HRP20151309T1 - Derivati imidazopiridina, postupak za njihovu pripravu i njihova terapeutska upotreba - Google Patents

Derivati imidazopiridina, postupak za njihovu pripravu i njihova terapeutska upotreba Download PDF

Info

Publication number
HRP20151309T1
HRP20151309T1 HRP20151309TT HRP20151309T HRP20151309T1 HR P20151309 T1 HRP20151309 T1 HR P20151309T1 HR P20151309T T HRP20151309T T HR P20151309TT HR P20151309 T HRP20151309 T HR P20151309T HR P20151309 T1 HRP20151309 T1 HR P20151309T1
Authority
HR
Croatia
Prior art keywords
formula
compound
alk
image
group
Prior art date
Application number
HRP20151309TT
Other languages
English (en)
Inventor
Chantal Alcouffe
Reinhard Kirsch
Corentin Herbert
Gilbert Lassale
Original Assignee
Sanofi
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=43383651&utm_source=***_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=HRP20151309(T1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Sanofi filed Critical Sanofi
Publication of HRP20151309T1 publication Critical patent/HRP20151309T1/hr

Links

Classifications

    • 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
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/517—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with carbocyclic ring systems, e.g. quinazoline, perimidine
    • 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
    • A61K31/4353—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 ortho- or peri-condensed with heterocyclic ring systems
    • A61K31/437—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 ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
    • 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
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/20—Pills, tablets, discs, rods
    • A61K9/2004—Excipients; Inactive ingredients
    • A61K9/2013—Organic compounds, e.g. phospholipids, fats
    • A61K9/2018—Sugars, or sugar alcohols, e.g. lactose, mannitol; Derivatives thereof, e.g. polysorbates
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/20—Pills, tablets, discs, rods
    • A61K9/2004—Excipients; Inactive ingredients
    • A61K9/2022—Organic macromolecular compounds
    • A61K9/205—Polysaccharides, e.g. alginate, gums; Cyclodextrin
    • A61K9/2054—Cellulose; Cellulose derivatives, e.g. hydroxypropyl methylcellulose
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/20—Pills, tablets, discs, rods
    • A61K9/2004—Excipients; Inactive ingredients
    • A61K9/2022—Organic macromolecular compounds
    • A61K9/205—Polysaccharides, e.g. alginate, gums; Cyclodextrin
    • A61K9/2059—Starch, including chemically or physically modified derivatives; Amylose; Amylopectin; Dextrin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00—Drugs for disorders of the urinary system
    • A61P13/08—Drugs for disorders of the urinary system of the prostate
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00—Drugs for disorders of the urinary system
    • A61P13/12—Drugs for disorders of the urinary system of the kidneys
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/06—Antipsoriatics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/04—Centrally acting analgesics, e.g. opioids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/04—Anorexiants; Antiobesity agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A61P35/02—Antineoplastic agents specific for leukemia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A61P35/04—Antineoplastic agents specific for metastasis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/80—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D211/82—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/80—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D211/84—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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
    • C07D211/90—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two 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
    • C07D233/88—Nitrogen atoms, e.g. allantoin
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two 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
    • C07D233/90—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • 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

Claims (18)

