ME02479B - Nova jedinjenja kao inhibitori diacilglicerol-aciltransferaze - Google Patents
Nova jedinjenja kao inhibitori diacilglicerol-aciltransferazeInfo
- Publication number
- ME02479B ME02479B MEP-2016-159A MEP2016159A ME02479B ME 02479 B ME02479 B ME 02479B ME P2016159 A MEP2016159 A ME P2016159A ME 02479 B ME02479 B ME 02479B
- Authority
- ME
- Montenegro
- Prior art keywords
- amino
- pirimido
- oksazepin
- indol
- piridin
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims 11
- 102000002148 Diacylglycerol O-acyltransferase Human genes 0.000 title 1
- 108010001348 Diacylglycerol O-acyltransferase Proteins 0.000 title 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 17
- -1 C3-C7cycloalkyl Chemical group 0.000 claims 12
- 125000005843 halogen group Chemical group 0.000 claims 12
- 150000001408 amides Chemical class 0.000 claims 9
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 9
- 150000003839 salts Chemical class 0.000 claims 9
- 229910052739 hydrogen Inorganic materials 0.000 claims 7
- 239000001257 hydrogen Substances 0.000 claims 7
- 125000004043 oxo group Chemical group O=* 0.000 claims 6
- QHXILXDHCYOAQA-UHFFFAOYSA-N 2h-1,4-oxazepin-5-one Chemical compound O=C1C=COCC=N1 QHXILXDHCYOAQA-UHFFFAOYSA-N 0.000 claims 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims 5
- 125000004104 aryloxy group Chemical group 0.000 claims 5
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- 125000003118 aryl group Chemical group 0.000 claims 4
- 125000001072 heteroaryl group Chemical group 0.000 claims 4
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 3
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 150000002431 hydrogen Chemical class 0.000 claims 3
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims 2
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 2
- 125000001070 dihydroindolyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims 2
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims 2
- 125000001041 indolyl group Chemical group 0.000 claims 2
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims 2
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims 2
- KDOPAZIWBAHVJB-UHFFFAOYSA-N 5h-pyrrolo[3,2-d]pyrimidine Chemical compound C1=NC=C2NC=CC2=N1 KDOPAZIWBAHVJB-UHFFFAOYSA-N 0.000 claims 1
- 208000008589 Obesity Diseases 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims 1
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 claims 1
- 125000002619 bicyclic group Chemical group 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 125000004609 dihydroquinazolinyl group Chemical group N1(CN=CC2=CC=CC=C12)* 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 235000020824 obesity Nutrition 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
- A61K31/553—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having at least one nitrogen and one oxygen as ring hetero atoms, e.g. loxapine, staurosporine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- 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
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Obesity (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Communicable Diseases (AREA)
- Child & Adolescent Psychology (AREA)
- Oncology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Claims (11)
1.Jedinjenje formule (I):gde R1 je biciklični sistem prstenova koji sadrži 9 do 11 članova prstena uključujući 1 do 4 heteroatoma, nezavisno izabranih iz grupe koju čine N, O, i S, gde pomenuti biciklični sistem može biti supstituisan sa 1 do 3 grupe izabrane iz grupe koju čine C1-C6alkil, supstituisani C1-C6alkil, C3-C7cikloalkil, halo, hidroksil, okso, amid, karboksilna kiselina, -C(O)Ra, -SO2Ra, arilalkil, -(C1-C3alkil)ariloksi, aril, heteroaril i C1-C4alkoksi,gde svaki Ra je nezavisno C1-C6alkil, supstituisani C1-C6alkil ili nesupstituisani C3-C7cikloalkil;svaki R2i R3je nezavisno vodonik, C1-C6alkil, supstituisani C1-C6alkil, halo, hidroksil, amid, karboksilna kiselina, ili C1-C4alkoksi; im je 0-2;ili njegova farmaceutski prihvatljiva so.
