NO328600B1 - Substituerte sykloheksan-1,4-diaminderivater, anvendelse derav, fremgangsmate for fremstilling derav og legemidler inneholdende slike derivater - Google Patents

Info

Publication number

NO328600B1

NO328600B1 NO20034930A NO20034930A NO328600B1 NO 328600 B1 NO328600 B1 NO 328600B1 NO 20034930 A NO20034930 A NO 20034930A NO 20034930 A NO20034930 A NO 20034930A NO 328600 B1 NO328600 B1 NO 328600B1

Authority

NO

Norway

Prior art keywords

unsubstituted

polysubstituted

singly

case

saturated

Prior art date

2001-05-09

Links

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• VKIRRGRTJUUZHS-UHFFFAOYSA-N cyclohexane-1,4-diamine Chemical class NC1CCC(N)CC1 VKIRRGRTJUUZHS-UHFFFAOYSA-N 0.000 title claims description 125
• 239000003814 drug Substances 0.000 title claims description 52
• 229940079593 drug Drugs 0.000 title claims description 34
• 238000000034 method Methods 0.000 title claims description 15
• 238000002360 preparation method Methods 0.000 title claims description 12
• 230000008569 process Effects 0.000 title claims description 8
• 229920006395 saturated elastomer Polymers 0.000 claims description 548
• 125000001072 heteroaryl group Chemical group 0.000 claims description 535
• 125000003118 aryl group Chemical group 0.000 claims description 524
• 125000000217 alkyl group Chemical group 0.000 claims description 284
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 280
• -1 acenaphthyl Chemical group 0.000 claims description 260
• 239000000203 mixture Substances 0.000 claims description 140
• 150000003839 salts Chemical class 0.000 claims description 108
• 229910052739 hydrogen Inorganic materials 0.000 claims description 106
• 229910052799 carbon Inorganic materials 0.000 claims description 88
• 125000002541 furyl group Chemical group 0.000 claims description 88
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 82
• 125000002947 alkylene group Chemical group 0.000 claims description 81
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 80
• 125000001544 thienyl group Chemical group 0.000 claims description 76
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 75
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 75
• 239000002253 acid Substances 0.000 claims description 70
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 69
• 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 69
• 125000006239 protecting group Chemical group 0.000 claims description 65
• 150000007513 acids Chemical class 0.000 claims description 64
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 63
• 150000001875 compounds Chemical class 0.000 claims description 63
• 125000001041 indolyl group Chemical group 0.000 claims description 63
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 63
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 63
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 62
• 125000000623 heterocyclic group Chemical group 0.000 claims description 57
• 125000001624 naphthyl group Chemical group 0.000 claims description 57
• 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 50
• 125000004076 pyridyl group Chemical group 0.000 claims description 49
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 42
• 101100448208 Human herpesvirus 6B (strain Z29) U69 gene Proteins 0.000 claims description 40
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 38
• YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 36
• 150000001768 cations Chemical class 0.000 claims description 35
• 125000004429 atom Chemical group 0.000 claims description 34
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 32
• 238000002156 mixing Methods 0.000 claims description 31
• 150000004677 hydrates Chemical class 0.000 claims description 30
• 208000002193 Pain Diseases 0.000 claims description 29
• 239000012453 solvate Substances 0.000 claims description 29
• 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 claims description 28
• 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims description 26
• 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 25
