HRP20120992T1 - Aril metil benzokinazolinon kao pozitivni alosterni modulatori receptora m1 - Google Patents
Aril metil benzokinazolinon kao pozitivni alosterni modulatori receptora m1 Download PDFInfo
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- HRP20120992T1 HRP20120992T1 HRP20120992AT HRP20120992T HRP20120992T1 HR P20120992 T1 HRP20120992 T1 HR P20120992T1 HR P20120992A T HRP20120992A T HR P20120992AT HR P20120992 T HRP20120992 T HR P20120992T HR P20120992 T1 HRP20120992 T1 HR P20120992T1
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- alkyl
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- quinazolin
- methyl
- pharmaceutically acceptable
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- 230000003281 allosteric effect Effects 0.000 title 1
- 125000005002 aryl methyl group Chemical group 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 33
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 28
- 150000003839 salts Chemical class 0.000 claims 23
- 125000000217 alkyl group Chemical group 0.000 claims 16
- 125000003118 aryl group Chemical group 0.000 claims 16
- 229910052736 halogen Inorganic materials 0.000 claims 15
- 125000001072 heteroaryl group Chemical group 0.000 claims 15
- 150000002367 halogens Chemical class 0.000 claims 14
- 229910052757 nitrogen Inorganic materials 0.000 claims 13
- 229910052760 oxygen Inorganic materials 0.000 claims 11
- 229910052717 sulfur Inorganic materials 0.000 claims 11
- 229910052739 hydrogen Inorganic materials 0.000 claims 10
- 239000001257 hydrogen Substances 0.000 claims 10
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 8
- 229910052799 carbon Inorganic materials 0.000 claims 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims 8
- BJVYARVTSUNBMW-UHFFFAOYSA-N samoquasine a Chemical compound C1=CC=CC2=CC=C3C(=O)N=CNC3=C21 BJVYARVTSUNBMW-UHFFFAOYSA-N 0.000 claims 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 5
- 125000003342 alkenyl group Chemical group 0.000 claims 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 5
- 125000003367 polycyclic group Chemical group 0.000 claims 5
- 125000006413 ring segment Chemical group 0.000 claims 5
- 125000000623 heterocyclic group Chemical group 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 3
- 125000004429 atom Chemical group 0.000 claims 3
- 125000004122 cyclic group Chemical group 0.000 claims 3
- 208000035475 disorder Diseases 0.000 claims 3
- QMNUDYFKZYBWQX-UHFFFAOYSA-N 1H-quinazolin-4-one Chemical compound C1=CC=C2C(=O)N=CNC2=C1 QMNUDYFKZYBWQX-UHFFFAOYSA-N 0.000 claims 2
- JUVQLZBJFOGEEO-DHIUTWEWSA-N 3-[(1r,2r)-2-hydroxycyclohexyl]-6-[(6-methylpyridin-3-yl)methyl]benzo[h]quinazolin-4-one Chemical compound C1=NC(C)=CC=C1CC(C1=CC=CC=C11)=CC(C2=O)=C1N=CN2[C@H]1[C@H](O)CCCC1 JUVQLZBJFOGEEO-DHIUTWEWSA-N 0.000 claims 2
- YFKSJHGQSODSAP-DNQXCXABSA-N 3-[(1r,2r)-2-hydroxycyclohexyl]-6-[(6-pyrazol-1-ylpyridin-3-yl)methyl]benzo[h]quinazolin-4-one Chemical compound O[C@@H]1CCCC[C@H]1N1C(=O)C2=CC(CC=3C=NC(=CC=3)N3N=CC=C3)=C3C=CC=CC3=C2N=C1 YFKSJHGQSODSAP-DNQXCXABSA-N 0.000 claims 2
