ME02181B - Ne-nukleozidni inhibitori reverzne transkriptaze - Google Patents
Ne-nukleozidni inhibitori reverzne transkriptazeInfo
- Publication number
- ME02181B ME02181B MEP-2015-76A MEP7615A ME02181B ME 02181 B ME02181 B ME 02181B ME P7615 A MEP7615 A ME P7615A ME 02181 B ME02181 B ME 02181B
- Authority
- ME
- Montenegro
- Prior art keywords
- alkyl
- independently
- haloalkyl
- cycq
- halogen
- Prior art date
Links
- 229940042402 non-nucleoside reverse transcriptase inhibitor Drugs 0.000 title 1
- 239000002726 nonnucleoside reverse transcriptase inhibitor Substances 0.000 title 1
- 229910052799 carbon Inorganic materials 0.000 claims 25
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 22
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 22
- 150000001875 compounds Chemical class 0.000 claims 19
- 229910052736 halogen Inorganic materials 0.000 claims 17
- 150000002367 halogens Chemical class 0.000 claims 17
- 125000001424 substituent group Chemical group 0.000 claims 17
- 125000000217 alkyl group Chemical group 0.000 claims 14
- 229910052757 nitrogen Inorganic materials 0.000 claims 14
- 150000003839 salts Chemical class 0.000 claims 13
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 8
- 229910052739 hydrogen Inorganic materials 0.000 claims 8
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 7
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 7
- 125000005842 heteroatom Chemical group 0.000 claims 6
- 238000011321 prophylaxis Methods 0.000 claims 6
- 238000011282 treatment Methods 0.000 claims 6
- 125000003118 aryl group Chemical group 0.000 claims 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 5
- 229910052717 sulfur Inorganic materials 0.000 claims 5
- 125000003709 fluoroalkyl group Chemical group 0.000 claims 4
- 229910052760 oxygen Inorganic materials 0.000 claims 4
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 3
- 208000030507 AIDS Diseases 0.000 claims 3
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 3
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 3
- 208000031886 HIV Infections Diseases 0.000 claims 3
- 208000037357 HIV infectious disease Diseases 0.000 claims 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims 3
- 125000001072 heteroaryl group Chemical group 0.000 claims 3
- 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 claims 3
- 229920006395 saturated elastomer Polymers 0.000 claims 3
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 2
- 101100273648 Mus musculus Ccna2 gene Proteins 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 125000001624 naphthyl group Chemical group 0.000 claims 2
- 125000006574 non-aromatic ring group Chemical group 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 125000002733 (C1-C6) fluoroalkyl group Chemical group 0.000 claims 1