2.Jedinjenje prema zahtevu 1, koje je predstavljeno formulom (I) (A) gde je A 5- ili 6-člani heterociklični prsten, koji može imati 0 do 3 dvostrukih veza i može biti supstituisan sa 1 do 3 grupe izabrane iz grupe koju čine C1-C6alkil, supstituisani C1-C6alkil, C3-C7cikloalkil, halo, hidroksil, okso, amid, karboksilna kiselina, -C(O)Ra, -SO2Ra, arilalkil, -(C1-C3alkil)ariloksi, aril, heteroaril i C1-C4alkoksi, gde je svaki Ra nezavisno C1-C6alkil, supstituisani C1-C6alkil ili nesupstituisani C3-C7cikloalkil; svaki R2i R3je nezavisno vodonik, C1-C6alkil, supstituisani C1-C6alkil, halo, hidroksil, amid, karboksilna kiselina ili C1-C4alkoksi; R4je halo ili alkoksi; X je N ili CH; i m je 0-2; n je 0-2; ili njegova farmaceutski prihvatljiva so.
3.Jedinjenje prema zahtevu 2, gde je A 5-člani heterociklični prsten, koji može imati 0-2 dvostruke veze i može biti supstituisan sa 1-3 grupe izabrane iz grupe koju čine C1-C6alkil, supstituisani C1-C6alkil, C3-C7cikloalkil, halo, hidroksil, okso, amid, karboksilna kiselina, -C(O)Ra, -SO2Ra, arilalkil, -(C1-C3alkil)ariloksi, aril, heteroaril i C1-C4alkoksi, gde je svaki Ra nezavisno C1-C6alkil, supstituisani C1-C6alkil ili nesupstitusiani C3-C7cikloalkil; svaki R2 i R3 je nezavisno vovonik, C1-C6alkil, supstituisani C1-C6alkil, halo, hidroksil, amid, karboksilna kiselina ili C1-C4alkoksi; R4 je halo ili alkoksi; X je N ili CH; i m je 0-2; n je 0-2; ili njegova farmaceutski prihvaltljiva so.
4.Jedinjenje prema zahtevu 2, što je A 6-člani heterociklični prsten, koji može imati 0-3 dvostruke veze i može biti supstituisan sa 1 do 3 grupe iz grupe koju čine C1-C6alkil, supstituisani C1-C6alkil,C3-C7cikloalkil, halo, hidroksil, okso, amid, karboksilna kiselina, -C(O)Ra, -SO2Ra, arilalkil, -(C1-C3alkil)ariloksi, aril,heteroaril i C1-C4alkoksi, gde je svaki Ranezavisno C1-C6alkil, supstituisani C1-C6alkil ili nesupstitusiani C3-C7cikloalkil; svaki R2i R3je nezavisno vodonik, C1-C6alkil, supstituisani C1-C6alkil, halo, hidroksil, amid, karboksilna kiselina ili C1-C4alkoksi; R4je halo ili alkoksi; X je N ili CH; i m je 0-2; n je 0-2; ili njegova farmaceutski prihvatljiva so.
5.Jedinjenje prema bilo kom od zahteva 2-4, gde m je 0; n je 0; R3 je vodonik; i X je N; ili njegova farmaceutski prihvatljiva so.
6.Jedinjenje prema bilo kom od zahteva 2-4, gde m je 0; n je 0; R3 je vodonik i X je CH; ili njegova farmaceutski prihvatljiva so.
7.Jedinjenje prema zahtevu 1, gde m je 0; R3 je vodonik; R1 je biciklični sistem prstenova izabran iz grupe koju čine tetrahidroizohinolinil, tetrahidrohinolinil, indolil, dihidroindolil, indazolil, dihidroindazolil, benzotiofenil, benzodiazolil, dihidrobenzodiazolil, benzimidazolil,indolinil, benzotriazolil, pirolopiridinil, benzotiazolil, benzofuranil, dihidrohinazolinil, i pirolopirimidinil; gde pomenuti biciklični sistem prstenova može biti supstituisan sa 1 do 3 grupe izabrane iz grupe koju čine C1-C6alkil, supstituisani C1-C6alkil, C3-C7cikloalkil, halo, hidroksil, okso, amid, karboksilna kiselina, -C(O)Ra, -SO2Ra, arilalkil,-(C1-C3alkil)ariloksi, aril, heteroaril i C1-C4alkoksi, gde svaki Raje nezavisno C1-C6alkil, supstituisani C1-C6alkil ili nesupstituisani C3-C7cikloalkil; ili njegova farmaceutski prihvatljiva so.