1. Spoj s formulom (I): [image] naznačen time da: - R1 predstavlja . atom vodika ili atom halogena, . alkil skupinu proizvoljno supstituiranu s -COOR5, . alkenil skupinu proizvoljno supstituiranu s -COOR5, . -COOR5 ili -CONR5R6 skupinu, . -NR5COR6 ili -NR5-SO2R6 skupinu, ili . aril skupinu, naročito fenil, ili heteroaril skupinu, navedena aril ili heteroaril skupina je proizvoljno supstituirana s jednom ili više skupina izabranih od: halogenih atoma, alkil skupine, cikloalkil skupine, -COOR5, -CF3, -OCF3, -CN,-C(NH2)NOH, -OR5, -O-Alk-COOR5, -O-Alk-NR5R6, -O-Alk-NR7R8, -Alk-OR5,-Alk-COOR5, -CONR5R6, -CO-NR5-OR6, -CO-NR5-SO2R7, -CONR5-Alk-NR5R6,-CONR5-Alk-NR7R8, -Alk-NR5R6, -NR5R6, -NC(O)N(CH3)2, -CO-Alk, -CO(OAlk)nOH, COO-Alk-NR5R6, COO-Alk-NR7R8 i 5-članih heteroaril skupina, navedene heteroaril skupine su proizvoljno supstituirane s jednom ili više skupina izabranih od halogenih atoma i alkila, -CF3, -CN, -COOR5, -Alk-OR5, -Alk-COOR5, -CONR5R6, -CONR7R8, -CO-NR5-OR6, -CO-NR5-SO2R6, -NR5R6 i -Alk-NR5R6 skupina, ili s hidroksil skupinom ili s kisikovim atomom, - n je cijeli broj u rasponu od 1 do 3, - R2 i R3 zajedno tvore, s ugljikovim atomima fenilne jezgre na koje su spojeni, 6-člani heterocikal koji sadrži dušik koji odgovara jednoj od formula (A), (B) ili (C) ispod: [image] u kojima valovite crte predstavljaju fenilnu jezgru na koju su spojeni R2 i R3 i: . Ra predstavlja vodikov atom ili alkil, haloalkil, -Alk-CF3, -Alk-COOR5, -Alk'-COOR5, -Alk-CONR5R6, -Alk'-CONR5R6, -Alk-CONR7R8, -Alk-NR5R6, -AlkCONR5-OR6, -Alk-NR7R8, -Alk-cikloalkil, -Alk-O-R5, -Alk-S-R5, -Alk-CN, -OR5, -OAlkCOOR5, -NR5R6, -NR5-COOR6, -Alk-aril, -Alk-O-aril, -Alk-O-heteroaril, -Alk-heteroaril ili heteroaril skupinu, gdje je aril ili heteroaril skupina proizvoljno supstituirana s jednim ili više atoma halogena i/ili alkil, cikloalkil, -CF3, -OCF3, -O-R5 ili -S-R5 skupinama, . Ra' predstavlja vodikov atom ili linearnu, razgranatu, cikličku ili djelomično cikličku alkil skupinu, ili -Alk-OR5, -Alk-NR5R6 ili -Alk-NR7R8 skupinu, Ra' je proizvoljno supstituiran s jednim ili više atoma halogena, . Rb predstavlja vodikov atom ili alkil ili -Alk-COOR5 skupinu, . Rb' predstavlja vodikov atom ili alkil, haloalkil, cikloalkil, fenil ili -Alk-COOR5 skupinu, . RC predstavlja vodikov atom ili alkil, -CN, -COOR5, -CO-NR5R6, -CONR7R8 -CO-NR5-Alk-NR5R6, -CONR5-Alk-OR5, -CONR5SO2R5, -Alk-aril ili -Alk-heteroaril skupinu, gdje je aril ili heteroaril skupina proizvoljno supstituirana s jednim ili više atoma halogena i/ili alkil, cikloalkil, -CF3, -OCF3, -O-alkil ili -S-alkil skupinama, . RC' predstavlja vodikov atom ili alkil skupinu, . RC" predstavlja vodikov atom ili alkil, alkenil, haloalkil, cikloalkil, -Alk-NR5R6, -Alk-NR7R8, -Alk-OR5 ili-Alk-SR5 skupinu, - R4, smješten na položaju 6, 7 ili 8 jezgre imidazopiridina, predstavlja: . vodikov atom, . -COOR5 skupinu, . -CO-NR5-Alk-NR5R6 skupinu, . -CO-NR5-Alk-NR7R8 skupinu, ili . -CO-NR5-Alk-OR6 skupinu, - R5 i R6, koji mogu biti isti ili različiti, predstavljaju vodikove atome, haloalkil skupine ili alkil skupine, cikloalkil skupine ili Ms skupinu, - R7 i R8, koji mogu biti isti ili različiti, predstavljaju vodikove atome ili alkil ili fenil skupine, ili još R7 i R8 zajedno tvore 3- do 8-člani zasićeni prsten koji može proizvoljno sadržavati heteroatom, - Alk predstavlja linearni ili razgranati alkilenski lanac, i - Alk' predstavlja linearni, razgranati, ciklički ili djelomično ciklički alkilenski lanac, proizvoljno u obliku njegove farmaceutski prihvatljive soli.
2. Spoj prema zahtjevu 1, naznačen time da R1 predstavlja: . atom vodika ili atom halogena, . alkil skupinu koja je nesupstituirana ili supstituirana s -COOR5, . alkenil skupinu koja je nesupstituirana ili supstituirana s -COOR5, . -COOR5 skupinu, . -CONR5R6 skupinu, . -NR5-SO2R6 skupinu, ili . fenil skupinu proizvoljno supstituiranu s jednom ili dvije skupine izabrane od: • atoma halogena; • alkil skupine proizvoljno supstituirane s -COOR5; • -CN, -C(NH2)NOH, -COOR5, -CONR5R6, -CO-NR5-OR6,-CO-NR5-SO2R6, -COAlk, -CO(OAlk)nOH, -OR5, -OCF3 ,-O-Alk-COOR5, -Alk-OR5, -NR5R6 ili -NC(O)N(CH3)2 skupine, • 5-člane heteroarile proizvoljno supstituirane s alkil skupinom i/ili hidroksil skupinom ili kisikov atom, gdje R5 i R6, koji mogu biti isti ili različiti, predstavljaju vodikove atome, ili alkil skupine proizvoljno supstituirane s -NR7R8 skupinom, R7 predstavlja vodikov atom, alkil skupinu koja sadrži 1 ili 2 ugljikova atoma ili fenil skupinu, n je cijeli broj u rasponu od 1 do 3, ili . heteroaril skupinu koja je proizvoljno kondenzirana i/ili proizvoljno supstituirana s jednom ili dvije skupine izabrane od alkil skupine, OR5, -COOR5,-NR5R6 i cikloalkil atoma, te kisikovog atoma, u kojem R5 i R6, koji mogu biti isti ili različiti, predstavljaju vodikove atome ili alkil skupine koje sadrže 1 ili 2 ugljikova atoma, proizvoljno u obliku njegove farmaceutski prihvatljive soli.
3. Spoj prema zahtjevu 1, naznačen time da R2 i R3 zajedno tvore, s ugljikovim atomima fenilne jezgre na koje su spojeni, 6-člani heterocikal koji sadrži dušik koji odgovara bilo kojoj od formula (A) i (B) kako je definirano u zahtjevu 1, proizvoljno u obliku njegove farmaceutski prihvatljive soli.