- 125000000081 (C5-C8) cycloalkenyl group Chemical group 0.000 claims 1
- DBTDEFJAFBUGPP-UHFFFAOYSA-N Methanethial Chemical compound S=C DBTDEFJAFBUGPP-UHFFFAOYSA-N 0.000 claims 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims 1
- 125000002619 bicyclic group Chemical group 0.000 claims 1
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
Classifications
-
- 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
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- 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
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
-
- 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
- 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
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Virology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- General Chemical & Material Sciences (AREA)
- AIDS & HIV (AREA)
- Molecular Biology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Steroid Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Saccharide Compounds (AREA)
Claims (16)
1. Jedinjenje formule I: ili njegova farmaceutski prihvatljiva so, gde: R1 je C1-10 alkil, CycA, ili AryA; CycA je C3-8 cikloalkil, gde je cikloalkil izborno supstituisan sa od 1 do 4 supstituenta, od kojih je svaki nezavisno halogen, C1-6 alkil, OH, O-C1-6 alkil, C1-6 haloalkil, ili O-C1-6 haloalkil; AryA je aril koji je izborno supstituisan sa ukupno od 1 do 6 supstituenata, gde: (i) od nula do 6 supstituenata su svaki nezavisno: (1) C1-6 alkil, (2) C1-6 haloalkil, (3) C1-6 alkil supstituisan sa od 1 do 3 supstituenta od kojih je svaki nezavisno OH, O-C1-6 alkil, O-C1-6 haloalkil, CN, NO2, N(RA)RB, C(O)N(RA)RB, C(O)RA, CO2RA, SRA, S(O)RA, S(O)2RA, S(O)2N(RA)RB, N(RA)C(O)RB, N(RA)CO2RB, N(RA)S(O)2RB, N(RA)S(O)2N(RA)RB, OC(O)N(RA)RB, N(RA)C(O)N(RA)RB, ili N(RA)C(O)C(O)N(RA)RB, (4) C2-6 alkenil, (5) C2-6 alkenil supstituisan sa od 1 do 3 supstituenta od kojih je svaki nezavisno OH, O-C1-6 alkil, O-C1-6 haloalkil, CN, NO2, N(RA)RB, C(O)N(RA)RB, C(O)RA, CO2RA, SRA, S(O)RA, S(O)2RA, S(O)2N(RA)RB, N(RA)C(O)RB, N(RA)CO2RB, N(RA)S(O)2RB, N(RA)S(O)2N(RA)RB, OC(O)N(RA)RB, N(RA)C(O)N(RA)RB, ili N(RA)C(O)C(O)N(RA)RB, (6) C2-6 alkinil, (7) C2-6 alkinil supstituisan sa od 1 do 3 supstituenta od kojih je svaki nezavisno OH, O-C1-6 alkil, O-C1-6 haloalkil, CN, NO2, N(RA)RB, C(O)N(RA)RB, C(O)RA, CO2RA, SRA, S(O)RA, S(O)2RA, S(O)2N(RA)RB, N(RA)C(O)RB, N(RA)CO2RB, N(RA)S(O)2RB, N(RA)S(O)2N(RA)RB, OC(O)N(RA)RB, N(RA)C(O)N(RA)RB, ili N(RA)C(O)C(O)N(RA)RB, (8) O-C1-6 alkil, (9) O-C1-6 haloalkil, (10) OH, (11) halogen, (12) CN, (13) NO2, (14) N(RA)RB, (15) C(O)N(RA)RB, (16) C(O)RA, (17) C(O)-C1-6 haloalkil, (18) C(O)ORA, (19) OC(O)N(RA)RB, (20) SRA, (21) S(O)RA, (22) S(O)2RA, (23) S(O)2N(RA)RB, (24) N(RA)S(O)2RB, (25) N(RA)S(O)2N(RA)RB, (26) N(RA)C(O)RB, (27) N(RA)C(O)N(RA)RB, (28) N(RA)C(O)-C(O)N(RA)RB, ili (29) N(RA)CO2RB, i (ii) od nula do 2 supstituenta su svaki nezavisno: (1) CycQ, (2) AryQ, (3) HetQ, (4) HetR, (5) J-CycQ, (6) J-AryQ, (7) J-HetQ, (8) J-HetR, (9) C1-6 alkil supstituisan sa CycQ, AryQ, HetQ, HetR, J-CycQ, J-AryQ, J-HetQ, ili J-HetR, (10) C2-6 alkenil supstituisan sa CycQ, AryQ, HetQ, HetR, J-CycQ, J-AryQ, J-HetQ, ili J-HetR, ili (11) C2-6 alkinil supstituisan sa CycQ, AryQ, HetQ, HetR, J-CycQ, J-AryQ, J-HetQ, ili J-HetR; svaki CycQ je nezavisno C3-8 cikloalkil ili C5-8 cikloalkenil, pri čemu je cikloalkil ili cikloalkenil izborno supstituisan sa od 1 do 4 supstituenta, od kojih je svaki nezavisno halogen, C1-6 alkil, OH, O-C1-6 alkil, C1-6 haloalkil, ili O-C1-6 haloalkil; svaki AryQ je nezavisno fenil ili naftil, pri čemu fenil ili naftil je izborno supstituisan sa od 1 do 5 supstituenata od kojih je svaki nezavisno halogen, CN, NO2, C1-6 alkil, C1-6 haloalkil, OH, O-C1-6 alkil, O-C1-6 haloalkil, N(RA)RB, C(O)N(RA)RB, C(O)RA, CO2RA, SRA, S(O)RA, SO2RA, SO2N(RA)RB, ili SO2N(RA)C(O)RB; svaki HetQ je nezavisno heteroaril koji je izborno supstituisan sa od 1 do 4 supstituenta od kojih je svaki nezavisno halogen, C1-6 alkil, C1-6 haloalkil, OH, O-C1-6 alkil, O-C1-6 haloalkil, N(RA)RB, C(O)N(RA)RB, C(O)RA, CO2RA, SO2RA, N(RA)C(O)N(RA)RB, ili N(RA)CO2RB; svaki HetR je nezavisno 4- do 7-člani, zasićeni ili nezasićeni, nearomatični heterociklični prsten koji sadrži najmanje jedan atom ugljenika i od 1 do 4 heteroatoma nezavisno izabrana od N, O i S, gde je svaki S izborno oksidovan do S(O) ili S(O)2, i pri čemu je zasićeni ili nezasićeni heterociklični prsten izborno supstituisan sa od 1 do 4 supstituenta od kojih je svaki nezavisno halogen, CN, C1-6 alkil, OH, okso, O-C1-6 alkil, C1-6 haloalkil, O-C1-6 haloalkil, C(O)N(RA)RB, C(O)RA, CO2RA, ili SO2RA; svaki J je nezavisno: (i) O, (ii) S, (iii) S(O), (iv) S(O)2, (v) O-C1-6 alkilen, (vi) S-C1-6 alkilen, (vii) S(O)-C1-6 alkilen, (viii) S(O)2-C1-6 alkilen, (ix) N(RA), ili (x) N(RA)-C1-6 alkilen; R2 i R3 su svaki nezavisno: (1) H, (2) C1-6 alkil, (3) C1-6 haloalkil, (4) C1-6 alkil supstituisan sa od 1 do 3 supstituenta od kojih je svaki nezavisno OH, O-C1-6 alkil, O-C1-6 haloalkil, CN, NO2, N(RA)RB, C(O)N(RA)RB, C(O)RA, CO2RA, SRA, S(O)RA, S(O)2RA, S(O)2N(RA)RB, N(RA)C(O)RB, N(RA)CO2RB, N(RA)S(O)2RB,N(RA)S(O)2N(RA)RB, OC(O)N(RA)RB, N(RA)C(O)N(RA)RB, ili N(RA)C(O)C(O)N(RA)RB, (5) O-C1-6 alkil u kome je alkil izborno supstituisan sa OH, O-C1-6 alkil, O-C1-6 haloalkil, CN, N(RA)RB, C(O)N(RA)RB, C(O)RA, CO2RA, SRA, S(O)RA, S(O)2RA, ili S(O)2N(RA)RB, (6) O-C1-6 haloalkil, (7) halogen, (8) CN, (9) NO2, (10) N(RA)RB, (11) C(O)N(RA)RB, (12) C(O)RA, (13) C(O)-C1-6 