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 25
• 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 25
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 25
• 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 24
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 24
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 22
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 22
• 229910052760 oxygen Inorganic materials 0.000 claims description 21
• 125000005605 benzo group Chemical group 0.000 claims description 20
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 19
• 125000001424 substituent group Chemical group 0.000 claims description 19
• 229910052717 sulfur Inorganic materials 0.000 claims description 19
• 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 claims description 18
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 17
• SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 16
• 238000004519 manufacturing process Methods 0.000 claims description 16
• 239000013543 active substance Substances 0.000 claims description 15
• FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 14
• UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 14
• KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 14
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 14
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 14
• IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 14
• 229910052801 chlorine Inorganic materials 0.000 claims description 14
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 14
• 229910052731 fluorine Inorganic materials 0.000 claims description 14
• AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 14
• 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 13
• 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 13
• 229910052794 bromium Inorganic materials 0.000 claims description 13
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 13
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 13
• 229940126601 medicinal product Drugs 0.000 claims description 13
• 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 12
• 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 claims description 12
• 125000005879 dioxolanyl group Chemical group 0.000 claims description 12
• 229910052740 iodine Inorganic materials 0.000 claims description 12
• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 12
• 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims description 12
• 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 12
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 12
• 125000000335 thiazolyl group Chemical group 0.000 claims description 12
• 125000006704 (C5-C6) cycloalkyl group Chemical group 0.000 claims description 11
• 230000036407 pain Effects 0.000 claims description 11
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 11
• 238000011260 co-administration Methods 0.000 claims description 10
• 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 10
• 208000004296 neuralgia Diseases 0.000 claims description 10
• 208000021722 neuropathic pain Diseases 0.000 claims description 10
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 9
• 208000000094 Chronic Pain Diseases 0.000 claims description 9
• 229910003204 NH2 Inorganic materials 0.000 claims description 9
• 230000001154 acute effect Effects 0.000 claims description 9
• 208000005298 acute pain Diseases 0.000 claims description 9
• 239000000654 additive Substances 0.000 claims description 9
• 230000002981 neuropathic effect Effects 0.000 claims description 9
• 239000000126 substance Substances 0.000 claims description 9
• BWWVPRAFFGGRNT-UHFFFAOYSA-N 1-n,1-n-dimethyl-4-n-[(1-methylindol-3-yl)methyl]-1-phenylcyclohexane-1,4-diamine Chemical compound C1CC(NCC=2C3=CC=CC=C3N(C)C=2)CCC1(N(C)C)C1=CC=CC=C1 BWWVPRAFFGGRNT-UHFFFAOYSA-N 0.000 claims description 8
• SIMLFUJOTUODCL-UHFFFAOYSA-N 4-n-(1h-indol-3-ylmethyl)-1-n,1-n-dimethyl-1-phenylcyclohexane-1,4-diamine Chemical compound C1CC(NCC=2C3=CC=CC=C3NC=2)CCC1(N(C)C)C1=CC=CC=C1 SIMLFUJOTUODCL-UHFFFAOYSA-N 0.000 claims description 8
