CA2566297C - Substituted cyclohexyl-1,4-diamine derivatives - Google Patents
Substituted cyclohexyl-1,4-diamine derivatives Download PDFInfo
- Publication number
- CA2566297C CA2566297C CA2566297A CA2566297A CA2566297C CA 2566297 C CA2566297 C CA 2566297C CA 2566297 A CA2566297 A CA 2566297A CA 2566297 A CA2566297 A CA 2566297A CA 2566297 C CA2566297 C CA 2566297C
- Authority
- CA
- Canada
- Prior art keywords
- cyclohexyl
- benzyl
- dimethylamino
- succinamide
- chloro
- 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.)
- Expired - Fee Related
Links
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 28
- 238000000034 method Methods 0.000 claims abstract description 18
- 230000008569 process Effects 0.000 claims abstract description 10
- -1 hydrogen radicals Chemical class 0.000 claims description 166
- 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 111
- 125000000217 alkyl group Chemical group 0.000 claims description 52
- 150000003839 salts Chemical class 0.000 claims description 45
- 125000003118 aryl group Chemical group 0.000 claims description 39
- 229920006395 saturated elastomer Polymers 0.000 claims description 38
- 239000000203 mixture Substances 0.000 claims description 35
- 125000001072 heteroaryl group Chemical group 0.000 claims description 30
- 208000002193 Pain Diseases 0.000 claims description 28
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 28
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 23
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 21
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 20
- 125000001544 thienyl group Chemical group 0.000 claims description 18
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 17
- 239000002253 acid Substances 0.000 claims description 16
- 125000002541 furyl group Chemical group 0.000 claims description 16
- 125000004076 pyridyl group Chemical group 0.000 claims description 15
- 239000003814 drug Substances 0.000 claims description 13
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 12
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 11
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 11
- 125000001041 indolyl group Chemical group 0.000 claims description 11
- 125000001624 naphthyl group Chemical group 0.000 claims description 11
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 11
- 229940005483 opioid analgesics Drugs 0.000 claims description 10
- 150000003254 radicals Chemical class 0.000 claims description 10
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 9
- 208000007271 Substance Withdrawal Syndrome Diseases 0.000 claims description 9
- 230000003444 anaesthetic effect Effects 0.000 claims description 9
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 9
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 9
- 238000006467 substitution reaction Methods 0.000 claims description 9
- 239000001384 succinic acid Substances 0.000 claims description 9
- 208000024827 Alzheimer disease Diseases 0.000 claims description 8
- 208000000094 Chronic Pain Diseases 0.000 claims description 8
- 125000005842 heteroatom Chemical group 0.000 claims description 8
- 230000001777 nootropic effect Effects 0.000 claims description 8
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 7
- 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 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 7
- YFDWJWZYIJKUCN-UHFFFAOYSA-N N'-[4-benzyl-4-(dimethylamino)cyclohexyl]-N-[2-(2-fluorophenyl)ethyl]pentanediamide hydrochloride Chemical compound Cl.C1CC(NC(=O)CCCC(=O)NCCC=2C(=CC=CC=2)F)CCC1(N(C)C)CC1=CC=CC=C1 YFDWJWZYIJKUCN-UHFFFAOYSA-N 0.000 claims description 6
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 6
- 150000008064 anhydrides Chemical class 0.000 claims description 6
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 6
- 125000004429 atom Chemical group 0.000 claims description 6
- 208000009132 Catalepsy Diseases 0.000 claims description 5
- 206010012335 Dependence Diseases 0.000 claims description 5
- 206010012735 Diarrhoea Diseases 0.000 claims description 5
- 208000026139 Memory disease Diseases 0.000 claims description 5
- 208000004880 Polyuria Diseases 0.000 claims description 5
- 206010046543 Urinary incontinence Diseases 0.000 claims description 5
- 206010047853 Waxy flexibility Diseases 0.000 claims description 5
- 230000001154 acute effect Effects 0.000 claims description 5
- 208000005298 acute pain Diseases 0.000 claims description 5
- 208000022531 anorexia Diseases 0.000 claims description 5
- 230000008878 coupling Effects 0.000 claims description 5
- 238000010168 coupling process Methods 0.000 claims description 5