- JUVQLZBJFOGEEO-GOTSBHOMSA-N 3-[(1s,2s)-2-hydroxycyclohexyl]-6-[(6-methylpyridin-3-yl)methyl]benzo[h]quinazolin-4-one Chemical compound C1=NC(C)=CC=C1CC(C1=CC=CC=C11)=CC(C2=O)=C1N=CN2[C@@H]1[C@@H](O)CCCC1 JUVQLZBJFOGEEO-GOTSBHOMSA-N 0.000 claims 2
- DVCCSLYSLDPDQI-DHIUTWEWSA-N 5-[[3-[(1r,2r)-2-hydroxycyclohexyl]-4-oxobenzo[h]quinazolin-6-yl]methyl]pyridine-2-carbonitrile Chemical compound O[C@@H]1CCCC[C@H]1N1C(=O)C2=CC(CC=3C=NC(=CC=3)C#N)=C3C=CC=CC3=C2N=C1 DVCCSLYSLDPDQI-DHIUTWEWSA-N 0.000 claims 2
- YMNHBRMXJGOJKH-UHFFFAOYSA-N 6-[(4-methoxyphenyl)methyl]-3-pyridin-3-ylbenzo[h]quinazolin-4-one Chemical compound C1=CC(OC)=CC=C1CC(C1=CC=CC=C11)=CC(C2=O)=C1N=CN2C1=CC=CN=C1 YMNHBRMXJGOJKH-UHFFFAOYSA-N 0.000 claims 2
- -1 6-chloropyridin-3-yl Chemical group 0.000 claims 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- SZXKGKXWTKFAGM-FGZHOGPDSA-N 3-[(1r,2r)-2-hydroxycyclohexyl]-6-[(1-methyl-6-oxopyridin-3-yl)methyl]benzo[h]quinazolin-4-one Chemical compound C1=CC(=O)N(C)C=C1CC(C1=CC=CC=C11)=CC(C2=O)=C1N=CN2[C@H]1[C@H](O)CCCC1 SZXKGKXWTKFAGM-FGZHOGPDSA-N 0.000 claims 1
- WHYIGHMTAVOOII-FGZHOGPDSA-N 3-[(1r,2r)-2-hydroxycyclohexyl]-6-[(6-methoxypyridin-3-yl)methyl]benzo[h]quinazolin-4-one Chemical compound C1=NC(OC)=CC=C1CC(C1=CC=CC=C11)=CC(C2=O)=C1N=CN2[C@H]1[C@H](O)CCCC1 WHYIGHMTAVOOII-FGZHOGPDSA-N 0.000 claims 1
- SXJQBWJPNSOKQV-CLJLJLNGSA-N 3-[(1r,2r)-2-hydroxycyclohexyl]-6-[[6-(1-methylpyrazol-4-yl)pyridin-3-yl]methyl]benzo[h]quinazolin-4-one Chemical compound C1=NN(C)C=C1C(N=C1)=CC=C1CC(C1=CC=CC=C11)=CC(C2=O)=C1N=CN2[C@H]1[C@H](O)CCCC1 SXJQBWJPNSOKQV-CLJLJLNGSA-N 0.000 claims 1
- GYMLQDYQTNGMDJ-DHIUTWEWSA-N 3-[(1r,2r)-2-hydroxycyclohexyl]-6-[[6-(hydroxymethyl)pyridin-3-yl]methyl]benzo[h]quinazolin-4-one Chemical compound C1=NC(CO)=CC=C1CC(C1=CC=CC=C11)=CC(C2=O)=C1N=CN2[C@H]1[C@H](O)CCCC1 GYMLQDYQTNGMDJ-DHIUTWEWSA-N 0.000 claims 1
- DJUWOLPWLMUYOT-VXKWHMMOSA-N 3-[(1s,2s)-2-hydroxycyclohexyl]-6-(pyridin-2-ylmethyl)benzo[h]quinazolin-4-one Chemical compound O[C@H]1CCCC[C@@H]1N1C(=O)C2=CC(CC=3N=CC=CC=3)=C3C=CC=CC3=C2N=C1 DJUWOLPWLMUYOT-VXKWHMMOSA-N 0.000 claims 1
- IQLPODPYUQUZHE-GOTSBHOMSA-N 3-[(1s,2s)-2-hydroxycyclohexyl]-6-[(6-methyl-1-oxidopyridin-1-ium-3-yl)methyl]benzo[h]quinazolin-4-one Chemical compound C1=[N+]([O-])C(C)=CC=C1CC(C1=CC=CC=C11)=CC(C2=O)=C1N=CN2[C@@H]1[C@@H](O)CCCC1 IQLPODPYUQUZHE-GOTSBHOMSA-N 0.000 claims 1
- YGKSUTJODBUYMT-VXKWHMMOSA-N 6-[(6-chloropyridin-3-yl)methyl]-3-[(1s,2s)-2-hydroxycyclohexyl]-2-methylbenzo[h]quinazolin-4-one Chemical compound C1=C2C(=O)N([C@@H]3[C@H](CCCC3)O)C(C)=NC2=C2C=CC=CC2=C1CC1=CC=C(Cl)N=C1 YGKSUTJODBUYMT-VXKWHMMOSA-N 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 102000007207 Muscarinic M1 Receptor Human genes 0.000 claims 1
- 108010008406 Muscarinic M1 Receptor Proteins 0.000 claims 1