8.Jedinjenje prema zahtevu 7, gde m je 0; R3 je vodonik; R1 je biciklični sistem prstenova izabran iz grupe koju čine tetrahidroizohinolinil, tetrahidrohinolinil, indolil,dihidroindolil, indazolil, dihidroindazolil, i pirolopiridinil; gde pomenuti biciklični sistemprstenova može biti supstituisan sa 1 do 3 grupe izabrane iz grupe koju čine C1-C6alkil, supstituisani C1-C6alkil, C3-C7cikloalkil, halo, hidroksil, okso, amid, karboksilna kiselina, -C(O)Ra, -SO2Ra, arilalkil,-(C1-C3alkil)ariloksi, aril, heteroaril i C1-C4alkoksi, gde svaki Raje nezavisno C1-C6alkil, supstituisani C1-C6alkil ilinesupstituisani C3-C7cikloalkil; ili njegova farmaceutski prihvatljiva so.
9.Jedinjenje prema zahtevu 1 izabrano iz grupe koju čine: 2-(6-{4-amino-5-okso-5H,6H,7H,8H-pirimido[5,4-f][1,4]oksazepin-6-il}-1-okso-1,2,3,4-tetrahidroizohinolin-2-il)sirćetna kiselina; etil 2-(6-{4-amino-5-okso-5H,6H,7H,8H-pirimido[5,4-f][1,4]oksazepin-6-il}-2-okso-1,2,3,4-tetrahidrohinolin-1-il)acetat; 2-(6-{4-amino-5-okso-5H,6H,7H,8H-pirimido[5,4-f][1,4]oksazepin-6-il}-2-okso-1,2,3,4-tetrahidrohinolin-1-il)sirćetna kiselina; etil 2-(6-{4-amino-5-okso-5H,6H,7H,8H-pirimido[5,4-f][1,4]oksazepin-6-il}-1-okso-1,2,3,4-tetrahidroizohinolin-2-il)acetat; 6-{4-amino-5-okso-5H,6H,7H,8H-pirimido[5,4-f][1,4]oksazepin-6-il}-1-metil-1,2,3,4-tetrahidrohinolin-2-on; 6-{4-amino-5-okso-5H,6H,7H,8H-pirimido[5,4-f][1,4]oksazepin-6-il}-2-metil-1,2,3,4-tetrahudroizohinolin-1-on; 6-{4-amino-5-okso-5H,6H,7H,8H-pirimido[5,4-f][1,4]oksazepin-6-il}-2-benzil-1,2,3,4-tetrahidroizohinolin-1-on; 6-{4-amino-5-okso-5H,6H,7H,8H-pirimido[5,4-f][1,4]oksazepin-6-il}-2-propil-1,2,3,4-tetrahidroizohinolin-1-on; 6-{4-amino-5-okso-5H,6H,7H,8H-pirimido[5,4-f][1,4]oksazepin-6-il}-l-propil-1,2,3,4-tetrahidrohinolin-2-on; 5-{4-amino-5-okso-5H,6H,7H,8H-pirimido[5,4-f][1,4]oksazepin-6-il}-2-benzil-1-(prop-2-en-1-il)-2,3-dihidro-1H-indazol-3-on; 5-{4-amino-5-okso-5H,6H,7H,8H-pirimido[5,4-f][1,4]oksazepin-6-il}-1-propil-2,3-dihidro-1H-indazol-3-on; 4-amino-6-(1-propil-1H-indol-5-il)-5H,6H,7H,8H-pirimido[5,4-f][1,4]oksazepin-5-on; 4-amino-6-(1-propil-1H-indazol-5-il)-5H,6H,7H,8H-pirimido[5,4-f][1,4]oksazepin-5-on; 4-amino-6-(1-benzotiofen-5-il)-5H,6H,7H,8H-pirimido[[5,4-f][1,4]oksazepin-5-on; 