haloalkil, (14) C(O)ORA, (15) OC(O)RA, (16) OC(O)N(RA)RB, (17) SRA, (18) S(O)RA, (19) S(O)2RA, (20) S(O)2N(RA)RB, (21) N(RA)S(O)2RB, (22) N(RA)S(O)2N(RA)RB, (23) N(RA)C(O)RB, (24) N(RA)C(O)N(RA)RB, (25) N(RA)C(O)-C(O)N(RA)RB, (26) N(RA)CO2RB, (27) N(RC)RD, (28) C(O)N(RC)RD, (29) OC(O)N(RC)RD, (30) S(O)2N(RC)RD, (31) N(RA)S(O)2N(RC)RD, (32) N(RA)C(O)N(RC)RD, (33) N(RA)C(O)-C(O)N(RC)RD, (34) C3-8 cikloalkil, (35) O-C3-8 cikloalkil, (36) AryX, ili (37) HetX; gde AryX nezavisno ima istu definiciju kao AryQ, i HetX nezavisno ima istu definiciju kao HetQ; R4 je H, C1-6 alkil, AryZ, HetZ, halogen, CN, ili C1-6 fluoroalkil; AryZ nezavisno ima istu definiciju kao AryQ; HetZ nezavisno ima istu definiciju kao HetQ; R5 je H ili C1-6 alkil; svaki aril je nezavisno (i) fenil, (ii) 9- ili 10-člani biciklični, fuzionisani karbociklični sistem prstena u kome je najmanje jedan prsten aromatičan, ili (iii) 11- do 14-člani triciklični, fuzionisani karbociklični sistem prstena u kome je najmanje jedan prsten aromatičan; svaki heteroaril je nezavisno (i) 5- ili 6-člani heteroaromatični prsten koji sadrži od 1 do 4 heteroatoma nezavisno izabrana od N, O i S, pri čemu je svaki N izborno u obliku oksida, ili (ii) 9- ili 10-člani heterobiciklični, fuzionisani sistem prstena koji sadrži od 1 do 6 heteroatoma nezavisno izabranih od N, O i S, pri čemu bilo koji ili oba prstena sadrže jedan ili više heteroatoma, najmanje jedan prsten je aromatičan, svaki N je izborno u obliku oksida, i svaki S u prstenu koji nije aromatičan je izborno S(O) ili S(O)2; svaki RA je nezavisno H ili C1-6 alkil; svaki RB je nezavisno H ili C1-6 alkil; i svaki par od RC i RD zajedno sa azotom za koji su oba vezani formiraju 4- do 7-člani zasićeni ili nezasićeni, ne-aromatični prsten koji izborno sadrži heteroatom pored N za koji su RC i RD vezani, gde je dodatni heteroatom izabran od N, O i S; gde je prsten izborno supstituisan sa 1 ili 2 supstituenta od kojih je svaki nezavisno C1-6 alkil, C(O)RA, C(O)ORA, C(O)N(RA)RB, ili S(O)2RA; i gde je izborni S u prstenu izborno u obliku S(O) ili S(O)2.
2. Jedinjenje prema patentnom zahtevu 1, ili njegova farmaceutski prihvatljiva so, gde AryA je fenil, gde je fenil izborno supstituisan sa od 1 do 3 supstituenta od kojih je svaki nezavisno: (1) C1-4 alkil, (2) C1-4 haloalkil, (3) O-C1-4 alkil, (4) halogen, (5) CN, (6) S-C1-4 alkil, ili (7) CycQ, uz uslov da ne više od jednog supstituenta je CycQ, i gde CycQ je C3-7 cikloalkil.
3. Jedinjenje prema patentnom zahtevu 1, ili njegova farmaceutski prihvatljiva so, gde: R2 je: (1) C1-4 alkil, (2) C1-4 haloalkil, (3) O-C1-4 alkil, (4) O-C1-4 halooalkil, (5) halogen, (6) S-C1-4 alkil, ili (7) C3-7 cikloalkil; R3 je: (1) H, (2) C1-4 alkil, (3) C1-4 haloalkil, (4) O-C1-4 alkil, (5) O-C1-4 haloalkil, (6) halogen, (7) S-C1-4 alkil, ili (8) C3-7 cikloalkil; i R4 je H.