4. Spoj prema zahtjevu 1, naznačen time da R2 i R3 zajedno tvore, s ugljikovim atomima fenilne jezgre na koje su spojeni, 6-člani heterocikal koji sadrži dušik koji odgovara formuli (A) kako je definirano u zahtjevu 1, proizvoljno u obliku njegove farmaceutski prihvatljive soli.
5. Spoj prema bilo kojem od prethodnih patentnih zahtjeva, naznačen time da formula (A) ili (B) je takva da: . Ra predstavlja vodikov atom ili alkil skupinu, proizvoljno supstituiranu s jednim ili više halogena; -AlkCONR5R6; haloalkil; -CH2-COOR5; -Alk-heteroaril, -Alk-O-fenil ili -Alk-fenil, gdje je fenilna skupina proizvoljno supstituirana s jednom ili dvije alkil skupine i/ili OR5 i/ili atomima halogena; -Alk-cikloalkil, . Ra' predstavlja vodikov atom ili linearnu, razgranatu, cikličku ili djelomično cikličku alkil skupinu, ili -CH2-OR5 ili -Alk-NR5R6 skupinu, . Rb predstavlja vodikov atom ili alkil skupinu, . Rb' predstavlja vodikov atom ili alkil, fenil ili -CH2-COOR5 skupinu, gdje alkil skupine sadrže 1 do 6 ugljikovih atoma, R5 je kako je opisano u zahtjevu 1, proizvoljno u obliku njegove farmaceutski prihvatljive soli.
6. Spoj prema bilo kojem od prethodnih patentnih zahtjeva, naznačen time da R4 predstavlja vodikov atom ili -COOH, -CO-NH-Alk-NR7R8 ili -CO-NH-Alk-OH skupinu, ili još predstavlja alkil skupinu, koja poželjno sadrži 1 do 3 ugljikova atoma, koja je nesupstituirana, u kojoj Alk, R7 i R8 su kako je opisano u zahtjevu 1.
7. Spoj prema jednom od prethodnih patentnih zahtjeva, naznačen time da je izabran od slijedećih spojeva: 6-(imidazo[1,5-a]piridin-3-ilkarbonil)-3-propilkinazolin-2,4(1H,3H)-diona, 3-{3-[(2,4-diokso-3-propil-1,2,3,4-tetrahidrokinazolin-6-il)karbonil]imidazo[1,5-a]piridin-1-il}benzojeve kiseline, 3-[(2,4-diokso-3-propil-1,2,3,4-tetrahidrokinazolin-6-il)karbonil]imidazo[1,5-a]piridin-6-karboksilne kiseline, 3-(3-{[3-(4-fluorobenzil)-1-metil-2,4-diokso-1,2,3,4-tetrahidrokinazolin-6-il]karbonil}imidazo[1,5-a]piridin-1-il)benzojeve kiseline, 3-{3[(2,4-diokso-3-propil-1,2,3,4-tetrahidrokinazolin-6-il)karbonil]imidazo[1,5-a]piridin-1-il}benzamida, 6-({1-[3-(5-metil-1,3,4-oksadiazol-2-il)fenil]imidazo[1,5-a]piridin-3-il}karbonil-3-propilkinazolin-2,4(1H, 3H)-diona, 6-({1-[3-(3-metil-1,2,4-oksadiazol-5-il)fenil]imidazo[1,5-a]piridin-3-il}karbonil)-3-propilkinazolin-2,4(1H, 3H)-diona, N-{3-[(2,4-diokso-3-propil-1,2,3,4-tetrahidrokinazolin-6-il)karbonil]imidazo[1,5-a]piridin-1-il}metansulfonamida, 2-morfolin-4-il-etil 3-(3-{[3-(4-fluorobenzil)-1-metil-2,4-diokso-1,2,3,4-tetrahidrokinazolin-6-il]karbonil}imidazo[1,5-a]piridin-1-il)benzoata, N-[2-(dimetilamino)etil]-3-(3-{[3-(4-fluorobenzil)-1-metil-2,4-diokso-1,2,3,4-tetrahidrokinazolin-6-il]karbonil}imidazo[1,5-a]piridin-1-il)benzamida, 3-(3-{[3-(4-fluorobenzil)-1-propil-2,4-diokso-1,2,3,4-tetrahidrokinazolin-6-il]karbonil}imidazo[1,5-a]piridin-1-il)benzojeve kiseline, 3-(4-fluorobenzil)-1-metil-6-[(1-piridin-3-ilimidazo[1,5-a]piridin-3-il)karbonil]kinazolin-2,4(1H, 3H)-diona, 3-{3-[(2-metil-4-okso-3-propil-3,4-dihidrokinazolin-6-il)karbonil]imidazo[1,5-a]piridin-1-il}benzojeve kiseline, 3-{3-[(2-metil-4-okso-3-propil-3,4-dihidrokinazolin-6-il)karbonil]imidazo[1,5-a]piridin-1-il}benzamida, 6-(imidazo[1,5-a]piridin-3-ilkarbonil)kinazolin-4(3H)-on, N,N,1,2-tetrametil-4-okso-6-{[1-(piridin-3-il)imidazo[1,5-a]piridin-3-il]karbonil}-1,4-dihidrokinolin-3-karboksamida, 3-[3-({3-[2-(4-fluorofenoksi)etil]-1-propil-2,4-diokso-1,2,3,4-tetrahidrokinazolin-6-il}karbonil)imidazo[1,5-a]piridin-1-il]benzojeve kiseline, proizvoljno u obliku njihove farmaceutski prihvatljive soli.
8. Postupak za pripravu spojeva formule (I) prema bilo kojem od zahtjeva 1 do 7 u kojem R2 i R3 zajedno tvore heterocikal s dušikom prema formuli (A) kako je definirano u zahtjevu 1, u kojem R1 i Ra' predstavljaju vodikove atome, naznačen time da: - spoj s formulom (IV) [image] u kojem R4 je kako je definirano u zahtjevu 1, se kondenzira sa spojem s formulom (V) [image] kako bi se dobilo spoj s formulom (VI) [image] - spoj s formulom (VI) se podvrgava bazičnoj reakciji hidrolize kako bi se dobilo spoj s formulom (VII): [image] - reakcija esterifikacije spoja s formulom (VII) provodi se tako da se dobije spoj s formulom (VIII) [image] - spoj s formulom (VIII) se podvrgava djelovanju trifosgena tako da se tvori izocijanat koji odgovara spoju (VIII), te se zatim ovaj izocijanat kondenzira s aminom s formulom RaNH2, Ra je kako je definirano u zahtjevu 1, kako bi se dobilo ureu s formulom (IX), [image] - urea s formulom (IX) se podvrgava reakciji ciklizacije u bazičnom mediju.