- 238000005859 coupling reaction Methods 0.000 claims description 5
- 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 5
- 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 5
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 5
- 206010061428 decreased appetite Diseases 0.000 claims description 5
- 208000035475 disorder Diseases 0.000 claims description 5
- 230000035619 diuresis Effects 0.000 claims description 5
- 229940079593 drug Drugs 0.000 claims description 5
- 206010015037 epilepsy Diseases 0.000 claims description 5
- 230000037023 motor activity Effects 0.000 claims description 5
- 208000004296 neuralgia Diseases 0.000 claims description 5
- 230000004770 neurodegeneration Effects 0.000 claims description 5
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 5
- 230000002981 neuropathic effect Effects 0.000 claims description 5
- 208000021722 neuropathic pain Diseases 0.000 claims description 5
- 230000003957 neurotransmitter release Effects 0.000 claims description 5
- 125000004193 piperazinyl group Chemical group 0.000 claims description 5
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 5
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 5
- 150000003335 secondary amines Chemical class 0.000 claims description 5
- 125000006180 3-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1[H])C([H])([H])[H])C([H])([H])* 0.000 claims description 4
- 208000019901 Anxiety disease Diseases 0.000 claims description 4
- 206010006895 Cachexia Diseases 0.000 claims description 4
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 4
- 206010020772 Hypertension Diseases 0.000 claims description 4
- 208000001953 Hypotension Diseases 0.000 claims description 4
- 208000020358 Learning disease Diseases 0.000 claims description 4
- 208000019695 Migraine disease Diseases 0.000 claims description 4
- 208000008589 Obesity Diseases 0.000 claims description 4
- 208000003251 Pruritus Diseases 0.000 claims description 4
- 229910006069 SO3H Inorganic materials 0.000 claims description 4
- 206010039966 Senile dementia Diseases 0.000 claims description 4
- 201000001880 Sexual dysfunction Diseases 0.000 claims description 4
- 208000009205 Tinnitus Diseases 0.000 claims description 4
- 238000010521 absorption reaction Methods 0.000 claims description 4
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 4
- 230000002082 anti-convulsion Effects 0.000 claims description 4
- 230000036506 anxiety Effects 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 238000011260 co-administration Methods 0.000 claims description 4
- 208000010877 cognitive disease Diseases 0.000 claims description 4
- 230000002950 deficient Effects 0.000 claims description 4
- 230000036543 hypotension Effects 0.000 claims description 4
- 230000001771 impaired effect Effects 0.000 claims description 4
- 230000008991 intestinal motility Effects 0.000 claims description 4
- 201000003723 learning disability Diseases 0.000 claims description 4
- 230000003137 locomotive effect Effects 0.000 claims description 4
- 206010027599 migraine Diseases 0.000 claims description 4
- 239000003158 myorelaxant agent Substances 0.000 claims description 4
- 235000015097 nutrients Nutrition 0.000 claims description 4
- 235000020824 obesity Nutrition 0.000 claims description 4
- 239000000014 opioid analgesic Substances 0.000 claims description 4
- 231100000872 sexual dysfunction Toxicity 0.000 claims description 4
- 125000003107 substituted aryl group Chemical group 0.000 claims description 4
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 4
- 208000011580 syndromic disease Diseases 0.000 claims description 4
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 4
- 231100000886 tinnitus Toxicity 0.000 claims description 4
- NIYFVTGQGJSFBN-UHFFFAOYSA-N 4-[4-(4-chlorobenzoyl)piperidin-1-yl]-n-[4-(dimethylamino)-4-[(3-methylphenyl)methyl]cyclohexyl]-4-oxobutanamide Chemical compound C1CC(NC(=O)CCC(=O)N2CCC(CC2)C(=O)C=2C=CC(Cl)=CC=2)CCC1(N(C)C)CC1=CC=CC(C)=C1 NIYFVTGQGJSFBN-UHFFFAOYSA-N 0.000 claims description 3
- SSYLTJOEHJJOSO-UHFFFAOYSA-N 5-(3,4-dihydro-1h-isoquinolin-2-yl)-n-[4-(dimethylamino)-4-thiophen-2-ylcyclohexyl]-5-oxopentanamide Chemical compound C1CC(NC(=O)CCCC(=O)N2CC3=CC=CC=C3CC2)CCC1(N(C)C)C1=CC=CS1 SSYLTJOEHJJOSO-UHFFFAOYSA-N 0.000 claims description 3
- RZKUUXMTGXSUHF-UHFFFAOYSA-N N'-[4-benzyl-4-(dimethylamino)cyclohexyl]-N-[2-(4-chlorophenyl)ethyl]pentanediamide hydrochloride Chemical compound Cl.C1CC(NC(=O)CCCC(=O)NCCC=2C=CC(Cl)=CC=2)CCC1(N(C)C)CC1=CC=CC=C1 RZKUUXMTGXSUHF-UHFFFAOYSA-N 0.000 claims description 3