• GKKDBSVWRIIQDJ-UHFFFAOYSA-N 4-n-[2-(1h-indol-3-yl)ethyl]-1-n,1-n-dimethyl-1-phenylcyclohexane-1,4-diamine Chemical compound C1CC(NCCC=2C3=CC=CC=C3NC=2)CCC1(N(C)C)C1=CC=CC=C1 GKKDBSVWRIIQDJ-UHFFFAOYSA-N 0.000 claims description 8
• 238000006243 chemical reaction Methods 0.000 claims description 8
• 239000003153 chemical reaction reagent Substances 0.000 claims description 8
• 125000005842 heteroatom Chemical group 0.000 claims description 8
• PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 8
• RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 8
• 229910052757 nitrogen Inorganic materials 0.000 claims description 8
• 239000000014 opioid analgesic Substances 0.000 claims description 8
• FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical compound C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 claims description 7
• SLROLMCJBPHLBQ-UHFFFAOYSA-N 4-n-[1-(1h-indol-3-yl)propan-2-yl]-1-n,1-n-dimethyl-1-phenylcyclohexane-1,4-diamine Chemical compound C=1NC2=CC=CC=C2C=1CC(C)NC(CC1)CCC1(N(C)C)C1=CC=CC=C1 SLROLMCJBPHLBQ-UHFFFAOYSA-N 0.000 claims description 7
• PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 7
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 7
• RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 claims description 7
• XSCHRSMBECNVNS-UHFFFAOYSA-N benzopyrazine Natural products N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims description 7
• QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 claims description 7
• 239000012964 benzotriazole Substances 0.000 claims description 7
• LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical compound C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 claims description 7
• LYKMMUBOEFYJQG-UHFFFAOYSA-N piperoxan Chemical compound C1OC2=CC=CC=C2OC1CN1CCCCC1 LYKMMUBOEFYJQG-UHFFFAOYSA-N 0.000 claims description 7
• 238000006467 substitution reaction Methods 0.000 claims description 7
• VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims description 7
• 229930192474 thiophene Natural products 0.000 claims description 7
• FTHZKCMAGMIUOU-UHFFFAOYSA-N 4-n-(1-benzothiophen-3-ylmethyl)-1-benzyl-1-n,1-n-dimethylcyclohexane-1,4-diamine;dihydrochloride Chemical compound Cl.Cl.C1CC(NCC=2C3=CC=CC=C3SC=2)CCC1(N(C)C)CC1=CC=CC=C1 FTHZKCMAGMIUOU-UHFFFAOYSA-N 0.000 claims description 6
• YSIKTFCRHQNQEP-UHFFFAOYSA-N 4-n-(1-benzothiophen-3-ylmethyl)-1-n,1-n-dimethyl-1-phenylcyclohexane-1,4-diamine;dihydrochloride Chemical compound Cl.Cl.C1CC(NCC=2C3=CC=CC=C3SC=2)CCC1(N(C)C)C1=CC=CC=C1 YSIKTFCRHQNQEP-UHFFFAOYSA-N 0.000 claims description 6
• YWKWGULBAVUUNJ-UHFFFAOYSA-N 4-n-(1h-indol-3-ylmethyl)-1-n,1-n-dimethyl-1-phenylcyclohexane-1,4-diamine;dihydrochloride Chemical compound Cl.Cl.C1CC(NCC=2C3=CC=CC=C3NC=2)CCC1(N(C)C)C1=CC=CC=C1 YWKWGULBAVUUNJ-UHFFFAOYSA-N 0.000 claims description 6
• ZDSRRNGYNZJQML-UHFFFAOYSA-N 4-n-[2-(1h-indol-3-yl)ethyl]-1-n,1-n-dimethyl-1-phenylcyclohexane-1,4-diamine;dihydrochloride Chemical compound Cl.Cl.C1CC(NCCC=2C3=CC=CC=C3NC=2)CCC1(N(C)C)C1=CC=CC=C1 ZDSRRNGYNZJQML-UHFFFAOYSA-N 0.000 claims description 6
• WZZNQPJROHVWBF-UHFFFAOYSA-N 4-n-benzyl-1-n,1-n-dimethyl-1-phenylcyclohexane-1,4-diamine;hydrochloride Chemical compound Cl.C1CC(N(C)C)(C=2C=CC=CC=2)CCC1NCC1=CC=CC=C1 WZZNQPJROHVWBF-UHFFFAOYSA-N 0.000 claims description 6
• XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 6
• 230000003444 anaesthetic effect Effects 0.000 claims description 6
• 229910052736 halogen Inorganic materials 0.000 claims description 6
• 150000002367 halogens Chemical class 0.000 claims description 6
• GJDBQWAQDWEWLG-UHFFFAOYSA-N methyl 2-[[4-(dimethylamino)-4-phenylcyclohexyl]amino]-3-(1h-indol-3-yl)propanoate;dihydrochloride Chemical compound Cl.Cl.C=1NC2=CC=CC=C2C=1CC(C(=O)OC)NC(CC1)CCC1(N(C)C)C1=CC=CC=C1 GJDBQWAQDWEWLG-UHFFFAOYSA-N 0.000 claims description 6
• BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 claims description 6
