JP2003502272A5 - - Google Patents
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- JP2003502272A5 JP2003502272A5 JP2000530520A JP2000530520A JP2003502272A5 JP 2003502272 A5 JP2003502272 A5 JP 2003502272A5 JP 2000530520 A JP2000530520 A JP 2000530520A JP 2000530520 A JP2000530520 A JP 2000530520A JP 2003502272 A5 JP2003502272 A5 JP 2003502272A5
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- JP
- Japan
- Prior art keywords
- alkyl
- cycloalkyl
- alkoxy
- aryl
- con
- 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.)
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- 125000000217 alkyl group Chemical group 0.000 description 881
- 125000000753 cycloalkyl group Chemical group 0.000 description 776
- 125000003545 alkoxy group Chemical group 0.000 description 331
- 125000001072 heteroaryl group Chemical group 0.000 description 247
- 125000003118 aryl group Chemical group 0.000 description 224
- 125000004104 aryloxy group Chemical group 0.000 description 177
- 229910052739 hydrogen Inorganic materials 0.000 description 149
- 239000001257 hydrogen Substances 0.000 description 149
- 125000005843 halogen group Chemical group 0.000 description 129
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 98
- 125000000623 heterocyclic group Chemical group 0.000 description 65
- 150000002431 hydrogen Chemical class 0.000 description 51
- 150000001875 compounds Chemical class 0.000 description 41
- 229910052717 sulfur Inorganic materials 0.000 description 38
- 125000005336 allyloxy group Chemical group 0.000 description 29
- 125000001309 chloro group Chemical group Cl* 0.000 description 26
- 125000001153 fluoro group Chemical group F* 0.000 description 26
- 125000004432 carbon atom Chemical group C* 0.000 description 23
- -1 methoxyphenyl Chemical group 0.000 description 23
- 229910052760 oxygen Inorganic materials 0.000 description 21
- 150000003839 salts Chemical class 0.000 description 19
- 229910052799 carbon Inorganic materials 0.000 description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 18
- 150000002148 esters Chemical class 0.000 description 17
- 239000008194 pharmaceutical composition Substances 0.000 description 17
- 239000012453 solvate Substances 0.000 description 17
- 125000004423 acyloxy group Chemical group 0.000 description 16
- 125000003107 substituted aryl group Chemical group 0.000 description 14
- 125000002618 bicyclic heterocycle group Chemical group 0.000 description 12
- 125000002950 monocyclic group Chemical group 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 11
- 238000000034 method Methods 0.000 description 10
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 10
- 125000001424 substituent group Chemical group 0.000 description 9