9. Postupak za pripravu derivata formule (I) prema jednom od zahtjeva 1 do 7 u kojem R2 i R3 zajedno tvore heterocikal s dušikom prema formuli (A) kako je definirano u zahtjevu 1, R1 je kako je definirano u zahtjevu 1, uz uvjet da R1 ne predstavlja vodikov atom, i R4 je kako je definirano u zahtjevu 1, naznačen time da: - spoj s formulom (IV) [image] u kojem R4 je kako je definirano u zahtjevu 1, se kondenzira sa spojem s formulom (V) [image] kako bi se dobilo spoj s formulom (VI) [image] - spoj s formulom (VI) se podvrgava bazičnoj reakciji hidrolize kako bi se dobilo spoj s formulom (VII): [image] - reakcija esterifikacije spoja s formulom (VII) provodi se tako da se dobije spoj s formulom (VIII) [image] - spoj s formulom (VIII) se podvrgava reakciji bromiranja kako bi se dobilo spoj s formulom (X): [image] - derivat s formulom (X) se podvrgava djelovanju trifosgena i nastaje izocijanat koji odgovara spoju s formulom (X), koji je kondenziran s aminom s formulom RaNH2, Ra je kako je definirano u zahtjevu 1, kako bi se dobilo ureu s formulom (XI): [image] - spoj s formulom (XI) se podvrgava reakciji ciklizacije u bazičnom mediju kako bi se dobilo spoj s formulom (XII), [image] - spoj s formulom (XII) se podvrgava reakciji alkilacije u prisutnosti baze i halogeniranog derivata Ra'X, Ra' je kako je definirano u zahtjevu 1, kako bi se dobilo spoj s formulom (XIII): [image] - spoj s formulom (XIII) se podvrgava, u prisutnosti paladijeva katalizatora, liganda i baze: . reakciji sa fenilboratnim ili heteroarilboratnim ili fenilboronatnim esterom ili derivatima heteroarilboronatnog estera u skladu sa Suzuki spajanjem, . ili drugačije reakciji iminacije s benzofenoniminom, nakon čega slijedi kisela hidroliza i reakciji alkilacije sa sulfonil kloridom s formulom R6SO2Cl, . ili drugačije reakciji cijanacije s cinkovim cijanidom, nakon čega slijedi kisela hidroliza i esterifikaciji ili peptidnom spajanju s aminom R5R6NH2, R5 i R6 su definirani u zahtjevu 1.
10. Postupak za pripravu spojeva formule (I) prema bilo kojem od zahtjeva 1 do 7 u kojem R2 i R3 zajedno tvore heterocikal s dušikom prema formuli (A) kako je definirano u zahtjevu 1, i u kojem R1 i R4 predstavljaju skupine kako je definirano u zahtjevu 1, uz uvjet da R1 nije vodikov atom, naznačen time da: - spoj s formulom (IV) [image] u kojem R4 je kako je definirano u zahtjevu 1, se kondenzira sa spojem s formulom (V) [image] kako bi se dobilo spoj s formulom (VI) [image] - spoj s formulom (VI) se podvrgava bazičnoj reakciji hidrolize kako bi se dobilo spoj s formulom (VII): [image] - reakcija esterifikacije spoja s formulom (VII) provodi se tako da se dobije spoj s formulom (VIII): [image] - spoj s formulom (VIII) se podvrgava reakciji bromiranja kako bi se dobilo spoj s formulom (X): [image] - spoj s formulom (X) se podvrgava, u prisutnosti paladijeva katalizatora, liganda i baze: . reakciji s fenilboratnim ili heteroarilboratnim ili fenilboronatnim esterom ili derivatima heteroarilboronatnog estera u skladu sa Suzuki spajanjem, . ili drugačije reakciji iminacije s benzofenoniminom, nakon čega slijedi kisela hidroliza i reakciji alkilacije sa sulfonil kloridom s formulom R6SO2Cl, . ili drugačije reakciji cijanacije s cinkovim kloridom, nakon čega slijedi kisela hidroliza i esterifikaciji ili peptidnom spajanju s aminom R5R6NH2, R5 i R6 su definirani u zahtjevu 1, kako bi se dobilo spoj s formulom (XIV): [image] - derivat s formulom (XIV) se podvrgava djelovanju trifosgena tako da se tvori odgovarajući izocijanat, tako dobiveni izocijanat kondenzira s aminom s formulom RaNH2 kako bi se dobilo ureu s formulom (XV), Ra je kako je definirano u zahtjevu 1: [image] - derivat s formulom (XV) se podvrgava reakciji ciklizacije u bazičnom mediju kako bi se dobilo spoj s formulom (XVI): [image] - spoj s formulom (XVI) se podvrgava reakciji alkilacije u prisutnosti baze i halogeniranog derivata Ra'X, Ra' je kako je definirano u zahtjevu 1 i X je halogen.
11. Postupak za pripravu spojeva formule (I) prema zahtjevima 1 do 7 gdje R2 i R3 zajedno tvore heterocikal s dušikom prema formuli (A) i u kojem R1 predstavlja skupinu kako je definirano u zahtjevu 1, uz uvjet da R1 ne predstavlja vodikov atom, R4 je kako je definirano u zahtjevu, naznačen time da: - spoj s formulom (IV) [image] u kojem R4 je kako je definirano u zahtjevu 1, se kondenzira sa spojem s formulom (V) [image] kako bi se dobilo spoj s formulom (VI) [image] - spoj s formulom (VI) se podvrgava bazičnoj reakciji hidrolize kako bi se dobilo spoj s formulom (VII): [image] - reakcija esterifikacije spoja s formulom (VII) provodi se tako da se dobije spoj s formulom (VIII) [image] - spoj s formulom (VIII) se podvrgava reakciji bromiranja kako bi se dobilo spoj s formulom (X): [image] - derivat s formulom (X) se podvrgava djelovanju trifosgena i nastaje izocijanat koji odgovara spoju s formulom (X), koji je kondenziran s aminom s formulom RaNH2, Ra je kako je definirano u zahtjevu 1, kako bi se dobilo ureu s formulom (XI): [image] - spoj s formulom (XI) se podvrgava reakciji ciklizacije u bazičnom mediju kako bi se dobilo spoj s formulom (XII) [image] - spoj s formulom (XII) se podvrgava, u prisutnosti paladijeva katalizatora, liganda i baze, - reakciji sa fenilboratnim ili heteroarilboratnim ili fenilboronatnim esterom ili derivatima heteroarilboronatnog estera u skladu sa Suzuki spajanjem, - ili drugačije reakciji iminacije s benzofenoniminom, nakon čega slijedi kisela hidroliza i reakciji sulfonilacije sa sulfonil kloridom s formulom R6SO2Cl, - ili drugačije reakciji cijanacije s cinkovim cijanidom, nakon čega slijedi kisela hidroliza i esterifikaciji ili peptidnom spajanju s aminom R5R6NH2, R5 i R6 je kako je definirano u zahtjevu 1, kako bi se dobilo spoj s formulom (XVI) u kojem R1 je kako je definirano u zahtjevu 1, uz uvjet da R1 ne predstavlja vodikov atom, [image] - spoj s formulom (XVI) se podvrgava reakciji alkilacije u prisutnosti baze i halogeniranog derivata Ra'X, Ra' je kako je definirano u zahtjevu 1 i X je halogen.