- 208000002193 Pain Diseases 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- HVEKLNAQIIHGKO-DHIUTWEWSA-N [(1R,2R)-2-[6-[(6-chloropyridin-3-yl)methyl]-4-oxobenzo[h]quinazolin-3-yl]cyclohexyl] acetate Chemical compound CC(=O)O[C@@H]1CCCC[C@H]1N1C(=O)C2=CC(CC=3C=NC(Cl)=CC=3)=C3C=CC=CC3=C2N=C1 HVEKLNAQIIHGKO-DHIUTWEWSA-N 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- PQIUGRLKNKSKTC-UHFFFAOYSA-N benzo[h]quinazoline Chemical compound N1=CN=C2C3=CC=CC=C3C=CC2=C1 PQIUGRLKNKSKTC-UHFFFAOYSA-N 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 150000002431 hydrogen Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 230000001404 mediated effect Effects 0.000 claims 1
- WYNJRCASJLJTNA-GOTSBHOMSA-N n-[(1s,2s)-2-[6-[(6-chloropyridin-3-yl)methyl]-4-oxobenzo[h]quinazolin-3-yl]cyclohexyl]acetamide Chemical compound CC(=O)N[C@H]1CCCC[C@@H]1N1C(=O)C2=CC(CC=3C=NC(Cl)=CC=3)=C3C=CC=CC3=C2N=C1 WYNJRCASJLJTNA-GOTSBHOMSA-N 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 239000001301 oxygen Chemical group 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 201000000980 schizophrenia Diseases 0.000 claims 1
- 239000011593 sulfur Chemical group 0.000 claims 1
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- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
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- 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
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- A61P25/20—Hypnotics; Sedatives
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C53/00—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
- C07C53/08—Acetic acid
- C07C53/10—Salts thereof
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C53/00—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
- C07C53/15—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen containing halogen
- C07C53/19—Acids containing three or more carbon atoms
- C07C53/21—Acids containing three or more carbon atoms containing fluorine
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- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/86—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
- C07D239/88—Oxygen atoms
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- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- 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
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Claims (25)
1. Spoj formule (I):
[image]
ili njegova farmaceutski prihvatljiva sol, u kojem
svako X, Y i Z su CH i Q je C, ili jedan od X, Y, Q i Z je N i drugi su CH ili C, ili X i Y su CH i Q, R1 i Z su vezani zajedno tako da formiraju naftil grupu;
R1 je izabran iz grupe koju čine
(1) vodik,
(2) aril,
(3) heteroaril grupa koja je ciklična ili policiklična grupa, koja ima od pet do dvanaest atoma u prstenu, pri čemu su navedeni atomi izabrani od C, O, N ili S, pri čemu je najmanje jedan od njih O, N ili S,
(4) halogen,
(5) -CN,
(6) -O-C1-6 alkil,
(7) -C 1-6 alkil,
(8)-C2-6 alkenil
(9) -S(=O)n-R4,
(10) -NR5AR5B,