- ZXZSSVLBDJNMFS-UHFFFAOYSA-N N-[4-(dimethylamino)-4-thiophen-2-ylcyclohexyl]-N'-(2-phenylcyclopropyl)pentanediamide Chemical compound C1CC(N(C)C)(C=2SC=CC=2)CCC1NC(=O)CCCC(=O)NC1CC1C1=CC=CC=C1 ZXZSSVLBDJNMFS-UHFFFAOYSA-N 0.000 claims description 3
- 229910006074 SO2NH2 Inorganic materials 0.000 claims description 3
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 3
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 3
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 claims description 3
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 3
- 239000003153 chemical reaction reagent Substances 0.000 claims description 3
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- VKIRRGRTJUUZHS-UHFFFAOYSA-N cyclohexane-1,4-diamine Chemical class NC1CCC(N)CC1 VKIRRGRTJUUZHS-UHFFFAOYSA-N 0.000 claims description 3
- 125000005879 dioxolanyl group Chemical group 0.000 claims description 3
- YHNUVZDMTLKABS-UHFFFAOYSA-N ethyl 3-[[4-[[4-(dimethylamino)-4-[(4-methylphenyl)methyl]cyclohexyl]amino]-4-oxobutanoyl]amino]propanoate Chemical compound C1CC(NC(=O)CCC(=O)NCCC(=O)OCC)CCC1(N(C)C)CC1=CC=C(C)C=C1 YHNUVZDMTLKABS-UHFFFAOYSA-N 0.000 claims description 3
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 3
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 claims description 3
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 3
- 150000004820 halides Chemical class 0.000 claims description 3
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000002757 morpholinyl group Chemical group 0.000 claims description 3
- MHOAWCGZEUPVOO-UHFFFAOYSA-N n-[4-(dimethylamino)-4-[(3-methylphenyl)methyl]cyclohexyl]-4-(4-methylpiperidin-1-yl)-4-oxobutanamide Chemical compound C1CC(C)CCN1C(=O)CCC(=O)NC1CCC(CC=2C=C(C)C=CC=2)(N(C)C)CC1 MHOAWCGZEUPVOO-UHFFFAOYSA-N 0.000 claims description 3
- YPOVHGGVHUVTBF-UHFFFAOYSA-N n-[4-(dimethylamino)-4-[(4-methylphenyl)methyl]cyclohexyl]-n'-(3-methylbutan-2-yl)butanediamide Chemical compound C1CC(NC(=O)CCC(=O)NC(C)C(C)C)CCC1(N(C)C)CC1=CC=C(C)C=C1 YPOVHGGVHUVTBF-UHFFFAOYSA-N 0.000 claims description 3
- JXPDWYNLKGUGQB-UHFFFAOYSA-N n-[4-[(3-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]-n'-[1-(4-methylphenyl)ethyl]butanediamide Chemical compound C=1C=C(C)C=CC=1C(C)NC(=O)CCC(=O)NC(CC1)CCC1(N(C)C)CC1=CC=CC(Cl)=C1 JXPDWYNLKGUGQB-UHFFFAOYSA-N 0.000 claims description 3
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000003367 polycyclic group Chemical group 0.000 claims description 3
- 150000003141 primary amines Chemical class 0.000 claims description 3
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000000335 thiazolyl group Chemical group 0.000 claims description 3
- 125000006704 (C5-C6) cycloalkyl group Chemical group 0.000 claims description 2
- 125000003852 3-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])* 0.000 claims description 2
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 2
- UPEIWIQESOIEGN-UHFFFAOYSA-N 4-(3,6-dihydro-2h-pyridin-1-yl)-n-[4-(dimethylamino)-4-[(4-methylphenyl)methyl]cyclohexyl]-4-oxobutanamide Chemical compound C1CC(NC(=O)CCC(=O)N2CC=CCC2)CCC1(N(C)C)CC1=CC=C(C)C=C1 UPEIWIQESOIEGN-UHFFFAOYSA-N 0.000 claims description 2
- NVMUFWSVKCVQTE-UHFFFAOYSA-N 4-(4-benzylpiperidin-1-yl)-n-[4-(dimethylamino)-4-thiophen-2-ylcyclohexyl]-4-oxobutanamide Chemical compound C1CC(N(C)C)(C=2SC=CC=2)CCC1NC(=O)CCC(=O)N(CC1)CCC1CC1=CC=CC=C1 NVMUFWSVKCVQTE-UHFFFAOYSA-N 0.000 claims description 2
- KDKSLISDSVTIOQ-UHFFFAOYSA-N 4-[4-(4-acetylphenyl)piperazin-1-yl]-n-[4-(dimethylamino)-4-[(4-methylphenyl)methyl]cyclohexyl]-4-oxobutanamide Chemical compound C1CC(NC(=O)CCC(=O)N2CCN(CC2)C=2C=CC(=CC=2)C(C)=O)CCC1(N(C)C)CC1=CC=C(C)C=C1 KDKSLISDSVTIOQ-UHFFFAOYSA-N 0.000 claims description 2
- HPUGEVLRLBFKQL-UHFFFAOYSA-N 4-[4-(4-chlorobenzoyl)piperidin-1-yl]-n-[4-[(3-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]-4-oxobutanamide Chemical compound C1CC(NC(=O)CCC(=O)N2CCC(CC2)C(=O)C=2C=CC(Cl)=CC=2)CCC1(N(C)C)CC1=CC=CC(Cl)=C1 HPUGEVLRLBFKQL-UHFFFAOYSA-N 0.000 claims description 2
- KYAHSKKDTMFBQK-UHFFFAOYSA-N 4-[4-(4-chlorophenyl)piperazin-1-yl]-n-[4-(dimethylamino)-4-[(3-methylphenyl)methyl]cyclohexyl]-4-oxobutanamide Chemical compound C1CC(NC(=O)CCC(=O)N2CCN(CC2)C=2C=CC(Cl)=CC=2)CCC1(N(C)C)CC1=CC=CC(C)=C1 KYAHSKKDTMFBQK-UHFFFAOYSA-N 0.000 claims description 2
- ZUQIFNPUSDCPSM-UHFFFAOYSA-N 4-[4-(4-chlorophenyl)piperazin-1-yl]-n-[4-(dimethylamino)-4-[(4-methylphenyl)methyl]cyclohexyl]-4-oxobutanamide Chemical compound C1CC(NC(=O)CCC(=O)N2CCN(CC2)C=2C=CC(Cl)=CC=2)CCC1(N(C)C)CC1=CC=C(C)C=C1 ZUQIFNPUSDCPSM-UHFFFAOYSA-N 0.000 claims description 2