12. Postupak za pripravu spojeva formule (I) prema zahtjevima 1 do 7, gdje R2 i R3 zajedno tvore heterocikal s dušikom prema formuli (B) kako je definirano u zahtjevu 1, R4 je kako je definirano u zahtjevu 1, i R1 predstavlja vodikov atom, naznačen time da: - spoj s formulom (IV) [image] u kojem R4 je kako je definirano u zahtjevu 1, se kondenzira sa spojem s formulom (V) [image] kako bi se dobilo spoj s formulom (VI) [image] - spoj s formulom (VI) se podvrgava bazičnoj reakciji hidrolize kako bi se dobilo spoj s formulom (VII): [image] - reakcija esterifikacije spoja s formulom (VII) se provodi tako da se dobije spoj s formulom (VIII) [image] - spoj (VIII) se podvrgava reakciji saponifikacije kako bi se dobilo spoj (XXIV): [image] - spoj (XXIV) se zatim podvrgava reakciji kondenzacije sa alkil ili aril anhidridom (Rb'CO)2O kako bi se dobilo spoj s formulom (XVII), [image] - spoj s formulom (XVII) se podvrgava reakciji kondenzacije s aminom RbNH2, Rb i Rb' je kako je definirano u zahtjevu 1.
13. Postupak za pripravu spojeva formule (I) prema zahtjevima 1 do 7, gdje R2 i R3 zajedno tvore heterocikal s dušikom prema formuli (B) kako je definirano u zahtjevu 1, R4 je kako je definirano u zahtjevu 1 i R1 je kako je definirano u zahtjevu 1, uz uvjet da R1 ne predstavlja vodikov atom, naznačen time da: - spoj s formulom (IV) [image] u kojem R4 je kako je definirano u zahtjevu 1, se kondenzira sa spojem s formulom (V): [image] kako bi se dobilo spoj s formulom (VI): [image] - spoj s formulom (VI) se podvrgava bazičnoj reakciji hidrolize kako bi se dobilo spoj s formulom (VII): [image] - reakcija esterifikacije spoja s formulom (VII) provodi se tako da se dobije spoj s formulom (VIII): [image] - spoj s formulom (VIII) se podvrgava reakciji bromiranja kako bi se dobilo spoj s formulom (X): [image] - spoj s formulom (X) se podvrgava, u prisutnosti paladijeva katalizatora, liganda i baze, - reakciji sa fenilboratnim ili heteroarilboratnim ili fenilboronatnim esterom ili derivatima heteroarilboronatnog estera u skladu sa Suzuki spajanjem, - ili drugačije reakciji iminacije s benzofenoniminom, nakon čega slijedi kisela hidroliza i reakciji alkilacije sa sulfonil kloridom s formulom R6SO2Cl, - ili drugačije reakciji cijanacije s cinkovim kloridom, nakon čega slijedi kisela hidroliza i esterifikaciji ili peptidnom spajanju s aminom R5R6NH2, R5 i R6 su definirani u zahtjevu 1, - kako bi se dobilo spoj s formulom XIV: [image] - spoj (XIV) se podvrgava reakciji saponifikacije kako bi se dobilo spoj (XXV): [image] - spoj (XXV) se zatim podvrgava reakciji kondenzacije sa alkil ili aril anhidridom (Rb'CO)2O, Rb' je kako je definirano u zahtjevu 1, kako bi se dobilo spoj s formulom (XVIII): [image] - spoj s formulom (XVIII) se podvrgava reakciji kondenzacije s aminom RbNH2, Rb je kako je definirano u zahtjevu 1.
14. Farmaceutski pripravak naznačen time da sadrži, kao aktivnu tvar, spoj s formulom (I) prema bilo kojem od zahtjeva 1 do 7, proizvoljno u kombinaciji s jednim ili više pogodnih inertnih pomoćnih sredstava.
15. Spoj prema bilo kojem od zahtjeva 1 do 7, naznačen time da je za njegovu upotrebu za liječenje i sprječavanje bolesti koje zahtijevaju modulaciju b-FGFs.
16. Spoj prema bilo kojem od zahtjeva 1 do 7, naznačen time da je za upotrebu za liječenje i sprječavanje karcinoma, naročito karcinoma koji imaju visok stupanj vaskularizacije, kao što su rak pluća, rak dojke, rak prostate, rak gušterače, rak debelog crijeva, rak bubrega i ezofagealni karcinomi, te karcinomi koji induciraju metastaze, kao što su rak debelog crijeva, rak jetre i rak želuca, melanomi, gliomi, limfomi, leukemije, te također trombopenije.
17. Spoj prema zahtjevu 16, naznačen time da je za upotrebu u kombinaciji s jednim ili više antikancerogenih aktivnih sastojaka i/ili s radioterapijom i/ili s bilo kojim anti-VEGF tretmanom.
18. Spoj prema bilo kojem od zahtjeva 1 do 7, naznačen time da je za upotrebu za liječenje i sprječavanje kardiovaskularnih bolesti, poput ateroskleroze ili postangioplastične restenoze, bolesti povezanih s komplikacijama koje se javljaju nakon implantacije endovaskularnih stentova i/ili aortokoronarnih premosnica ili drugih vaskularnih transplantata, srčane hipertrofije, vaskularnih komplikacija dijabetesa, kao što je dijabetička retinopatija, fibroza jetre, fibroza bubrega i fibroza pluća, neuropatska bol, kroničnih upalnih bolesti kao što je reumatoidni artritis ili IBD, hiperplazije prostate, psorijaze, akantoma svijetlih stanica, osteoartritisa, ahondroplazija (ACH), hipohondroplazija (HCH), TD (tanatoforičnih displazija), pretilosti, te makularne degeneracije, kao što je makularna degeneracija povezana sa starenjem (ARMD).
HRP20151309TT 2010-07-06 2015-12-01 Derivati imidazopiridina, postupak za njihovu pripravu i njihova terapeutska upotreba HRP20151309T1 (hr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
FR1055475A FR2962437B1 (fr) 2010-07-06 2010-07-06 Derives d'imidazopyridine, leur procede de preparation et leur application en therapeutique
PCT/IB2011/052954 WO2012004732A1 (en) 2010-07-06 2011-07-04 Imidazopyridine derivatives, process for the preparation thereof and therapeutic use thereof
EP11743633.7A EP2590976B1 (en) 2010-07-06 2011-07-04 Imidazopyridine derivatives, process for the preparation thereof and therapeutic use thereof