4. Jedinjenje prema patentnom zahtevu 1, ili njegova farmaceutski prihvatljiva so, koje je jedinjenje formule II: gde: X1 i X2 su svaki nezavisno: (1) H, (2) C1-4 alkil, (3) C1-4 haloalkil, (4) C2-4 alkenil, (5) C2-4 alkenil supstituisan sa CN, (6) OH, (7) O-C1-4 alkil, (8) O-C1-4 haloalkil, (9) halogen, (10) CN, (11) NO2, (12) N(RA)RB, (13) C(O)N(RA)RB, (14) C(O)RA, (15) CO2RA, (16) SRA, (17) S(O)RA, (18) SO2RA, (19) SO2N(RA)RB, (20) SO2N(RA)C(O)RB, ili (21) CycQ; gde: svaki CycQ je C3-7 cikloalkil, gde je cikloalkil izborno supstituisan sa od 1 do 3 supstituenta, od kojih je svaki nezavisno halogen, C1-4 alkil, OH, O-C1-4 alkil, C1-4 haloalkil, ili O-C1-4 haloalkil; R2 i R3 su svaki nezavisno: (1) H, (2) C1-4 alkil, (3) C1-4 haloalkil, (4) CH2OH, (5) CH2O-C1-4 alkil, (6) CH2CN, (7) CH2N(RA)RB, (8) CH2C(O)N(RA)RB, (9) CH2C(O)RA, (10) CH2CO2RA, (11) CH2S(O)2RA, (12) O-C1-4 alkil, (13) O-C1-4 haloalkil, (14) halogen, (15) CN, (16) NO2, (17) N(RA)RB, (18) C(O)N(RA)RB, (19) C(O)RA, (20) C(O)-C1-4 haloalkil, (21) C(O)ORA, (22) SRA, (23) S(O)2RA, (24) (25) (26) (27) (28) (29) (30) (31) (32) (33) (34) (35) ili (36) C3-7 cikloalkil; svaki V je nezavisno H, CH3, C(O)CH3, C(O)OCH3, ili S(O)2CH3; R5 je H ili C1-4 alkil; svaki RA je nezavisno H ili C1-4 alkil; i svaki RB je nezavisno H ili C1-4 alkil.
5. Jedinjenje prema bilo kom od patentnih zahteva 1 ili 4 ili njegova farmaceutski prihvatljiva so, gde: X1 i X2 su svaki nezavisno: (1) C1-4 alkil, (2) C1-4 fluoroalkil, (3) O-C1-4 alkil, (4) halogen, (5) CN, (6) S-C1-4 alkil, ili (7) CycQ; i uz uslov da (i) ne više od jednog supstituenta je CycQ, i gde CycQ je C3-7 cikloalkil; i (ii) najmanje jedan od X1 i X2 se razlikuje od H; R2 je: (1) C1-4 alkil, (2) C1-4 fluoroalkil, (3) O-C1-4 alkil, (4) O-C1-4 fluoroalkil, (5) halogen, (6) S-C1-4 alkil, ili (7) C3-7 cikloalkil; R3 je: (1) H, (2) C1-4 alkil, (3) C1-4 haloalkil, (4) O-C1-4 alkil, (5) O-C1-4 fluoroalkil, (6) halogen, (7) S-C1-4 alkil, ili (8) C3-7 cikloalkil; i R5 je H ili C1-3 alkil.
6. Jedinjenje prema bilo kom od patentnih zahteva 1, 4 ili 5, ili njegova farmaceutski prihvatljiva so, gde jedinjenje je jedinjenje formule III:
7. Jedinjenje prema bilo kom od patentnih zahteva 1, 4-6 ili njegova farmaceutski prihvatljiva so, gde R5 je CH3 ili CH2CH3.
8. Jedinjenje prema bilo kom od patentnih zahteva 1, 4-7, ili njegova farmaceutski prihvatljiva so, gde R3 je H.
9. Jedinjenje formule I prema patentnom zahtevu 1, gde je jedinjenje izabrano iz grupe koju čine: i njegove farmaceutski prihvatljive soli.
10. Jedinjenje formule I prema patentnom zahtevu 1 koje je
11. Farmaceutski prihvatljiva so jedinjenja formule I prema patentnom zahtevu 1 koje je
12. Farmaceutska kompozicija koja sadrži efikasnu količinu jedinjenja prema bilo kom od patentnih zahteva 1-10, ili njegove farmaceutski prihvatljive soli, i farmaceutski prihvatljiv nosač.
13. Farmaceutska kompozicija koja sadrži efikasnu količinu jedinjenja prema patentnom zahtevu 10 i farmaceutski prihvatljiv nosač.
14. Jedinjenje prema bilo kom od patentnih zahteva 1-10, ili njegova farmaceutski prihvatljiva so, za upotrebu u profilaksi ili tretmanu infekcije HIV-om ili za profilaksu, tretman ili odlaganje početka SIDA-e kod subjekta kod koga postoji potreba za tim.