pri čemu je navedena aril, heteroaril, alkil and alkenil grupa izborno supstituirana sa jednim ili više
(a) halogena,
(b) hidroksi,
(c)-O-C1-6 alkil,
(d) -C1-6 alkil,
(e) -C(=O)-(O)m-R6,
(f) -N(R5AR5B),
(g) -S(=O)n-R8, ili
(h) okso,
uz uvjet da kada je Q jednako N, tada je R1 odsutan;
R2 je izabran iz grupe koju čine
(1) vodik,
(2) aril,
(3) heteroaril grupa koja je ciklična ili policiklična grupa, koja ima od pet do dvanaest atoma u prstenu, pri čemu su navedeni atomi izabrani od C, O, N ili S, pri čemu je najmanje jedan od njih O, N ili S,
(4) heterociklična grupa, koja je nearomatična ciklična ili policiklična grupa koja ima od pet do dvanaest atoma u prstenu izabranih od C, O, N ili S, pri čemu je najmanje jedan od njih O, N ili S,
(5) -O-C1-6 alkil,
(6) -C1-6 alkil,
(7)-C2-6 alkenil,
(8) -S(=O)n-R4,
(9) -C3-8 cikloalkil,
(10) -C5-8 cikloalkenil,
(11) -NR5AR5B,
pri čemu je navedena aril, heteroaril, heterociklil, alkil, alkenil, cikloalkil i cikloalkenil grupa izborno supstituirana sa jednim ili više
(a) halogena,
(b) hidroksi,
(c) -O-C 1-6 alkil,
(d) -C1-6 alkil,
(e)-S(=O)n-R8,
(f) -C2-6 alkenil,
(g) -CN,
(h) -C(=O)-(O)m-R6,
(i) -NR5AR5B,
(j) okso,
(k) aril,
(l) heteroaril grupa koja je ciklična ili policiklična grupa, koja ima od pet do dvanaest atoma u prstenu, pri čemu su navedeni atomi izabrani od C, O, N ili S, pri čemu je najmanje jedan od njih O, N ili S,
(m) heterociklična grupa, koja je nearomatična ciklična ili policiklična grupa koja ima od pet do dvanaest atoma u prstenu izabranih od C, O, N ili S, pri čemu je najmanje jedan od njih O, N ili S
(n) -OC(=O)- R6,
pri čemu je alkil, alkenil, aril, heteroaril ili heterociklična grupa izborno supstituirana sa jednim ili više
(i) halogena,
(ii) -C1-6 alkil, ili
(iii) -OC1-6 alkil;
R3 je izabran iz grupe koju čine
(1) vodik,
(2) -C1-6 alkil, i
(3)-S(O)n-R4,
pri čemu je navedena R3 alkil grupa je izborno supstituirana sa jednim ili više
(a) halogena,
(b) cijano, i
(c) -O-C1-6 alkil, pri čemu je navedena alkil izborno supstituiran sa jednim ili više halo;
R4, R6 i R8 su nezavisno izabrani iz grupe koju čine
(1) vodik,
(2) -C1-6 alkil, i
(3) -(CH2)n-aril,
pri čemu je navedena R4, R6 ili R8 alkil ili aril grupa izborno supstituirana sa jednim ili više
(a) halogena,
(b) cijano, i
(c) -O-C1-6 alkil, pri čemu je navedena alkil izborno supstituiran sa jednim ili više halogena;
R5A i R5B su izabrani iz grupe koju čine
(1) vodik,
(2) -C1-6 alkil,
(3) -C3-6 cikloalkil,
(4) -C(=O)-O- R6,
(5) -S(O)2-R6,
ili R5A i R5B su vezani zajedno sa dušikom za koji su oba vezani tako da formiraju 2-6-člani karbocikličan prsten, gdje su jedan ili dva od ugljikovih atoma iz prstena izborno zamijenjeni sa dušikom, kisikom ili sumporom;
m je 0 ili 1; i
n je 0, 1 ili 2.
2. Spoj prema patentnom zahtjevu 1, ili njegova farmaceutski prihvatljiva sol, gdje je Q jednako C, svako X i Y su CH i Z je N.
3. Spoj prema patentnom zahtjevu 1, ili njegova farmaceutski prihvatljiva sol, gdje su svako X, Y i Z jednaki CH, i Q je C.
