PT1919907E - Composto heterocíclico - Google Patents

Info

Publication number

PT1919907E

PT1919907E PT06797580T PT06797580T PT1919907E PT 1919907 E PT1919907 E PT 1919907E PT 06797580 T PT06797580 T PT 06797580T PT 06797580 T PT06797580 T PT 06797580T PT 1919907 E PT1919907 E PT 1919907E

Authority

PT

Portugal

Prior art keywords

group

alkyl

groups

alkyl group

substituent

Prior art date

2005-08-31

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• 150000002391 heterocyclic compounds Chemical class 0.000 title claims abstract description 19
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 680
• 150000001875 compounds Chemical class 0.000 claims abstract description 183
• 150000003839 salts Chemical class 0.000 claims abstract description 81
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 7
• 208000015114 central nervous system disease Diseases 0.000 claims abstract description 6
• -1 tetrahydrobenzothiazolyl group Chemical group 0.000 claims description 2028
• 125000001424 substituent group Chemical group 0.000 claims description 228
• 125000005843 halogen group Chemical group 0.000 claims description 154
• 125000003118 aryl group Chemical group 0.000 claims description 153
• 125000002252 acyl group Chemical group 0.000 claims description 147
• 125000004043 oxo group Chemical group O=* 0.000 claims description 115
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 111
• 125000003277 amino group Chemical group 0.000 claims description 95
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 78
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 71
• 229910052736 halogen Chemical group 0.000 claims description 66
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 63
• 125000005936 piperidyl group Chemical group 0.000 claims description 63
• 238000006243 chemical reaction Methods 0.000 claims description 59
• 125000004193 piperazinyl group Chemical group 0.000 claims description 58
• 125000004076 pyridyl group Chemical group 0.000 claims description 56
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 50
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 48
• 125000002883 imidazolyl group Chemical group 0.000 claims description 42
• 125000003435 aroyl group Chemical group 0.000 claims description 41
• 125000003342 alkenyl group Chemical group 0.000 claims description 34
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 34
• 125000002541 furyl group Chemical group 0.000 claims description 33
• 201000000980 schizophrenia Diseases 0.000 claims description 32
• 125000004104 aryloxy group Chemical group 0.000 claims description 28
• 125000002757 morpholinyl group Chemical group 0.000 claims description 28
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 25
• 125000001544 thienyl group Chemical group 0.000 claims description 24
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 22
• 125000005236 alkanoylamino group Chemical group 0.000 claims description 21
• 238000000034 method Methods 0.000 claims description 21
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 19
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 19
• 125000000335 thiazolyl group Chemical group 0.000 claims description 19
• 125000002971 oxazolyl group Chemical group 0.000 claims description 18
• JPRPJUMQRZTTED-UHFFFAOYSA-N 1,3-dioxolanyl Chemical group [CH]1OCCO1 JPRPJUMQRZTTED-UHFFFAOYSA-N 0.000 claims description 17
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 17
• 125000001624 naphthyl group Chemical group 0.000 claims description 17
• 208000028698 Cognitive impairment Diseases 0.000 claims description 16
• 125000002393 azetidinyl group Chemical group 0.000 claims description 16
• 208000010877 cognitive disease Diseases 0.000 claims description 16
• 208000007415 Anhedonia Diseases 0.000 claims description 14
• 208000020925 Bipolar disease Diseases 0.000 claims description 14
• 208000035475 disorder Diseases 0.000 claims description 14
• 208000024714 major depressive disease Diseases 0.000 claims description 14
• 230000001149 cognitive effect Effects 0.000 claims description 13
• 230000007812 deficiency Effects 0.000 claims description 13
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 13