- YBXYBODUAKFOQF-UHFFFAOYSA-N 4-[4-(5-chloro-2-methylphenyl)piperazin-1-yl]-n-[4-(dimethylamino)-4-[(3-methylphenyl)methyl]cyclohexyl]-4-oxobutanamide Chemical compound C1CC(NC(=O)CCC(=O)N2CCN(CC2)C=2C(=CC=C(Cl)C=2)C)CCC1(N(C)C)CC1=CC=CC(C)=C1 YBXYBODUAKFOQF-UHFFFAOYSA-N 0.000 claims description 2
- CEIZZGGZQDUGPI-UHFFFAOYSA-N 4-[4-(5-chloro-2-methylphenyl)piperazin-1-yl]-n-[4-[(3-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]-4-oxobutanamide Chemical compound C1CC(NC(=O)CCC(=O)N2CCN(CC2)C=2C(=CC=C(Cl)C=2)C)CCC1(N(C)C)CC1=CC=CC(Cl)=C1 CEIZZGGZQDUGPI-UHFFFAOYSA-N 0.000 claims description 2
- BJZMTOCGNYANHS-UHFFFAOYSA-N 4-[4-[(4-tert-butylphenyl)methyl]piperazin-1-yl]-n-[4-(dimethylamino)-4-phenylcyclohexyl]-4-oxobutanamide Chemical compound C1CC(N(C)C)(C=2C=CC=CC=2)CCC1NC(=O)CCC(=O)N(CC1)CCN1CC1=CC=C(C(C)(C)C)C=C1 BJZMTOCGNYANHS-UHFFFAOYSA-N 0.000 claims description 2
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims description 2
- 125000006181 4-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- GABVZMHCFBLNMP-UHFFFAOYSA-N N'-[1-(1-adamantyl)ethyl]-N-[4-(dimethylamino)-4-thiophen-2-ylcyclohexyl]pentanediamide Chemical compound C1C(C2)CC(C3)CC2CC13C(C)NC(=O)CCCC(=O)NC(CC1)CCC1(N(C)C)C1=CC=CS1 GABVZMHCFBLNMP-UHFFFAOYSA-N 0.000 claims description 2
- AZZFGLNZJCMZBA-UHFFFAOYSA-N N'-[4-(dimethylamino)-4-thiophen-2-ylcyclohexyl]-N-(2,2-diphenylpropyl)pentanediamide Chemical compound C1CC(N(C)C)(C=2SC=CC=2)CCC1NC(=O)CCCC(=O)NCC(C)(C=1C=CC=CC=1)C1=CC=CC=C1 AZZFGLNZJCMZBA-UHFFFAOYSA-N 0.000 claims description 2
- VKGGDQZXHYWQRZ-UHFFFAOYSA-N N'-[4-(dimethylamino)-4-thiophen-2-ylcyclohexyl]-N-(3,3-diphenylpropyl)pentanediamide Chemical compound C1CC(N(C)C)(C=2SC=CC=2)CCC1NC(=O)CCCC(=O)NCCC(C=1C=CC=CC=1)C1=CC=CC=C1 VKGGDQZXHYWQRZ-UHFFFAOYSA-N 0.000 claims description 2
- HHBAOLKIIPVQLF-UHFFFAOYSA-N N-[(3-bromophenyl)methyl]-N'-[4-(dimethylamino)-4-thiophen-2-ylcyclohexyl]pentanediamide Chemical compound C1CC(N(C)C)(C=2SC=CC=2)CCC1NC(=O)CCCC(=O)NCC1=CC=CC(Br)=C1 HHBAOLKIIPVQLF-UHFFFAOYSA-N 0.000 claims description 2
- FRKREZPYOXJLNF-UHFFFAOYSA-N N-[(3-chlorophenyl)methyl]-N'-[4-(dimethylamino)-4-thiophen-2-ylcyclohexyl]pentanediamide Chemical compound C1CC(N(C)C)(C=2SC=CC=2)CCC1NC(=O)CCCC(=O)NCC1=CC=CC(Cl)=C1 FRKREZPYOXJLNF-UHFFFAOYSA-N 0.000 claims description 2
- DCQODIUCWRTWNO-UHFFFAOYSA-N N-[4-benzyl-4-(dimethylamino)cyclohexyl]-N'-(4-methylpentan-2-yl)pentanediamide Chemical compound C1CC(NC(=O)CCCC(=O)NC(C)CC(C)C)CCC1(N(C)C)CC1=CC=CC=C1 DCQODIUCWRTWNO-UHFFFAOYSA-N 0.000 claims description 2
- 125000005605 benzo group Chemical group 0.000 claims description 2
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
- GFKSAPVGRHTBLO-UHFFFAOYSA-N benzyl 2-[[5-[[4-(dimethylamino)-4-thiophen-2-ylcyclohexyl]amino]-5-oxopentanoyl]amino]-4-methylpentanoate Chemical compound C=1C=CC=CC=1COC(=O)C(CC(C)C)NC(=O)CCCC(=O)NC(CC1)CCC1(N(C)C)C1=CC=CS1 GFKSAPVGRHTBLO-UHFFFAOYSA-N 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- 125000001070 dihydroindolyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- SHKNFKYIDVFGCD-UHFFFAOYSA-N ethyl 2-[[4-[[4-[(4-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]amino]-4-oxobutanoyl]amino]propanoate Chemical compound C1CC(NC(=O)CCC(=O)NC(C)C(=O)OCC)CCC1(N(C)C)CC1=CC=C(Cl)C=C1 SHKNFKYIDVFGCD-UHFFFAOYSA-N 0.000 claims description 2
- BFJVKOVCQODSCO-UHFFFAOYSA-N ethyl 4-[4-[[4-[(3-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]amino]-4-oxobutanoyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCN1C(=O)CCC(=O)NC1CCC(CC=2C=C(Cl)C=CC=2)(N(C)C)CC1 BFJVKOVCQODSCO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- BZSOALZSMIFNRV-UHFFFAOYSA-N n'-(2,3-dihydro-1h-inden-1-yl)-n-[4-(dimethylamino)-4-[(3-methylphenyl)methyl]cyclohexyl]butanediamide Chemical compound C1CC(NC(=O)CCC(=O)NC2C3=CC=CC=C3CC2)CCC1(N(C)C)CC1=CC=CC(C)=C1 BZSOALZSMIFNRV-UHFFFAOYSA-N 0.000 claims description 2
- NVAYHQISYYAFNG-UHFFFAOYSA-N n'-(2,3-dihydro-1h-inden-1-yl)-n-[4-(dimethylamino)-4-thiophen-2-ylcyclohexyl]pentanediamide Chemical compound C1CC(NC(=O)CCCC(=O)NC2C3=CC=CC=C3CC2)CCC1(N(C)C)C1=CC=CS1 NVAYHQISYYAFNG-UHFFFAOYSA-N 0.000 claims description 2
- VPDCPDFXPDYGGS-UHFFFAOYSA-N n'-(4-benzyl-4-morpholin-4-ylcyclohexyl)-n-(2-morpholin-4-ylethyl)butanediamide Chemical compound C1COCCN1CCNC(=O)CCC(=O)NC(CC1)CCC1(N1CCOCC1)CC1=CC=CC=C1 VPDCPDFXPDYGGS-UHFFFAOYSA-N 0.000 claims description 2
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- RTPVTBIRORKJLE-UHFFFAOYSA-N n'-[1-[(2,6-dichlorophenyl)methyl]pyrrolidin-3-yl]-n-[4-(dimethylamino)-4-[(4-methylphenyl)methyl]cyclohexyl]butanediamide Chemical compound C1CC(NC(=O)CCC(=O)NC2CN(CC=3C(=CC=CC=3Cl)Cl)CC2)CCC1(N(C)C)CC1=CC=C(C)C=C1 RTPVTBIRORKJLE-UHFFFAOYSA-N 0.000 claims description 2
