-C3 halogenalkilna skupina, C3-C4 cikloalkil, te C3-C4 cikloalkoksi, b) fenilna skupina koja može biti supstituirana s jednim ili više supstituenata koje se bira iz skupine koju čine atom halogena, skupina cijano, skupina -COOH, nerazgranata ili razgranata C1-C3 alkilna skupina, nerazgranati ili razgranati C1-C3 alkoksi, nerazgranata ili razgranata C1-C3 halogenalkilna skupina, C3-C4 cikloalkil, C3-C4 cikloalkoksi, c) petero- ili šesteročlani zasićeni heterociklički prsten koji sadrži jedan ili dva heteroatoma koje se bira između N i O kao dio prstena, gdje navedeni heterocikl može biti supstituiran skupinom koju se bira između C1-C3 alkilne skupine, te C3-C4 cikloalkilne skupine, te d) -C3-C6 cikloalkilna skupina; – R3, R4 i R5 se neovisno bira iz skupine koju čine atom vodika, atom halogena, nerazgranata ili razgranata C1-C3 alkilna skupina, C3-C4 cikloalkilna skupina i skupina cijano, i njihove farmaceutski prihvatljive soli.
2. Spoj u skladu s patentnim zahtjevom 1, naznačen time što se R3, R4 i R5 neovisno bira iz skupine koju čine atom vodika i atom halogena.
3. Spoj u skladu s bilo kojim od patentnih zahtjeva 1 do 2, naznačen time što su R3, R4 i R5 atomi vodika.
4. Spoj u skladu s bilo kojim od patentnih zahtjeva 1 do 3, naznačen time što G1 predstavlja N atom, a G2 predstavlja skupinu -CR9, gdje se R9 bira između: a) fenilna skupina koja može biti supstituirana s jednim ili više supstituenata koje se bira iz skupine koju čine atom halogena, skupina -COOH, b) piridilni prsten koji može biti supstituiran s jednim ili više supstituenata koje se bira iz skupine koju čine atom halogena i skupina cijano, c) morfolinil i piperazinilna skupina koja može biti supstituirana s a skupina koju se bira između C1-C3 alkilne skupine i C3-C6 cikloalkilne skupine.
5. Spoj u skladu s bilo kojim od patentnih zahtjeva 1 do 3, naznačen time što G2 predstavlja N atom, a G1 predstavlja skupinu -CR9, gdje se R9 bira između: a) fenilna skupina koja može biti supstituirana s jednim ili više supstituenata koje se bira iz skupine koju čine atom halogena i skupina -COOH, b) piridinilni prsten koji može biti supstituiran s jednim ili više supstituenata koje se bira iz skupine koju čine atom halogena i skupina cijano, c) morfolinilna i piperazinilna skupina koja može biti supstituirana skupinom koju se bira između C1-C3 alkilne skupine i C3-C6 cikloalkilne skupine.
6. Spoj u skladu s patentnim zahtjevom 1, naznačen time što R1 predstavlja skupinu cijano, R3, R4 i R5 predstavljaju atome vodika, G1 predstavlja N atom, a G2 predstavlja skupinu -CR9, gdje R9 predstavlja fenilna skupina koja može biti supstituirana s jednim ili više supstituenata koje se bira iz skupine koju čine atom halogena, skupina -COOH i skupina cijano.
7. Spoj u skladu s patentnim zahtjevom 1, naznačen time što R1 predstavlja skupinu cijano, R3, R4 i R5 neovisno predstavljaju atom vodika, G1 predstavlja N atom, a G2 predstavlja skupinu -CR9, gdje R9 predstavlja piridilni prsten koji može biti supstituiran s jednim ili više supstituenata koje se bira iz skupine koju čine atom halogena, skupina cijano.