Publications (1)

Publication Number Publication Date
HRP20151309T1 true HRP20151309T1 (hr) 2016-01-01

Family

ID=43383651

Family Applications (1)

Application Number Title Priority Date Filing Date
HRP20151309TT HRP20151309T1 (hr) 2010-07-06 2015-12-01 Derivati imidazopiridina, postupak za njihovu pripravu i njihova terapeutska upotreba

Country Status (36)

Country Link
US (2) US8759344B2 (hr)
EP (1) EP2590976B1 (hr)
JP (1) JP5889295B2 (hr)
KR (1) KR101820548B1 (hr)
CN (1) CN103080111B (hr)
AR (1) AR082112A1 (hr)
AU (1) AU2011275427B2 (hr)
BR (1) BR112013000273B1 (hr)
CA (1) CA2804915C (hr)
CL (1) CL2013000016A1 (hr)
CO (1) CO6650360A2 (hr)
CR (1) CR20120643A (hr)
CY (1) CY1117374T1 (hr)
DK (1) DK2590976T3 (hr)
EA (1) EA022690B1 (hr)
EC (1) ECSP13012363A (hr)
ES (1) ES2556754T3 (hr)
FR (1) FR2962437B1 (hr)
GT (1) GT201200346A (hr)
HR (1) HRP20151309T1 (hr)
HU (1) HUE025639T2 (hr)
IL (1) IL223832A (hr)
MA (1) MA34450B1 (hr)
MX (1) MX2012015120A (hr)
NI (1) NI201200192A (hr)
NZ (1) NZ604973A (hr)
PE (1) PE20130651A1 (hr)
PL (1) PL2590976T3 (hr)
PT (1) PT2590976E (hr)
SG (1) SG186396A1 (hr)
SI (1) SI2590976T1 (hr)
TN (1) TN2012000608A1 (hr)
TW (1) TWI520961B (hr)
UY (1) UY33488A (hr)
WO (1) WO2012004732A1 (hr)
ZA (1) ZA201209632B (hr)