15. Jedinjenje prema patentnom zahtevu 10 za upotrebu u profilaksi ili tretmanu infekcije HIV-om ili za profilaksu, tretman ili odlaganje početka SIDA-e kod subjekta kod koga postoji potreba za tim.
16. Jedinjenje prema bilo kom od patentnih zahteva 1-10, ili njegova farmaceutski prihvatljiva so, za upotrebu u pripremi leka za profilaksu ili tretman infekcije HIV-om ili za profilaksu, tretman ili odlaganje početka SIDA-e kod subjekta kod koga postoji potreba za tim.
Applications Claiming Priority (4)
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| US31882410P | 2010-03-30 | 2010-03-30 | |
| US32157310P | 2010-04-07 | 2010-04-07 | |
| EP11761856.1A EP2552902B1 (en) | 2010-03-30 | 2011-03-28 | Non-nucleoside reverse transcriptase inhibitors |
| PCT/CA2011/000320 WO2011120133A1 (en) | 2010-03-30 | 2011-03-28 | Non-nucleoside reverse transcriptase inhibitors |
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| ME02181B true ME02181B (me) | 2015-10-20 |
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| MEP-2016-282A ME02570B (me) | 2010-03-30 | 2011-03-28 | Farmaceutska kompozicija koja sadrži ne-nukleozidni inhibitor reverzne transkriptaze |
| MEP-2015-76A ME02181B (me) | 2010-03-30 | 2011-03-28 | Ne-nukleozidni inhibitori reverzne transkriptaze |
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| MEP-2016-282A ME02570B (me) | 2010-03-30 | 2011-03-28 | Farmaceutska kompozicija koja sadrži ne-nukleozidni inhibitor reverzne transkriptaze |
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| KR101421861B1 (ko) * | 2010-03-30 | 2014-07-22 | 머크 캐나다 인크. | 비-뉴클레오시드 역전사효소 억제제 |
| CN103517990A (zh) | 2010-10-07 | 2014-01-15 | 通用医疗公司 | 癌症生物标志物 |
| CN109384765A (zh) * | 2012-09-26 | 2019-02-26 | 默沙东公司 | 逆转录酶抑制剂的晶型 |
| JO3470B1 (ar) | 2012-10-08 | 2020-07-05 | Merck Sharp & Dohme | مشتقات 5- فينوكسي-3h-بيريميدين-4-أون واستخدامها كمثبطات ناسخ عكسي ل hiv |
| MX355439B (es) * | 2012-12-05 | 2018-04-18 | Merck Sharp & Dohme | Proceso para preparar inhibidores de la transcriptasa inversa. |
| US20160287568A1 (en) * | 2013-11-22 | 2016-10-06 | Merck Sharp & Dohme Corp. | Composition of a non-nucleoside reverse transcriptase inhibitor |
| US9598397B2 (en) | 2013-12-04 | 2017-03-21 | Merck Sharp & Dohme Corp. | Process for making reverse transcriptase inhibitors |
| SI3125894T1 (sl) * | 2014-04-01 | 2020-12-31 | Merck Sharp & Dohme Corp. | Predzdravila inhibitorjev reverzne transkriptaze HIV |
| US10301624B2 (en) | 2014-06-25 | 2019-05-28 | The General Hospital Corporation | Targeting human satellite II (HSATII) |
| WO2017095761A1 (en) | 2015-12-02 | 2017-06-08 | Merck Sharp & Dohme Corp. | Pharmaceutical compositions containing doravirine, tenofovir disoproxil fumarate and lamivudine |
| US11077050B2 (en) | 2017-03-24 | 2021-08-03 | Merck Sharp & Dohme Corp. | Formulation for parenteral administration |
| EP3612226A1 (en) | 2017-04-18 | 2020-02-26 | Cipla Limited | Combination therapy for use in treating retroviral infections |