• 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 13
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 12
• 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 12
• 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 12
• 125000005052 dihydropyrazolyl group Chemical group N1(NCC=C1)* 0.000 claims description 12
• 238000006467 substitution reaction Methods 0.000 claims description 12
• 208000027520 Somatoform disease Diseases 0.000 claims description 11
• 125000001589 carboacyl group Chemical group 0.000 claims description 11
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 11
• 208000024827 Alzheimer disease Diseases 0.000 claims description 10
• 208000020706 Autistic disease Diseases 0.000 claims description 10
• 208000018737 Parkinson disease Diseases 0.000 claims description 10
• 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 10
• 208000012839 conversion disease Diseases 0.000 claims description 10
• 230000004770 neurodegeneration Effects 0.000 claims description 10
• 208000015122 neurodegenerative disease Diseases 0.000 claims description 10
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
• 125000000160 oxazolidinyl group Chemical group 0.000 claims description 10
• 208000019906 panic disease Diseases 0.000 claims description 10
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 9
• 208000020401 Depressive disease Diseases 0.000 claims description 9
• 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 claims description 9
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
• 125000001425 triazolyl group Chemical group 0.000 claims description 9
• 239000004480 active ingredient Substances 0.000 claims description 8
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 8
• 125000004619 benzopyranyl group Chemical group O1C(C=CC2=C1C=CC=C2)* 0.000 claims description 8
• 229940079593 drug Drugs 0.000 claims description 8
• 239000003814 drug Substances 0.000 claims description 8
• 125000002632 imidazolidinyl group Chemical group 0.000 claims description 8
• 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 8
• 239000008194 pharmaceutical composition Substances 0.000 claims description 8
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 8
• 206010000117 Abnormal behaviour Diseases 0.000 claims description 7
• 201000001880 Sexual dysfunction Diseases 0.000 claims description 7
• 210000003169 central nervous system Anatomy 0.000 claims description 7
• 125000001786 isothiazolyl group Chemical group 0.000 claims description 7
• 231100000872 sexual dysfunction Toxicity 0.000 claims description 7
• 208000011117 substance-related disease Diseases 0.000 claims description 7
• 125000001113 thiadiazolyl group Chemical group 0.000 claims description 7
• 125000001984 thiazolidinyl group Chemical group 0.000 claims description 7
• 125000000464 thioxo group Chemical group S=* 0.000 claims description 7
• 208000002193 Pain Diseases 0.000 claims description 6
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 6
• 125000004598 dihydrobenzofuryl group Chemical group O1C(CC2=C1C=CC=C2)* 0.000 claims description 6
• 125000004639 dihydroindenyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 6
• 125000001041 indolyl group Chemical group 0.000 claims description 6
• 230000036961 partial effect Effects 0.000 claims description 6
• 125000005554 pyridyloxy group Chemical group 0.000 claims description 6
• 125000005493 quinolyl group Chemical group 0.000 claims description 6
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 6
• 208000008811 Agoraphobia Diseases 0.000 claims description 5
• 206010001605 Alcohol poisoning Diseases 0.000 claims description 5
• 208000007848 Alcoholism Diseases 0.000 claims description 5
• 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims description 5
• 206010003805 Autism Diseases 0.000 claims description 5
• 206010012218 Delirium Diseases 0.000 claims description 5
• 201000010374 Down Syndrome Diseases 0.000 claims description 5
• 208000010228 Erectile Dysfunction Diseases 0.000 claims description 5
• 208000026097 Factitious disease Diseases 0.000 claims description 5
• 208000011688 Generalised anxiety disease Diseases 0.000 claims description 5
• 201000001916 Hypochondriasis Diseases 0.000 claims description 5