4. Spoj prema patentnom zahtjevu 1, ili njegova farmaceutski prihvatljiva sol, gdje su svako X i Z jednaki CH, Q je C i Y je N.
5. Spoj prema bilo kojem od patentnih zahtjeva 1 do 4, ili njegova farmaceutski prihvatljiva sol, gdje je R1 izabran iz grupe koju čine
(1) halogen,
(2) -CN,
(3) -O-C1-6 alkil, ili
(4) -C1-6 alkil,
pri čemu je navedeni alkil izborno supstituiran sa jednim ili više
(a) halogena,
(b) hidroksi,
(c) -O-C 1-6 alkil,
(d) -C1-6 alkil,
(e) -C(=O)-(0)m-R6,
(f) -NR5AR5B, ili
(g) okso.
6. Spoj prema bilo kojem od patentnih zahtjeva 1 do 4, ili njegova farmaceutski prihvatljiva sol, gdje je R1 izabran iz grupe koju čine
(1) aril, ili
(2) heteroaril, gdje je R1 aril ili heteroaril grupa izborno supstituirana sa jednim ili više
(a) halogena,
(b) hidroksi,
(c) -O-C1-6 alkil,
(d) -C1-6 alkil, ili
(e) -S(O)n-R8.
7. Spoj prema bilo kojem od patentnih zahtjeva 1 do 6, ili njegova farmaceutski prihvatljiva sol, gdje je R2 jednako -C3-8 cikloalkil, izborno supstituiran sa jednim ili više
(a) hidroksi,
(b) -O-C1-6 alkil, ili
(c) okso.
8. Spoj prema bilo kojem od patentnih zahtjeva 1 do 6, ili njegova farmaceutski prihvatljiva sol, gdje je R2 izabran iz grupe koju čine
(1) aril,
(2) heteroaril, ili
(3) -C1-6 alkil, pri čemu je navedeni aril, heteroaril ili alkil izborno supstituiran sa jednim ili više
(a) halogena,
(b) hidroksi,
(c)-O-C 1-6 alkil,
(d) -C1-6 alkil,
(e) -CN,
(f) -C(=O)-(O)m-R6,
(g) -NR5AR5B,
(h) okso,
(i) aril, i
(j) heteroaril.
9. Spoj prema patentnom zahtjevu 1 ili njegova farmaceutski prihvatljiva sol, gdje je R3 jednako vodik.
10. Spoj prema patentnom zahtjevu 1, ili njegova farmaceutski prihvatljiva sol, koje je izabrano iz grupe koju čine
rac-3-[trans-2-hidroksicikloheksil]-6-[(6-metilpiridin-3-il)metil]benzo[h]hinazolin-4(3H)-on;
3-[(1S,2S)-2-hidroksicikloheksil]-6-[(6-metilpiridin-3-il)metil]benzo[h]hinazolin-4(3H)-on;
6-(4-metoksibenzil)-3-(5-metil)-1H-pirazol-3-il)benzo[h]hinazolin-4(3H)-on;
6-(4-metoksibenzil)-3-piridin-3-ilbenzo[h]hinazolin-4(3H)-on;
rac-3-[trans-2-hidroksicikloheksil]-6-{[6-(1-metil-1H-pirazol-4-il)piridin-3-il]metil}benzo[h]hinazolin-4(3H)-on;
rac-3-[trans-2-hidroksicikloheksil]-6-{[6-(1H-pirazol-1-il)piridin-3-il]metil}benzo[h]hinazolin-4(3H)-on;
rac-5-({3-[trans-2-hidroksicikloheksil]-4-okso-3,4-dihidrobenzo[h]hinazolin-6-il}metil)piridin-2-karbonitril;
rac-3-[trans-2-hidroksicikloheksil]-6-{[6-metilsulfonil)piridin-3-il]metil}benzo[h]hinazolin-4(3H)-on;
rac-3-[trans-2-hidroksicikloheksil]-6-[(6-metoksipiridin-3-il)metil]benzo[h]hinazolin-4(3H)-on;