- JXCCQRLAPAKYAR-UHFFFAOYSA-N n'-[2-(3,4-dimethoxyphenyl)ethyl]-n-[4-(dimethylamino)-4-[(3-methylphenyl)methyl]cyclohexyl]-n'-methylbutanediamide Chemical compound C1=C(OC)C(OC)=CC=C1CCN(C)C(=O)CCC(=O)NC1CCC(CC=2C=C(C)C=CC=2)(N(C)C)CC1 JXCCQRLAPAKYAR-UHFFFAOYSA-N 0.000 claims description 2
- ZFZYXHILMRRQHO-UHFFFAOYSA-N n'-[4-(diethoxyphosphorylmethyl)phenyl]-n-[4-(dimethylamino)-4-[(3-methylphenyl)methyl]cyclohexyl]butanediamide Chemical compound C1=CC(CP(=O)(OCC)OCC)=CC=C1NC(=O)CCC(=O)NC1CCC(CC=2C=C(C)C=CC=2)(N(C)C)CC1 ZFZYXHILMRRQHO-UHFFFAOYSA-N 0.000 claims description 2
- UJXSSHKRPFYPKA-UHFFFAOYSA-N n'-[4-(dimethylamino)-4-[(3-methylphenyl)methyl]cyclohexyl]-n-(2-thiophen-2-ylethyl)butanediamide Chemical compound C1CC(NC(=O)CCC(=O)NCCC=2SC=CC=2)CCC1(N(C)C)CC1=CC=CC(C)=C1 UJXSSHKRPFYPKA-UHFFFAOYSA-N 0.000 claims description 2
- PUYXRGMYGDXVLH-UHFFFAOYSA-N n'-[4-(dimethylamino)-4-[(3-methylphenyl)methyl]cyclohexyl]-n-[(2,3-dimethylphenyl)methyl]butanediamide Chemical compound C1CC(NC(=O)CCC(=O)NCC=2C(=C(C)C=CC=2)C)CCC1(N(C)C)CC1=CC=CC(C)=C1 PUYXRGMYGDXVLH-UHFFFAOYSA-N 0.000 claims description 2
- DTXOQURLLYEQCY-UHFFFAOYSA-N n'-[4-(dimethylamino)-4-[(3-methylphenyl)methyl]cyclohexyl]-n-[2-(2-ethoxyphenyl)ethyl]butanediamide Chemical compound CCOC1=CC=CC=C1CCNC(=O)CCC(=O)NC1CCC(CC=2C=C(C)C=CC=2)(N(C)C)CC1 DTXOQURLLYEQCY-UHFFFAOYSA-N 0.000 claims description 2
- JJNKIYUKXVRQAJ-UHFFFAOYSA-N n'-[4-(dimethylamino)-4-[(3-methylphenyl)methyl]cyclohexyl]-n-[2-(4-fluorophenyl)ethyl]butanediamide Chemical compound C1CC(NC(=O)CCC(=O)NCCC=2C=CC(F)=CC=2)CCC1(N(C)C)CC1=CC=CC(C)=C1 JJNKIYUKXVRQAJ-UHFFFAOYSA-N 0.000 claims description 2
- APOJAVQDRSKHIP-UHFFFAOYSA-N n'-[4-(dimethylamino)-4-[(4-methylphenyl)methyl]cyclohexyl]-n-(oxolan-2-ylmethyl)butanediamide Chemical compound C1CC(NC(=O)CCC(=O)NCC2OCCC2)CCC1(N(C)C)CC1=CC=C(C)C=C1 APOJAVQDRSKHIP-UHFFFAOYSA-N 0.000 claims description 2
- CXIFYUKMMHWCIO-UHFFFAOYSA-N n'-[4-(dimethylamino)-4-phenylcyclohexyl]-n-[2-(3-fluorophenyl)ethyl]butanediamide Chemical compound C1CC(N(C)C)(C=2C=CC=CC=2)CCC1NC(=O)CCC(=O)NCCC1=CC=CC(F)=C1 CXIFYUKMMHWCIO-UHFFFAOYSA-N 0.000 claims description 2
- BPFXGBQUIPDJIK-UHFFFAOYSA-N n'-[4-(dimethylamino)-4-thiophen-2-ylcyclohexyl]-n-[3-(n-methylanilino)propyl]butanediamide Chemical compound C1CC(N(C)C)(C=2SC=CC=2)CCC1NC(=O)CCC(=O)NCCCN(C)C1=CC=CC=C1 BPFXGBQUIPDJIK-UHFFFAOYSA-N 0.000 claims description 2
- CZSPNLZGJNSGBW-UHFFFAOYSA-N n'-[4-[(3-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]-n-(2-phenylethyl)butanediamide Chemical compound C1CC(NC(=O)CCC(=O)NCCC=2C=CC=CC=2)CCC1(N(C)C)CC1=CC=CC(Cl)=C1 CZSPNLZGJNSGBW-UHFFFAOYSA-N 0.000 claims description 2
- HVPQURZCBRRTKI-UHFFFAOYSA-N n'-[4-[(3-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]-n-(2-pyridin-2-ylethyl)butanediamide Chemical compound C1CC(NC(=O)CCC(=O)NCCC=2N=CC=CC=2)CCC1(N(C)C)CC1=CC=CC(Cl)=C1 HVPQURZCBRRTKI-UHFFFAOYSA-N 0.000 claims description 2
- DUPRJWWXHZXKAR-UHFFFAOYSA-N n'-[4-[(3-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]-n-(2-thiophen-2-ylethyl)butanediamide Chemical compound C1CC(NC(=O)CCC(=O)NCCC=2SC=CC=2)CCC1(N(C)C)CC1=CC=CC(Cl)=C1 DUPRJWWXHZXKAR-UHFFFAOYSA-N 0.000 claims description 2
- INMFDXLHVLUHRA-UHFFFAOYSA-N n'-[4-[(3-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]-n-[(3,4-difluorophenyl)methyl]butanediamide Chemical compound C1CC(NC(=O)CCC(=O)NCC=2C=C(F)C(F)=CC=2)CCC1(N(C)C)CC1=CC=CC(Cl)=C1 INMFDXLHVLUHRA-UHFFFAOYSA-N 0.000 claims description 2
- ZGIRRPHVVJYWNA-UHFFFAOYSA-N n'-[4-[(3-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]-n-[2-[(2,6-dichlorophenyl)methylsulfanyl]ethyl]butanediamide Chemical compound C1CC(NC(=O)CCC(=O)NCCSCC=2C(=CC=CC=2Cl)Cl)CCC1(N(C)C)CC1=CC=CC(Cl)=C1 ZGIRRPHVVJYWNA-UHFFFAOYSA-N 0.000 claims description 2
- ZITGJDJYJQRUIK-UHFFFAOYSA-N n'-[4-[(3-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]-n-[3-(n-methylanilino)propyl]butanediamide Chemical compound C1CC(NC(=O)CCC(=O)NCCCN(C)C=2C=CC=CC=2)CCC1(N(C)C)CC1=CC=CC(Cl)=C1 ZITGJDJYJQRUIK-UHFFFAOYSA-N 0.000 claims description 2
- ZCLKDHAKNDPSCL-UHFFFAOYSA-N n'-[4-[(4-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]-n'-[2-(1h-indol-3-yl)ethyl]butanediamide Chemical compound C1CC(N(CCC=2C3=CC=CC=C3NC=2)C(=O)CCC(N)=O)CCC1(N(C)C)CC1=CC=C(Cl)C=C1 ZCLKDHAKNDPSCL-UHFFFAOYSA-N 0.000 claims description 2
- SWWRZPPTVNYSEE-UHFFFAOYSA-N n'-[4-[(4-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]-n-(3-methoxypropyl)butanediamide Chemical compound C1CC(NC(=O)CCC(=O)NCCCOC)CCC1(N(C)C)CC1=CC=C(Cl)C=C1 SWWRZPPTVNYSEE-UHFFFAOYSA-N 0.000 claims description 2
