CA2617760C - Pyrimidine compounds as serotonin receptor modulators - Google Patents

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Publication number

CA2617760C

CA2617760C CA2617760A CA2617760A CA2617760C CA 2617760 C CA2617760 C CA 2617760C CA 2617760 A CA2617760 A CA 2617760A CA 2617760 A CA2617760 A CA 2617760A CA 2617760 C CA2617760 C CA 2617760C

Authority

CA

Canada

Prior art keywords

tetrahydro

phenyl

pyrido

pyrimidine

fluoro

Prior art date

2005-08-04

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Expired - Fee Related

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• 102000040125 5-hydroxytryptamine receptor family Human genes 0.000 title abstract description 17
• 108091032151 5-hydroxytryptamine receptor family Proteins 0.000 title abstract description 17
• 150000003230 pyrimidines Chemical class 0.000 title description 17
• 150000001875 compounds Chemical class 0.000 claims abstract description 199
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 35
• QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims abstract description 20
• 230000001404 mediated effect Effects 0.000 claims abstract description 15
• 201000010099 disease Diseases 0.000 claims abstract description 13
• 229940076279 serotonin Drugs 0.000 claims abstract description 6
• -1 phenoxy, pyridyl Chemical group 0.000 claims description 254
• 238000000034 method Methods 0.000 claims description 65
• 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 54
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 48
• 150000001721 carbon Chemical group 0.000 claims description 42
• 125000001424 substituent group Chemical group 0.000 claims description 38
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 36
• 125000005843 halogen group Chemical group 0.000 claims description 36
• 150000001408 amides Chemical class 0.000 claims description 29
• 125000003386 piperidinyl group Chemical group 0.000 claims description 29
• 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
• 125000004193 piperazinyl group Chemical group 0.000 claims description 27
• 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 27
• 229910052757 nitrogen Inorganic materials 0.000 claims description 26
• 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 24
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 22
• 208000035475 disorder Diseases 0.000 claims description 22
• 150000002148 esters Chemical class 0.000 claims description 20
• 229910052739 hydrogen Inorganic materials 0.000 claims description 18
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 18
• 125000004076 pyridyl group Chemical group 0.000 claims description 16
• 239000001257 hydrogen Substances 0.000 claims description 14
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 13
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Substances N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 13
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 12
• 125000001931 aliphatic group Chemical group 0.000 claims description 12
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 10
• 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 10
• 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
• 239000003814 drug Substances 0.000 claims description 10
• 125000002971 oxazolyl group Chemical group 0.000 claims description 10
• 125000001544 thienyl group Chemical group 0.000 claims description 10
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 9
• 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 8
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 8
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 8
• 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 8
• 241000124008 Mammalia Species 0.000 claims description 8
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 8
• 125000000217 alkyl group Chemical group 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
• 230000002265 prevention Effects 0.000 claims description 8
• 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 8
• 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 8
• 208000019901 Anxiety disease Diseases 0.000 claims description 7
• 230000036506 anxiety Effects 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
• 208000002551 irritable bowel syndrome Diseases 0.000 claims description 7
• 239000008194 pharmaceutical composition Substances 0.000 claims description 7
• 239000012453 solvate Substances 0.000 claims description 7