• 208000004356 Hysteria Diseases 0.000 claims description 5
• 208000036626 Mental retardation Diseases 0.000 claims description 5
• 208000019695 Migraine disease Diseases 0.000 claims description 5
• 208000019022 Mood disease Diseases 0.000 claims description 5
• 208000008589 Obesity Diseases 0.000 claims description 5
• 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims description 5
• 206010033664 Panic attack Diseases 0.000 claims description 5
• 208000028017 Psychotic disease Diseases 0.000 claims description 5
• 206010041250 Social phobia Diseases 0.000 claims description 5
• 208000033039 Somatisation disease Diseases 0.000 claims description 5
• 208000000323 Tourette Syndrome Diseases 0.000 claims description 5
• 208000016620 Tourette disease Diseases 0.000 claims description 5
• 208000031674 Traumatic Acute Stress disease Diseases 0.000 claims description 5
• 208000028552 Treatment-Resistant Depressive disease Diseases 0.000 claims description 5
• 206010047700 Vomiting Diseases 0.000 claims description 5
• 208000026345 acute stress disease Diseases 0.000 claims description 5
• 230000006978 adaptation Effects 0.000 claims description 5
• 206010001584 alcohol abuse Diseases 0.000 claims description 5
• 208000025746 alcohol use disease Diseases 0.000 claims description 5
• 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims description 5
• 125000004852 dihydrofuranyl group Chemical group O1C(CC=C1)* 0.000 claims description 5
• 208000018459 dissociative disease Diseases 0.000 claims description 5
• 206010013663 drug dependence Diseases 0.000 claims description 5
• 208000024732 dysthymic disease Diseases 0.000 claims description 5
• 230000004970 emotional disturbance Effects 0.000 claims description 5
• 208000029364 generalized anxiety disease Diseases 0.000 claims description 5
• 230000000642 iatrogenic effect Effects 0.000 claims description 5
• 201000001881 impotence Diseases 0.000 claims description 5
• 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 5
• 125000003965 isoxazolidinyl group Chemical group 0.000 claims description 5
• 201000003995 melancholia Diseases 0.000 claims description 5
• 230000003340 mental effect Effects 0.000 claims description 5
• 206010027599 migraine Diseases 0.000 claims description 5
• 235000020824 obesity Nutrition 0.000 claims description 5
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 5
• 208000028173 post-traumatic stress disease Diseases 0.000 claims description 5
• 208000019116 sleep disease Diseases 0.000 claims description 5
• 208000022925 sleep disturbance Diseases 0.000 claims description 5
• 208000016994 somatization disease Diseases 0.000 claims description 5
• 208000016686 tic disease Diseases 0.000 claims description 5
• 230000008673 vomiting Effects 0.000 claims description 5
• 208000000103 Anorexia Nervosa Diseases 0.000 claims description 4
• 206010006550 Bulimia nervosa Diseases 0.000 claims description 4
• 239000003937 drug carrier Substances 0.000 claims description 4
• 201000003104 endogenous depression Diseases 0.000 claims description 4
• 150000002367 halogens Chemical class 0.000 claims description 4
• 125000004634 hexahydroazepinyl group Chemical group N1(CCCCCC1)* 0.000 claims description 4
• 229910052739 hydrogen Inorganic materials 0.000 claims description 4
• 239000001257 hydrogen Substances 0.000 claims description 4
• 238000002156 mixing Methods 0.000 claims description 4
• 208000027753 pain disease Diseases 0.000 claims description 4
• 230000008569 process Effects 0.000 claims description 4
• 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 4
• 102000049773 5-HT2A Serotonin Receptor Human genes 0.000 claims description 3
• 108010072564 5-HT2A Serotonin Receptor Proteins 0.000 claims description 3
• 208000032841 Bulimia Diseases 0.000 claims description 3
• 229940096895 Dopamine D2 receptor agonist Drugs 0.000 claims description 3
• 230000037007 arousal Effects 0.000 claims description 3
• 125000001769 aryl amino group Chemical group 0.000 claims description 3
• 208000026725 cyclothymic disease Diseases 0.000 claims description 3
• 239000002288 dopamine 2 receptor stimulating agent Substances 0.000 claims description 3