8. Spoj u skladu s patentnim zahtjevom 1, naznačen time što R1 predstavlja skupinu cijano, R3, R4 i R5 neovisno predstavljaju atom vodika, G2 predstavlja N atom, a G1 predstavlja skupinu -CR9, gdje se R9 bira između: a) fenilna skupina koja može biti supstituirana s jednim ili više supstituenata koje se bira iz skupine koju čine atom halogena, skupina -COOH i skupina cijano, b) piridilni prsten koji može biti supstituiran s jednim ili više supstituenata koje se bira iz skupine koju čine atom halogena, skupina cijano.
9. Spoj u skladu s patentnim zahtjevom 1, naznačen time što je jedan od: 2-klor-5-cijano-N-(2-fenilpiridin-4-il)benzamida 2-klor-5-cijano-N-(6-fenilpiridin-3-il)benzamida 2-klor-5-cijano-N-(2-(4-fluorfenil)piridin-4-il)benzamida 2-klor-5-cijano-N-(6-(4-fluorfenil)piridin-3-il)benzamida N-([2,3′-bipiridin]-5-il)-2-klor-5-cijanobenzamida N-([2,3′-bipiridin]-4-il)-2-klor-5-cijanobenzamida N-([2,4′-bipiridin]-5-il)-2-klor-5-cijanobenzamida N-([2,4′-bipiridin]-4-il)-2-klor-5-cijanobenzamida N-([2,3′-bipiridin]-5-il)-5-cijano-2-fluorbenzamida 5-cijano-2-fluor-N-(6-(4-fluorfenil)piridin-3-il)benzamida 5-cijano-2-fluor-N-(2-(4-fluorfenil)piridin-4-il)benzamida N-([2,3′-bipiridin]-4-il)-5-cijano-2-fluorbenzamida N-([2,2′-bipiridin]-5-il)-2-klor-5-cijanobenzamida 2-klor-5-cijano-N-(6-(4-metilpiperazin-1-il)piridin-3-il)benzamida 2-klor-5-cijano-N-(2-(4-metilpiperazin-1-il)piridin-4-il)benzamida 2-klor-5-cijano-N-(2-morfolinopiridin-4-il)benzamida 2-klor-5-cijano-N-(6-morfolinopiridin-3-il)benzamida N-([2,4′-bipiridin]-4-il)-5-cijano-2-fluorbenzamida N-([2,4′-bipiridin]-5-il)-5-cijano-2-fluorbenzamida 2-klor-5-cijano-N-(piridazin-4-il)benzamida 5-cijano-2-fluor-N-(piridazin-4-il)benzamida 2-klor-5-cijano-N-(6-ciklopropilpiridin-3-il)benzamida 3-(5-(2-klor-5-cijanobenzamido)piridin-2-il)benzojeve kiseline 4-(5-(2-klor-5-cijanobenzamido)piridin-2-il)benzojeve kiseline i njihovih farmaceutski prihvatljivih soli.
10. Spoj u skladu s bilo kojim od patentnih zahtjeva 1 do 9, naznačen time što je namijenjen upotrebi u liječenju ili sprječavanju bolesti ili patološkog stanja kojeg se može ublažiti moduliranjem receptora PPARγ, gdje se navedenu bolest ili patološko stanje bira iz skupine koju čine rak kojeg se bira između raka dojke, raka gušterače, raka jajnika, raka prostate, bubrežnog raka, raka mokraćnog mjehura, raka testisa, urothelial rak raka kože, melanoma, raka debelog crijeva, raka bubrega, raka ili raka krvotvornog tkiva, kojeg se bira između limfoma, multiplog mijeloma i leukemije; metaboličke bolesti koje se bira između osteoporoze, rahitisa, artroze, pretilosti, dijabetesa melitusa tip I i tip II, poremećaja metabolizma lipida, pankreatitisa, poremećaja metabolizma glukoze, dijabetične neuropatije, komplikacija dijabetesa, hiperurikemije, upalnih bolesti poput upalnih kožnih bolesti koje se bira između psorijaze, atopičnog dermatitisa, egzema, običnih akni, drugih dermatitisa i svrbeža, plućnih poremećaja koje se bira između astme i kronične opstruktivne plućne bolesti, autoimune bolesti, neurodegenerativne bolesti koju se bira između multiple skleroze, Alzheimerove bolesti, Parkinsonove bolesti, kardiovaskularnih bolesti koje se bira između ateroskleroze, venskih i arterijskih okluzivnih bolesti, restenoze nakon invazivnih zahvata, kardiomiopatije, fibroze miokarda, kongestivne srčane insuficijencije, angiogeneze i neovaskularizacije kod neoplastičnih bolesti i bubrežnih bolesti.
