NZ565334A - Pyrimidine compounds as serotonin receptor modulators - Google Patents

Info

Publication number

NZ565334A

NZ565334A NZ565334A NZ56533406A NZ565334A NZ 565334 A NZ565334 A NZ 565334A NZ 565334 A NZ565334 A NZ 565334A NZ 56533406 A NZ56533406 A NZ 56533406A NZ 565334 A NZ565334 A NZ 565334A

Authority

NZ

New Zealand

Prior art keywords

tetrahydro

phenyl

pyrido

pyrimidine

fluoro

Prior art date

2005-08-04

Links

• Espacenet
• Global Dossier
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• 150000003230 pyrimidines Chemical class 0.000 title abstract description 18
• 102000040125 5-hydroxytryptamine receptor family Human genes 0.000 title abstract description 16
• 108091032151 5-hydroxytryptamine receptor family Proteins 0.000 title abstract description 16
• 150000001875 compounds Chemical class 0.000 claims abstract description 191
• 208000019901 Anxiety disease Diseases 0.000 claims abstract description 12
• 230000036506 anxiety Effects 0.000 claims abstract description 12
• 208000019116 sleep disease Diseases 0.000 claims abstract description 8
• 230000005856 abnormality Effects 0.000 claims abstract description 5
• 208000015114 central nervous system disease Diseases 0.000 claims abstract description 5
• 230000027288 circadian rhythm Effects 0.000 claims abstract description 5
• -1 phenoxy, pyridyl Chemical group 0.000 claims description 245
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 58
• 229910052799 carbon Inorganic materials 0.000 claims description 53
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 48
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 41
• 150000001721 carbon Chemical group 0.000 claims description 40
• 125000001424 substituent group Chemical group 0.000 claims description 38
• 125000005843 halogen group Chemical group 0.000 claims description 36
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 35
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 32
• 125000003386 piperidinyl group Chemical group 0.000 claims description 31
• 125000002757 morpholinyl group Chemical group 0.000 claims description 28
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 28
• 150000003839 salts Chemical class 0.000 claims description 28
• 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 28
• 150000001408 amides Chemical class 0.000 claims description 27
• 229910052757 nitrogen Inorganic materials 0.000 claims description 27
• 208000035475 disorder Diseases 0.000 claims description 26
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 24
• 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 24
• 125000004432 carbon atom Chemical group C* 0.000 claims description 24
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 24
• 125000002950 monocyclic group Chemical group 0.000 claims description 24
• 125000006413 ring segment Chemical group 0.000 claims description 24
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 23
• QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims description 22
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 21
• 150000002148 esters Chemical class 0.000 claims description 20
• 229910052739 hydrogen Inorganic materials 0.000 claims description 19
• 229910052701 rubidium Inorganic materials 0.000 claims description 17
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Substances N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 16
• 201000010099 disease Diseases 0.000 claims description 15
• 230000001404 mediated effect Effects 0.000 claims description 15
• 125000004076 pyridyl group Chemical group 0.000 claims description 15
• 239000001257 hydrogen Substances 0.000 claims description 14
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 13
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
• 241000124008 Mammalia Species 0.000 claims description 12
• 125000001931 aliphatic group Chemical group 0.000 claims description 12
• 125000000217 alkyl group Chemical group 0.000 claims description 11
• 239000003814 drug Substances 0.000 claims description 11
• 230000002265 prevention Effects 0.000 claims description 11
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 10
• 208000019695 Migraine disease Diseases 0.000 claims description 10
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 10