6-[(6-kloropiridin-3-il)metil]-3-(2-oksicikloheksil)benzo[h]hinazolin-4(3H)-on;
trans-2-[6-[(6-kloropiridin-3-il)metil]-4-oksobenzo[h]hinazolin-3(4H)-il]cikloheksil rac-acetat;
N-{(1S,2S)-2-[6-[(6-kloropiridin-3-il)metil]-4-oksobenzo[h]hinazolin-3(4H)-il]cikloheksil}acetamid;
3-[(1S,2S)-2-hidroksicikloheksil]-6-[(6-izopropilpiridin-3-il)metilbenzo[h]hinazolin-4(3H)-on;
3-[(1S,2S)-2-hidroksicikloheksil]-6-{[(6-(1-hidroksi-1-metiletil)piridin-3-il]metil}benzo[h]hinazolin-4(3H)-on;
rac-3-[trans-2-hidroksicikloheksil]-6-{[6-(hidroksimetil)piridin-3-il]metil}benzo[h]hinazolin-4(3H)-on;
rac-3-[trans-2-hidroksicikloheksil]-6-[(1-metil-6-okso-1,6-dihidropiridin-3-il)metil]benzo[h]hinazolin-4(3H)-on;
3-[(1S,2S)-2-hidroksicikloheksil]-6-[(6-metil-1-oksidopiridin-3-il)metil]benzo[h] hinazolin-4(3H)-on;
3-[(1S,2S)-2-hidroksicikloheksil]-6-(piridin-2-ilmetil)benzo[h]hinazolin-4(3H)-on;
6-[(6-kloropiridin-3-il)metil]-3-[(1S,2S)-2-hidroksicikloheksil]-2-metilbenzo[h] hinazolin-4(3H)-on;
ili njegova farmaceutski prihvatljiva sol.
11. Spoj prema patentnom zahtjevu 1, ili njegova farmaceutski prihvatljiva sol, koji je izabran iz grupe koju čine
rac-3-[trans-2-hidroksicikloheksil]-6-[(6-metilpiridin-3-il)metil]benzo[h]hinazolin-4(3H)-on;
3-[(1S,2S)-2-hidroksicikloheksil]-6-[(6-metilpiridin-3-il)metil]benzo[h]hinazolin-4(3H)-on;
6-(4-metoksibenzil)-3-(5-metil)-1H-pirazol-3-il)benzo[h]hinazolin-4(3H)-on;
6-(4-metoksibenzil)-3-piridin-3-ilbenzo[h]hinazolin-4(3H)-on;
rac-3-[trans-2-hidroksicikloheksil]-6-{[6-(-metil-1H-pirazol-4-il)piridin-3-il]metil}benzo[h]hinazolin-4(3H)-on;
rac-3-[trans-2-hidroksicikloheksil]-6-{[6-(1H-pirazol-1-il)piridin-3-il]metil }benzo[h]hinazolin-4(3H)-on;
rac-5-({3-[trans-2-hidroksicikloheksil]-4-okso-3,4-dihidrobenzo[h]hinazolin-6-il}metil)piridin-2-karbonitril;
ili njegova farmaceutski prihvatljiva sol.
12. Spoj prema patentnom zahtjevu 1, gdje su X i Y jednaki CH, Q je C, i R1, R2, R3 i Z su prikazani u daljem tekstu:
[image]
13. Spoj prema patentnom zahtjevu 1, gdje je spoj formule (I) – spoj formule (II):
[image]
ili njegova farmaceutski prihvatljiva sol, gdje
R7 je izabran iz grupe koju čine
(1) vodik,
(2) aril,
(3) heteroaril,
(4) halogen,
(5) -CN,
(6) -O-C1-6 alkil,
(7) -C1-6 alkil,
(8) -C2-6 alkenil
(9) -S(=O)n-R4, i (10) -NR5AR5B,
pri čemu je navedena aril, heteroaril, alkil i alkenil grupa izborno supstituirana sa jednim ili više
(a) halogena,
(b) hidroksi,
(c) -O-C1-6 alkil,
(d)-C1-6 alkil,
(e) -C(=O)-(O)m-R6,
(f) -N(R5AR5B),
(g) -S(=O)n-R8, i
(h) okso.
