JP2009503076A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2009503076A5 JP2009503076A5 JP2008525054A JP2008525054A JP2009503076A5 JP 2009503076 A5 JP2009503076 A5 JP 2009503076A5 JP 2008525054 A JP2008525054 A JP 2008525054A JP 2008525054 A JP2008525054 A JP 2008525054A JP 2009503076 A5 JP2009503076 A5 JP 2009503076A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- phenyl
- tetrahydro
- pyrido
- pyrimidine
- Prior art date
- 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.)
- Granted
Links
- 125000000217 alkyl group Chemical group 0.000 claims 326
- -1 —C 3-6 cycloalkyl Chemical group 0.000 claims 120
- 229910052799 carbon Inorganic materials 0.000 claims 79
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 58
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 56
- 150000001875 compounds Chemical class 0.000 claims 54
- 150000001721 carbon Chemical group 0.000 claims 51
- 125000005843 halogen group Chemical group 0.000 claims 42
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 40
- 125000001424 substituent group Chemical group 0.000 claims 36
- 125000003342 alkenyl group Chemical group 0.000 claims 35
- 125000000753 cycloalkyl group Chemical group 0.000 claims 35
- 125000003386 piperidinyl group Chemical group 0.000 claims 32
- 125000004193 piperazinyl group Chemical group 0.000 claims 30
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 30
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims 30
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 28
- 125000002947 alkylene group Chemical group 0.000 claims 28
- 125000000304 alkynyl group Chemical group 0.000 claims 28
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims 28
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 28
- 125000004093 cyano group Chemical group *C#N 0.000 claims 28
- 125000002950 monocyclic group Chemical group 0.000 claims 28
- 229910052757 nitrogen Inorganic materials 0.000 claims 28
- 125000006413 ring segment Chemical group 0.000 claims 28
- 125000004432 carbon atom Chemical group C* 0.000 claims 26
- 125000002757 morpholinyl group Chemical group 0.000 claims 24
- 150000001408 amides Chemical class 0.000 claims 21
- 125000001931 aliphatic group Chemical group 0.000 claims 14
- 125000004076 pyridyl group Chemical group 0.000 claims 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 11
- 150000003839 salts Chemical class 0.000 claims 11
- 229910052739 hydrogen Inorganic materials 0.000 claims 9
- 125000002971 oxazolyl group Chemical group 0.000 claims 9
- 238000006467 substitution reaction Methods 0.000 claims 9
- 125000001544 thienyl group Chemical group 0.000 claims 9
- 125000004122 cyclic group Chemical group 0.000 claims 8
- 208000035475 disorder Diseases 0.000 claims 8
- 125000004450 alkenylene group Chemical group 0.000 claims 7
- 125000004419 alkynylene group Chemical group 0.000 claims 7
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims 7
- 125000003118 aryl group Chemical group 0.000 claims 7
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 7
- 125000005724 cycloalkenylene group Chemical group 0.000 claims 7
- 125000002993 cycloalkylene group Chemical group 0.000 claims 7
- 150000002148 esters Chemical class 0.000 claims 7
- 125000001072 heteroaryl group Chemical group 0.000 claims 7
- 125000005842 heteroatom Chemical group 0.000 claims 7
- 239000001257 hydrogen Substances 0.000 claims 7
- 229910052760 oxygen Inorganic materials 0.000 claims 7
- 239000012453 solvate Substances 0.000 claims 7
- 229910052717 sulfur Inorganic materials 0.000 claims 7
- 125000003831 tetrazolyl group Chemical group 0.000 claims 7
- 238000009472 formulation Methods 0.000 claims 6
- 239000000203 mixture Substances 0.000 claims 6
- 239000008194 pharmaceutical composition Substances 0.000 claims 6
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 5
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims 5
- 241000124008 Mammalia Species 0.000 claims 5
- 239000004480 active ingredient Substances 0.000 claims 5
- 150000002431 hydrogen Chemical class 0.000 claims 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 5
- 238000011282 treatment Methods 0.000 claims 5
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims 4
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 4
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 4
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims 4
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 4
- 208000019901 Anxiety disease Diseases 0.000 claims 4
- 230000036506 anxiety Effects 0.000 claims 4
- 230000002265 prevention Effects 0.000 claims 4
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims 4
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 3
- 208000019695 Migraine disease Diseases 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 3
- 206010027599 migraine Diseases 0.000 claims 3
- 208000019116 sleep disease Diseases 0.000 claims 3
- 208000020685 sleep-wake disease Diseases 0.000 claims 3
- 125000004502 1,2,3-oxadiazolyl group Chemical group 0.000 claims 2
- 125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 claims 2
- 125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 claims 2
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 claims 2
- 125000004506 1,2,5-oxadiazolyl group Chemical group 0.000 claims 2
- 125000001781 1,3,4-oxadiazolyl group Chemical group 0.000 claims 2
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims 2
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims 2
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 claims 2
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 2
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims 2
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims 2
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 2
- 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 claims 2
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims 2
- 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 2
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims 2
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims 2
- 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 2
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 2
- 125000004863 4-trifluoromethoxyphenyl group Chemical group [H]C1=C([H])C(OC(F)(F)F)=C([H])C([H])=C1* 0.000 claims 2
- 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 2
- 208000020925 Bipolar disease Diseases 0.000 claims 2
- 208000019888 Circadian rhythm sleep disease Diseases 0.000 claims 2
- 208000030814 Eating disease Diseases 0.000 claims 2
- 208000019454 Feeding and Eating disease Diseases 0.000 claims 2