• 206010027599 migraine Diseases 0.000 claims description 10
• 125000001544 thienyl group Chemical group 0.000 claims description 10
• 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 9
• 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 9
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 8
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 8
• 125000004122 cyclic group Chemical group 0.000 claims description 8
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
• 125000002971 oxazolyl group Chemical group 0.000 claims description 8
• 201000000980 schizophrenia Diseases 0.000 claims description 8
• 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 7
• 208000030814 Eating disease Diseases 0.000 claims description 7
• 208000019454 Feeding and Eating disease Diseases 0.000 claims description 7
• 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims description 7
• 235000014632 disordered eating Nutrition 0.000 claims description 7
• 125000001072 heteroaryl group Chemical group 0.000 claims description 7
• 125000005842 heteroatom Chemical group 0.000 claims description 7
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
• 239000008194 pharmaceutical composition Substances 0.000 claims description 7
• 239000012453 solvate Substances 0.000 claims description 7
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 6
• 208000020925 Bipolar disease Diseases 0.000 claims description 6
• 208000011688 Generalised anxiety disease Diseases 0.000 claims description 6
• 208000019022 Mood disease Diseases 0.000 claims description 6
• 208000018262 Peripheral vascular disease Diseases 0.000 claims description 6
• 208000028017 Psychotic disease Diseases 0.000 claims description 6
• 201000001880 Sexual dysfunction Diseases 0.000 claims description 6
• 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 6
• 125000003118 aryl group Chemical group 0.000 claims description 6
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 6
• 230000030135 gastric motility Effects 0.000 claims description 6
• 208000029364 generalized anxiety disease Diseases 0.000 claims description 6
• 150000004677 hydrates Chemical class 0.000 claims description 6
• 208000002551 irritable bowel syndrome Diseases 0.000 claims description 6
• 229910052760 oxygen Inorganic materials 0.000 claims description 6
• 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 6
• 231100000872 sexual dysfunction Toxicity 0.000 claims description 6
• 229910052717 sulfur Inorganic materials 0.000 claims description 6
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 6
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 5
• 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 5
• 208000019888 Circadian rhythm sleep disease Diseases 0.000 claims description 5
• 208000001456 Jet Lag Syndrome Diseases 0.000 claims description 5
• 206010046543 Urinary incontinence Diseases 0.000 claims description 5
• 208000033915 jet lag type circadian rhythm sleep disease Diseases 0.000 claims description 5
• ROSDSFDQCJNGOL-UHFFFAOYSA-N protonated dimethyl amine Natural products CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 5
• 229940076279 serotonin Drugs 0.000 claims description 5
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 5
• 125000004502 1,2,3-oxadiazolyl group Chemical group 0.000 claims description 4
• 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 claims description 4
• 125000001781 1,3,4-oxadiazolyl group Chemical group 0.000 claims description 4
• 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 claims description 4
• 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 4
• 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 4
• 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 4
• 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims description 4
• 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 claims description 4
• 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 4
• 125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 claims description 4
• 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 4
• 125000004863 4-trifluoromethoxyphenyl group Chemical group [H]C1=C([H])C(OC(F)(F)F)=C([H])C([H])=C1* 0.000 claims description 4
• 208000007848 Alcoholism Diseases 0.000 claims description 4