5-{4-amino-5-okso-5H,6H,7H,8H-pirimido[5,4-f][1,4]oksazepin-6-il}-1,3-dipropil-2,3-dihidro-1H-1,3-benzodiazol-2-on; 4-amino-6-(2-propil-2H-indazol-5-il)-5H,6H,7H,8H-pirimido[5,4-f][1,4]oksazepin-5-on; 4-amino-6-(1,3-benzotiazol-6-il)-5H,6H,7H,8H-pirimido[5,4-f][1,4]oksazepin-5-on; 5-{4-amino-5-okso-5H,6H,7H,8H-pirimido[5,4-f][1,4]oksazepin-6-il}-1-propil-2,3-dihidro-1H-indol-2,3-dion; 4-amino-6-(1-benzofuran-5-il)-5H,6H,7H,8H-pirimido[5,4-f][1,4]oksazepin-5-on; 4-amino-6-(1-ciklopropil-1,2,3,4-tetrahidrohinolin-6-il)-5H,6H,7H,8H-pirimido[5,4-f][1,4]oksazepin-5-on; 4-amino-6-(2-propil-1,2,3,4-tetrahidroizohinolin-6-il)-5H,6H,7H,8H-pirimido[5,4-f][1,4]oksazepin-5-on; 4-amino-6-[1-(2,2-difluoroetil)-1,2,3,4-tetrahidrohinolin-6-il]-5H,6H,7H,8H-pirimido[5,4-f][1,4]oksazepin-5-on; 5-{4-amino-5-okso-5H,6H,7H,8H-oksepino[2,3-d]pirimidin-6-il}-1-(propan-2-il)-2,3-dihidro-1H-indazol-3-on; 5-{4-amino-5-okso-5H,6H,7H,8H-oksepino[2,3-d]pirimidin-6-il}-1-(2-metoksietil)-2,3-dihidro-1H-indazol-3-on; 5-{4-amino-5-okso-5H,6H,7H,8H-pirimido[5,4-f][1,4]oksazepin-6-il}-1-(2,2-difluoroetil)-2,3-dihidro-1H-indazol-3-on; 5-{4-amino-5-okso-5H,6H,7H,8H-pirimido[5,4-f][1,4]oksazepin-6-il}-1-ciklopropil-2,3-dihidro-1H-indazol-3-on; 6-amino-4-(1-propil-1H-1,3-benzodiazol-5-il)-2,3,4,5-tetrahidro-1,4-benzoksazepin-5-on; 4-amino-6-(1-propil-1H-1,3-benzodiazol-6-il)-5H,6H,7H,8H-pirimido[5,4-f][1,4]oksazepin-5-on; 4-amino-6-(2-propil-2H-1,2,3-benzotriazol-5-il)-5H,6H,7H,8H-pirimido[5,4-f][1,4]oksazepin-5-on; 4-amino-6-(1-propil-1H-1,2,3-benzotriazol-6-il)-5H,6H,7H,8H-pirimido[5,4-f][1,4]oksazepin-5-one; 4-amino-6-(2-metil-1,3-benzotiazol-5-il)-5H,6H,7H,8H-pirimido[5,4-f][1,4]oksazepin-5-on; 4-amino-6-[1-(2,2-difluoroetil)-1H-pirolo[2,3-b]piridin-5-il]-5H,6H,7H,8H-pirimido[5,4-f][1,4]oksazepin-5-on; 4-amino-6-{1-ciklopropil-1H-pirolo[2,3-b]piridin-5-il}-5H,6H,7H,8H-pirimido[5,4-f][1,4]oksazepin-5-on; 4-amino-6-[1-(ciklopropilmetil)-1H-indol-5-il]-5H,6H,7H,8H-pirimido[5,4-f][1,4]oksazepin-5-on; 3-(5-{4-amino-5-okso-5H,6H,7H,8H-pirimido[5,4-f][1,4]oksazepin-6-il}-1H-indol-1-il)propanska kiselina; 4-amino-6-[1-(cikloheksilmetil)-1H-indol-5-il]-5H,6H,7H,8H-pirimido[5,4-f][1,4]oksazepin-5-on; 