- 208000011688 Generalised anxiety disease Diseases 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims 2
- 208000001456 Jet Lag Syndrome Diseases 0.000 claims 2
- 208000019022 Mood disease Diseases 0.000 claims 2
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims 2
- 208000018262 Peripheral vascular disease Diseases 0.000 claims 2
- 201000001880 Sexual dysfunction Diseases 0.000 claims 2
- 206010046543 Urinary incontinence Diseases 0.000 claims 2
- 230000005856 abnormality Effects 0.000 claims 2
- 125000005605 benzo group Chemical group 0.000 claims 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 230000002060 circadian Effects 0.000 claims 2
- 125000004976 cyclobutylene group Chemical group 0.000 claims 2
- 125000004979 cyclopentylene group Chemical group 0.000 claims 2
- 125000004980 cyclopropylene group Chemical group 0.000 claims 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 2
- 235000014632 disordered eating Nutrition 0.000 claims 2
- 125000002541 furyl group Chemical group 0.000 claims 2
- 230000030135 gastric motility Effects 0.000 claims 2
- 208000029364 generalized anxiety disease Diseases 0.000 claims 2
- 125000002883 imidazolyl group Chemical group 0.000 claims 2
- 208000002551 irritable bowel syndrome Diseases 0.000 claims 2
- 125000001786 isothiazolyl group Chemical group 0.000 claims 2
- 125000000842 isoxazolyl group Chemical group 0.000 claims 2
- 208000033915 jet lag type circadian rhythm sleep disease Diseases 0.000 claims 2
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims 2
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 2
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims 2
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 2
- 238000002600 positron emission tomography Methods 0.000 claims 2
- 208000020016 psychiatric disease Diseases 0.000 claims 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims 2
- 125000002098 pyridazinyl group Chemical group 0.000 claims 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims 2
- 201000000980 schizophrenia Diseases 0.000 claims 2
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims 2
- 231100000872 sexual dysfunction Toxicity 0.000 claims 2
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 2
- 125000000335 thiazolyl group Chemical group 0.000 claims 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 2
- ASRQEWDFKBMFCD-UHFFFAOYSA-N 1-[2-[(4-fluorophenyl)methyl]-4-(4-methylphenyl)pyrimidin-5-yl]-n,n-dimethylmethanamine Chemical compound N1=C(C=2C=CC(C)=CC=2)C(CN(C)C)=CN=C1CC1=CC=C(F)C=C1 ASRQEWDFKBMFCD-UHFFFAOYSA-N 0.000 claims 1
- YBTQDQATZUHXFT-UHFFFAOYSA-N 1-[2-benzyl-6-(4-methylphenyl)pyrimidin-4-yl]-n,n-dimethylmethanamine Chemical compound N=1C(CN(C)C)=CC(C=2C=CC(C)=CC=2)=NC=1CC1=CC=CC=C1 YBTQDQATZUHXFT-UHFFFAOYSA-N 0.000 claims 1
- JFCYVJNLMFBSIT-UHFFFAOYSA-N 1-[6-(4-fluorophenyl)-2-propan-2-ylpyrimidin-4-yl]-n-methylmethanamine Chemical compound CC(C)C1=NC(CNC)=CC(C=2C=CC(F)=CC=2)=N1 JFCYVJNLMFBSIT-UHFFFAOYSA-N 0.000 claims 1
- LDMOEFOXLIZJOW-UHFFFAOYSA-N 1-dodecanesulfonic acid Chemical compound CCCCCCCCCCCCS(O)(=O)=O LDMOEFOXLIZJOW-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- NRANKSPLOJQBFM-UHFFFAOYSA-N 2,7-dibenzyl-4-(4-methylphenyl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidine Chemical compound C1=CC(C)=CC=C1C1=NC(CC=2C=CC=CC=2)=NC2=C1CCN(CC=1C=CC=CC=1)C2 NRANKSPLOJQBFM-UHFFFAOYSA-N 0.000 claims 1
- NQFBXIROFMVGNW-UHFFFAOYSA-N 2,7-dibenzyl-4-phenyl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidine Chemical compound C=1C=CC=CC=1CN(C1)CCC(C(=N2)C=3C=CC=CC=3)=C1N=C2CC1=CC=CC=C1 NQFBXIROFMVGNW-UHFFFAOYSA-N 0.000 claims 1
- GOHOJAZROIPQEW-UHFFFAOYSA-N 2-(2-methylpropyl)-4-pyridin-4-yl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine Chemical compound N=1C(CC(C)C)=NC=2CCNCC=2C=1C1=CC=NC=C1 GOHOJAZROIPQEW-UHFFFAOYSA-N 0.000 claims 1
- CGVHACFRBMBKCJ-UHFFFAOYSA-N 2-(2-methylpropyl)-4-thiophen-2-yl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine Chemical compound N=1C(CC(C)C)=NC=2CCNCC=2C=1C1=CC=CS1 CGVHACFRBMBKCJ-UHFFFAOYSA-N 0.000 claims 1
- YDCBPAZBKRIIJQ-UHFFFAOYSA-N 2-(2-methylpropyl)-4-thiophen-3-yl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine Chemical compound N=1C(CC(C)C)=NC=2CCNCC=2C=1C=1C=CSC=1 YDCBPAZBKRIIJQ-UHFFFAOYSA-N 0.000 claims 1
- HTFORLXUESCAKA-UHFFFAOYSA-N 2-(2-propan-2-yl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl)-1,3-oxazole Chemical compound N=1C(C(C)C)=NC=2CCNCC=2C=1C1=NC=CO1 HTFORLXUESCAKA-UHFFFAOYSA-N 0.000 claims 1
- XHSCZYJVMANUEJ-UHFFFAOYSA-N 2-(2-propan-2-yl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl)-1,3-thiazole Chemical compound N=1C(C(C)C)=NC=2CCNCC=2C=1C1=NC=CS1 XHSCZYJVMANUEJ-UHFFFAOYSA-N 0.000 claims 1
- CHQLWFOCWHEVFP-UHFFFAOYSA-N 2-(3,3-difluorocyclopentyl)-4-(4-fluorophenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine Chemical compound C1=CC(F)=CC=C1C1=NC(C2CC(F)(F)CC2)=NC2=C1CNCC2 CHQLWFOCWHEVFP-UHFFFAOYSA-N 0.000 claims 1
- RQMNDTPEHPXZBI-UHFFFAOYSA-N 2-(3-fluorophenyl)-4-(4-fluorophenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine Chemical compound C1=CC(F)=CC=C1C1=NC(C=2C=C(F)C=CC=2)=NC2=C1CNCC2 RQMNDTPEHPXZBI-UHFFFAOYSA-N 0.000 claims 1
- CFJYTYOMZJWLJA-UHFFFAOYSA-N 2-(4,4-difluorocyclohexyl)-4-(4-fluorophenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine Chemical compound C1=CC(F)=CC=C1C1=NC(C2CCC(F)(F)CC2)=NC2=C1CNCC2 CFJYTYOMZJWLJA-UHFFFAOYSA-N 0.000 claims 1
- NEAQVXCKMIBFBH-UHFFFAOYSA-N 2-(4-fluorocyclohexyl)-4-(4-fluorophenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine Chemical compound C1CC(F)CCC1C(N=C1C=2C=CC(F)=CC=2)=NC2=C1CNCC2 NEAQVXCKMIBFBH-UHFFFAOYSA-N 0.000 claims 1
- BOJLLFFKHKHUGQ-UHFFFAOYSA-N 2-[2-benzyl-6-(4-methylphenyl)pyrimidin-4-yl]ethanamine Chemical compound C1=CC(C)=CC=C1C1=CC(CCN)=NC(CC=2C=CC=CC=2)=N1 BOJLLFFKHKHUGQ-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- WIUYYTPGPBRRGB-UHFFFAOYSA-N 2-[4-(4-fluorophenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-yl]-2-methylpropanoic acid Chemical compound N=1C(C(C)(C(O)=O)C)=NC=2CCNCC=2C=1C1=CC=C(F)C=C1 WIUYYTPGPBRRGB-UHFFFAOYSA-N 0.000 claims 1
- XBANPAVNUYYALV-UHFFFAOYSA-N 2-[4-(4-fluorophenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-yl]propan-2-ol Chemical compound N=1C(C(C)(O)C)=NC=2CCNCC=2C=1C1=CC=C(F)C=C1 XBANPAVNUYYALV-UHFFFAOYSA-N 0.000 claims 1
- ZCPJSJOPVXVKAG-UHFFFAOYSA-N 2-[4-(4-fluorophenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-yl]propanoic acid Chemical compound N=1C(C(C(O)=O)C)=NC=2CCNCC=2C=1C1=CC=C(F)C=C1 ZCPJSJOPVXVKAG-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- HWTYXTNYMDWWFE-UHFFFAOYSA-N 2-benzyl-4-(3-fluorophenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine Chemical compound FC1=CC=CC(C=2C=3CNCCC=3N=C(CC=3C=CC=CC=3)N=2)=C1 HWTYXTNYMDWWFE-UHFFFAOYSA-N 0.000 claims 1