• 206010020772 Hypertension Diseases 0.000 claims description 4
• VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 4
• MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 4
• 208000002193 Pain Diseases 0.000 claims description 4
• XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 claims description 4
• 125000005605 benzo group Chemical group 0.000 claims description 4
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
• 125000004979 cyclopentylene group Chemical group 0.000 claims description 4
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 4
• 239000003937 drug carrier Substances 0.000 claims description 4
• 125000002541 furyl group Chemical group 0.000 claims description 4
• 125000002883 imidazolyl group Chemical group 0.000 claims description 4
• 125000001786 isothiazolyl group Chemical group 0.000 claims description 4
• 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 4
• 230000002503 metabolic effect Effects 0.000 claims description 4
• 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 4
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 4
• 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims description 4
• 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 4
• 238000002600 positron emission tomography Methods 0.000 claims description 4
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 4
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 4
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 4
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
• 125000000335 thiazolyl group Chemical group 0.000 claims description 4
• VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 4
• 125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 claims description 3
• 125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 claims description 3
• 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 3
• 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 3
• AQXXZBYTNOCOCR-UHFFFAOYSA-N 2,7-dibenzyl-4-(4-fluorophenyl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidine;hydrochloride Chemical compound Cl.C1=CC(F)=CC=C1C1=NC(CC=2C=CC=CC=2)=NC2=C1CCN(CC=1C=CC=CC=1)C2 AQXXZBYTNOCOCR-UHFFFAOYSA-N 0.000 claims description 3
• ASZNFJMUDLKXJH-UHFFFAOYSA-N 2-[2-tert-butyl-6-(4-fluorophenyl)pyrimidin-4-yl]-n-methylethanamine Chemical compound CC(C)(C)C1=NC(CCNC)=CC(C=2C=CC(F)=CC=2)=N1 ASZNFJMUDLKXJH-UHFFFAOYSA-N 0.000 claims description 3
• 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 3
• 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 3
• DIRZXJKOIYZCSA-UHFFFAOYSA-N 4-(3-chlorophenyl)-2-methyl-6,7,8,9-tetrahydro-5h-pyrimido[4,5-d]azepine Chemical compound N=1C(C)=NC=2CCNCCC=2C=1C1=CC=CC(Cl)=C1 DIRZXJKOIYZCSA-UHFFFAOYSA-N 0.000 claims description 3
• JIFKNIUMZVRGTD-UHFFFAOYSA-N 4-(4-fluorophenyl)-2-[(4-fluorophenyl)methyl]-7-methyl-5,6,8,9-tetrahydropyrimido[4,5-d]azepine Chemical compound N=1C(C=2C=CC(F)=CC=2)=C2CCN(C)CCC2=NC=1CC1=CC=C(F)C=C1 JIFKNIUMZVRGTD-UHFFFAOYSA-N 0.000 claims description 3
• FOGYKSDLSLGJOJ-UHFFFAOYSA-N 4-(4-fluorophenyl)-2-propan-2-yl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine 2-hydroxypropane-1,2,3-tricarboxylic acid Chemical compound OC(=O)CC(O)(CC(O)=O)C(O)=O.CC(C)c1nc2CCNCc2c(n1)-c1ccc(F)cc1 FOGYKSDLSLGJOJ-UHFFFAOYSA-N 0.000 claims description 3
• MSRIOUIZJVELSU-UHFFFAOYSA-N 4-(4-fluorophenyl)-2-propan-2-yl-6,7,8,9-tetrahydro-5h-pyrimido[4,5-c]azepine;hydrochloride Chemical compound Cl.N=1C(C(C)C)=NC=2CNCCCC=2C=1C1=CC=C(F)C=C1 MSRIOUIZJVELSU-UHFFFAOYSA-N 0.000 claims description 3
• UDDNBGLDSGXOCT-UHFFFAOYSA-N 4-(4-fluorophenyl)-2-propan-2-yl-7-pyrrolidin-1-yl-5,6,7,8-tetrahydroquinazoline Chemical compound N=1C(C(C)C)=NC=2CC(N3CCCC3)CCC=2C=1C1=CC=C(F)C=C1 UDDNBGLDSGXOCT-UHFFFAOYSA-N 0.000 claims description 3
• 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 3
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 3
• 206010012688 Diabetic retinal oedema Diseases 0.000 claims description 3
• 206010012689 Diabetic retinopathy Diseases 0.000 claims description 3
• 206010012735 Diarrhoea Diseases 0.000 claims description 3
• 239000005977 Ethylene Substances 0.000 claims description 3
• VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 3
• 208000010412 Glaucoma Diseases 0.000 claims description 3
• 208000001953 Hypotension Diseases 0.000 claims description 3