• 208000019695 Migraine disease 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
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
• 150000004677 hydrates Chemical class 0.000 claims description 6
• 206010027599 migraine Diseases 0.000 claims description 6
• 201000000980 schizophrenia Diseases 0.000 claims description 6
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 6
• 208000030814 Eating disease Diseases 0.000 claims description 5
• 208000019454 Feeding and Eating disease Diseases 0.000 claims description 5
• VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 5
• 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims description 5
• 235000014632 disordered eating Nutrition 0.000 claims description 5
• 208000019116 sleep disease Diseases 0.000 claims description 5
• 125000004502 1,2,3-oxadiazolyl group Chemical group 0.000 claims description 4
• 125000004504 1,2,4-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
• 125000004506 1,2,5-oxadiazolyl group Chemical group 0.000 claims description 4
• 125000001781 1,3,4-oxadiazolyl group Chemical group 0.000 claims description 4
• 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 4
• 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 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
• 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=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
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=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
• 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 4
• LKGBTCMMESGPGL-UHFFFAOYSA-N 4-(4-fluorophenyl)-2-phenyl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine Chemical compound C1=CC(F)=CC=C1C1=NC(C=2C=CC=CC=2)=NC2=C1CNCC2 LKGBTCMMESGPGL-UHFFFAOYSA-N 0.000 claims description 4
• 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 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
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 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
• 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims description 4
• 208000007848 Alcoholism Diseases 0.000 claims description 4
• 208000020925 Bipolar disease Diseases 0.000 claims description 4
• 208000019888 Circadian rhythm sleep disease Diseases 0.000 claims description 4
• 208000011688 Generalised anxiety disease Diseases 0.000 claims description 4
• 208000001456 Jet Lag Syndrome Diseases 0.000 claims description 4
• 208000019022 Mood disease Diseases 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
• 208000018262 Peripheral vascular disease Diseases 0.000 claims description 4
• 208000028017 Psychotic disease Diseases 0.000 claims description 4
• 201000001880 Sexual dysfunction Diseases 0.000 claims description 4
• 206010046543 Urinary incontinence Diseases 0.000 claims description 4
• 230000005856 abnormality Effects 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
• 208000015114 central nervous system disease Diseases 0.000 claims description 4
• 230000027288 circadian rhythm Effects 0.000 claims description 4
• 125000004979 cyclopentylene group Chemical group 0.000 claims description 4
• 125000004980 cyclopropylene 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
• 230000030135 gastric motility Effects 0.000 claims description 4
• 208000029364 generalized anxiety disease Diseases 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
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 4
• 208000033915 jet lag type circadian rhythm sleep disease Diseases 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
• 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
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 4
• 231100000872 sexual dysfunction Toxicity 0.000 claims description 4
• 125000001412 tetrahydropyranyl 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
• GKFRWQCMHCHZMP-UHFFFAOYSA-N 4-(4-fluorophenyl)-2-[fluoro(phenyl)methyl]-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine Chemical compound N=1C=2CCNCC=2C(C=2C=CC(F)=CC=2)=NC=1C(F)C1=CC=CC=C1 GKFRWQCMHCHZMP-UHFFFAOYSA-N 0.000 claims description 3
• RKPRFJORBOCCDX-UHFFFAOYSA-N 4-(4-fluorophenyl)-2-propan-2-yl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine Chemical group N=1C(C(C)C)=NC=2CCNCC=2C=1C1=CC=C(F)C=C1 RKPRFJORBOCCDX-UHFFFAOYSA-N 0.000 claims description 3
• CZFYSRJTOJIVPQ-UHFFFAOYSA-N 4-(4-fluorophenyl)-2-propan-2-yl-5,6,7,8-tetrahydroquinazoline Chemical compound N=1C(C(C)C)=NC=2CCCCC=2C=1C1=CC=C(F)C=C1 CZFYSRJTOJIVPQ-UHFFFAOYSA-N 0.000 claims description 3