11. Farmaceutski pripravak, naznačen time što sadrži spoj u skladu s bilo kojim od patentnih zahtjeva 1 do 9, farmaceutski prihvatljivi razrjeđivač ili nosač i izborno terapijski djelotvornu količinu dodatnih kemoterapijskih sredstava, protuupalnih sredstava, steroida, imunoterapijskog sredstva i drugih sredstava poput terapijskih protutijela.
12. Kombinacijski proizvod, naznačen time što sadrži spoj u skladu s bilo kojim od patentnih zahtjeva 1 do 9, ili njegovu farmaceutski prihvatljivu sol, i u najmanju ruku terapijsko sredstvo kojeg se bira iz skupine koju čine kemoterapijska sredstva, protuupalna sredstva, steroidi, imunosupresivi, imunoterapijska sredstva, terapijska protutijela i modulatori PPAR, osobito oni koje se bira iz skupine koju čine protutijela protiv CTLA4, koja se bira između ipilimumaba i tremelimumaba, protutijela protiv PD1, poput MDX-1106 (nivolumab), MK3475 (pembrolizumab), CT-011 (pidilizumab) i AMP-224, protutijela protiv PDL1 koja se bira između MPDL3280A, MEDI4736 i MDX-1105; karboplatin, karmustin (BCNU), cisplatin, ciklofosfamid, etopozid, irinotekan, lomustin (CCNU), metotreksat, prokarbazin, temozolomid, vinkristin.
HRP20220329TT 2017-12-12 2018-12-11 Novi derivati benzamida kao modulatori ppar-gama HRP20220329T1 (hr)

Applications Claiming Priority (3)

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EP17382845.0A EP3498694A1 (en) 2017-12-12 2017-12-12 New benzamide derivatives as ppar-gamma modulators
EP18812195.8A EP3724165B1 (en) 2017-12-12 2018-12-11 New benzamide derivatives as ppar-gamma modulators
PCT/EP2018/084290 WO2019115498A1 (en) 2017-12-12 2018-12-11 New benzamide derivatives as ppar-gamma modulators

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US (1) US11267808B2 (hr)
EP (2) EP3498694A1 (hr)
JP (1) JP7212235B2 (hr)
KR (1) KR20200098557A (hr)
CN (1) CN111630030B (hr)
AU (1) AU2018382461B2 (hr)
BR (1) BR112020011558A2 (hr)
CA (1) CA3084879A1 (hr)
CY (1) CY1125060T1 (hr)
DK (1) DK3724165T3 (hr)
EA (1) EA202091433A1 (hr)
ES (1) ES2908938T3 (hr)
HR (1) HRP20220329T1 (hr)
HU (1) HUE058004T2 (hr)
LT (1) LT3724165T (hr)
MX (1) MX2020006235A (hr)
PL (1) PL3724165T3 (hr)
PT (1) PT3724165T (hr)
RS (1) RS63021B1 (hr)
SI (1) SI3724165T1 (hr)
WO (1) WO2019115498A1 (hr)

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JP2023549123A (ja) * 2020-11-09 2023-11-22 エーザイ・アール・アンド・ディー・マネジメント株式会社 ＰＰＡＲγ調節薬及び使用方法
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