Families Citing this family (28)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2962437B1 (fr) 2010-07-06 2012-08-17 Sanofi Aventis Derives d'imidazopyridine, leur procede de preparation et leur application en therapeutique
US8754114B2 (en) 2010-12-22 2014-06-17 Incyte Corporation Substituted imidazopyridazines and benzimidazoles as inhibitors of FGFR3
FR2985185B1 (fr) * 2012-01-04 2013-12-27 Sanofi Sa Utilisation en therapeutique de derives d'imidazopyridine
UA117347C2 (uk) 2012-06-13 2018-07-25 Інсайт Холдинґс Корпорейшн Заміщені трициклічні сполуки як інгібітори fgfr
WO2014026125A1 (en) 2012-08-10 2014-02-13 Incyte Corporation Pyrazine derivatives as fgfr inhibitors
US9266892B2 (en) 2012-12-19 2016-02-23 Incyte Holdings Corporation Fused pyrazoles as FGFR inhibitors
AR094812A1 (es) 2013-02-20 2015-08-26 Eisai R&D Man Co Ltd Derivado de piridina monocíclico como inhibidor del fgfr
CN105263931B (zh) 2013-04-19 2019-01-25 因赛特公司 作为fgfr抑制剂的双环杂环
EP3044224A1 (en) * 2013-09-11 2016-07-20 F. Hoffmann-La Roche AG KETO-IMIDAZOPYRIDINE DERIVATIVES AS RORc MODULATORS
RU2658821C1 (ru) 2014-08-18 2018-06-25 Эйсай Ар Энд Ди Менеджмент Ко., Лтд. Соль моноциклического производного пиридина и ее кристалл
US10851105B2 (en) 2014-10-22 2020-12-01 Incyte Corporation Bicyclic heterocycles as FGFR4 inhibitors
UA121669C2 (uk) 2015-02-20 2020-07-10 Інсайт Корпорейшн Біциклічні гетероцикли як інгібітори fgfr
WO2016134294A1 (en) 2015-02-20 2016-08-25 Incyte Corporation Bicyclic heterocycles as fgfr4 inhibitors
MA41551A (fr) 2015-02-20 2017-12-26 Incyte Corp Hétérocycles bicycliques utilisés en tant qu'inhibiteurs de fgfr4
US9640143B1 (en) * 2016-01-22 2017-05-02 Sony Corporation Active video projection screen coordinating grayscale values of screen with color pixels projected onto screen
AR111960A1 (es) 2017-05-26 2019-09-04 Incyte Corp Formas cristalinas de un inhibidor de fgfr y procesos para su preparación
EP3777860A4 (en) 2018-03-28 2021-12-15 Eisai R&D Management Co., Ltd. THERAPEUTIC FOR HEPATOCELLULAR CARCINOMA
MA52493A (fr) 2018-05-04 2021-03-10 Incyte Corp Sels d'un inhibiteur de fgfr
SG11202010636VA (en) 2018-05-04 2020-11-27 Incyte Corp Solid forms of an fgfr inhibitor and processes for preparing the same
US11628162B2 (en) 2019-03-08 2023-04-18 Incyte Corporation Methods of treating cancer with an FGFR inhibitor
WO2021007269A1 (en) 2019-07-09 2021-01-14 Incyte Corporation Bicyclic heterocycles as fgfr inhibitors
PE20221085A1 (es) 2019-10-14 2022-07-05 Incyte Corp Heterociclos biciclicos como inhibidores de fgfr
WO2021076728A1 (en) 2019-10-16 2021-04-22 Incyte Corporation Bicyclic heterocycles as fgfr inhibitors
CN115151539A (zh) 2019-12-04 2022-10-04 因赛特公司 Fgfr抑制剂的衍生物
WO2021113479A1 (en) 2019-12-04 2021-06-10 Incyte Corporation Tricyclic heterocycles as fgfr inhibitors
CN114380752A (zh) * 2020-10-22 2022-04-22 南开大学 一种制备n-取代-2，4-喹唑啉二酮类化合物的合成方法
CA3220274A1 (en) 2021-06-09 2022-12-15 Incyte Corporation Tricyclic heterocycles as fgfr inhibitors
CN114016060B (zh) * 2021-11-23 2023-05-02 南昌大学 一种酚类化合物的合成方法

Family Cites Families (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SE0102808D0 (sv) 2001-08-22 2001-08-22 Astrazeneca Ab New compounds
FR2838123B1 (fr) 2002-04-04 2005-06-10 Sanofi Synthelabo Nouveaux derives d'indolozine-1,2,3 substituee, inhibiteurs selectifs du b-fgf
FR2851563B1 (fr) 2003-02-26 2005-04-22 Sod Conseils Rech Applic Nouveaux derives de benzimidazole et d'imidazo-pyridine et leur utilisation en tant que medicament
FR2859997B1 (fr) 2003-09-18 2006-02-03 Sanofi Synthelabo Nouveaux derives d'indolizine 1,2,3,6,7,8 substituee, inhibiteurs des fgfs, leur procede de preparation et les compositions pharmaceutiques les contenant.
WO2005028479A2 (en) 2003-09-25 2005-03-31 Janssen Pharmaceutica N.V. Hiv replication inhibiting purine derivatives
FR2865934B1 (fr) 2004-02-05 2006-05-05 Sanofi Synthelabo Utilisation de derives d'indolizine 1,2,3 substitues, inhibiteurs des fgfs, pour la preparation de medicaments utiles pour le traitement de maladies liees a une angiogenese pathologique choroidienne
KR20070086595A (ko) * 2004-11-22 2007-08-27 쓰레솔드 파마슈티컬스, 인코포레이티드 튜불린 결합 항암제 및 이의 전구약물
FR2883286B1 (fr) * 2005-03-16 2008-10-03 Sanofi Aventis Sa NOUVEAUX DERIVES D'IMIDAZO[1,5-a]PYRIDINES, INHIBITEURS DE FGFs, LEUR PROCEDE DE PREPARATION ET LES COMPOSITIONS PHARMACEUTIQUES LES CONTENANT
CN1733742A (zh) * 2005-07-12 2006-02-15 浙江大学 苯并三嗪衍生物的制备及用途
FR2893616B1 (fr) 2005-11-23 2008-01-04 Sanofi Aventis Sa Nouveaux derives d'indolizine, leur procede de preparation et les compositions therapeutiques les comprenant
FR2896247B1 (fr) * 2006-01-13 2008-02-29 Sanofi Aventis Sa Composes dimeres agonistes des recepteurs des fgfs (fgfrs), leur procede de preparation et leur application en therapeutique
EP1891955A1 (en) 2006-07-24 2008-02-27 Sanofi-Aventis Use of 1,2,3-substituted indolizine derivatives, inhibitors of FGFs, for the preparation of a medicament intended for the treatment of degenerative joint diseases
CN1887878A (zh) * 2006-07-26 2007-01-03 浙江大学 三嗪氮氧化物及合成方法和用途
WO2008085302A1 (en) 2006-12-20 2008-07-17 Merck & Co., Inc. Imidazopyridine analogs as cb2 receptor modulators, useful in the treatment of pain, respiratory and non-respiratory diseases
CN101239978A (zh) 2008-03-05 2008-08-13 南方医科大学 一种咪唑并吡啶类化合物
WO2011055320A1 (en) 2009-11-06 2011-05-12 Piramal Life Sciences Limited Imidazopyridine derivatives
FR2962437B1 (fr) 2010-07-06 2012-08-17 Sanofi Aventis Derives d'imidazopyridine, leur procede de preparation et leur application en therapeutique