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• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 3
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• QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 3
• 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims description 3
• 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 3
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• 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
• OKDGFVNMESDAJU-UHFFFAOYSA-N 2-[difluoro(phenyl)methyl]-4-(4-fluorophenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine Chemical compound C1=CC(F)=CC=C1C1=NC(C(F)(F)C=2C=CC=CC=2)=NC2=C1CNCC2 OKDGFVNMESDAJU-UHFFFAOYSA-N 0.000 claims description 2
• ZTVYQILIXFGEAY-UHFFFAOYSA-N 2-butan-2-yl-4-(4-methoxyphenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine Chemical compound N=1C(C(C)CC)=NC=2CCNCC=2C=1C1=CC=C(OC)C=C1 ZTVYQILIXFGEAY-UHFFFAOYSA-N 0.000 claims description 2
• VNJZFZKBKNWIGU-UHFFFAOYSA-N 2-butan-2-yl-4-[4-(trifluoromethoxy)phenyl]-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine Chemical compound N=1C(C(C)CC)=NC=2CCNCC=2C=1C1=CC=C(OC(F)(F)F)C=C1 VNJZFZKBKNWIGU-UHFFFAOYSA-N 0.000 claims description 2
• HDQLXMMAVVHCAJ-UHFFFAOYSA-N 2-methyl-4-phenyl-6,7,8,9-tetrahydro-5h-pyrimido[4,5-d]azepine Chemical compound N=1C(C)=NC=2CCNCCC=2C=1C1=CC=CC=C1 HDQLXMMAVVHCAJ-UHFFFAOYSA-N 0.000 claims description 2
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• 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
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• LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical group NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 claims description 2
• 125000004820 3-methylbutylene group Chemical group [H]C([H])([H])C([H])(C([H])([H])[*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims description 2
• MGZQSLINEFMJIE-UHFFFAOYSA-N 4-(2,4-difluorophenyl)-2-propan-2-yl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine Chemical compound N=1C(C(C)C)=NC=2CCNCC=2C=1C1=CC=C(F)C=C1F MGZQSLINEFMJIE-UHFFFAOYSA-N 0.000 claims description 2
• UUIYDVDXDBJJSY-UHFFFAOYSA-N 4-(2-fluorophenyl)-2-propan-2-yl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine Chemical compound N=1C(C(C)C)=NC=2CCNCC=2C=1C1=CC=CC=C1F UUIYDVDXDBJJSY-UHFFFAOYSA-N 0.000 claims description 2
• YUSDAWLYMZIEMC-UHFFFAOYSA-N 4-(3,4-dichlorophenyl)-2-propan-2-yl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine;hydrochloride Chemical compound Cl.N=1C(C(C)C)=NC=2CCNCC=2C=1C1=CC=C(Cl)C(Cl)=C1 YUSDAWLYMZIEMC-UHFFFAOYSA-N 0.000 claims description 2
• GGEQUEGGJKAVPW-UHFFFAOYSA-N 4-(3-chloro-4-fluorophenyl)-8-methyl-2-propan-2-yl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine;hydrochloride Chemical compound Cl.N=1C(C(C)C)=NC=2C(C)CNCC=2C=1C1=CC=C(F)C(Cl)=C1 GGEQUEGGJKAVPW-UHFFFAOYSA-N 0.000 claims description 2
• UBOMIPBQLOKTME-UHFFFAOYSA-N 4-(3-fluorophenyl)-2-propan-2-yl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine Chemical compound N=1C(C(C)C)=NC=2CCNCC=2C=1C1=CC=CC(F)=C1 UBOMIPBQLOKTME-UHFFFAOYSA-N 0.000 claims description 2
• ZUEGJLFXFLMUCB-UHFFFAOYSA-N 4-(4-chlorophenyl)-2-methyl-6,7,8,9-tetrahydro-5h-pyrimido[4,5-d]azepine Chemical compound N=1C(C)=NC=2CCNCCC=2C=1C1=CC=C(Cl)C=C1 ZUEGJLFXFLMUCB-UHFFFAOYSA-N 0.000 claims description 2
• ZJGUHDRASYVSOE-UHFFFAOYSA-N 4-(4-chlorophenyl)-2-propan-2-yl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine Chemical compound N=1C(C(C)C)=NC=2CCNCC=2C=1C1=CC=C(Cl)C=C1 ZJGUHDRASYVSOE-UHFFFAOYSA-N 0.000 claims description 2
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• HLJYXAOJQGEBFE-UHFFFAOYSA-N 4-(3,4-difluorophenyl)-2-propan-2-yl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine;hydrochloride Chemical compound Cl.N=1C(C(C)C)=NC=2CCNCC=2C=1C1=CC=C(F)C(F)=C1 HLJYXAOJQGEBFE-UHFFFAOYSA-N 0.000 claims 1
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• ZDPBTEIZPOIEQO-UHFFFAOYSA-N 4-(4-fluorophenyl)-2-(2-phenylpropan-2-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine Chemical compound N=1C=2CCNCC=2C(C=2C=CC(F)=CC=2)=NC=1C(C)(C)C1=CC=CC=C1 ZDPBTEIZPOIEQO-UHFFFAOYSA-N 0.000 claims 1
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• BZIBDCRNNKVCTK-UHFFFAOYSA-N 4-(4-fluorophenyl)-6-methyl-2-propan-2-yl-7,8-dihydro-5h-pyrido[4,3-d]pyrimidine Chemical compound N=1C(C(C)C)=NC=2CCN(C)CC=2C=1C1=CC=C(F)C=C1 BZIBDCRNNKVCTK-UHFFFAOYSA-N 0.000 claims 1
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