• QHLWXDXBURXTFJ-UHFFFAOYSA-N n-[4-(dimethylamino)-4-phenylcyclohexyl]-n-propylbenzamide;hydrochloride Chemical compound Cl.C=1C=CC=CC=1C(=O)N(CCC)C(CC1)CCC1(N(C)C)C1=CC=CC=C1 QHLWXDXBURXTFJ-UHFFFAOYSA-N 0.000 claims description 6
• LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 claims description 6
• 238000006268 reductive amination reaction Methods 0.000 claims description 6
• 125000005329 tetralinyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 6
• LFPWQFOSDUIQPT-UHFFFAOYSA-N 1-n,1-n-dimethyl-4-n-[2-(7-methyl-1h-indol-3-yl)ethyl]-1-phenylcyclohexane-1,4-diamine;dihydrochloride Chemical compound Cl.Cl.C1CC(NCCC=2C3=CC=CC(C)=C3NC=2)CCC1(N(C)C)C1=CC=CC=C1 LFPWQFOSDUIQPT-UHFFFAOYSA-N 0.000 claims description 5
• COKSNCUEIFGHPQ-UHFFFAOYSA-N 4-n-(1,2-dihydroacenaphthylen-1-yl)-1-n,1-n-dimethyl-1-phenylcyclohexane-1,4-diamine;dihydrochloride Chemical compound Cl.Cl.C1CC(NC2C=3C=CC=C4C=CC=C(C=34)C2)CCC1(N(C)C)C1=CC=CC=C1 COKSNCUEIFGHPQ-UHFFFAOYSA-N 0.000 claims description 5
• QCCXRNLUJPYHIT-UHFFFAOYSA-N 4-n-[2-(6-fluoro-1h-indol-3-yl)ethyl]-1-n,1-n-dimethyl-1-phenylcyclohexane-1,4-diamine;dihydrochloride Chemical compound Cl.Cl.C1CC(NCCC=2C3=CC=C(F)C=C3NC=2)CCC1(N(C)C)C1=CC=CC=C1 QCCXRNLUJPYHIT-UHFFFAOYSA-N 0.000 claims description 5
• 230000015572 biosynthetic process Effects 0.000 claims description 5
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 5
• NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 claims description 5
• HASHIQANERBSQC-UHFFFAOYSA-N 1-n,1-n-dimethyl-1-phenyl-4-n-[2-(5-phenylmethoxy-1h-indol-3-yl)ethyl]cyclohexane-1,4-diamine Chemical compound C1CC(N(C)C)(C=2C=CC=CC=2)CCC1NCCC(C1=C2)=CNC1=CC=C2OCC1=CC=CC=C1 HASHIQANERBSQC-UHFFFAOYSA-N 0.000 claims description 4
• OTCYOBLTAQTFPW-UHFFFAOYSA-N 4-aminocyclohexan-1-one Chemical class NC1CCC(=O)CC1 OTCYOBLTAQTFPW-UHFFFAOYSA-N 0.000 claims description 4
• WCCMVPWCXQERET-UHFFFAOYSA-N 4-n-(2,3-dihydro-1h-inden-5-yl)-1-n,1-n-dimethyl-1-phenylcyclohexane-1,4-diamine Chemical compound C1CC(NC=2C=C3CCCC3=CC=2)CCC1(N(C)C)C1=CC=CC=C1 WCCMVPWCXQERET-UHFFFAOYSA-N 0.000 claims description 4
• XCMBEDKJGGNRJD-UHFFFAOYSA-N 4-n-(2h-benzotriazol-5-yl)-1-n,1-n-dimethyl-1-phenylcyclohexane-1,4-diamine;hydrochloride Chemical compound Cl.C1CC(NC=2C=C3NN=NC3=CC=2)CCC1(N(C)C)C1=CC=CC=C1 XCMBEDKJGGNRJD-UHFFFAOYSA-N 0.000 claims description 4
• GCWMSDSVVBVTSU-UHFFFAOYSA-N 4-n-(9h-fluoren-1-yl)-1-n,1-n-dimethyl-1-phenylcyclohexane-1,4-diamine;dihydrochloride Chemical compound Cl.Cl.C1CC(NC=2C3=C(C4=CC=CC=C4C3)C=CC=2)CCC1(N(C)C)C1=CC=CC=C1 GCWMSDSVVBVTSU-UHFFFAOYSA-N 0.000 claims description 4
• WTMUVVVADPHWFA-UHFFFAOYSA-N 4-n-[1-(1h-indol-3-yl)propan-2-yl]-1-n,1-n-dimethyl-1-phenylcyclohexane-1,4-diamine;dihydrochloride Chemical compound Cl.Cl.C=1NC2=CC=CC=C2C=1CC(C)NC(CC1)CCC1(N(C)C)C1=CC=CC=C1 WTMUVVVADPHWFA-UHFFFAOYSA-N 0.000 claims description 4
• BCLWHBNQUOVGQP-UHFFFAOYSA-N 4-n-[2-(5-methoxy-1h-indol-3-yl)ethyl]-1-n,1-n-dimethyl-1-phenylcyclohexane-1,4-diamine;dihydrochloride Chemical compound Cl.Cl.C12=CC(OC)=CC=C2NC=C1CCNC(CC1)CCC1(N(C)C)C1=CC=CC=C1 BCLWHBNQUOVGQP-UHFFFAOYSA-N 0.000 claims description 4
• 208000004880 Polyuria Diseases 0.000 claims description 4
• DCZFGQYXRKMVFG-UHFFFAOYSA-N cyclohexane-1,4-dione Chemical compound O=C1CCC(=O)CC1 DCZFGQYXRKMVFG-UHFFFAOYSA-N 0.000 claims description 4
• JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexyloxide Natural products O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 4
• 230000035619 diuresis Effects 0.000 claims description 4
• 206010015037 epilepsy Diseases 0.000 claims description 4
• 125000001979 organolithium group Chemical group 0.000 claims description 4
• 125000002524 organometallic group Chemical group 0.000 claims description 4
• 208000011117 substance-related disease Diseases 0.000 claims description 4
• AAAODFPLXSUBKU-UHFFFAOYSA-N 1-benzyl-4-n-(2,3-dihydro-1h-inden-5-yl)-1-n,1-n-dimethylcyclohexane-1,4-diamine;hydrochloride Chemical compound Cl.C1CC(NC=2C=C3CCCC3=CC=2)CCC1(N(C)C)CC1=CC=CC=C1 AAAODFPLXSUBKU-UHFFFAOYSA-N 0.000 claims description 3
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