• 230000035987 intoxication Effects 0.000 claims description 3
• 231100000566 intoxication Toxicity 0.000 claims description 3
• 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 3
• 230000002265 prevention Effects 0.000 claims description 3
• 239000003772 serotonin uptake inhibitor Substances 0.000 claims description 3
• 230000035946 sexual desire Effects 0.000 claims description 3
• 230000001568 sexual effect Effects 0.000 claims description 3
• 239000000021 stimulant Substances 0.000 claims description 3
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
• 125000000129 anionic group Chemical group 0.000 claims description 2
• 239000003420 antiserotonin agent Substances 0.000 claims description 2
• 229940121356 serotonin receptor antagonist Drugs 0.000 claims description 2
• 229940126570 serotonin reuptake inhibitor Drugs 0.000 claims description 2
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 336
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 90
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 52
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 10
• 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 9
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 9
• 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 6
• 125000006624 (C1-C6) alkoxycarbonylamino group Chemical group 0.000 claims 4
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 3
• 208000012902 Nervous system disease Diseases 0.000 claims 3
• 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 3
• 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 2
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 2
• 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims 2
• 125000006727 (C1-C6) alkenyl group Chemical group 0.000 claims 1
• 125000006590 (C2-C6) alkenylene group Chemical group 0.000 claims 1
• YWSBWHMBCHGEGX-UHFFFAOYSA-N 1,4-dioxa-8-azaspiro[4.5]decyl Chemical group [O+]1=CCOC11CC[N-]CC1 YWSBWHMBCHGEGX-UHFFFAOYSA-N 0.000 claims 1
• UBZKMAIJHFLIAH-UHFFFAOYSA-N 1-(1-benzothiophen-4-yl)-4-[3-(2-methoxy-6-methyl-4-piperidin-1-ylphenoxy)propyl]piperazine Chemical compound C=1C(C)=C(OCCCN2CCN(CC2)C=2C=3C=CSC=3C=CC=2)C(OC)=CC=1N1CCCCC1 UBZKMAIJHFLIAH-UHFFFAOYSA-N 0.000 claims 1
• UNOXKZWRSRTOBM-UHFFFAOYSA-N 1-[4-[4-[3-[4-(1-benzothiophen-4-yl)piperazin-1-yl]propoxy]-3-methoxy-5-methylphenyl]piperazin-1-yl]ethanone Chemical compound C=1C(C)=C(OCCCN2CCN(CC2)C=2C=3C=CSC=3C=CC=2)C(OC)=CC=1N1CCN(C(C)=O)CC1 UNOXKZWRSRTOBM-UHFFFAOYSA-N 0.000 claims 1
• CEZRSDASDVUETF-UHFFFAOYSA-N 4-[3-[4-(1-benzothiophen-4-yl)piperazin-1-yl]propoxy]-3-methoxy-n,5-dimethylaniline Chemical compound COC1=CC(NC)=CC(C)=C1OCCCN1CCN(C=2C=3C=CSC=3C=CC=2)CC1 CEZRSDASDVUETF-UHFFFAOYSA-N 0.000 claims 1
• GGKWEBSKDYFMOS-UHFFFAOYSA-N 4-[3-[4-(1-benzothiophen-4-yl)piperazin-1-yl]propoxy]-3-methoxy-n,n,5-trimethylaniline Chemical compound COC1=CC(N(C)C)=CC(C)=C1OCCCN1CCN(C=2C=3C=CSC=3C=CC=2)CC1 GGKWEBSKDYFMOS-UHFFFAOYSA-N 0.000 claims 1
• QRAFGRXCWMHBEO-UHFFFAOYSA-N 4-[3-[4-(1-benzothiophen-4-yl)piperazin-1-yl]propoxy]-n-(2,2-dimethoxyethyl)-3-methoxy-5-methylbenzamide Chemical compound COC1=CC(C(=O)NCC(OC)OC)=CC(C)=C1OCCCN1CCN(C=2C=3C=CSC=3C=CC=2)CC1 QRAFGRXCWMHBEO-UHFFFAOYSA-N 0.000 claims 1
• 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims 1
• 125000003320 C2-C6 alkenyloxy group Chemical group 0.000 claims 1
• 125000004103 aminoalkyl group Chemical group 0.000 claims 1
• 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
• 239000005557 antagonist Substances 0.000 claims 1
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
• KJNCFURRTYFBKI-UHFFFAOYSA-N methyl 4-[4-[3-[4-(1-benzothiophen-4-yl)piperazin-1-yl]propoxy]-3-formyl-5-methoxyphenyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC)CCN1C(C=C1C=O)=CC(OC)=C1OCCCN1CCN(C=2C=3C=CSC=3C=CC=2)CC1 KJNCFURRTYFBKI-UHFFFAOYSA-N 0.000 claims 1
• IWMGIJONIYLYFS-UHFFFAOYSA-N methyl 4-[4-[3-[4-(1-benzothiophen-4-yl)piperazin-1-yl]propoxy]-3-methoxy-5-methylphenyl]-3-oxopiperazine-1-carboxylate Chemical compound O=C1CN(C(=O)OC)CCN1C(C=C1OC)=CC(C)=C1OCCCN1CCN(C=2C=3C=CSC=3C=CC=2)CC1 IWMGIJONIYLYFS-UHFFFAOYSA-N 0.000 claims 1
• 125000005476 oxopyrrolidinyl group Chemical group 0.000 claims 1
• DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 1