4-amino-6-[1-(pentan-3-il)-1H-indol-5-il]-5H,6H,7H,8H-pirimido[5,4-f][1,4]oksazepin-5-on; 4-amino-6-{1-[(4-metoksifenil)metil]-1H-indol-5-il}-5H,6H,7H,8H-pirimido[5,4-f][1,4]oksazepin-5-on; 4-amino-6-{1-[(4-fluorofenil)metil]-1H-indol-5-il}-5H,6H,7H,8H-pirimido[5,4-f][1,4]oksazepin-5-on; 4-amino-6-{1-[2-(benziloksi)etil]-1H-indol-5-il}-5H,6H,7H,8H-pirimido[5,4-f][1,4]oksazepin-5-on; 4-amino-6-(1-benzil-1H-indol-5-il)-5H,6H,7H,8H-pirimido[5,4-f][1,4]oksazepin-5-on; 4-amino-6-[1-(3-metoksipropil)-1H-indol-5-il]-5H,6H,7H,8H-pirimido[5,4-f][1,4]oksazepin-5-on; 4-amino-6-[1-(2,2-difluoroetil)-1H-indol-5-il]-5H,6H,7H,8H-pirimido[5,4-f][1,4]oksazepin-5-on; 4-amino-6-(1-metil-1H-indol-5-il)-5H,6H,7H,8H-pirimido[5,4-f][1,4]oksazepin-5-on; 4-amino-6-[1-(2-metoksietil)-1H-indol-5-il]-5H,6H,7H,8H-pirimido[5,4-f][1,4]oksazepin-5-on; 4-amino-6-[1-(propan-2-il)-1H-indol-5-il]-5H,6H,7H,8H-pirimido[5,4-f][1,4]oksazepin-5-on; 4-amino-6-(1H-indol-5-il)-5H,6H,7H,8H-pirimido[5,4-f][1,4]oksazepin-5-on; 4-amino-6-(1-propil-2,3-dihidro-1H-indol-5-il)-5H,6H,7H,8H-pirimido[5,4-f][1,4]oksazepin-5-on; 4-amino-6-(2,3-dihidro-1H-indol-5-il)-5H,6H,7H,8H-pirimido[5,4-f][1,4]oksazepin-5-on; 4-amino-6-[1-(2-metoksietil)-2,3-dihidro-1H-indol-5-il]-5H,6H,7H,8H-pirimido [5,4-f][1,4]oksazepin-5-on; 4-amino-6-(1,2-dimetil-1H-indol-5-il)-5H,6H,7H,8H-pirimido[5,4-f][1,4]oksazepin-5-on; 4-amino-6-[1-(ciklopropilmetil)-1H-pirolo[2,3-b]piridin-5-il]-5H,6H,7H,8H-pirimido[5,4-f][1,4]oksazepin-5-on; 4-amino-6-{1-propil-1H-pirolo[2,3-b]piridin-5-il}-5H,6H,7H,8H-pirimido[5,4-f][1,4]oksazepin-5-on; 4-amino-6-[1-(2-metoksietil)-1H-pirolo[2,3-b]piridin-5-il]-5H,6H,7H,8H-pirimido[5,4-f][1,4]oksazepin-5-on; 4-amino-6-[1-(cikloheksilmetil)-1H-pirolo[2,3-b]piridin-5-il]-5H,6H,7H,8H-pirimido[5,4-f][1,4]oksazepin-5-on; 4-amino-6-{1-cikloheksil-1H-pirolo[2,3-b]piridin-5-il}-5H,6H,7H,8H-pirimido[5,4-f][1,4]oksazepin-5-on; 4-amino-6-[1-(propan-2-il)-1H-pirolo[2,3-b]piridin-5-il]-5H,6H,7H,8H-pirimido[5,4-f][1,4]oksazepin-5-on; 4-amino-6-[1-(2-hidroksietil)-1H-pirolo[2,3-b]piridin-5-il]-5H,6H,7H,8H-pirimido[5,4-f][1,4]oksazepin-5-on; 4-amino-6-(1-metanesulfonil-1H-indol-5-il)-5H,6H,7H,8H-pirimido[5,4-f][1,4]oksazepin-5-on; 4-amino-6-(1-ciklopropil-1H-indol-5-il)-5H,6H,7H,8H-pirimido[5,4-f][1,4]oksazepin-5-on; 