- 229910052727 yttrium Inorganic materials 0.000 description 9
- KCTZOTUQSGYWLV-UHFFFAOYSA-N N1C=NC=C2N=CC=C21 Chemical compound N1C=NC=C2N=CC=C21 KCTZOTUQSGYWLV-UHFFFAOYSA-N 0.000 description 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 208000008589 Obesity Diseases 0.000 description 6
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 6
- 125000001246 bromo group Chemical group Br* 0.000 description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 description 6
- 235000020824 obesity Nutrition 0.000 description 6
- 150000001204 N-oxides Chemical class 0.000 description 5
- 125000002527 bicyclic carbocyclic group Chemical group 0.000 description 5
- 230000002265 prevention Effects 0.000 description 5
- 241000725303 Human immunodeficiency virus Species 0.000 description 4
- 206010020751 Hypersensitivity Diseases 0.000 description 4
- 206010028980 Neoplasm Diseases 0.000 description 4
- 208000028389 Nerve injury Diseases 0.000 description 4
- 208000026935 allergic disease Diseases 0.000 description 4
- 206010012601 diabetes mellitus Diseases 0.000 description 4
- 201000010099 disease Diseases 0.000 description 4
- 208000027866 inflammatory disease Diseases 0.000 description 4
- LOTBYPQQWICYBB-UHFFFAOYSA-N methyl n-hexyl-n-[2-(hexylamino)ethyl]carbamate Chemical compound CCCCCCNCCN(C(=O)OC)CCCCCC LOTBYPQQWICYBB-UHFFFAOYSA-N 0.000 description 4
- 230000008764 nerve damage Effects 0.000 description 4
- 208000011580 syndromic disease Diseases 0.000 description 4
- 208000024827 Alzheimer disease Diseases 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 206010012735 Diarrhoea Diseases 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- 208000028017 Psychotic disease Diseases 0.000 description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 3
- 208000035475 disorder Diseases 0.000 description 3
- 230000004634 feeding behavior Effects 0.000 description 3
- 238000003780 insertion Methods 0.000 description 3
- 230000037431 insertion Effects 0.000 description 3
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 2
- DMGOZCOEMMLYBQ-UHFFFAOYSA-N 2-methyl-6-phenyl-4-pyrrolidin-1-yl-5h-pyrrolo[3,2-d]pyrimidine Chemical compound C=12NC(C=3C=CC=CC=3)=CC2=NC(C)=NC=1N1CCCC1 DMGOZCOEMMLYBQ-UHFFFAOYSA-N 0.000 description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 2
- 208000020925 Bipolar disease Diseases 0.000 description 2
- 206010007559 Cardiac failure congestive Diseases 0.000 description 2
- 206010008874 Chronic Fatigue Syndrome Diseases 0.000 description 2
- 206010010904 Convulsion Diseases 0.000 description 2
- 208000001640 Fibromyalgia Diseases 0.000 description 2
- 206010019233 Headaches Diseases 0.000 description 2
- 206010019280 Heart failures Diseases 0.000 description 2