- WLLVRJWRAXBDKZ-UHFFFAOYSA-N n'-[4-[(4-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]-n-(naphthalen-1-ylmethyl)butanediamide Chemical compound C1CC(NC(=O)CCC(=O)NCC=2C3=CC=CC=C3C=CC=2)CCC1(N(C)C)CC1=CC=C(Cl)C=C1 WLLVRJWRAXBDKZ-UHFFFAOYSA-N 0.000 claims description 2
- ASZBFHALYJAPFH-UHFFFAOYSA-N n'-[4-[(4-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]-n-[(2-methylphenyl)methyl]butanediamide Chemical compound C1CC(NC(=O)CCC(=O)NCC=2C(=CC=CC=2)C)CCC1(N(C)C)CC1=CC=C(Cl)C=C1 ASZBFHALYJAPFH-UHFFFAOYSA-N 0.000 claims description 2
- PSXHIFCLUFOYAG-UHFFFAOYSA-N n'-[4-[(4-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]-n-[2-(2-fluorophenyl)ethyl]butanediamide Chemical compound C1CC(NC(=O)CCC(=O)NCCC=2C(=CC=CC=2)F)CCC1(N(C)C)CC1=CC=C(Cl)C=C1 PSXHIFCLUFOYAG-UHFFFAOYSA-N 0.000 claims description 2
- YSCZVLJIHGRINB-UHFFFAOYSA-N n'-[4-[(4-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]-n-[2-(3-fluorophenyl)ethyl]butanediamide Chemical compound C1CC(NC(=O)CCC(=O)NCCC=2C=C(F)C=CC=2)CCC1(N(C)C)CC1=CC=C(Cl)C=C1 YSCZVLJIHGRINB-UHFFFAOYSA-N 0.000 claims description 2
- SESWGKNDJXBJFS-UHFFFAOYSA-N n'-benzhydryl-n-[4-[(3-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]butanediamide Chemical compound C1CC(NC(=O)CCC(=O)NC(C=2C=CC=CC=2)C=2C=CC=CC=2)CCC1(N(C)C)CC1=CC=CC(Cl)=C1 SESWGKNDJXBJFS-UHFFFAOYSA-N 0.000 claims description 2
- QATKCGWMFLSEHC-UHFFFAOYSA-N n'-benzyl-n'-(2-cyanoethyl)-n-[4-(dimethylamino)-4-[(4-methylphenyl)methyl]cyclohexyl]butanediamide Chemical compound C1CC(NC(=O)CCC(=O)N(CCC#N)CC=2C=CC=CC=2)CCC1(N(C)C)CC1=CC=C(C)C=C1 QATKCGWMFLSEHC-UHFFFAOYSA-N 0.000 claims description 2
- MPOFLRHOOCWNPT-UHFFFAOYSA-N n'-benzyl-n-[4-(dimethylamino)-4-[(3-methylphenyl)methyl]cyclohexyl]-n'-methylbutanediamide Chemical compound C1CC(NC(=O)CCC(=O)N(C)CC=2C=CC=CC=2)CCC1(N(C)C)CC1=CC=CC(C)=C1 MPOFLRHOOCWNPT-UHFFFAOYSA-N 0.000 claims description 2
- XHGRUPWFGSOGBV-UHFFFAOYSA-N n'-benzyl-n-[4-(dimethylamino)-4-phenylcyclohexyl]-n'-(2-phenylethyl)butanediamide Chemical compound C1CC(N(C)C)(C=2C=CC=CC=2)CCC1NC(=O)CCC(=O)N(CC=1C=CC=CC=1)CCC1=CC=CC=C1 XHGRUPWFGSOGBV-UHFFFAOYSA-N 0.000 claims description 2
- WPTRPBSPVWIYRF-UHFFFAOYSA-N n'-benzyl-n-[4-[(3-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]-n'-(2-cyanoethyl)butanediamide Chemical compound C1CC(NC(=O)CCC(=O)N(CCC#N)CC=2C=CC=CC=2)CCC1(N(C)C)CC1=CC=CC(Cl)=C1 WPTRPBSPVWIYRF-UHFFFAOYSA-N 0.000 claims description 2
- GRDNCWJULHPUJC-UHFFFAOYSA-N n-(1-adamantylmethyl)-n'-(4-benzyl-4-morpholin-4-ylcyclohexyl)butanediamide Chemical compound C1C(C2)CC(C3)CC2CC13CNC(=O)CCC(=O)NC(CC1)CCC1(N1CCOCC1)CC1=CC=CC=C1 GRDNCWJULHPUJC-UHFFFAOYSA-N 0.000 claims description 2
- GLIFUARQRMYBLF-UHFFFAOYSA-N n-(4-benzyl-4-morpholin-4-ylcyclohexyl)-4-oxo-4-[2-(pyrrolidin-1-ylmethyl)pyrrolidin-1-yl]butanamide Chemical compound C1CC(CC=2C=CC=CC=2)(N2CCOCC2)CCC1NC(=O)CCC(=O)N1CCCC1CN1CCCC1 GLIFUARQRMYBLF-UHFFFAOYSA-N 0.000 claims description 2
- XXDXRBOWSDLBGR-UHFFFAOYSA-N n-(4-benzyl-4-morpholin-4-ylcyclohexyl)-n'-(2,3-dihydro-1h-inden-1-yl)butanediamide Chemical compound C1CC2=CC=CC=C2C1NC(=O)CCC(=O)NC(CC1)CCC1(N1CCOCC1)CC1=CC=CC=C1 XXDXRBOWSDLBGR-UHFFFAOYSA-N 0.000 claims description 2
- GGXQLMMHKSLLOS-UHFFFAOYSA-N n-[(2-chloro-6-methylphenyl)methyl]-n'-[4-[(3-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]butanediamide Chemical compound C1CC(NC(=O)CCC(=O)NCC=2C(=CC=CC=2C)Cl)CCC1(N(C)C)CC1=CC=CC(Cl)=C1 GGXQLMMHKSLLOS-UHFFFAOYSA-N 0.000 claims description 2
- SXAOMKDJBZSXRL-UHFFFAOYSA-N n-[(3-bromophenyl)methyl]-n'-[4-(dimethylamino)-4-[(3-methylphenyl)methyl]cyclohexyl]butanediamide Chemical compound C1CC(NC(=O)CCC(=O)NCC=2C=C(Br)C=CC=2)CCC1(N(C)C)CC1=CC=CC(C)=C1 SXAOMKDJBZSXRL-UHFFFAOYSA-N 0.000 claims description 2
- WACHWIUPFWHAFQ-UHFFFAOYSA-N n-[2-(2-chlorophenyl)ethyl]-n'-[4-(dimethylamino)-4-phenylcyclohexyl]butanediamide Chemical compound C1CC(N(C)C)(C=2C=CC=CC=2)CCC1NC(=O)CCC(=O)NCCC1=CC=CC=C1Cl WACHWIUPFWHAFQ-UHFFFAOYSA-N 0.000 claims description 2
- DXILTXIKWMGREV-UHFFFAOYSA-N n-[2-(3,4-dichlorophenyl)ethyl]-n'-[4-(dimethylamino)-4-[(3-methylphenyl)methyl]cyclohexyl]butanediamide Chemical compound C1CC(NC(=O)CCC(=O)NCCC=2C=C(Cl)C(Cl)=CC=2)CCC1(N(C)C)CC1=CC=CC(C)=C1 DXILTXIKWMGREV-UHFFFAOYSA-N 0.000 claims description 2
- WNGMBWFBHPWENB-UHFFFAOYSA-N n-[2-(3-chlorophenyl)ethyl]-n'-[4-[(3-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]butanediamide Chemical compound C1CC(NC(=O)CCC(=O)NCCC=2C=C(Cl)C=CC=2)CCC1(N(C)C)CC1=CC=CC(Cl)=C1 WNGMBWFBHPWENB-UHFFFAOYSA-N 0.000 claims description 2