5-{4-amino-5-okso-5H,6H,7H,8H-pirimido[5,4-f][1,4]oksazepin-6-il}-1-propil-1H-indol-2-karboksilna kiselina; 4-amino-6-[1-propil-3-(trifluoroacetil)-1H-indol-5-il]-5H,6H,7H,8H-pirimido[5,4-f][1,4]oksazepin-5-on; 4-amino-6-[1-propil-3-(1,1,1-trifluoro-2-metoksipropan-2-il)-1H-indol-5-il]-5H,6H,7H,8H-pirimido[5,4-f][1,4]oksazepin-5-on; 4-amino-6-(1-fenil-1H-indol-5-il)-5H,6H,7H,8H-pirimido[5,4-f][1,4]oksazepin-5-on; 4-amino-6-{1-[4-(trifluorometil)fenil]-1H-pirolo[2,3-b]piridin-5-il}-5H,6H,7H,8H-pirimido[5,4-f][1,4]oksazepin-5-on; 4-amino-6-[1-(4-fluorofenil)-1H-pirolo[2,3-b]piridin-5-il]-5H,6H,7H,8H-pirimido[5,4-f][1,4]oksazepin-5-on; 4-amino-6-[1-(3-hlorofenil)-1H-pirolo[2,3-b]piridin-5-il]-5H,6H,7H,8H-pirimido[5,4-f][1,4]oksazepin-5-on; 4-amino-6-[1-(3-hlorofenil)-1H-indol-5-il]-5H,6H,7H,8H-pirimido[5,4-f][1,4]oksazepin-5-on; 4-amino-6-[1-(2-metoksifenil)-1H-pirolo[2,3-b]piridin-5-il]-5H,6H,7H,8H-pirimido[5,4-f][1,4]oksazepin-5-on; 4-amino-6-[1-(2-metoksifenil)-1H-indol-5-il]-5H,6H,7H,8H-pirimido[5,4-f][1,4]oksazepin-5-on; 4-amino-6-{1-fenil-1H-pirolo[2,3-b]piridin-5-il}-5H,6H,7H,8H-pirimido[5,4-f][1,4]oksazepin-5-on; 4-amino-6-[1-(2-fluorofenil)-1H-pirolo[2,3-b]piridin-5-il]-5H,6H,7H,8H-pirimido[5,4-f][1,4]oksazepin-5-on; 4-amino-6-[1-(3,4-difluorofenil)-1H-indol-5-il]-5H,6H,7H,8H-pirimido [5,4-f][1,4]oksazepin-5-on; 4-amino-6-[1-(3,4-difluorofenil)-1H-pirolo[2,3-b]piridin-5-il]-5H,6H,7H,8H-pirimido[5,4-f][1,4]oksazepin-5-on; 4-amino-6-[1-(2-fluorofenil)-1H-indol-5-il]-5H,6H,7H,8H-pirimido [5,4-f][1,4]oksazepin-5-on; 4-amino-6-{1-[4-(trifluorometil)fenil]-1H-indol-5-il}-5H,6H,7H,8H-pirimido[5,4-f][1,4]oksazepin-5-on; 4-amino-6-[1-(4-hlorofenil)-1H-pirolo[2,3-b]piridin-5-il]-5H,6H,7H,8H-pirimido[5,4-f][1,4]oksazepin-5-on; 4-amino-6-{1-[3-(trifluorometil)fenil]-1H-indol-5-il}-5H,6H,7H,8H-pirimido[5,4-f][1,4]oksazepin-5-on; 4-amino-6-{1-[3-(trifluorometil)fenil]-1H-pirolo[2,3-b]piridin-5-il}-5H,6H,7H,8H-pirimido[5,4-f][1,4]oksazepin-5-on; 4-amino-6-[1-(1,3-tiazol-2-il)-1H-indol-5-il]-5H,6H,7H,8H-pirimido[5,4-f][1,4]oksazepin-5-on; 4-amino-6-{1-[6-(trifluorometil)piridin-3-il]-1H-indol-5-il}-5H,6H,7H,8H-pirimido[5,4-f][1,4]oksazepin-5-on; 