- 208000023105 Huntington disease Diseases 0.000 description 2
- 208000013016 Hypoglycemia Diseases 0.000 description 2
- 206010061598 Immunodeficiency Diseases 0.000 description 2
- 208000029462 Immunodeficiency disease Diseases 0.000 description 2
- 208000019022 Mood disease Diseases 0.000 description 2
- 206010027951 Mood swings Diseases 0.000 description 2
- 208000007101 Muscle Cramp Diseases 0.000 description 2
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 description 2
- 208000001132 Osteoporosis Diseases 0.000 description 2
- 208000002193 Pain Diseases 0.000 description 2
- 208000018737 Parkinson disease Diseases 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- 201000004681 Psoriasis Diseases 0.000 description 2
- 206010037660 Pyrexia Diseases 0.000 description 2
- 208000005392 Spasm Diseases 0.000 description 2
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 2
- 208000029650 alcohol withdrawal Diseases 0.000 description 2
- 125000004414 alkyl thio group Chemical group 0.000 description 2
- 230000007815 allergy Effects 0.000 description 2
- 230000001142 anti-diarrhea Effects 0.000 description 2
- 208000006673 asthma Diseases 0.000 description 2
- 201000011510 cancer Diseases 0.000 description 2
- 230000001684 chronic effect Effects 0.000 description 2
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 2
- 206010015037 epilepsy Diseases 0.000 description 2
- 231100000318 excitotoxic Toxicity 0.000 description 2
- 230000003492 excitotoxic effect Effects 0.000 description 2
- 231100000869 headache Toxicity 0.000 description 2
- 229940088597 hormone Drugs 0.000 description 2
- 239000005556 hormone Substances 0.000 description 2
- 230000009610 hypersensitivity Effects 0.000 description 2
- 230000002218 hypoglycaemic effect Effects 0.000 description 2
- 230000007813 immunodeficiency Effects 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- 208000002551 irritable bowel syndrome Diseases 0.000 description 2
- 230000000302 ischemic effect Effects 0.000 description 2
- 125000002757 morpholinyl group Chemical group 0.000 description 2
- 208000029766 myalgic encephalomeyelitis/chronic fatigue syndrome Diseases 0.000 description 2
- 230000004770 neurodegeneration Effects 0.000 description 2
- 208000015122 neurodegenerative disease Diseases 0.000 description 2
- 201000008482 osteoarthritis Diseases 0.000 description 2
- 230000036407 pain Effects 0.000 description 2
- 125000003386 piperidinyl group Chemical group 0.000 description 2
- 125000003373 pyrazinyl group Chemical group 0.000 description 2
- 125000002098 pyridazinyl group Chemical group 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 description 2