- MGZMUMCFSFOPHM-UHFFFAOYSA-N n-[2-[(2,6-dichlorophenyl)methylsulfanyl]ethyl]-n'-[4-(dimethylamino)-4-[(4-methylphenyl)methyl]cyclohexyl]butanediamide Chemical compound C1CC(NC(=O)CCC(=O)NCCSCC=2C(=CC=CC=2Cl)Cl)CCC1(N(C)C)CC1=CC=C(C)C=C1 MGZMUMCFSFOPHM-UHFFFAOYSA-N 0.000 claims description 2
- DGTAIVCXILDHEO-UHFFFAOYSA-N n-[4-(dimethylamino)-4-[(3-methylphenyl)methyl]cyclohexyl]-4-(8-fluoro-1,3,4,5-tetrahydropyrido[4,3-b]indol-2-yl)-4-oxobutanamide Chemical compound C1CC(NC(=O)CCC(=O)N2CC=3C4=CC(F)=CC=C4NC=3CC2)CCC1(N(C)C)CC1=CC=CC(C)=C1 DGTAIVCXILDHEO-UHFFFAOYSA-N 0.000 claims description 2
- SEVSYNLBHWMXLH-UHFFFAOYSA-N n-[4-(dimethylamino)-4-[(3-methylphenyl)methyl]cyclohexyl]-4-[4-[(3-fluoro-4-methoxyphenyl)methyl]piperazin-1-yl]-4-oxobutanamide Chemical compound C1=C(F)C(OC)=CC=C1CN1CCN(C(=O)CCC(=O)NC2CCC(CC=3C=C(C)C=CC=3)(CC2)N(C)C)CC1 SEVSYNLBHWMXLH-UHFFFAOYSA-N 0.000 claims description 2
- CZQVZVSUGLAUCM-UHFFFAOYSA-N n-[4-(dimethylamino)-4-[(3-methylphenyl)methyl]cyclohexyl]-4-oxo-4-(4-phenyl-3,6-dihydro-2h-pyridin-1-yl)butanamide Chemical compound C1CC(NC(=O)CCC(=O)N2CC=C(CC2)C=2C=CC=CC=2)CCC1(N(C)C)CC1=CC=CC(C)=C1 CZQVZVSUGLAUCM-UHFFFAOYSA-N 0.000 claims description 2
- XYNJGFVWZRPTOB-UHFFFAOYSA-N n-[4-(dimethylamino)-4-[(3-methylphenyl)methyl]cyclohexyl]-n'-(4-phenylbutan-2-yl)butanediamide Chemical compound C1CC(CC=2C=C(C)C=CC=2)(N(C)C)CCC1NC(=O)CCC(=O)NC(C)CCC1=CC=CC=C1 XYNJGFVWZRPTOB-UHFFFAOYSA-N 0.000 claims description 2
- MCGWJJNDFGNBOQ-UHFFFAOYSA-N n-[4-(dimethylamino)-4-[(3-methylphenyl)methyl]cyclohexyl]-n'-[(2-fluorophenyl)methyl]-n'-(furan-2-ylmethyl)butanediamide Chemical compound C1CC(NC(=O)CCC(=O)N(CC=2OC=CC=2)CC=2C(=CC=CC=2)F)CCC1(N(C)C)CC1=CC=CC(C)=C1 MCGWJJNDFGNBOQ-UHFFFAOYSA-N 0.000 claims description 2
- RHSKBVHFPHRNAD-UHFFFAOYSA-N n-[4-(dimethylamino)-4-[(4-methylphenyl)methyl]cyclohexyl]-4-[4-(4-methoxyphenyl)piperazin-1-yl]-4-oxobutanamide Chemical compound C1=CC(OC)=CC=C1N1CCN(C(=O)CCC(=O)NC2CCC(CC=3C=CC(C)=CC=3)(CC2)N(C)C)CC1 RHSKBVHFPHRNAD-UHFFFAOYSA-N 0.000 claims description 2
- JRSZVJTWIGCBCR-UHFFFAOYSA-N n-[4-(dimethylamino)-4-[(4-methylphenyl)methyl]cyclohexyl]-4-[4-(5-methylpyrazine-2-carbonyl)piperazin-1-yl]-4-oxobutanamide Chemical compound C1CC(NC(=O)CCC(=O)N2CCN(CC2)C(=O)C=2N=CC(C)=NC=2)CCC1(N(C)C)CC1=CC=C(C)C=C1 JRSZVJTWIGCBCR-UHFFFAOYSA-N 0.000 claims description 2
- QNPANRMTHVWYPI-UHFFFAOYSA-N n-[4-(dimethylamino)-4-[(4-methylphenyl)methyl]cyclohexyl]-4-[4-[(7-methoxy-1,3-benzodioxol-5-yl)methyl]piperazin-1-yl]-4-oxobutanamide Chemical compound C=1C=2OCOC=2C(OC)=CC=1CN(CC1)CCN1C(=O)CCC(=O)NC(CC1)CCC1(N(C)C)CC1=CC=C(C)C=C1 QNPANRMTHVWYPI-UHFFFAOYSA-N 0.000 claims description 2
- YSEHYFDTELTWMD-UHFFFAOYSA-N n-[4-(dimethylamino)-4-[(4-methylphenyl)methyl]cyclohexyl]-4-oxo-4-(4-phenyl-3,6-dihydro-2h-pyridin-1-yl)butanamide Chemical compound C1CC(NC(=O)CCC(=O)N2CC=C(CC2)C=2C=CC=CC=2)CCC1(N(C)C)CC1=CC=C(C)C=C1 YSEHYFDTELTWMD-UHFFFAOYSA-N 0.000 claims description 2
- CZBGPAHFPVSIKQ-UHFFFAOYSA-N n-[4-(dimethylamino)-4-[(4-methylphenyl)methyl]cyclohexyl]-4-oxo-4-[4-[[(2,2,2-trifluoroacetyl)amino]methyl]piperidin-1-yl]butanamide Chemical compound C1CC(NC(=O)CCC(=O)N2CCC(CNC(=O)C(F)(F)F)CC2)CCC1(N(C)C)CC1=CC=C(C)C=C1 CZBGPAHFPVSIKQ-UHFFFAOYSA-N 0.000 claims description 2
- PWWPFFXFYWWKNC-UHFFFAOYSA-N n-[4-(dimethylamino)-4-[(4-methylphenyl)methyl]cyclohexyl]-n'-[2-(1h-indol-3-yl)ethyl]-n'-methylbutanediamide Chemical compound C1CC(NC(=O)CCC(=O)N(C)CCC=2C3=CC=CC=C3NC=2)CCC1(N(C)C)CC1=CC=C(C)C=C1 PWWPFFXFYWWKNC-UHFFFAOYSA-N 0.000 claims description 2
- XYJJPLNPZYLVOY-UHFFFAOYSA-N n-[4-(dimethylamino)-4-[(4-methylphenyl)methyl]cyclohexyl]-n'-methyl-n'-[2-[(2,2,2-trifluoroacetyl)amino]ethyl]butanediamide Chemical compound C=1C=C(C)C=CC=1CC1(N(C)C)CCC(NC(=O)CCC(=O)N(C)CCNC(=O)C(F)(F)F)CC1 XYJJPLNPZYLVOY-UHFFFAOYSA-N 0.000 claims description 2
- NKLIALXVBULHNW-UHFFFAOYSA-N n-[4-[(3-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]-4-(4-methylpiperidin-1-yl)-4-oxobutanamide Chemical compound C1CC(C)CCN1C(=O)CCC(=O)NC1CCC(CC=2C=C(Cl)C=CC=2)(N(C)C)CC1 NKLIALXVBULHNW-UHFFFAOYSA-N 0.000 claims description 2
- GVYRHRURIQNBLK-UHFFFAOYSA-N n-[4-[(3-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]-4-(8-fluoro-1,3,4,5-tetrahydropyrido[4,3-b]indol-2-yl)-4-oxobutanamide Chemical compound C1CC(NC(=O)CCC(=O)N2CC=3C4=CC(F)=CC=C4NC=3CC2)CCC1(N(C)C)CC1=CC=CC(Cl)=C1 GVYRHRURIQNBLK-UHFFFAOYSA-N 0.000 claims description 2
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- CYUZEVDRERQCKR-UHFFFAOYSA-N N-[4-(dimethylamino)-4-thiophen-2-ylcyclohexyl]-N'-(2-phenylmethoxycyclopentyl)pentanediamide Chemical compound C1CC(N(C)C)(C=2SC=CC=2)CCC1NC(=O)CCCC(=O)NC1CCCC1OCC1=CC=CC=C1 CYUZEVDRERQCKR-UHFFFAOYSA-N 0.000 claims 1