4-amino-6-[1-(piridin-2-il)-1H-indol-5-il]-5H,6H,7H,8H-pirimido[5,4-f][1,4]oksazepin-5-on; 4-amino-6-[1-(piridin-2-il)-1H-pirolo[2,3-b]piridin-5-il]-5H,6H,7H,8H-pirimido[5,4-f][1,4]oksazepin-5-on; 4-amino-6-[1-(pirazin-2-il)-1H-pirolo [2,3-b]piridin-5-il]-5H,6H,7H,8H-pirimido[5,4-f][1,4]oksazepin-5-on; 4-amino-6-[1-(pirazin-2-il)-1H-indol-5-il]-5H,6H,7H,8H-pirimido[5,4-f][1,4]oksazepin-5-on; 4-amino-6-{1-[5-(trifluorometil)piridin-2-il]-1H-indol-5-il}-5H,6H,7H,8H-pirimido[5,4-f][1,4]oksazepin-5-on; 4-amino-6-{1-[5-(trifluorometil)piridin-2-il]-1H-pirolo[2,3-b]piridin-5-il}-5H,6H,7H,8H-pirimido[5,4-f][1,4]oksazepin-5-on; 4-amino-6-[1-(1,3-tiazol-2-il)-1H-pirolo[2,3-b]piridin-5-il]-5H,6H,7H,8H-pirimido[5,4-f][1,4]oksazepin-5-on; 4-amino-6-{1-[6-(trifluorometil)piridin-3-il]-1H-pirolo[2,3-b]piridin-5-il}-5H,6H,7H,8H-pirimido[5,4-f][1,4]oksazepin-5-on; 4-amino-6-[1-fenil-3-(propan-2-il)-1H-indol-5-il]-5H,6H,7H,8H-pirimido[5,4-f][1,4]oksazepin-5-on; 4-amino-6-(2-fenil-1-propil-1H-indol-5-il)-5H,6H,7H,8H-pirimido[5,4-f][1,4]oksazepin-5-on; 4-amino-6-(6-fluoro-1-fenil-1H-indol-5-il)-5H,6H,7H,8H-pirimido[5,4-f][1,4]oksazepin-5-on; 6-{4-amino-5-okso-5H,6H,7H,8H-pirimido[5,4-f][1,4]oksazepin-6-il}-3-benzil-3,4-dihidrohinazolin-4-on; 6-{4-amino-5-okso-5H,6H,7H,8H-pirimido[5,4-f][1,4]oksazepin-6-il}-3,4-dihidrohinazolin-4-on; 4-amino-6-(1-benzil-6-fluoro-1H-indol-5-il)-5H,6H,7H,8H-pirimido[5,4-f][1,4]oksazepin-5-on; 4-amino-6-{5-propil-5H-pirolo[3,2-d]pirimidin-2-il}-5H,6H,7H,8H-pirimido[5,4-f][1,4]oksazepin-5-on; 4-amino-6-(1-propil-1H-pirolo[3,2-b]piridin-5-il)-7,8-dihidropirimido[5,4-f][1,4]oksazepin-5(6H)-on; 4-amino-6-(1-(6-metilpiridin-3-il)-1H-indol-5-il)-7,8-dihidropirimido[5,4-f][1,4]oksazepin-5(6H)-on; 4-amino-6-(1-(4-(difluorometil)fenil)-1H-indol-5-il)-7,8-dihidropirimido[5,4-f][1,4]oksazepin-5(6H)-on; 4-amino-6-(1-(4-(difluorometil)fenil)-1H-pirolo[2,3-b]piridin-5-il)-7,8-dihidropirimido[5,4-f][1,4]oksazepin-5(6H)-on; i 4-amino-6-(1-(4-(trifluorometil)piridin-2-il)-1H-pirolo[2,3-b]piridin-5-il)-7,8-dihidropirimido[5,4-f][1,4]oksazepin-5(6H)-on; ili njegova farmaceutski prihvatljiva so.
10.Jedinjenje prema bilokom od zahteva 1-9, ili njegove farmaceutsko prihvatljive soli, za upotrebu u lečenju gojaznosti.