• 206010061218 Inflammation Diseases 0.000 claims description 3
• 206010028813 Nausea Diseases 0.000 claims description 3
• 208000008589 Obesity Diseases 0.000 claims description 3
• 208000022873 Ocular disease Diseases 0.000 claims description 3
• 208000003435 Optic Neuritis Diseases 0.000 claims description 3
• XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 3
• 206010040070 Septic Shock Diseases 0.000 claims description 3
• 206010064930 age-related macular degeneration Diseases 0.000 claims description 3
• 206010001584 alcohol abuse Diseases 0.000 claims description 3
• 208000025746 alcohol use disease Diseases 0.000 claims description 3
• 125000004429 atom Chemical group 0.000 claims description 3
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 3
• AKCLJLKZMKSIRX-UHFFFAOYSA-N dodeca-2,4,6-triene Chemical compound CCCCCC=CC=CC=CC AKCLJLKZMKSIRX-UHFFFAOYSA-N 0.000 claims description 3
• 230000002526 effect on cardiovascular system Effects 0.000 claims description 3
• 230000002496 gastric effect Effects 0.000 claims description 3
• 230000003054 hormonal effect Effects 0.000 claims description 3
• 230000036543 hypotension Effects 0.000 claims description 3
• 230000004054 inflammatory process Effects 0.000 claims description 3
• 208000028867 ischemia Diseases 0.000 claims description 3
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 3
• 208000017169 kidney disease Diseases 0.000 claims description 3
• 208000002780 macular degeneration Diseases 0.000 claims description 3
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 3
• 230000008693 nausea Effects 0.000 claims description 3
• 235000020824 obesity Nutrition 0.000 claims description 3
• QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 3
• 208000028173 post-traumatic stress disease Diseases 0.000 claims description 3
• 230000036303 septic shock Effects 0.000 claims description 3
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• 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 3
• NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 3
• 230000002792 vascular Effects 0.000 claims description 3
• 125000004506 1,2,5-oxadiazolyl group Chemical group 0.000 claims description 2
• GFXWGEWGSPGJJN-UHFFFAOYSA-N 2,7-dibenzyl-4-(4-methoxyphenyl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidine Chemical compound C1=CC(OC)=CC=C1C1=NC(CC=2C=CC=CC=2)=NC2=C1CCN(CC=1C=CC=CC=1)C2 GFXWGEWGSPGJJN-UHFFFAOYSA-N 0.000 claims description 2
• UTWOKDMZZMEEIR-UHFFFAOYSA-N 2-benzyl-4-(3,4-difluorophenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine Chemical compound C1=C(F)C(F)=CC=C1C1=NC(CC=2C=CC=CC=2)=NC2=C1CNCC2 UTWOKDMZZMEEIR-UHFFFAOYSA-N 0.000 claims description 2
• NCYDQOYVSVVPGD-UHFFFAOYSA-N 2-cyclopentyl-4-(4-methoxyphenyl)-7-methyl-5,6,8,9-tetrahydropyrimido[4,5-d]azepine Chemical compound C1=CC(OC)=CC=C1C1=NC(C2CCCC2)=NC2=C1CCN(C)CC2 NCYDQOYVSVVPGD-UHFFFAOYSA-N 0.000 claims description 2
• YXTJOVZVHZIUNM-UHFFFAOYSA-N 2-tert-butyl-4-(4-fluorophenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine Chemical compound N=1C(C(C)(C)C)=NC=2CCNCC=2C=1C1=CC=C(F)C=C1 YXTJOVZVHZIUNM-UHFFFAOYSA-N 0.000 claims description 2
• 125000005809 3,4,5-trimethoxyphenyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 2
• IADWJBWZKVBDQW-UHFFFAOYSA-N 4-(4-fluorophenyl)-2-(oxolan-3-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine Chemical compound C1=CC(F)=CC=C1C1=NC(C2COCC2)=NC2=C1CNCC2 IADWJBWZKVBDQW-UHFFFAOYSA-N 0.000 claims description 2
• ZYNZTCJIOCPGGJ-UHFFFAOYSA-N 4-(4-fluorophenyl)-2-propan-2-yl-6,7,8,9-tetrahydro-5h-pyrimido[4,5-d]azepine;hydrochloride Chemical compound Cl.N=1C(C(C)C)=NC=2CCNCCC=2C=1C1=CC=C(F)C=C1 ZYNZTCJIOCPGGJ-UHFFFAOYSA-N 0.000 claims description 2
• FPWNLURCHDRMHC-UHFFFAOYSA-N 4-chlorobiphenyl Chemical group C1=CC(Cl)=CC=C1C1=CC=CC=C1 FPWNLURCHDRMHC-UHFFFAOYSA-N 0.000 claims description 2
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
• 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims description 2
• OEUCUJNXNFPIIZ-UHFFFAOYSA-N 6-benzyl-8-methyl-2-propan-2-yl-4-thiophen-3-yl-7,8-dihydro-5h-pyrido[4,3-d]pyrimidine Chemical compound C1C=2C(C3=CSC=C3)=NC(C(C)C)=NC=2C(C)CN1CC1=CC=CC=C1 OEUCUJNXNFPIIZ-UHFFFAOYSA-N 0.000 claims description 2
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