- AVPPTWMKPBULGJ-UHFFFAOYSA-N 2-benzyl-4-(4-fluorophenyl)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine;hydrochloride Chemical compound Cl.C1=CC(F)=CC=C1C1=NC(CC=2C=CC=CC=2)=NC2=C1CCNC2 AVPPTWMKPBULGJ-UHFFFAOYSA-N 0.000 claims 1
- ZUHRRJVOTSODOR-UHFFFAOYSA-N 2-benzyl-4-(4-fluorophenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine Chemical compound C1=CC(F)=CC=C1C1=NC(CC=2C=CC=CC=2)=NC2=C1CNCC2 ZUHRRJVOTSODOR-UHFFFAOYSA-N 0.000 claims 1
- CSVHQMLHJMXBPD-UHFFFAOYSA-N 2-benzyl-4-(4-fluorophenyl)-6,7,8,9-tetrahydro-5h-pyrimido[4,5-c]azepine;hydrochloride Chemical compound Cl.C1=CC(F)=CC=C1C1=NC(CC=2C=CC=CC=2)=NC2=C1CCCNC2 CSVHQMLHJMXBPD-UHFFFAOYSA-N 0.000 claims 1
- UFNOVPGGHCFBLJ-UHFFFAOYSA-N 2-benzyl-4-(4-fluorophenyl)-6,7,8,9-tetrahydro-5h-pyrimido[4,5-d]azepine Chemical compound C1=CC(F)=CC=C1C1=NC(CC=2C=CC=CC=2)=NC2=C1CCNCC2 UFNOVPGGHCFBLJ-UHFFFAOYSA-N 0.000 claims 1
- RYTJQWWDIOORSK-UHFFFAOYSA-N 2-benzyl-4-(4-fluorophenyl)-6,7,8,9-tetrahydro-5h-pyrimido[5,4-c]azepine;hydrochloride Chemical compound Cl.C1=CC(F)=CC=C1C1=NC(CC=2C=CC=CC=2)=NC2=C1CNCCC2 RYTJQWWDIOORSK-UHFFFAOYSA-N 0.000 claims 1
- RRAZYWPASMFMAG-UHFFFAOYSA-N 2-benzyl-4-(4-fluorophenyl)-7-methyl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidine;hydrochloride Chemical compound Cl.C1N(C)CCC(C(=N2)C=3C=CC(F)=CC=3)=C1N=C2CC1=CC=CC=C1 RRAZYWPASMFMAG-UHFFFAOYSA-N 0.000 claims 1
- HUQNDSRJDBPDEL-UHFFFAOYSA-N 2-benzyl-4-(4-fluorophenyl)-7-propan-2-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidine Chemical compound C1N(C(C)C)CCC(C(=N2)C=3C=CC(F)=CC=3)=C1N=C2CC1=CC=CC=C1 HUQNDSRJDBPDEL-UHFFFAOYSA-N 0.000 claims 1
- QXVGJFVHHANYAX-UHFFFAOYSA-N 2-benzyl-4-(4-methoxyphenyl)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine Chemical compound C1=CC(OC)=CC=C1C1=NC(CC=2C=CC=CC=2)=NC2=C1CCNC2 QXVGJFVHHANYAX-UHFFFAOYSA-N 0.000 claims 1
- QPESUDDKGRENDA-UHFFFAOYSA-N 2-benzyl-4-(4-methylphenyl)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine;hydrochloride Chemical compound Cl.C1=CC(C)=CC=C1C1=NC(CC=2C=CC=CC=2)=NC2=C1CCNC2 QPESUDDKGRENDA-UHFFFAOYSA-N 0.000 claims 1
- ZKSMAPWVBJQLNO-UHFFFAOYSA-N 2-benzyl-4-(4-methylphenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine Chemical compound C1=CC(C)=CC=C1C1=NC(CC=2C=CC=CC=2)=NC2=C1CNCC2 ZKSMAPWVBJQLNO-UHFFFAOYSA-N 0.000 claims 1
- DCODHURRXZDVAZ-UHFFFAOYSA-N 2-benzyl-4-(4-methylphenyl)-6,7,8,9-tetrahydro-5h-pyrimido[4,5-d]azepine Chemical compound C1=CC(C)=CC=C1C1=NC(CC=2C=CC=CC=2)=NC2=C1CCNCC2 DCODHURRXZDVAZ-UHFFFAOYSA-N 0.000 claims 1
- KYSIDQYDCRTDJH-UHFFFAOYSA-N 2-benzyl-4-(4-methylphenyl)-6-[(4-methylpiperazin-1-yl)methyl]pyrimidine Chemical compound C1CN(C)CCN1CC1=CC(C=2C=CC(C)=CC=2)=NC(CC=2C=CC=CC=2)=N1 KYSIDQYDCRTDJH-UHFFFAOYSA-N 0.000 claims 1
- LJIDCYCHNQXEPW-UHFFFAOYSA-N 2-benzyl-4-[4-(trifluoromethyl)phenyl]-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=NC(CC=2C=CC=CC=2)=NC2=C1CNCC2 LJIDCYCHNQXEPW-UHFFFAOYSA-N 0.000 claims 1
- MKVDTCNMTYYTHU-UHFFFAOYSA-N 2-benzyl-4-[4-(trifluoromethyl)phenyl]-6,7,8,9-tetrahydro-5h-pyrimido[4,5-d]azepine Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=NC(CC=2C=CC=CC=2)=NC2=C1CCNCC2 MKVDTCNMTYYTHU-UHFFFAOYSA-N 0.000 claims 1
- KPAGUIDGAONHKM-UHFFFAOYSA-N 2-benzyl-4-phenyl-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine Chemical compound N=1C=2CNCCC=2C(C=2C=CC=CC=2)=NC=1CC1=CC=CC=C1 KPAGUIDGAONHKM-UHFFFAOYSA-N 0.000 claims 1
- XNOSXOVNQUXCIU-UHFFFAOYSA-N 2-benzyl-4-phenyl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine Chemical compound N=1C=2CCNCC=2C(C=2C=CC=CC=2)=NC=1CC1=CC=CC=C1 XNOSXOVNQUXCIU-UHFFFAOYSA-N 0.000 claims 1
- TVFDKRFXXSXNQG-UHFFFAOYSA-N 2-benzyl-7-methyl-4-(4-methylphenyl)-5,6,8,9-tetrahydropyrimido[4,5-d]azepine Chemical compound N=1C(C=2C=CC(C)=CC=2)=C2CCN(C)CCC2=NC=1CC1=CC=CC=C1 TVFDKRFXXSXNQG-UHFFFAOYSA-N 0.000 claims 1
- RYXQZPCZRUZASP-UHFFFAOYSA-N 2-butan-2-yl-4-(3-fluorophenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine Chemical compound N=1C(C(C)CC)=NC=2CCNCC=2C=1C1=CC=CC(F)=C1 RYXQZPCZRUZASP-UHFFFAOYSA-N 0.000 claims 1
- AFXYGEHWOKMZQS-UHFFFAOYSA-N 2-butan-2-yl-4-(4-fluorophenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine;hydrochloride Chemical compound Cl.N=1C(C(C)CC)=NC=2CCNCC=2C=1C1=CC=C(F)C=C1 AFXYGEHWOKMZQS-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- VPCIQDQLKTYYFI-UHFFFAOYSA-N 2-butan-2-yl-4-(4-methylphenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine;hydrochloride Chemical compound Cl.N=1C(C(C)CC)=NC=2CCNCC=2C=1C1=CC=C(C)C=C1 VPCIQDQLKTYYFI-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- YWDIQXUBGTZIJI-UHFFFAOYSA-N 2-cyclobutyl-4-(4-fluorophenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine;hydrochloride Chemical compound Cl.C1=CC(F)=CC=C1C1=NC(C2CCC2)=NC2=C1CNCC2 YWDIQXUBGTZIJI-UHFFFAOYSA-N 0.000 claims 1
- VAIXQGRVMRRZAE-UHFFFAOYSA-N 2-cyclobutyl-4-(4-methylphenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine Chemical compound C1=CC(C)=CC=C1C1=NC(C2CCC2)=NC2=C1CNCC2 VAIXQGRVMRRZAE-UHFFFAOYSA-N 0.000 claims 1
- RMODCJATEPQNLZ-UHFFFAOYSA-N 2-cyclopent-3-en-1-yl-4-(4-fluorophenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine Chemical compound C1=CC(F)=CC=C1C1=NC(C2CC=CC2)=NC2=C1CNCC2 RMODCJATEPQNLZ-UHFFFAOYSA-N 0.000 claims 1
- JHWYCTGSHIXUNV-UHFFFAOYSA-N 2-cyclopentyl-4-(4-fluorophenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine Chemical compound C1=CC(F)=CC=C1C1=NC(C2CCCC2)=NC2=C1CNCC2 JHWYCTGSHIXUNV-UHFFFAOYSA-N 0.000 claims 1
- ZFKHQIZFZFIFOQ-UHFFFAOYSA-N 2-cyclopentyl-4-(4-fluorophenyl)-6,7,8,9-tetrahydro-5h-pyrimido[4,5-d]azepine Chemical compound C1=CC(F)=CC=C1C1=NC(C2CCCC2)=NC2=C1CCNCC2 ZFKHQIZFZFIFOQ-UHFFFAOYSA-N 0.000 claims 1
- ZSSZWXKEDYMMFD-UHFFFAOYSA-N 2-cyclopentyl-4-(4-fluorophenyl)-7-methyl-5,6,8,9-tetrahydropyrimido[4,5-d]azepine Chemical compound C=12CCN(C)CCC2=NC(C2CCCC2)=NC=1C1=CC=C(F)C=C1 ZSSZWXKEDYMMFD-UHFFFAOYSA-N 0.000 claims 1
- CKIFZFSVSAWWTF-UHFFFAOYSA-N 2-cyclopentyl-4-(4-methoxyphenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine Chemical compound C1=CC(OC)=CC=C1C1=NC(C2CCCC2)=NC2=C1CNCC2 CKIFZFSVSAWWTF-UHFFFAOYSA-N 0.000 claims 1
- ZLXCOEKWZRBKGI-UHFFFAOYSA-N 2-cyclopentyl-4-(4-methoxyphenyl)-6,7,8,9-tetrahydro-5h-pyrimido[4,5-d]azepine Chemical compound C1=CC(OC)=CC=C1C1=NC(C2CCCC2)=NC2=C1CCNCC2 ZLXCOEKWZRBKGI-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- LXDDSFXYHSIAHR-UHFFFAOYSA-N 2-cyclopentyl-4-(4-methylphenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine Chemical compound C1=CC(C)=CC=C1C1=NC(C2CCCC2)=NC2=C1CNCC2 LXDDSFXYHSIAHR-UHFFFAOYSA-N 0.000 claims 1