- 206010039073 rheumatoid arthritis Diseases 0.000 description 2
- 208000020431 spinal cord injury Diseases 0.000 description 2
- 208000024891 symptom Diseases 0.000 description 2
- 230000006016 thyroid dysfunction Effects 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- KLSNEFPIXYMBHH-UHFFFAOYSA-N 1-(2-methyl-6-phenyl-5h-pyrrolo[3,2-d]pyrimidin-4-yl)pyrrolidin-3-ol Chemical compound C=12NC(C=3C=CC=CC=3)=CC2=NC(C)=NC=1N1CCC(O)C1 KLSNEFPIXYMBHH-UHFFFAOYSA-N 0.000 description 1
- LRDJPMBFLOIIRG-UHFFFAOYSA-N 1-hydroxy-2-(2-methyl-6-phenylpiperidin-4-yl)-2h-thieno[3,2-d]pyrimidine Chemical compound N1C(C)CC(C2N(C=3C=CSC=3C=N2)O)CC1C1=CC=CC=C1 LRDJPMBFLOIIRG-UHFFFAOYSA-N 0.000 description 1
- HQALSHVZJLQPFN-UHFFFAOYSA-N 1-hydroxy-2-(2-methyl-6-phenylpiperidin-4-yl)pyrrolo[3,2-d]pyrimidine Chemical compound N1C(C)CC(C=2N(C3=CC=NC3=CN=2)O)CC1C1=CC=CC=C1 HQALSHVZJLQPFN-UHFFFAOYSA-N 0.000 description 1
- LSELFBQZZQRNQO-UHFFFAOYSA-N 14-methyl-10-phenyl-2,9,13,15-tetrazatetracyclo[7.6.1.02,7.012,16]hexadeca-1(15),10,12(16),13-tetraene Chemical compound C=1C(C=23)=NC(C)=NC=2N2CCCCC2CN3C=1C1=CC=CC=C1 LSELFBQZZQRNQO-UHFFFAOYSA-N 0.000 description 1
- NRFWKHLSQWNDNN-UHFFFAOYSA-N 2-(2-methyl-6-phenyl-5h-pyrrolo[3,2-d]pyrimidin-4-yl)-1,3-thiazole Chemical compound C=12NC(C=3C=CC=CC=3)=CC2=NC(C)=NC=1C1=NC=CS1 NRFWKHLSQWNDNN-UHFFFAOYSA-N 0.000 description 1
- VQABLVZTEBQHDS-UHFFFAOYSA-N 2-(2-methyl-6-phenylpiperidin-4-yl)furo[3,2-d]pyrimidine Chemical compound N1C(C)CC(C=2N=C3C=COC3=CN=2)CC1C1=CC=CC=C1 VQABLVZTEBQHDS-UHFFFAOYSA-N 0.000 description 1
- GSZYQNUCJIAZJL-UHFFFAOYSA-N 2-(2-methyl-6-phenylpiperidin-4-yl)thieno[3,2-d]pyrimidine Chemical compound N1C(C)CC(C=2N=C3C=CSC3=CN=2)CC1C1=CC=CC=C1 GSZYQNUCJIAZJL-UHFFFAOYSA-N 0.000 description 1
- BVPAWPXJYCYODN-UHFFFAOYSA-N 2-(2-tert-butyl-6-methylpiperidin-4-yl)-1-hydroxy-2h-thieno[3,2-d]pyrimidine Chemical compound C1C(C(C)(C)C)NC(C)CC1C1N(O)C(C=CS2)=C2C=N1 BVPAWPXJYCYODN-UHFFFAOYSA-N 0.000 description 1
- VJTAHVDANNKYPH-UHFFFAOYSA-N 2-(2-tert-butyl-6-methylpiperidin-4-yl)thieno[3,2-d]pyrimidine Chemical compound C1C(C(C)(C)C)NC(C)CC1C1=NC=C(SC=C2)C2=N1 VJTAHVDANNKYPH-UHFFFAOYSA-N 0.000 description 1
- HFIVJEORNLARNN-UHFFFAOYSA-N 2-(4-fluorophenyl)-5-methyl-7-piperidin-1-yl-1h-pyrrolo[3,2-b]pyridine Chemical compound C=12NC(C=3C=CC(F)=CC=3)=CC2=NC(C)=CC=1N1CCCCC1 HFIVJEORNLARNN-UHFFFAOYSA-N 0.000 description 1
- FGISNVXRIOFKCD-UHFFFAOYSA-N 2-(cyclohexen-1-yl)-7-piperidin-1-yl-1h-pyrrolo[3,2-b]pyridine;hydrochloride Chemical compound Cl.C1CCCCN1C1=CC=NC2=C1NC(C=1CCCCC=1)=C2 FGISNVXRIOFKCD-UHFFFAOYSA-N 0.000 description 1
- UNZNOAPSLRPDPE-UHFFFAOYSA-N 2-[2-(4-chlorophenyl)-6-methylpiperidin-4-yl]-1-hydroxy-2h-thieno[3,2-d]pyrimidine Chemical compound N1C(C)CC(C2N(C=3C=CSC=3C=N2)O)CC1C1=CC=C(Cl)C=C1 UNZNOAPSLRPDPE-UHFFFAOYSA-N 0.000 description 1