14. Spoj prema patentnom zahtjevu 13, ili njegova farmaceutski prihvatljiva sol, gdje je R3 – vodik i R2 i R7 su spareni ko što je prikazano u daljem tekstu:
[image]
[image]
[image]
[image]
[image]
15. Spoj prema patentnom zahtjevu 1, gdje je spoj formule (I) – spoj formule (III):
[image]
[image]
ili njegova farmaceutski prihvatljiva sol, u kojem
R2 i R3 su kao što su opisani u prethodnom tekstu, i R7 je izabran iz grupe koju čine
(1) vodik,
(2) aril,
(3) heteroaril,
(4) halogen,
(5) -CN,
(6) -O-C1-6 alkil,
(7) -C1-6 alkil,
(8) -C2-6 alkenil
(9) -S(=O)n-R4, i
(10) -NR5AR5B,
pri čemu je navedena aril, heteroaril, alkil i alkenil grupa izborno supstituirana sa jednim ili više
(a) halogena,
(b) hidroksi,
(c) -O-C1-6 alkil,
(d) -C1-6 alkil,
(e) -C(=O)-(O)m-R6
(f) -N(R5AR5B),
(g) -S(=O)n-R8, i
(h) okso.
16. Spoj prema patentnom zahtjevu 15, gdje je R3 - vodik, i R2 i R7 su spareni iz grupe koju čine
[image]
[image]
[image]
ili njegova farmaceutski prihvatljiva sol.
17. Spoj prema patentnom zahtjevu 1, gdje je spoj formule (I) – spoj formule (IV):
[image]
ili njegova farmaceutski prihvatljiva sol, gdje su X, Y, Z, R1 i R3 kao što su definirani u patentnom zahtjevu 1.
18. Spoj prema patentnom zahtjevu 17, gdje je spoj formule (IV) –spoj formule (IVA)
[image]
gdje su veze između dušika u benzohinazolinu i 1-ugljika na cikloheksil prstenu, i veza između hidroksi i 2-ugljika na cikloheksil prstenu, - trans.
19. Spoj prema patentnom zahtjevu 17 ili 18, gdje su svako X i Y jednaki CH i Z je N.
20. Spoj prema patentnom zahtjevu 18 ili 19, gdje su svako X, Y i Z jednaki CH.
21. Spoj prema patentnom zahtjevu 18 gdje su svako X i Y jednaki CH, Z je N, R1 je CH3, i R3 je H; ili njegova farmaceutski prihvatljiva sol.
22. Spoj formule (V),
[image]
gdje su R2 i Q' spareni kao u daljem tekstu:
[image]
ili njegova farmaceutski prihvatljiva sol.
23. Farmaceutska kompozicija koja sadrži terapeutski efikasnu količinu spoja prema bilo kojem od patentnih zahtjeva 1-22, ili njegove farmaceutski prihvatljive soli, i farmaceutski prihvatljiv nosač.
24. Spoj prema bilo kojem od patentnih zahtjeva 1-22, ili njegova farmaceutski prihvatljiva sol, za uporabu u medicini.
25. Spoj prema bilo kojem od patentnih zahtjeva 1-22, ili njegova farmaceutski prihvatljiva sol, za uporabu u liječenju bolesti ili poremećaja posredovanog preko muskarinskog receptora M1, pri čemu je navedena bolest ili poremećaj izabran iz grupe koju čine Alzheimerova bolest, šizofrenija, bol ili poremećaji.