- DLYKTYPCAAZRLI-UHFFFAOYSA-N 2-cyclopentyl-4-(4-methylphenyl)-6,7,8,9-tetrahydro-5h-pyrimido[4,5-d]azepine Chemical compound C1=CC(C)=CC=C1C1=NC(C2CCCC2)=NC2=C1CCNCC2 DLYKTYPCAAZRLI-UHFFFAOYSA-N 0.000 claims 1
- JNJUOFQDQGGKPZ-UHFFFAOYSA-N 2-cyclopentyl-7-methyl-4-(4-methylphenyl)-5,6,8,9-tetrahydropyrimido[4,5-d]azepine Chemical compound C=12CCN(C)CCC2=NC(C2CCCC2)=NC=1C1=CC=C(C)C=C1 JNJUOFQDQGGKPZ-UHFFFAOYSA-N 0.000 claims 1
- UOSAXXBVFWTNNV-UHFFFAOYSA-N 2-cyclopropyl-4-(4-fluorophenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine Chemical compound C1=CC(F)=CC=C1C1=NC(C2CC2)=NC2=C1CNCC2 UOSAXXBVFWTNNV-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- JOSNPNNFENWBRX-UHFFFAOYSA-N 2-propan-2-yl-4-(1h-pyrazol-4-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine Chemical compound N=1C(C(C)C)=NC=2CCNCC=2C=1C=1C=NNC=1 JOSNPNNFENWBRX-UHFFFAOYSA-N 0.000 claims 1
- PUNOFUFQQRBCHV-UHFFFAOYSA-N 2-propan-2-yl-4-(1h-pyrazol-5-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine Chemical compound N=1C(C(C)C)=NC=2CCNCC=2C=1C1=CC=NN1 PUNOFUFQQRBCHV-UHFFFAOYSA-N 0.000 claims 1
- VQDGCYKQLKXMCP-UHFFFAOYSA-N 2-propan-2-yl-4-(2h-triazol-4-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine Chemical compound N=1C(C(C)C)=NC=2CCNCC=2C=1C1=CN=NN1 VQDGCYKQLKXMCP-UHFFFAOYSA-N 0.000 claims 1
- UDJYVDPONMAJAM-UHFFFAOYSA-N 2-propan-2-yl-4-[4-(trifluoromethyl)phenyl]-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine Chemical compound N=1C(C(C)C)=NC=2CCNCC=2C=1C1=CC=C(C(F)(F)F)C=C1 UDJYVDPONMAJAM-UHFFFAOYSA-N 0.000 claims 1
- KIEYOKIJSMSHPQ-UHFFFAOYSA-N 2-propan-2-yl-4-thiophen-3-yl-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine;hydrochloride Chemical compound Cl.N=1C(C(C)C)=NC=2CNCCC=2C=1C=1C=CSC=1 KIEYOKIJSMSHPQ-UHFFFAOYSA-N 0.000 claims 1
- CJKMUTXSZGDRJB-UHFFFAOYSA-N 2-propan-2-yl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine Chemical compound C1NCCC2=NC(C(C)C)=NC=C21 CJKMUTXSZGDRJB-UHFFFAOYSA-N 0.000 claims 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
- 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 1
- 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 1
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims 1
- 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 1
- HPFOUGSGHFIERX-UHFFFAOYSA-N 3-[4-(4-fluorophenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-yl]benzonitrile Chemical compound C1=CC(F)=CC=C1C1=NC(C=2C=C(C=CC=2)C#N)=NC2=C1CNCC2 HPFOUGSGHFIERX-UHFFFAOYSA-N 0.000 claims 1
- OFOJLMGAIPYVAY-UHFFFAOYSA-N 3-[4-(4-fluorophenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-yl]cyclohexan-1-ol Chemical compound C1C(O)CCCC1C(N=C1C=2C=CC(F)=CC=2)=NC2=C1CNCC2 OFOJLMGAIPYVAY-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- HPCGFVNDADOQEH-UHFFFAOYSA-N 4,5-dimethyl-2-(2-propan-2-yl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl)-1,3-oxazole Chemical compound N=1C(C(C)C)=NC=2CCNCC=2C=1C1=NC(C)=C(C)O1 HPCGFVNDADOQEH-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- WHVUYSHTXPYYBI-UHFFFAOYSA-N 4-(2-cyclopentyl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl)benzonitrile Chemical compound C1=CC(C#N)=CC=C1C1=NC(C2CCCC2)=NC2=C1CNCC2 WHVUYSHTXPYYBI-UHFFFAOYSA-N 0.000 claims 1
- HTNMVRVINOXEIN-UHFFFAOYSA-N 4-(2-cyclopentyl-6,7,8,9-tetrahydro-5h-pyrimido[4,5-d]azepin-4-yl)benzonitrile Chemical compound C1=CC(C#N)=CC=C1C1=NC(C2CCCC2)=NC2=C1CCNCC2 HTNMVRVINOXEIN-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- VSDHQMJLLCIXKF-UHFFFAOYSA-N 4-(2-phenoxyphenyl)-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=C1OC1=CC=CC=C1 VSDHQMJLLCIXKF-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- LOYKVYJEQFKDQZ-UHFFFAOYSA-N 4-(4-fluoro-3-methylphenyl)-2-(2-methylpropyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine Chemical compound N=1C(CC(C)C)=NC=2CCNCC=2C=1C1=CC=C(F)C(C)=C1 LOYKVYJEQFKDQZ-UHFFFAOYSA-N 0.000 claims 1
- VBFWZNBACARGQD-UHFFFAOYSA-N 4-(4-fluorophenyl)-2,6-di(propan-2-yl)-7,8-dihydro-5h-pyrido[4,3-d]pyrimidine Chemical compound C=12CN(C(C)C)CCC2=NC(C(C)C)=NC=1C1=CC=C(F)C=C1 VBFWZNBACARGQD-UHFFFAOYSA-N 0.000 claims 1
- UDWHMLMQXNEKBD-UHFFFAOYSA-N 4-(4-fluorophenyl)-2-(1,1,1,3,3,3-hexafluoropropan-2-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine Chemical compound C1=CC(F)=CC=C1C1=NC(C(C(F)(F)F)C(F)(F)F)=NC2=C1CNCC2 UDWHMLMQXNEKBD-UHFFFAOYSA-N 0.000 claims 1
- VEBIPTDXWIUNHW-UHFFFAOYSA-N 4-(4-fluorophenyl)-2-(1-methylcyclopropyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine Chemical compound N=1C=2CCNCC=2C(C=2C=CC(F)=CC=2)=NC=1C1(C)CC1 VEBIPTDXWIUNHW-UHFFFAOYSA-N 0.000 claims 1
- KAKBJMZQEXHHAS-UHFFFAOYSA-N 4-(4-fluorophenyl)-2-(1-methylpiperidin-4-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine Chemical compound C1CN(C)CCC1C(N=C1C=2C=CC(F)=CC=2)=NC2=C1CNCC2 KAKBJMZQEXHHAS-UHFFFAOYSA-N 0.000 claims 1
- QYWWGMHMNHZCHV-UHFFFAOYSA-N 4-(4-fluorophenyl)-2-(2-fluoropropan-2-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine Chemical compound N=1C(C(C)(F)C)=NC=2CCNCC=2C=1C1=CC=C(F)C=C1 QYWWGMHMNHZCHV-UHFFFAOYSA-N 0.000 claims 1
- UBXFSHYTJMAJGS-UHFFFAOYSA-N 4-(4-fluorophenyl)-2-(2-methoxyethyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine Chemical compound N=1C(CCOC)=NC=2CCNCC=2C=1C1=CC=C(F)C=C1 UBXFSHYTJMAJGS-UHFFFAOYSA-N 0.000 claims 1
- BNNDPEJQMKVBHK-UHFFFAOYSA-N 4-(4-fluorophenyl)-2-(2-methylphenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine Chemical compound CC1=CC=CC=C1C(N=C1C=2C=CC(F)=CC=2)=NC2=C1CNCC2 BNNDPEJQMKVBHK-UHFFFAOYSA-N 0.000 claims 1
- QRTRGDAIMCUVGH-UHFFFAOYSA-N 4-(4-fluorophenyl)-2-(2-methylpropyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine Chemical compound N=1C(CC(C)C)=NC=2CCNCC=2C=1C1=CC=C(F)C=C1 QRTRGDAIMCUVGH-UHFFFAOYSA-N 0.000 claims 1
- STRQOGVAXIWSAN-UHFFFAOYSA-N 4-(4-fluorophenyl)-2-(2-phenylethyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine Chemical compound C1=CC(F)=CC=C1C1=NC(CCC=2C=CC=CC=2)=NC2=C1CNCC2 STRQOGVAXIWSAN-UHFFFAOYSA-N 0.000 claims 1
- 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
- INPIJSFBWJOXNR-UHFFFAOYSA-N 4-(4-fluorophenyl)-2-(2-piperidin-1-ylethyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine Chemical compound C1=CC(F)=CC=C1C1=NC(CCN2CCCCC2)=NC2=C1CNCC2 INPIJSFBWJOXNR-UHFFFAOYSA-N 0.000 claims 1
- JQQWHVUKYBIUGY-UHFFFAOYSA-N 4-(4-fluorophenyl)-2-(4-methoxyphenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine Chemical compound C1=CC(OC)=CC=C1C(N=C1C=2C=CC(F)=CC=2)=NC2=C1CNCC2 JQQWHVUKYBIUGY-UHFFFAOYSA-N 0.000 claims 1
- YVKRQKSWHHIJCQ-UHFFFAOYSA-N 4-(4-fluorophenyl)-2-(oxan-3-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine Chemical compound C1=CC(F)=CC=C1C1=NC(C2COCCC2)=NC2=C1CNCC2 YVKRQKSWHHIJCQ-UHFFFAOYSA-N 0.000 claims 1