• 125000002947 alkylene group Chemical group 0.000 abstract description 10
• 125000004450 alkenylene group Chemical group 0.000 abstract description 5
• 231100000957 no side effect Toxicity 0.000 abstract description 2
• 238000001228 spectrum Methods 0.000 abstract description 2
• 208000020016 psychiatric disease Diseases 0.000 abstract 1
• 125000004432 carbon atom Chemical group C* 0.000 description 189
• 125000003545 alkoxy group Chemical group 0.000 description 135
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 117
• 230000000694 effects Effects 0.000 description 43
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 42
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 41
• 239000002904 solvent Substances 0.000 description 37
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 25
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 20
• 235000019441 ethanol Nutrition 0.000 description 20
• 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 description 19
• LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 17
• 125000004414 alkyl thio group Chemical group 0.000 description 16
• 239000003826 tablet Substances 0.000 description 16
• ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 15
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
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• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
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• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
• 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 15
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• 125000002911 monocyclic heterocycle group Chemical group 0.000 description 14
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• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 12
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 12
• 125000005186 naphthyloxy group Chemical group C1(=CC=CC2=CC=CC=C12)O* 0.000 description 12
• 239000000843 powder Substances 0.000 description 12
• 239000007858 starting material Substances 0.000 description 12
• GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 11
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 11
• 229910052783 alkali metal Inorganic materials 0.000 description 11
• 229910052757 nitrogen Inorganic materials 0.000 description 11
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
• WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 10
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
• LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 10
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
• WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 10
• 239000008103 glucose Substances 0.000 description 10
• 238000002360 preparation method Methods 0.000 description 10
• 229940044551 receptor antagonist Drugs 0.000 description 10
• 239000002464 receptor antagonist Substances 0.000 description 10
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 9
• 239000003795 chemical substances by application Substances 0.000 description 9
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• 239000011975 tartaric acid Substances 0.000 description 1
• 235000002906 tartaric acid Nutrition 0.000 description 1
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• 125000005942 tetrahydropyridyl group Chemical group 0.000 description 1
• 125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 description 1
• 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
• 125000005302 thiazolylmethyl group Chemical group [H]C1=C([H])N=C(S1)C([H])([H])* 0.000 description 1
• 125000005301 thienylmethyl group Chemical group [H]C1=C([H])C([H])=C(S1)C([H])([H])* 0.000 description 1
• 125000005033 thiopyranyl group Chemical group 0.000 description 1
• 230000000472 traumatic effect Effects 0.000 description 1
• 125000004784 trichloromethoxy group Chemical group ClC(O*)(Cl)Cl 0.000 description 1
• 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
• 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
• 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• 235000015112 vegetable and seed oil Nutrition 0.000 description 1
• 239000008158 vegetable oil Substances 0.000 description 1