11.Farmaceutska kompozicija koja sadrži jedinjenje prema bilo kom od zahteva 1-9, i farmaceutski prihvatljiv nosač. GlaxoSmithKline Zastupaju,
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| IN1452DE2011 | 2011-05-20 | ||
| US201161503728P | 2011-07-01 | 2011-07-01 | |
| PCT/US2012/038523 WO2012162129A1 (en) | 2011-05-20 | 2012-05-18 | Novel compounds as diacylglycerol acyltransferase inhibitors |
| EP12789931.8A EP2710013B1 (en) | 2011-05-20 | 2012-05-18 | Novel compounds as diacylglycerol acyltransferase inhibitors |
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| DK2710013T3 (en) | 2011-05-20 | 2016-09-26 | Glaxosmithkline Intellectual Property (No 2) Ltd | New compounds such as diacylglycerol-acyltransferase inhibitors |
| WO2014081996A1 (en) * | 2012-11-23 | 2014-05-30 | Glaxosmithkline Llc | Novel compounds as diacylglycerol acyltransferase inhibitors |
| JP6279600B2 (ja) * | 2012-11-23 | 2018-02-14 | グラクソスミスクライン・リミテッド・ライアビリティ・カンパニーＧｌａｘｏＳｍｉｔｈＫｌｉｎｅ ＬＬＣ | ジアシルグリセロールアシルトランスフェラーゼ阻害剤としての新規化合物 |
| US9796729B2 (en) | 2012-11-23 | 2017-10-24 | Glaxosmithkline Llc | Compounds as diacylglycerol acyltransferase inhibitors |
| CN103524431B (zh) * | 2013-09-24 | 2016-01-13 | 西安交通大学 | 3-苄基-4-喹唑啉酮类化合物及其合成方法和应用 |
| WO2015049668A1 (en) | 2013-10-03 | 2015-04-09 | Glaxosmithkline Intellectual Property (No.2) Limited | Novel compound as a diacylglycerol acyltransferase inhibitor |
| WO2015049667A1 (en) | 2013-10-03 | 2015-04-09 | Glaxosmithkline Intellectual Property (No.2) Limited | Novel compound as a diacylglycerol acyltransferase inhibitor |
| CN103880757B (zh) * | 2014-04-15 | 2016-02-24 | 上海毕得医药科技有限公司 | 一种5-羟基嘧啶-2-羧酸的合成方法 |
| WO2016181409A1 (en) | 2015-05-11 | 2016-11-17 | Cadila Healthcare Limited | Saroglitazar magnesium for the treatment of chylomicronemia syndrome - |
| WO2017064635A2 (en) | 2015-10-14 | 2017-04-20 | Cadila Healthcare Limited | Pyrrole compound, compositions and process for preparation thereof |
| CN105732461A (zh) * | 2016-02-03 | 2016-07-06 | 常州工程职业技术学院 | 5-甲氧基-6-卤代吲哚的制备方法 |
| CN106083707B (zh) * | 2016-06-01 | 2018-10-26 | 温州大学 | 一种非对称杂芳基硫醚的合成方法 |
| CN107619928B (zh) * | 2016-07-15 | 2020-08-07 | 中国科学院上海有机化学研究所 | 一种萃取组合物、萃取体系及其应用 |
| CN107619932B (zh) * | 2016-07-15 | 2020-08-07 | 中国科学院上海有机化学研究所 | 一种萃取组合物、萃取体系及其应用 |
| RU2706655C1 (ru) * | 2019-01-28 | 2019-11-19 | Акционерное общество "Гознак" (АО "Гознак") | Полимерсодержащее композиционное защищенное изделие |
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| US20090036425A1 (en) | 2007-08-02 | 2009-02-05 | Pfizer Inc | Substituted bicyclolactam compounds |
| US8232273B2 (en) * | 2008-12-19 | 2012-07-31 | Genentech, Inc. | Heterocyclic compounds and methods of use |
| WO2010086820A1 (en) | 2009-02-02 | 2010-08-05 | Pfizer Inc. | 4-amino-5-oxo-7, 8-dihydropyrimido [5,4-f] [1,4] oxazepin-6 (5h) -yl) phenyl derivatives, pharmaceutical compositions and uses thereof |
| AR075858A1 (es) * | 2009-03-18 | 2011-05-04 | Schering Corp | Compuestos biciclicos como inhibidores de diacilglicerol aciltransferasa |
| JP5497152B2 (ja) * | 2009-04-24 | 2014-05-21 | エフ．ホフマン−ラ ロシュ アーゲー | ブルトン型チロシンキナーゼの阻害薬 |
| DK2710013T3 (en) | 2011-05-20 | 2016-09-26 | Glaxosmithkline Intellectual Property (No 2) Ltd | New compounds such as diacylglycerol-acyltransferase inhibitors |
| US9796729B2 (en) | 2012-11-23 | 2017-10-24 | Glaxosmithkline Llc | Compounds as diacylglycerol acyltransferase inhibitors |
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