- AZUUIFBBCRIKLF-UHFFFAOYSA-N 4-(4-fluorophenyl)-2-(oxan-4-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine Chemical compound C1=CC(F)=CC=C1C1=NC(C2CCOCC2)=NC2=C1CNCC2 AZUUIFBBCRIKLF-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- ICXYYFPLSKPKJE-UHFFFAOYSA-N 4-(4-fluorophenyl)-2-[(4-fluorophenyl)methyl]-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine Chemical compound C1=CC(F)=CC=C1CC(N=C1C=2C=CC(F)=CC=2)=NC2=C1CNCC2 ICXYYFPLSKPKJE-UHFFFAOYSA-N 0.000 claims 1
- RCRKYHCZNIGMKD-UHFFFAOYSA-N 4-(4-fluorophenyl)-2-[(4-fluorophenyl)methyl]-6,7,8,9-tetrahydro-5h-pyrimido[4,5-d]azepine Chemical compound C1=CC(F)=CC=C1CC(N=C1C=2C=CC(F)=CC=2)=NC2=C1CCNCC2 RCRKYHCZNIGMKD-UHFFFAOYSA-N 0.000 claims 1
- SMFAJHKCMWLYEB-UHFFFAOYSA-N 4-(4-fluorophenyl)-2-[(4-fluorophenyl)methyl]-6-methyl-7,8-dihydro-5h-pyrido[4,3-d]pyrimidine Chemical compound N=1C(C=2C=CC(F)=CC=2)=C2CN(C)CCC2=NC=1CC1=CC=C(F)C=C1 SMFAJHKCMWLYEB-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- IKYSOVOQOJQTKX-UHFFFAOYSA-N 4-(4-fluorophenyl)-2-[(4-fluorophenyl)methyl]-7-methyl-9-methylidene-6,8-dihydro-5h-pyrimido[4,5-d]azepine Chemical compound N1=C2C(=C)CN(C)CCC2=C(C=2C=CC(F)=CC=2)N=C1CC1=CC=C(F)C=C1 IKYSOVOQOJQTKX-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- ABOAUXKAVARYLG-UHFFFAOYSA-N 4-(4-fluorophenyl)-2-piperidin-4-yl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine Chemical compound C1=CC(F)=CC=C1C1=NC(C2CCNCC2)=NC2=C1CNCC2 ABOAUXKAVARYLG-UHFFFAOYSA-N 0.000 claims 1
- OEVFNBGGUWXQNM-UHFFFAOYSA-N 4-(4-fluorophenyl)-2-propan-2-yl-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine;hydrochloride Chemical compound Cl.N=1C(C(C)C)=NC=2CNCCC=2C=1C1=CC=C(F)C=C1 OEVFNBGGUWXQNM-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- JNVXMELGLMGJFB-UHFFFAOYSA-N 4-(4-fluorophenyl)-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=C1 JNVXMELGLMGJFB-UHFFFAOYSA-N 0.000 claims 1
- RTCLSIGEZMGCPZ-UHFFFAOYSA-N 4-(4-fluorophenyl)-2-propan-2-yl-5,6,7,8-tetrahydroquinazolin-7-ol Chemical compound N=1C(C(C)C)=NC=2CC(O)CCC=2C=1C1=CC=C(F)C=C1 RTCLSIGEZMGCPZ-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- PWDAARRDZQYPES-UHFFFAOYSA-N 4-(4-fluorophenyl)-2-propan-2-yl-6,7-dihydro-5h-pyrrolo[3,4-d]pyrimidine;hydrochloride Chemical compound Cl.N=1C(C(C)C)=NC=2CNCC=2C=1C1=CC=C(F)C=C1 PWDAARRDZQYPES-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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
- LLMDRLXOXKLTKG-UHFFFAOYSA-N 4-(4-fluorophenyl)-7-methyl-2-propan-2-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidine;hydrochloride Chemical compound Cl.N=1C(C(C)C)=NC=2CN(C)CCC=2C=1C1=CC=C(F)C=C1 LLMDRLXOXKLTKG-UHFFFAOYSA-N 0.000 claims 1
- SDIUNQQQPPBBOZ-UHFFFAOYSA-N 4-(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=C1 SDIUNQQQPPBBOZ-UHFFFAOYSA-N 0.000 claims 1
- HBKLEPCDRRZECR-UHFFFAOYSA-N 4-(4-fluorophenyl)-n-methyl-2-propan-2-yl-5,6,7,8-tetrahydroquinazolin-6-amine;hydrochloride Chemical compound Cl.C=12CC(NC)CCC2=NC(C(C)C)=NC=1C1=CC=C(F)C=C1 HBKLEPCDRRZECR-UHFFFAOYSA-N 0.000 claims 1
- DHDABDNZSHWCMV-UHFFFAOYSA-N 4-(4-fluorophenyl)-n-methyl-2-propan-2-yl-5,6,7,8-tetrahydroquinazolin-7-amine;hydrochloride Chemical compound Cl.C1C(NC)CCC2=C1N=C(C(C)C)N=C2C1=CC=C(F)C=C1 DHDABDNZSHWCMV-UHFFFAOYSA-N 0.000 claims 1
- FHIZMNLYDQJTJK-UHFFFAOYSA-N 4-(4-methoxyphenyl)-2-(2-methylpropyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine Chemical compound C1=CC(OC)=CC=C1C1=NC(CC(C)C)=NC2=C1CNCC2 FHIZMNLYDQJTJK-UHFFFAOYSA-N 0.000 claims 1
- CRBVWRFHHOTVLG-UHFFFAOYSA-N 4-(4-methoxyphenyl)-2-propan-2-yl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine Chemical compound C1=CC(OC)=CC=C1C1=NC(C(C)C)=NC2=C1CNCC2 CRBVWRFHHOTVLG-UHFFFAOYSA-N 0.000 claims 1
- MCLALWBLJICXPT-UHFFFAOYSA-N 4-(4-methoxyphenyl)-2-propan-2-yl-6,7,8,9-tetrahydro-5h-pyrimido[4,5-c]azepine Chemical compound C1=CC(OC)=CC=C1C1=NC(C(C)C)=NC2=C1CCCNC2 MCLALWBLJICXPT-UHFFFAOYSA-N 0.000 claims 1
- RFMQFVQMGRDDCK-UHFFFAOYSA-N 4-(4-methylphenyl)-2-(2-methylpropyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine Chemical compound N=1C(CC(C)C)=NC=2CCNCC=2C=1C1=CC=C(C)C=C1 RFMQFVQMGRDDCK-UHFFFAOYSA-N 0.000 claims 1
- YXQDNVATQFNWPT-UHFFFAOYSA-N 4-(4-methylphenyl)-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(C)C=C1 YXQDNVATQFNWPT-UHFFFAOYSA-N 0.000 claims 1
- DORFJEXVKYBZDV-UHFFFAOYSA-N 4-(4-methylphenyl)-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(C)C=C1 DORFJEXVKYBZDV-UHFFFAOYSA-N 0.000 claims 1
- ZJIAPHFVAIECTL-UHFFFAOYSA-N 4-(5-fluoropyridin-2-yl)-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=N1 ZJIAPHFVAIECTL-UHFFFAOYSA-N 0.000 claims 1
- KUORMYAPPZFFMC-UHFFFAOYSA-N 4-(5-methylfuran-2-yl)-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(C)O1 KUORMYAPPZFFMC-UHFFFAOYSA-N 0.000 claims 1
- FPFRBZXIRXQLPV-UHFFFAOYSA-N 4-(5-methylthiophen-3-yl)-2-propan-2-yl-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine;hydrochloride Chemical compound Cl.N=1C(C(C)C)=NC=2CNCCC=2C=1C1=CSC(C)=C1 FPFRBZXIRXQLPV-UHFFFAOYSA-N 0.000 claims 1
- HGUIQXYOYVUCNG-UHFFFAOYSA-N 4-(furan-2-yl)-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=CO1 HGUIQXYOYVUCNG-UHFFFAOYSA-N 0.000 claims 1
- DJLGNLSGKUHUQZ-UHFFFAOYSA-N 4-(furan-3-yl)-2-propan-2-yl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine Chemical compound N=1C(C(C)C)=NC=2CCNCC=2C=1C=1C=COC=1 DJLGNLSGKUHUQZ-UHFFFAOYSA-N 0.000 claims 1
- ZMNKRECWDNJIOT-UHFFFAOYSA-N 4-[2-(2-methylpropyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl]benzonitrile Chemical compound N=1C(CC(C)C)=NC=2CCNCC=2C=1C1=CC=C(C#N)C=C1 ZMNKRECWDNJIOT-UHFFFAOYSA-N 0.000 claims 1
- BDMVKHWSOBWEPE-UHFFFAOYSA-N 4-[2-[(4-fluorophenyl)methyl]-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl]benzonitrile Chemical compound C1=CC(F)=CC=C1CC(N=C1C=2C=CC(=CC=2)C#N)=NC2=C1CNCC2 BDMVKHWSOBWEPE-UHFFFAOYSA-N 0.000 claims 1
- IQELHRYLGDMEFE-UHFFFAOYSA-N 4-[2-[(4-fluorophenyl)methyl]-6-methyl-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-4-yl]benzonitrile Chemical compound N=1C(C=2C=CC(=CC=2)C#N)=C2CN(C)CCC2=NC=1CC1=CC=C(F)C=C1 IQELHRYLGDMEFE-UHFFFAOYSA-N 0.000 claims 1
- FPWNLURCHDRMHC-UHFFFAOYSA-N 4-chlorobiphenyl Chemical group C1=CC(Cl)=CC=C1C1=CC=CC=C1 FPWNLURCHDRMHC-UHFFFAOYSA-N 0.000 claims 1
- NPQCVIDGFCIFNW-UHFFFAOYSA-N 4-phenyl-2-propan-2-yl-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine Chemical compound N=1C(C(C)C)=NC=2CNCCC=2C=1C1=CC=CC=C1 NPQCVIDGFCIFNW-UHFFFAOYSA-N 0.000 claims 1
- XBAQJEMMLBLSSA-UHFFFAOYSA-N 4-phenyl-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=C1 XBAQJEMMLBLSSA-UHFFFAOYSA-N 0.000 claims 1