- MYLPTZDXJPMVMW-UHFFFAOYSA-N 2-[2-(4-chlorophenyl)-6-methylpiperidin-4-yl]thieno[3,2-d]pyrimidine Chemical compound N1C(C)CC(C=2N=C3C=CSC3=CN=2)CC1C1=CC=C(Cl)C=C1 MYLPTZDXJPMVMW-UHFFFAOYSA-N 0.000 description 1
- YRYDJESLVLBPRI-UHFFFAOYSA-N 2-[2-(4-fluorophenyl)-6-methylpiperidin-4-yl]thieno[3,2-d]pyrimidine Chemical compound N1C(C)CC(C=2N=C3C=CSC3=CN=2)CC1C1=CC=C(F)C=C1 YRYDJESLVLBPRI-UHFFFAOYSA-N 0.000 description 1
- VHLAEBPEAQVKAB-UHFFFAOYSA-N 2-cyclohexyl-7-piperidin-1-yl-1h-pyrrolo[3,2-b]pyridine Chemical compound C1CCCCC1C1=CC2=NC=CC(N3CCCCC3)=C2N1 VHLAEBPEAQVKAB-UHFFFAOYSA-N 0.000 description 1
- RNQZOKCAVOJNSG-UHFFFAOYSA-N 2-methyl-4-(2-methylpyrrolidin-1-yl)-6-phenyl-5h-pyrrolo[3,2-d]pyrimidine Chemical compound CC1CCCN1C1=NC(C)=NC2=C1NC(C=1C=CC=CC=1)=C2 RNQZOKCAVOJNSG-UHFFFAOYSA-N 0.000 description 1
- KVZDNBWSPOUUHF-UHFFFAOYSA-N 2-methyl-6-phenyl-4-(4-phenylpiperazin-1-yl)-5h-pyrrolo[3,2-d]pyrimidine Chemical compound C=12NC(C=3C=CC=CC=3)=CC2=NC(C)=NC=1N(CC1)CCN1C1=CC=CC=C1 KVZDNBWSPOUUHF-UHFFFAOYSA-N 0.000 description 1
- WVUPXOVXHJCBCF-UHFFFAOYSA-N 2-methyl-6-phenyl-4-pyridin-3-yl-5h-pyrrolo[3,2-d]pyrimidine Chemical compound C=12NC(C=3C=CC=CC=3)=CC2=NC(C)=NC=1C1=CC=CN=C1 WVUPXOVXHJCBCF-UHFFFAOYSA-N 0.000 description 1
- CSABZLYAAMAGRM-UHFFFAOYSA-N 2-methyl-6-phenyl-4-thiophen-2-yl-5h-pyrrolo[3,2-d]pyrimidine Chemical compound C=12NC(C=3C=CC=CC=3)=CC2=NC(C)=NC=1C1=CC=CS1 CSABZLYAAMAGRM-UHFFFAOYSA-N 0.000 description 1
- BNFLOTVXLMSRMX-UHFFFAOYSA-N 2-phenyl-4-[2-(trifluoromethyl)thiophen-3-yl]piperidine Chemical compound S1C=CC(C2CC(NCC2)C=2C=CC=CC=2)=C1C(F)(F)F BNFLOTVXLMSRMX-UHFFFAOYSA-N 0.000 description 1
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 1
- FGVYRZPTQVFCBR-UHFFFAOYSA-N 3-(7-piperidin-1-yl-1h-pyrrolo[3,2-b]pyridin-2-yl)phenol Chemical compound OC1=CC=CC(C=2NC3=C(N4CCCCC4)C=CN=C3C=2)=C1 FGVYRZPTQVFCBR-UHFFFAOYSA-N 0.000 description 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
- PDORTDCGJIZCFI-UHFFFAOYSA-N 4-(3,4-dihydro-1h-isoquinolin-2-yl)-2-methyl-6-phenylthieno[3,2-d]pyrimidine Chemical compound C=1C2=NC(C)=NC(N3CC4=CC=CC=C4CC3)=C2SC=1C1=CC=CC=C1 PDORTDCGJIZCFI-UHFFFAOYSA-N 0.000 description 1
- NWZPSAYBNUDYIN-UHFFFAOYSA-N 4-(3,6-dihydro-2h-pyridin-1-yl)-2-methyl-6-phenylthieno[3,2-d]pyrimidine Chemical compound C=12SC(C=3C=CC=CC=3)=CC2=NC(C)=NC=1N1CCC=CC1 NWZPSAYBNUDYIN-UHFFFAOYSA-N 0.000 description 1
- TZGGZZBAQIYWER-UHFFFAOYSA-N 4-[6-(3,4-difluorophenyl)-2-methyl-5h-pyrrolo[3,2-d]pyrimidin-4-yl]morpholine Chemical compound C=12NC(C=3C=C(F)C(F)=CC=3)=CC2=NC(C)=NC=1N1CCOCC1 TZGGZZBAQIYWER-UHFFFAOYSA-N 0.000 description 1