| AU2019217875A1 (en) | 2018-02-06 | 2020-08-20 | Icahn School Of Medicine At Mount Sinai | Repeat RNA as biomarkers of tumor immune response |
| WO2020018352A1 (en) * | 2018-07-17 | 2020-01-23 | Merck Sharp & Dohme Corp. | Hiv drug combination for increasing barrier against resistance |
| PH12021551408A1 (en) | 2018-12-18 | 2022-05-16 | Merck Sharp & Dohme Llc | Pyrimidone derivatives as selective cytotoxic agents against hiv infected cells |
| CN110801455B (zh) * | 2019-11-12 | 2020-06-02 | 河北医科大学第二医院 | 用于治疗mrsa的药物组合物及其应用 |
| CN114163309B (zh) * | 2021-12-27 | 2023-04-25 | 甘肃皓天医药科技有限责任公司 | 一种多拉韦林中间体的制备方法 |
| CN114349690B (zh) * | 2022-02-15 | 2023-04-25 | 甘肃皓天医药科技有限责任公司 | 一种多拉韦林中间体合成方法 |
| CN116903590A (zh) * | 2023-06-06 | 2023-10-20 | 延边大学 | 一种含杂环结构的吡啶酮类化合物及其制备方法和用途 |
| CN120157613A (zh) * | 2023-12-15 | 2025-06-17 | 山东诚创蓝海医药科技有限公司 | 多拉韦林中间体及其应用和合成方法 |
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| SE9904045D0 (sv) | 1999-11-09 | 1999-11-09 | Astra Ab | Compounds |
| TW200423930A (en) * | 2003-02-18 | 2004-11-16 | Hoffmann La Roche | Non-nucleoside reverse transcriptase inhibitors |
| CN100469769C (zh) | 2003-03-24 | 2009-03-18 | 弗·哈夫曼-拉罗切有限公司 | 作为逆转录酶抑制剂的苄基-哒嗪酮 |
| TW200505441A (en) * | 2003-03-24 | 2005-02-16 | Hoffmann La Roche | Non-nucleoside reverse transcriptase inhibitorsⅠ |
| US7166738B2 (en) | 2004-04-23 | 2007-01-23 | Roche Palo Alto Llc | Non-nucleoside reverse transcriptase inhibitors |
| SG152263A1 (en) | 2004-04-23 | 2009-05-29 | Hoffmann La Roche | Non-nucleoside reverse transcriptase inhibitors |
| WO2006067587A2 (en) | 2004-12-22 | 2006-06-29 | Pfizer Limited | Nonnucleoside inhibitors of hiv-1 reverse transcriptase |
| AR057455A1 (es) | 2005-07-22 | 2007-12-05 | Merck & Co Inc | Inhibidores de la transcriptasa reversa de vih y composicion farmaceutica |
| AU2006303368B2 (en) | 2005-10-19 | 2011-05-26 | F. Hoffmann-La Roche Ag | Non-Nucleoside Reverse Transcriptase Inhibitors |
| ES2320042T3 (es) | 2005-10-19 | 2009-05-18 | F. Hoffmann-La Roche Ag | Inhibidores de transcriptasa reversa con nucleosidos de n-fenil fenilacetamida. |
| TW200831085A (en) | 2006-12-13 | 2008-08-01 | Merck & Co Inc | Non-nucleoside reverse transcriptase inhibitors |
| JP5539216B2 (ja) | 2007-11-20 | 2014-07-02 | メルク・シャープ・アンド・ドーム・コーポレーション | 非ヌクレオシド系逆転写酵素阻害剤 |
| KR101421861B1 (ko) * | 2010-03-30 | 2014-07-22 | 머크 캐나다 인크. | 비-뉴클레오시드 역전사효소 억제제 |
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2011
- 2011-03-28 KR KR1020127025733A patent/KR101421861B1/ko active Active
- 2011-03-28 CA CA2794377A patent/CA2794377C/en active Active
- 2011-03-28 DK DK15157348.2T patent/DK2924034T3/en active
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2013
- 2013-05-23 JP JP2013108533A patent/JP5886790B2/ja not_active Expired - Fee Related
- 2013-07-03 US US13/934,633 patent/US20130296382A1/en not_active Abandoned
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2014
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