- AIUMOQLDWXLQDO-UHFFFAOYSA-N 4-phenyl-2-propan-2-yl-6,7,8,9-tetrahydro-5h-pyrimido[4,5-c]azepine Chemical compound N=1C(C(C)C)=NC=2CNCCCC=2C=1C1=CC=CC=C1 AIUMOQLDWXLQDO-UHFFFAOYSA-N 0.000 claims 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims 1
- YNVYJOASCWNWPW-UHFFFAOYSA-N 6-benzyl-4-(3-chloro-4-fluorophenyl)-8-methyl-2-propan-2-yl-7,8-dihydro-5h-pyrido[4,3-d]pyrimidine Chemical compound C1C=2C(C=3C=C(Cl)C(F)=CC=3)=NC(C(C)C)=NC=2C(C)CN1CC1=CC=CC=C1 YNVYJOASCWNWPW-UHFFFAOYSA-N 0.000 claims 1
- XCSIQLDZIDTESJ-UHFFFAOYSA-N 6-benzyl-4-(4-chlorophenyl)-8-methyl-2-propan-2-yl-7,8-dihydro-5h-pyrido[4,3-d]pyrimidine Chemical compound C1C=2C(C=3C=CC(Cl)=CC=3)=NC(C(C)C)=NC=2C(C)CN1CC1=CC=CC=C1 XCSIQLDZIDTESJ-UHFFFAOYSA-N 0.000 claims 1
- OQXVNIUIVKXZSC-UHFFFAOYSA-N 6-benzyl-4-(4-fluorophenyl)-8-methyl-2-propan-2-yl-7,8-dihydro-5h-pyrido[4,3-d]pyrimidine Chemical compound C1C=2C(C=3C=CC(F)=CC=3)=NC(C(C)C)=NC=2C(C)CN1CC1=CC=CC=C1 OQXVNIUIVKXZSC-UHFFFAOYSA-N 0.000 claims 1
- QHHCBLDHUKHBBE-UHFFFAOYSA-N 6-benzyl-4-[4-(4-chlorophenyl)phenyl]-8-methyl-2-propan-2-yl-7,8-dihydro-5h-pyrido[4,3-d]pyrimidine Chemical compound C1C=2C(C=3C=CC(=CC=3)C=3C=CC(Cl)=CC=3)=NC(C(C)C)=NC=2C(C)CN1CC1=CC=CC=C1 QHHCBLDHUKHBBE-UHFFFAOYSA-N 0.000 claims 1
- SAOXZEZNHKCUSN-UHFFFAOYSA-N 6-benzyl-8-methyl-2-propan-2-yl-4-[4-(trifluoromethyl)phenyl]-7,8-dihydro-5h-pyrido[4,3-d]pyrimidine Chemical compound C1C=2C(C=3C=CC(=CC=3)C(F)(F)F)=NC(C(C)C)=NC=2C(C)CN1CC1=CC=CC=C1 SAOXZEZNHKCUSN-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- CDBFUKBSCYKYIA-UHFFFAOYSA-N 6-benzyl-8-methyl-4-(4-methylphenyl)-2-propan-2-yl-7,8-dihydro-5h-pyrido[4,3-d]pyrimidine Chemical compound C1C=2C(C=3C=CC(C)=CC=3)=NC(C(C)C)=NC=2C(C)CN1CC1=CC=CC=C1 CDBFUKBSCYKYIA-UHFFFAOYSA-N 0.000 claims 1
- ADGUVEUADACQDW-UHFFFAOYSA-N 6-benzyl-8-methyl-4-phenyl-2-propan-2-yl-7,8-dihydro-5h-pyrido[4,3-d]pyrimidine Chemical compound C1C=2C(C=3C=CC=CC=3)=NC(C(C)C)=NC=2C(C)CN1CC1=CC=CC=C1 ADGUVEUADACQDW-UHFFFAOYSA-N 0.000 claims 1
- LBEOSTXBOGGVDF-UHFFFAOYSA-N 6-butyl-4-(4-fluorophenyl)-2-propan-2-yl-7,8-dihydro-5h-pyrido[4,3-d]pyrimidine Chemical compound C=12CN(CCCC)CCC2=NC(C(C)C)=NC=1C1=CC=C(F)C=C1 LBEOSTXBOGGVDF-UHFFFAOYSA-N 0.000 claims 1
- WWNNYITXYXENBD-UHFFFAOYSA-N 6-cyclobutyl-4-(4-fluorophenyl)-2-propan-2-yl-7,8-dihydro-5h-pyrido[4,3-d]pyrimidine Chemical compound N=1C(C(C)C)=NC=2CCN(C3CCC3)CC=2C=1C1=CC=C(F)C=C1 WWNNYITXYXENBD-UHFFFAOYSA-N 0.000 claims 1
- FYXUDQIGCJZZGE-UHFFFAOYSA-N 6-cyclopentyl-4-(4-fluorophenyl)-2-propan-2-yl-7,8-dihydro-5h-pyrido[4,3-d]pyrimidine Chemical compound N=1C(C(C)C)=NC=2CCN(C3CCCC3)CC=2C=1C1=CC=C(F)C=C1 FYXUDQIGCJZZGE-UHFFFAOYSA-N 0.000 claims 1
- PQUUWTOSTRJHSK-UHFFFAOYSA-N 6-cyclopropyl-4-(4-fluorophenyl)-2-propan-2-yl-7,8-dihydro-5h-pyrido[4,3-d]pyrimidine Chemical compound N=1C(C(C)C)=NC=2CCN(C3CC3)CC=2C=1C1=CC=C(F)C=C1 PQUUWTOSTRJHSK-UHFFFAOYSA-N 0.000 claims 1
- BARBZTJVDGZBML-UHFFFAOYSA-N 7-benzyl-2-propan-2-yl-4-thiophen-3-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidine;hydrochloride Chemical compound Cl.C1CC=2C(C3=CSC=C3)=NC(C(C)C)=NC=2CN1CC1=CC=CC=C1 BARBZTJVDGZBML-UHFFFAOYSA-N 0.000 claims 1
- FRGQBPCBKYDGED-UHFFFAOYSA-N 7-benzyl-4-(4-fluorophenyl)-2-propan-2-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidine Chemical compound C1CC=2C(C=3C=CC(F)=CC=3)=NC(C(C)C)=NC=2CN1CC1=CC=CC=C1 FRGQBPCBKYDGED-UHFFFAOYSA-N 0.000 claims 1
- KWFBFWUTTMYONB-UHFFFAOYSA-N 7-benzyl-4-(5-methylthiophen-3-yl)-2-propan-2-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidine;hydrochloride Chemical compound Cl.C1CC=2C(C=3C=C(C)SC=3)=NC(C(C)C)=NC=2CN1CC1=CC=CC=C1 KWFBFWUTTMYONB-UHFFFAOYSA-N 0.000 claims 1
- BTOLKTWDIBDQQP-UHFFFAOYSA-N 7-benzyl-4-phenyl-2-propan-2-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidine Chemical compound C1CC=2C(C=3C=CC=CC=3)=NC(C(C)C)=NC=2CN1CC1=CC=CC=C1 BTOLKTWDIBDQQP-UHFFFAOYSA-N 0.000 claims 1
- GBIAIRRHUCVNPA-UHFFFAOYSA-N 7-methyl-2-propan-2-yl-4-thiophen-3-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidine;hydrochloride Chemical compound Cl.N=1C(C(C)C)=NC=2CN(C)CCC=2C=1C=1C=CSC=1 GBIAIRRHUCVNPA-UHFFFAOYSA-N 0.000 claims 1
- HHEXMPIGJJBUNK-UHFFFAOYSA-N 7-methyl-4-(5-methylthiophen-3-yl)-2-propan-2-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidine;hydrochloride Chemical compound Cl.N=1C(C(C)C)=NC=2CN(C)CCC=2C=1C1=CSC(C)=C1 HHEXMPIGJJBUNK-UHFFFAOYSA-N 0.000 claims 1
- YHYRIIRTVDSNOA-UHFFFAOYSA-N 7-methyl-4-phenyl-2-propan-2-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidine Chemical compound N=1C(C(C)C)=NC=2CN(C)CCC=2C=1C1=CC=CC=C1 YHYRIIRTVDSNOA-UHFFFAOYSA-N 0.000 claims 1
- WMQWEAVOBMOWLU-UHFFFAOYSA-N 8-methyl-2-propan-2-yl-4-[4-(trifluoromethyl)phenyl]-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine Chemical compound N=1C(C(C)C)=NC=2C(C)CNCC=2C=1C1=CC=C(C(F)(F)F)C=C1 WMQWEAVOBMOWLU-UHFFFAOYSA-N 0.000 claims 1
- NJXUCOROPNNDDB-UHFFFAOYSA-N 8-methyl-2-propan-2-yl-4-thiophen-3-yl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine Chemical compound N=1C(C(C)C)=NC=2C(C)CNCC=2C=1C=1C=CSC=1 NJXUCOROPNNDDB-UHFFFAOYSA-N 0.000 claims 1
- QXARTIXRRUPKRV-UHFFFAOYSA-N 8-methyl-4-(4-methylphenyl)-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(C)C=C1 QXARTIXRRUPKRV-UHFFFAOYSA-N 0.000 claims 1
- DHSLSXCZOGPCKZ-UHFFFAOYSA-N 8-methyl-4-phenyl-2-propan-2-yl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine Chemical compound N=1C(C(C)C)=NC=2C(C)CNCC=2C=1C1=CC=CC=C1 DHSLSXCZOGPCKZ-UHFFFAOYSA-N 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
- 208000007848 Alcoholism Diseases 0.000 claims 1
- 206010003591 Ataxia Diseases 0.000 claims 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 claims 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims 1
- 206010012335 Dependence Diseases 0.000 claims 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims 1
- 206010012688 Diabetic retinal oedema Diseases 0.000 claims 1
- 206010012689 Diabetic retinopathy Diseases 0.000 claims 1
- 206010012735 Diarrhoea Diseases 0.000 claims 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 1
- 239000005977 Ethylene Substances 0.000 claims 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims 1
- 208000010412 Glaucoma Diseases 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims 1
- 206010020772 Hypertension Diseases 0.000 claims 1
- 208000001953 Hypotension Diseases 0.000 claims 1
- 206010061218 Inflammation Diseases 0.000 claims 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 claims 1
- 241001465754 Metazoa Species 0.000 claims 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 1
- OXBUVRWHHXBACF-UHFFFAOYSA-N N=1C(C(C)C)=NC=2CC(N3)CCC3C=2C=1C1=CC=C(F)C=C1 Chemical compound N=1C(C(C)C)=NC=2CC(N3)CCC3C=2C=1C1=CC=C(F)C=C1 OXBUVRWHHXBACF-UHFFFAOYSA-N 0.000 claims 1