- KDDQRKBRJSGMQE-UHFFFAOYSA-N 4-thiazolyl Chemical group [C]1=CSC=N1 KDDQRKBRJSGMQE-UHFFFAOYSA-N 0.000 description 1
- JIJBNODYTQRFQR-UHFFFAOYSA-N 6-(4-fluorophenyl)-2-methyl-4-(2-methylpiperidin-1-yl)-5h-pyrrolo[3,2-d]pyrimidine Chemical compound CC1CCCCN1C1=NC(C)=NC2=C1NC(C=1C=CC(F)=CC=1)=C2 JIJBNODYTQRFQR-UHFFFAOYSA-N 0.000 description 1
- SZZDYFWEHMPCAS-UHFFFAOYSA-N 7-piperidin-1-yl-2-pyridin-2-yl-1h-pyrrolo[3,2-b]pyridine Chemical compound C1CCCCN1C1=CC=NC2=C1NC(C=1N=CC=CC=1)=C2 SZZDYFWEHMPCAS-UHFFFAOYSA-N 0.000 description 1
- 208000019901 Anxiety disease Diseases 0.000 description 1
- ZJSHGKFUEPNFHP-UHFFFAOYSA-N C(C)C1=NC(=C2C(N1)=CC(=N2)C2=CC=CC=C2)N2CC1=CC=CC=C1CC2 Chemical compound C(C)C1=NC(=C2C(N1)=CC(=N2)C2=CC=CC=C2)N2CC1=CC=CC=C1CC2 ZJSHGKFUEPNFHP-UHFFFAOYSA-N 0.000 description 1
- AREJQYKTNHEJRM-UHFFFAOYSA-N C1(=CC=CC=C1)C1CC(CCN1)C1=C2C(NC(=N1)NCCC)=CC=N2 Chemical compound C1(=CC=CC=C1)C1CC(CCN1)C1=C2C(NC(=N1)NCCC)=CC=N2 AREJQYKTNHEJRM-UHFFFAOYSA-N 0.000 description 1
- IULADUGXHYYHPM-UHFFFAOYSA-N C12(CC3CC(CC(C1)C3)C2)C2CC(CC(N2)C)C2=NC=C3C(N2)=CC=N3 Chemical compound C12(CC3CC(CC(C1)C3)C2)C2CC(CC(N2)C)C2=NC=C3C(N2)=CC=N3 IULADUGXHYYHPM-UHFFFAOYSA-N 0.000 description 1
- DYHKIZKGIGJEDE-UHFFFAOYSA-N C1=C2NC(C)=NC(N3C4CCC3CCC4)=C2N=C1C1=CC=CC=C1 Chemical compound C1=C2NC(C)=NC(N3C4CCC3CCC4)=C2N=C1C1=CC=CC=C1 DYHKIZKGIGJEDE-UHFFFAOYSA-N 0.000 description 1
- LJYNJEIJQYGDMT-UHFFFAOYSA-N C1CC(CC(N1)c1ccccc1)Nc1ncc2nccc2[nH]1 Chemical compound C1CC(CC(N1)c1ccccc1)Nc1ncc2nccc2[nH]1 LJYNJEIJQYGDMT-UHFFFAOYSA-N 0.000 description 1
- OXTKALMGVPAARX-UHFFFAOYSA-N C1CC1C1CC(CC(N1)c1ccccc1)c1ncc2nccc2[nH]1 Chemical compound C1CC1C1CC(CC(N1)c1ccccc1)c1ncc2nccc2[nH]1 OXTKALMGVPAARX-UHFFFAOYSA-N 0.000 description 1
- JJLRHWKCKULJLT-UHFFFAOYSA-N C1CN(CCN1C1CC(CC(N1)c1ccccc1)c1ncc2nccc2[nH]1)c1ccccc1 Chemical compound C1CN(CCN1C1CC(CC(N1)c1ccccc1)c1ncc2nccc2[nH]1)c1ccccc1 JJLRHWKCKULJLT-UHFFFAOYSA-N 0.000 description 1
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- HEKUQHJRYKYKHO-UHFFFAOYSA-N CC1CC(CC(C)N1)c1ncc2ncc(-c3ccc(F)cc3)c2[nH]1 Chemical compound CC1CC(CC(C)N1)c1ncc2ncc(-c3ccc(F)cc3)c2[nH]1 HEKUQHJRYKYKHO-UHFFFAOYSA-N 0.000 description 1
- VJCBUYUQMIBJAO-UHFFFAOYSA-N CC1CC(CC(CCc2ccccc2)N1)c1ncc2nccc2[nH]1 Chemical compound CC1CC(CC(CCc2ccccc2)N1)c1ncc2nccc2[nH]1 VJCBUYUQMIBJAO-UHFFFAOYSA-N 0.000 description 1
- FZIQSIBPOOEOHF-UHFFFAOYSA-N CC1CC(CC(Cc2ccc(F)cc2)N1)c1ncc2nccc2[nH]1 Chemical compound CC1CC(CC(Cc2ccc(F)cc2)N1)c1ncc2nccc2[nH]1 FZIQSIBPOOEOHF-UHFFFAOYSA-N 0.000 description 1
- SMYMWOJVKSYQAT-UHFFFAOYSA-N CC1CC(CC(N1)C(C)(C)C)c1ncc2nccc2[nH]1 Chemical compound CC1CC(CC(N1)C(C)(C)C)c1ncc2nccc2[nH]1 SMYMWOJVKSYQAT-UHFFFAOYSA-N 0.000 description 1
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