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| US19974008P | 2008-11-20 | 2008-11-20 | |
| PCT/US2009/065060 WO2010059773A1 (en) | 2008-11-20 | 2009-11-19 | Aryl methyl benzoquinazolinone m1 receptor positive allosteric modulators |
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ID=41565956
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| HRP20120992AT HRP20120992T1 (hr) | 2008-11-20 | 2012-12-03 | Aril metil benzokinazolinon kao pozitivni alosterni modulatori receptora m1 |
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| US8664387B2 (en) * | 2009-12-14 | 2014-03-04 | Merck Sharp & Dohme Corp. | Pyridoquinazolinone M1 receptor positive allosteric modulators |
| MX336774B (es) | 2009-12-17 | 2016-01-28 | Merck Sharp & Dohme | Moduladores alostericos positivos de receptores m1 de la quinolina amida. |
| EP2515656B1 (en) * | 2009-12-21 | 2014-08-06 | Merck Sharp & Dohme Corp. | Aminobenzoquinazolinone m1 receptor positive allosteric modulators |
| US8557992B2 (en) | 2010-06-15 | 2013-10-15 | Merck Sharp & Dohme Corp. | Heterocyclic fused phenanthrolinone M1 receptor positive allosteric modulators |
| WO2012003147A1 (en) | 2010-07-01 | 2012-01-05 | Merck Sharp & Dohme Corp. | Isoindolone m1 receptor positive allosteric modulators |
| WO2012047702A1 (en) * | 2010-10-04 | 2012-04-12 | Merck Sharp & Dohme Corp. | Dihydrobenzoquinazolinone m1 receptor positive allosteric modulators |
| US9284312B2 (en) | 2011-05-17 | 2016-03-15 | Merck Sharp & Dohme Corp. | N-methyl tetrahydroquinoline M1 receptor positive allosteric modulators |
| JP2014522873A (ja) | 2011-08-12 | 2014-09-08 | ビーエーエスエフ ソシエタス・ヨーロピア | アントラニルアミド化合物および殺虫剤としてのその使用 |
| US20140171316A1 (en) | 2011-08-12 | 2014-06-19 | Basf Se | Anthranilamide compounds and their use as pesticides |
| WO2013097052A1 (en) | 2011-12-30 | 2013-07-04 | Abbott Laboratories | Bromodomain inhibitors |
| WO2013105117A1 (en) * | 2012-01-10 | 2013-07-18 | Council Of Scientific & Industrial Research | Cu-MEDIATED ANNULATION FOR THE PRODUCTION OF 1-AMINO-2-NAPHTHALENECARBOXYLIC ACID DERIVATIVES |
| JP6211509B2 (ja) | 2012-03-02 | 2017-10-11 | 武田薬品工業株式会社 | 複素環化合物およびその用途 |
| JP6211530B2 (ja) | 2012-11-19 | 2017-10-11 | 武田薬品工業株式会社 | 含窒素複素環化合物 |
| GB201317363D0 (en) | 2013-10-01 | 2013-11-13 | Eisai Ltd | Novel compounds |
| CN106232572B (zh) * | 2014-04-17 | 2018-11-13 | 住友化学株式会社 | 硝基化合物的制造方法 |
| EP3265466A4 (en) * | 2015-03-06 | 2018-12-26 | Chase Pharmaceuticals Corporation | Peripheral-anticholinergic muscarinic agonist combination |
| UA121503C2 (uk) | 2015-06-26 | 2020-06-10 | Такеда Фармасьютікал Компані Лімітед | 2,3-дигідро-4h-1,3-бензоксазин-4-онові похідні як модулятори холінергічного мускаринового рецептора m1 |
| EP4019018A1 (en) | 2015-09-11 | 2022-06-29 | Chase Pharmaceuticals Corporation | Muscarinic combination and its use for combating hypocholinergic disorders of the central nervous system |
| US10308633B2 (en) | 2015-09-30 | 2019-06-04 | Merck Sharp & Dohme Corp. | Process for making M1 receptor positive allosteric modulators |
| US20180273507A1 (en) * | 2015-09-30 | 2018-09-27 | Merck Sharp & Dohme Corp. | Crystal forms of a m1 receptor positive allosteric modulator |
| JP6787913B2 (ja) * | 2015-10-20 | 2020-11-18 | 武田薬品工業株式会社 | 複素環化合物 |
| CN109071534B (zh) | 2016-04-15 | 2021-11-23 | 艾伯维公司 | 布罗莫结构域抑制剂 |
| TW201815787A (zh) | 2016-09-23 | 2018-05-01 | 美商基利科學股份有限公司 | 磷脂醯肌醇3-激酶抑制劑 |
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2009
- 2009-11-19 NZ NZ592961A patent/NZ592961A/xx not_active IP Right Cessation
- 2009-11-19 DK DK09761104.0T patent/DK2358686T3/da active
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