- GGHGARDJTHELMD-UHFFFAOYSA-N N=1C(C(C)C)=NC=2CC(N3)CCC3CC=2C=1C1=CC=C(F)C=C1 Chemical compound N=1C(C(C)C)=NC=2CC(N3)CCC3CC=2C=1C1=CC=C(F)C=C1 GGHGARDJTHELMD-UHFFFAOYSA-N 0.000 claims 1
- 229910002651 NO3 Inorganic materials 0.000 claims 1
- 206010028813 Nausea Diseases 0.000 claims 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims 1
- 208000008589 Obesity Diseases 0.000 claims 1
- 208000003435 Optic Neuritis Diseases 0.000 claims 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims 1
- 229910019142 PO4 Inorganic materials 0.000 claims 1
- 208000002193 Pain Diseases 0.000 claims 1
- 206010040070 Septic Shock Diseases 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 1
- ZOMSJGXZJFJUOV-UHFFFAOYSA-N [4-(4-fluorophenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-yl]-phenylmethanol Chemical compound N=1C=2CCNCC=2C(C=2C=CC(F)=CC=2)=NC=1C(O)C1=CC=CC=C1 ZOMSJGXZJFJUOV-UHFFFAOYSA-N 0.000 claims 1
- 229940022663 acetate Drugs 0.000 claims 1
- 206010064930 age-related macular degeneration Diseases 0.000 claims 1
- 201000007930 alcohol dependence Diseases 0.000 claims 1
- 125000000732 arylene group Chemical group 0.000 claims 1
- 125000003725 azepanyl group Chemical group 0.000 claims 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 1
- 239000004305 biphenyl Substances 0.000 claims 1
- 235000010290 biphenyl Nutrition 0.000 claims 1
- FATUQANACHZLRT-KMRXSBRUSA-L calcium glucoheptonate Chemical compound [Ca+2].OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)C([O-])=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)C([O-])=O FATUQANACHZLRT-KMRXSBRUSA-L 0.000 claims 1
- 210000003169 central nervous system Anatomy 0.000 claims 1
- 208000015114 central nervous system disease Diseases 0.000 claims 1
- 210000001072 colon Anatomy 0.000 claims 1
- 230000002920 convulsive effect Effects 0.000 claims 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 125000004977 cycloheptylene group Chemical group 0.000 claims 1
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 claims 1
- 125000004956 cyclohexylene group Chemical group 0.000 claims 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- LTVOKYUPTHZZQH-UHFFFAOYSA-N difluoromethane Chemical group F[C]F LTVOKYUPTHZZQH-UHFFFAOYSA-N 0.000 claims 1
- POULHZVOKOAJMA-UHFFFAOYSA-M dodecanoate Chemical compound CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000002526 effect on cardiovascular system Effects 0.000 claims 1
- 208000030533 eye disease Diseases 0.000 claims 1
- 230000002496 gastric effect Effects 0.000 claims 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-M hexadecanoate Chemical compound CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 claims 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 230000003054 hormonal effect Effects 0.000 claims 1
- 150000004677 hydrates Chemical class 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 claims 1
- 230000036543 hypotension Effects 0.000 claims 1
- 230000004054 inflammatory process Effects 0.000 claims 1
- 208000028867 ischemia Diseases 0.000 claims 1
- 229940070765 laurate Drugs 0.000 claims 1
- 208000002780 macular degeneration Diseases 0.000 claims 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims 1
- 230000001404 mediated effect Effects 0.000 claims 1
- 208000030159 metabolic disease Diseases 0.000 claims 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims 1
- 239000003068 molecular probe Substances 0.000 claims 1
- 125000005487 naphthalate group Chemical group 0.000 claims 1
- 230000008693 nausea Effects 0.000 claims 1
- 235000020824 obesity Nutrition 0.000 claims 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims 1
- 229940049964 oleate Drugs 0.000 claims 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims 1
- 229940039748 oxalate Drugs 0.000 claims 1
- 125000004287 oxazol-2-yl group Chemical group [H]C1=C([H])N=C(*)O1 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims 1
- 239000010452 phosphate Substances 0.000 claims 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 238000011321 prophylaxis Methods 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000002755 pyrazolinyl group Chemical group 0.000 claims 1
- 125000001422 pyrrolinyl group Chemical group 0.000 claims 1
- 230000008085 renal dysfunction Effects 0.000 claims 1
- 230000036303 septic shock Effects 0.000 claims 1
- 229940076279 serotonin Drugs 0.000 claims 1
- 230000035939 shock Effects 0.000 claims 1
- 238000002603 single-photon emission computed tomography Methods 0.000 claims 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 claims 1
- 229940095064 tartrate Drugs 0.000 claims 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 1
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 claims 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 1
- 229940070710 valerate Drugs 0.000 claims 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims 1
- 230000002792 vascular Effects 0.000 claims 1
- MFPNTSYWVHFIJZ-UHFFFAOYSA-N CCC(CC)C(C)NC Chemical compound CCC(CC)C(C)NC MFPNTSYWVHFIJZ-UHFFFAOYSA-N 0.000 description 1
- 0 CN(C)C(*)*(*)=* Chemical compound CN(C)C(*)*(*)=* 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US70571905P | 2005-08-04 | 2005-08-04 | |
| US60/705,719 | 2005-08-04 | ||
| PCT/US2006/029437 WO2007019083A1 (en) | 2005-08-04 | 2006-07-27 | Pyrimidine compounds as serotonin receptor modulators |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2009503076A JP2009503076A (ja) | 2009-01-29 |
| JP2009503076A5 true JP2009503076A5 (enExample) | 2009-08-13 |
| JP5066088B2 JP5066088B2 (ja) | 2012-11-07 |
Family
ID=37400981
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008525054A Expired - Fee Related JP5066088B2 (ja) | 2005-08-04 | 2006-07-27 | セロトニン受容体モジュレーターとしてのピリミジン化合物 |
Country Status (16)
| Country | Link |
|---|---|
| EP (1) | EP1928461B1 (enExample) |
| JP (1) | JP5066088B2 (enExample) |
| KR (1) | KR101353268B1 (enExample) |
| CN (1) | CN101277700B (enExample) |
| AT (1) | ATE539753T1 (enExample) |
| AU (1) | AU2006278759B2 (enExample) |
| BR (1) | BRPI0614397A2 (enExample) |
| CA (1) | CA2617760C (enExample) |
| CR (1) | CR9791A (enExample) |
| EA (1) | EA014495B1 (enExample) |
| IL (2) | IL189164A (enExample) |
| NO (1) | NO340744B1 (enExample) |
| NZ (1) | NZ565334A (enExample) |
| UA (1) | UA95247C2 (enExample) |
| WO (1) | WO2007019083A1 (enExample) |
| ZA (1) | ZA200802010B (enExample) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MXPA06003150A (es) | 2003-09-17 | 2006-08-31 | Johnson & Johnson | Compuestos heterociclicos fusionados. |