Also Published As

Publication number Publication date
CL2013000016A1 (es) 2013-04-19
ECSP13012363A (es) 2013-01-31
TWI520961B (zh) 2016-02-11
SI2590976T1 (sl) 2016-01-29
MX2012015120A (es) 2013-05-01
CN103080111B (zh) 2016-06-15
CO6650360A2 (es) 2013-04-15
AU2011275427B2 (en) 2016-04-21
GT201200346A (es) 2014-05-20
TW201217370A (en) 2012-05-01
HUE025639T2 (en) 2016-04-28
FR2962437B1 (fr) 2012-08-17
JP2013530211A (ja) 2013-07-25
TN2012000608A1 (en) 2014-04-01
FR2962437A1 (fr) 2012-01-13
US20140243328A1 (en) 2014-08-28
EP2590976B1 (en) 2015-09-16
CR20120643A (es) 2013-02-05
NI201200192A (es) 2013-05-13
MA34450B1 (fr) 2013-08-01
CY1117374T1 (el) 2017-04-26
NZ604973A (en) 2014-05-30
US20130116250A1 (en) 2013-05-09
US8759344B2 (en) 2014-06-24
SG186396A1 (en) 2013-01-30
IL223832A (en) 2017-03-30
UY33488A (es) 2012-01-31
PE20130651A1 (es) 2013-06-20
ZA201209632B (en) 2014-03-26
CN103080111A (zh) 2013-05-01
BR112013000273B1 (pt) 2020-09-29
US9452164B2 (en) 2016-09-27
PT2590976E (pt) 2016-01-20
JP5889295B2 (ja) 2016-03-22
CA2804915A1 (en) 2012-01-12
BR112013000273A8 (pt) 2018-04-24
DK2590976T3 (en) 2015-12-21
ES2556754T3 (es) 2016-01-20
PL2590976T3 (pl) 2016-03-31
AU2011275427A1 (en) 2013-01-24
CA2804915C (en) 2018-07-03
AR082112A1 (es) 2012-11-14
WO2012004732A1 (en) 2012-01-12
BR112013000273A2 (pt) 2017-10-31
EA022690B1 (ru) 2016-02-29
KR20130128363A (ko) 2013-11-26
KR101820548B1 (ko) 2018-01-19
EA201291414A1 (ru) 2013-05-30
EP2590976A1 (en) 2013-05-15

Similar Documents

Publication Publication Date Title
HRP20151309T1 (hr) Derivati imidazopiridina, postupak za njihovu pripravu i njihova terapeutska upotreba
HRP20151162T1 (hr) Derivati indolizina, postupak za njihovo pripremanje i terapijska primjena
ES2581848T3 (es) Derivados de pirrolo[2,3-d]pirimidina como inhibidores de quinasas relacionadas con tropomiosina
ES2335659T3 (es) Pirimidopirimidonas como inhibidores de quinasas.
JP2023512113A (ja) Ｋｒａｓ ｇ１２ｄ変異に対して阻害活性を有する化合物
ES2719444T3 (es) Derivados de pirazol, procedimientos para su preparación y su uso terapéutico
ES2243598T3 (es) Nuevos derivados de pirazolopiridina sustituidos con piridina.
ES2274913T3 (es) Aza y poliaza-naftalenil carboxamidas utiles como inhibidores de vih integrada.
IL224164A (en) Derivatives 3,2-Diphenyl-8,1-Naphthyridine and 8,4,1-Aza-Naphthyridine and Pharmaceuticals Containing Them
US20100331334A1 (en) Inhibitors of mek
JP6285013B2 (ja) ３，５−（非）置換−１Ｈ−ピロロ［２，３−ｂ］ピリジン、１Ｈ−ピラゾロ［３，４−ｂ］ピリジン、及び５Ｈ−ピロロ［２，３−ｂ］ピラジン、ＩＴＫ及びＪＡＫ３キナーゼの阻害剤
EP1812450A2 (en) Tgf-beta inhibitors
JP2013544261A5 (hr)
KR20110125670A (ko) Ｒａｆ 키나제의 억제를 위한 피롤로［２,３-ｂ］피리딘 유도체
NZ536068A (en) Quinolinone derivatives
JP2010533729A (ja) キナーゼ調節のための化合物と方法、及びそのための適応
IL185611A (en) Annotated 3- (phenylcarbonyl) - imidazo [5,1-a] pyridine, processes for preparation and pharmaceutical preparations containing them
CA2429313A1 (en) Novel sulfonamide-substituted pyrazolopyridine derivatives
JP2022551093A (ja) 四環系ピリミジノン類化合物、その製造方法、その組成物及び使用
JP2019524895A (ja) 縮合複素環誘導体、その調製方法、及びその医学的使用
AU2022222470A1 (en) Tyk2 inhibitors and uses thereof
TW201920141A (zh) Cdk4/6抑制劑及其用途
JP2008500944A (ja) ２−置換フェニル−５，７−ジアルキル−３，７−ジヒドロピロロ［２，３−ｄ］ピリミジン−４−オン誘導体、その製法およびその医薬用途
CA3184974A1 (en) Preparation and application of tricyclic pyrimidinone compound and its composition
CA3222404A1 (en) Heterocyclic jak inhibitor