JP2009503076A5 - - Google Patents
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- 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
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- 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
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| 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 |
| CN101652367A (zh) | 2007-03-23 | 2010-02-17 | 辉瑞有限公司 | 作为5-ht2c激动剂的嘧啶并[4,5-d]氮杂卓衍生物 |
| WO2009078999A1 (en) | 2007-12-17 | 2009-06-25 | Janssen Pharmaceutica N.V. | Imidazolo-, oxazolo-, and thiazolopyrimidine modulators of trpv1 |
| WO2011146089A1 (en) * | 2010-05-21 | 2011-11-24 | Abbott Laboratories | Modulators of 5-ht receptors and methods of use thereof |
| CN106103434B (zh) | 2014-05-29 | 2019-05-10 | 大鹏药品工业株式会社 | 四氢吡啶并嘧啶化合物或其盐 |
| 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 |
| IL309982A (en) * | 2016-11-15 | 2024-03-01 | Univ Temple | New modulators of 5-hydroxytryptamine receptor 7 and a method of using them |
| US10562896B2 (en) | 2017-05-31 | 2020-02-18 | Chemocentryx, Inc. | 6-5 fused rings as C5a inhibitors |
| WO2019126424A1 (en) * | 2017-12-22 | 2019-06-27 | Chemocentryx, Inc. | DIARYL SUBSTITUTED 6,5-FUSED RING COMPOUNDS AS C5aR INHIBITORS |
| HRP20240793T1 (hr) | 2018-04-18 | 2024-09-13 | Constellation Pharmaceuticals, Inc. | Modulatori enzima koji modificiraju metil, njihovi pripravci i upotreba |
| 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 |
| LT4003532T (lt) | 2019-07-24 | 2024-11-11 | Constellation Pharmaceuticals, Inc. | 7-chlor-2- (4-(3-metoksiazetidin-1-il)cikloheksil)-2,4-dimetil-n-((6-metil-4-(metiltio)-2-okso-1,2-dihidropiridin-3-il)metil)benzo[d][1,3]dioksol-5-karboksamido kristalinės formos |
| KR102483492B1 (ko) * | 2019-09-02 | 2023-01-02 | 한양대학교 에리카산학협력단 | 2,5-이치환된 피리미딘 유도체 및 이를 포함하는 약학적 조성물 |
| CA3161590A1 (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 |
| EP4681774A3 (en) | 2021-03-29 | 2026-03-25 | Gilead Sciences, Inc. | Khk inhibitors |
| US12516064B2 (en) * | 2022-02-02 | 2026-01-06 | SpringWorks Therapeutics Inc. | Tetrahydropyridopyrimidines and related analogs for inhibiting YAP/TAZ-TEAD |
| US12600723B2 (en) | 2022-07-18 | 2026-04-14 | Incyte Corporation | Tetracyclic compounds as DGK inhibitors |
| US12600722B2 (en) | 2022-07-18 | 2026-04-14 | Incyte Corporation | Tetracyclic compounds as DGK inhibitors |
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| 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 |
| CA2188427C (en) * | 1994-04-29 | 2000-06-27 | Robert A. Volkmann | Neurotransmitter release enhancers |
| WO1997047601A1 (en) * | 1996-06-11 | 1997-12-18 | Yoshitomi Pharmaceutical Industries, Ltd. | Fused heterocyclic compounds and medicinal uses thereof |
| PL350884A1 (en) * | 1999-04-01 | 2003-02-10 | Pfizer Prod Inc | Aminopyrimidines as sorbitol dehydrogenase inhibitors |
| US6806230B1 (en) * | 1999-09-09 | 2004-10-19 | Kumiai Chemical Industry Co., Ltd. | Pyrimidine derivatives and herbicides containing them |
| AU2001241128A1 (en) * | 2000-03-14 | 2001-09-24 | 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 |
| ES2319539T3 (es) * | 2003-09-17 | 2009-05-08 | Janssen Pharmaceutica Nv | Compuestos heterociclicos condensados como moduladores del receptor de serotonina. |
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