| US7598255B2 (en) * | 2005-08-04 | 2009-10-06 | Janssen Pharmaceutica Nv | Pyrimidine compounds as serotonin receptor modulators |
| PE20080145A1 (es) * | 2006-03-21 | 2008-02-11 | Janssen Pharmaceutica Nv | Tetrahidro-pirimidoazepinas como moduladores de trpv1 |
| KR20090121358A (ko) * | 2007-03-23 | 2009-11-25 | 화이자 리미티드 | 5-ｈｔ2ｃ 작용제로서 피리미도 [4,5-ｄ] 아제핀 유도체 |
| JP5562865B2 (ja) | 2007-12-17 | 2014-07-30 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | Ｔｒｐｖ１のイミダゾロ−、オキサゾロ−、及びチアゾロピリミジン・モジュレーター |
| WO2011146089A1 (en) * | 2010-05-21 | 2011-11-24 | Abbott Laboratories | Modulators of 5-ht receptors and methods of use thereof |
| ES2703168T3 (es) | 2014-05-29 | 2019-03-07 | Taiho Pharmaceutical Co Ltd | Nuevo compuesto de tetrahidropiridopirimidina o sal del mismo |
| CN107365314B (zh) * | 2016-05-11 | 2024-09-27 | 国药集团国瑞药业有限公司 | 一种吡唑类化合物、其晶型及其制备方法 |
| ES3050660T3 (en) * | 2016-11-15 | 2025-12-22 | Univ Temple | 3-(2-(4-phenylpiperazin-1-yl)ethyl)-2-oxa-8-azaspiro[4.5]decan-1-one derivatives and related compounds as 5-hydroxytryptamine receptor 7 (5-ht7) modulators for treating e.g. inflammatory bowel disease, circadian rhythm disorder or depression |
| JP7141130B2 (ja) | 2017-05-31 | 2022-09-22 | ケモセントリックス，インコーポレイティド | Ｃ５ａ阻害剤としての６－５融合環 |
| US10828285B2 (en) * | 2017-12-22 | 2020-11-10 | Chemocentryx, Inc. | Diaryl substituted 6,5-fused ring compounds as C5aR inhibitors |
| UA127357C2 (uk) | 2018-04-18 | 2023-07-26 | Констеллатіон Фармацеутікалс, Інк. | Модулятори метилмодифікуючих ферментів, композиції та їх використання |
| EP3797108B1 (en) | 2018-05-21 | 2022-07-20 | Constellation Pharmaceuticals, Inc. | Modulators of methyl modifying enzymes, compositions and uses thereof |
| KR102282569B1 (ko) * | 2019-02-08 | 2021-07-29 | (주)퓨쳐켐 | 새로운 18F-표지된 친디엔체와 테트라진 화합물과의 IeDDA 반응을 이용한 18F-표지 방법 |
| MD4003532T2 (ro) | 2019-07-24 | 2025-01-31 | Constellation Pharmaceuticals Inc | Forme cristaline de 7-clor-2-(4-(3-metoxiazetidin-1-il)ciclohexil)-2,4-dimetil-N-((6-metil-4-(metiltio)-2-oxo-1,2-dihidropiridin-3-il)metil)benzo[d][1,3]dioxol-5-carboxamidă |
| KR102483492B1 (ko) * | 2019-09-02 | 2023-01-02 | 한양대학교 에리카산학협력단 | 2,5-이치환된 피리미딘 유도체 및 이를 포함하는 약학적 조성물 |
| WO2021097117A2 (en) * | 2019-11-13 | 2021-05-20 | Temple University-Of The Commonwealth System Of Higher Education | Novel functionalized lactones as modulators of the 5-hydroxytryptamine receptor 7 and their method of use |
| EP4313967B1 (en) | 2021-03-29 | 2025-11-12 | Gilead Sciences, Inc. | Khk inhibitors |
| JP2025505163A (ja) * | 2022-02-02 | 2025-02-21 | ザ・カトリック・ユニヴェルシテイト・ルーバン | Ｙａｐ／ｔａｚ－ｔｅａｄを阻害するためのテトラヒドロピリドピリミジン及び関連類似体 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3969355A (en) * | 1974-11-01 | 1976-07-13 | Morton-Norwich Products, Inc. | 5-Aminoethyl-2,4-diphenylpyrimidine dihydrobromide |
| JPH03148265A (ja) * | 1989-11-01 | 1991-06-25 | Sumitomo Chem Co Ltd | ５，７―ジフェニル―４，６―ジアザインダン誘導体、その製造法およびそれを有効成分とする除草剤 |
| US5137890A (en) * | 1990-02-14 | 1992-08-11 | Ortho Pharmaceutical Corporation | 4-phenyl tetrahydropyrido(4,3-d)pyrimidines |
| DE69533284T2 (de) * | 1994-04-29 | 2005-07-21 | Pfizer Inc. | Neue cyclische und acyclische amide zur erhöhung der neurotransmitter ausschüttung |
| AU2980797A (en) * | 1996-06-11 | 1998-01-07 | Yoshitomi Pharmaceutical Industries, Ltd. | Fused heterocyclic compounds and medicinal uses thereof |
| KR20020005653A (ko) * | 1999-04-01 | 2002-01-17 | 실버스타인 아써 에이. | 소르비톨 디하이드로게나제 저해제로서의 아미노피리미딘 |
| DE60008550T2 (de) * | 1999-09-09 | 2004-08-05 | Kumiai Chemical Industry Co., Ltd. | Pyrimidinderivate und herbizide welche diese enthalten |
| WO2001068585A1 (en) * | 2000-03-14 | 2001-09-20 | Fujisawa Pharmaceutical Co., Ltd. | Novel amide compounds |
| DE10111842A1 (de) * | 2001-03-13 | 2002-09-19 | Boehringer Ingelheim Pharma | Antithrombotische Carbonsäureamide, deren Herstellung und deren Verwendung als Arzneimittel |
| MXPA06003150A (es) * | 2003-09-17 | 2006-08-31 | Johnson & Johnson | Compuestos heterociclicos fusionados. |
-
2006
- 2006-07-27 WO PCT/US2006/029437 patent/WO2007019083A1/en not_active Ceased
- 2006-07-27 UA UAA200801682A patent/UA95247C2/ru unknown
- 2006-07-27 AT AT06788808T patent/ATE539753T1/de active
- 2006-07-27 NZ NZ565334A patent/NZ565334A/en not_active IP Right Cessation
- 2006-07-27 CA CA2617760A patent/CA2617760C/en not_active Expired - Fee Related
- 2006-07-27 BR BRPI0614397-0A patent/BRPI0614397A2/pt not_active Application Discontinuation
- 2006-07-27 AU AU2006278759A patent/AU2006278759B2/en not_active Ceased
- 2006-07-27 CN CN2006800364302A patent/CN101277700B/zh not_active Expired - Fee Related
- 2006-07-27 JP JP2008525054A patent/JP5066088B2/ja not_active Expired - Fee Related
- 2006-07-27 EP EP06788808A patent/EP1928461B1/en active Active
- 2006-07-27 KR KR1020087005335A patent/KR101353268B1/ko not_active Expired - Fee Related
- 2006-07-27 EA EA200800525A patent/EA014495B1/ru unknown
-
2008
- 2008-01-31 IL IL189164A patent/IL189164A/en active IP Right Grant
- 2008-02-27 NO NO20081034A patent/NO340744B1/no not_active IP Right Cessation
- 2008-03-03 ZA ZA200802010A patent/ZA200802010B/xx unknown
- 2008-03-04 CR CR9791A patent/CR9791A/es not_active Application Discontinuation
-
2011
- 2011-06-21 IL IL213679A patent/IL213679A0/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2009503076A5 (enExample) | ||
| US7598255B2 (en) | Pyrimidine compounds as serotonin receptor modulators | |
| RU2431635C2 (ru) | Соединения и композиции в качестве ингибиторов активности каннабиноидного рецептора 1 | |
| US20100016281A1 (en) | Pyrimidine compounds as serotonin receptor modulators | |
| KR101353268B1 (ko) | 세로토닌 수용체 모듈레이터로서의 피리미딘 화합물 | |
| JP2020050682A (ja) | ドライアイおよび他の目に関連する疾患を治療するためのヤヌスキナーゼ阻害剤 | |
| AU2010245250B2 (en) | Use of PDE7 inhibitors for the treatment of movement disorders | |
| CN101557826A (zh) | 泌尿系统疾病的治疗药 | |
| JP2000038350A (ja) | 糖尿病治療薬 | |
| TW201333012A (zh) | 咪唑并吡咯啶酮化合物 | |
| AU2013230128A1 (en) | Pyrazolo[1,5-a]pyrimidine-based compounds, compositions comprising them, and methods of their use | |
| ZA200603031B (en) | Fused heterocyclic componds as serotonin receptor modulators | |
| CZ20022222A3 (cs) | Nové substituované pyrazolo [4,3-e] diazepiny, farmaceutické kompozice obsahující tyto diazepiny, jejich použití jako léčiva a způsoby jejich přípravy | |
| TWI325322B (en) | Substituted 2-pyrimidinyl-6,7,8,9-tetrahydropyrimido[1,2-a] pyrimidin-4-one; and 7-pyrimidiny-2,3-dihydroimidazo[1,2-a] pyrimidin-5(1h)one derivatives | |
| KR20250048344A (ko) | 만성 피로, 탈진 및/또는 운동 불내성과 연관된 질환의 치료 및 예방을 위한 포스포디에스테라제-7 억제 활성을 갖는 치료제의 용도 | |
| HK1118469B (en) | Pyrimidine compounds as serotonin receptor modulators | |
| CN101155787A (zh) | (3,4-二氢-喹唑啉-2-基)-茚满-1-基-胺 |