- DNODHIVGTZNHEV-UHFFFAOYSA-N N-[4-(dimethylamino)-4-thiophen-2-ylcyclohexyl]-N'-(3-phenoxyphenyl)pentanediamide Chemical compound C1CC(N(C)C)(C=2SC=CC=2)CCC1NC(=O)CCCC(=O)NC(C=1)=CC=CC=1OC1=CC=CC=C1 DNODHIVGTZNHEV-UHFFFAOYSA-N 0.000 claims 1
- ZWKYYKWXGMIVCQ-UHFFFAOYSA-N N-[4-(dimethylamino)-4-thiophen-2-ylcyclohexyl]-N'-(4-phenylbutan-2-yl)pentanediamide Chemical compound C1CC(C=2SC=CC=2)(N(C)C)CCC1NC(=O)CCCC(=O)NC(C)CCC1=CC=CC=C1 ZWKYYKWXGMIVCQ-UHFFFAOYSA-N 0.000 claims 1
- JMCKQSWUBPPOPK-UHFFFAOYSA-N N-[4-(dimethylamino)-4-thiophen-2-ylcyclohexyl]-N'-(4-phenylmethoxyphenyl)pentanediamide Chemical compound C1CC(N(C)C)(C=2SC=CC=2)CCC1NC(=O)CCCC(=O)NC(C=C1)=CC=C1OCC1=CC=CC=C1 JMCKQSWUBPPOPK-UHFFFAOYSA-N 0.000 claims 1
- WIEMXZHKYPJHJK-UHFFFAOYSA-N N-[4-benzyl-4-(dimethylamino)cyclohexyl]-5-[4-[(7-methoxy-1,3-benzodioxol-5-yl)methyl]piperazin-1-yl]-5-oxopentanamide Chemical compound C(C1=CC=CC=C1)C1(CCC(CC1)NC(CCCC(=O)N1CCN(CC1)CC1=CC2=C(OCO2)C(=C1)OC)=O)N(C)C WIEMXZHKYPJHJK-UHFFFAOYSA-N 0.000 claims 1
- IDVPDEFEPHJEDR-UHFFFAOYSA-N N-[4-benzyl-4-(dimethylamino)cyclohexyl]-N'-(1,2,3,4-tetrahydronaphthalen-1-yl)pentanediamide Chemical compound C1CC(NC(=O)CCCC(=O)NC2C3=CC=CC=C3CCC2)CCC1(N(C)C)CC1=CC=CC=C1 IDVPDEFEPHJEDR-UHFFFAOYSA-N 0.000 claims 1
- RIJDNICRSYCZBI-UHFFFAOYSA-N N-[4-benzyl-4-(dimethylamino)cyclohexyl]-N'-[1-[(2,6-dichlorophenyl)methyl]pyrrolidin-3-yl]pentanediamide Chemical compound C1CC(NC(=O)CCCC(=O)NC2CN(CC=3C(=CC=CC=3Cl)Cl)CC2)CCC1(N(C)C)CC1=CC=CC=C1 RIJDNICRSYCZBI-UHFFFAOYSA-N 0.000 claims 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 claims 1
- COCQEOKAISAZEW-UHFFFAOYSA-N benzyl 2-[[4-[[4-(dimethylamino)-4-thiophen-2-ylcyclohexyl]amino]-4-oxobutanoyl]amino]propanoate Chemical compound C=1C=CC=CC=1COC(=O)C(C)NC(=O)CCC(=O)NC(CC1)CCC1(N(C)C)C1=CC=CS1 COCQEOKAISAZEW-UHFFFAOYSA-N 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
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- LCXAUEPUJJGPDI-UHFFFAOYSA-N ethyl 3-(4-chlorophenyl)-2-[[5-[[4-(dimethylamino)-4-thiophen-2-ylcyclohexyl]amino]-5-oxopentanoyl]amino]propanoate Chemical compound C1CC(C=2SC=CC=2)(N(C)C)CCC1NC(=O)CCCC(=O)NC(C(=O)OCC)CC1=CC=C(Cl)C=C1 LCXAUEPUJJGPDI-UHFFFAOYSA-N 0.000 claims 1
- PYQSVUARSGFITK-UHFFFAOYSA-N methyl 3-(4-chlorophenyl)-2-[[4-[[4-(dimethylamino)-4-[(4-methylphenyl)methyl]cyclohexyl]amino]-4-oxobutanoyl]amino]propanoate Chemical compound C1CC(CC=2C=CC(C)=CC=2)(N(C)C)CCC1NC(=O)CCC(=O)NC(C(=O)OC)CC1=CC=C(Cl)C=C1 PYQSVUARSGFITK-UHFFFAOYSA-N 0.000 claims 1
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- ZQRDGRNRNUYDEV-UHFFFAOYSA-N n'-(4-benzyl-4-morpholin-4-ylcyclohexyl)-n-[(2-chloro-6-methylphenyl)methyl]butanediamide Chemical compound CC1=CC=CC(Cl)=C1CNC(=O)CCC(=O)NC1CCC(CC=2C=CC=CC=2)(N2CCOCC2)CC1 ZQRDGRNRNUYDEV-UHFFFAOYSA-N 0.000 claims 1
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- NKRYHECEGOVBGQ-UHFFFAOYSA-N n'-(4-benzyl-4-morpholin-4-ylcyclohexyl)-n-[2-(3-methoxyphenyl)ethyl]butanediamide Chemical compound COC1=CC=CC(CCNC(=O)CCC(=O)NC2CCC(CC=3C=CC=CC=3)(CC2)N2CCOCC2)=C1 NKRYHECEGOVBGQ-UHFFFAOYSA-N 0.000 claims 1
- ZQOQJUVTNNTFSB-UHFFFAOYSA-N n'-(4-benzyl-4-morpholin-4-ylcyclohexyl)-n-[2-(5-methoxy-1h-indol-3-yl)ethyl]butanediamide Chemical compound C12=CC(OC)=CC=C2NC=C1CCNC(=O)CCC(=O)NC(CC1)CCC1(N1CCOCC1)CC1=CC=CC=C1 ZQOQJUVTNNTFSB-UHFFFAOYSA-N 0.000 claims 1
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- ZPJBHXUJIOGYPT-UHFFFAOYSA-N n'-[4-(dimethylamino)-4-[(3-methylphenyl)methyl]cyclohexyl]-n-[[4-fluoro-2-(trifluoromethyl)phenyl]methyl]butanediamide Chemical compound C1CC(NC(=O)CCC(=O)NCC=2C(=CC(F)=CC=2)C(F)(F)F)CCC1(N(C)C)CC1=CC=CC(C)=C1 ZPJBHXUJIOGYPT-UHFFFAOYSA-N 0.000 claims 1
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- WOMSPBSSXLXAQQ-UHFFFAOYSA-N n'-[4-(dimethylamino)-4-thiophen-2-ylcyclohexyl]-n-[[3-(trifluoromethoxy)phenyl]methyl]pentanediamide Chemical compound C1CC(N(C)C)(C=2SC=CC=2)CCC1NC(=O)CCCC(=O)NCC1=CC=CC(OC(F)(F)F)=C1 WOMSPBSSXLXAQQ-UHFFFAOYSA-N 0.000 claims 1
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- JLVLNWLPOWKBAM-UHFFFAOYSA-N n'-[4-[(3-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]-n-(3-phenylpropyl)butanediamide Chemical compound C1CC(NC(=O)CCC(=O)NCCCC=2C=CC=CC=2)CCC1(N(C)C)CC1=CC=CC(Cl)=C1 JLVLNWLPOWKBAM-UHFFFAOYSA-N 0.000 claims 1
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- GKAWYEOBECKPBV-UHFFFAOYSA-N n'-[4-[(3-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]-n-(oxolan-2-ylmethyl)butanediamide Chemical compound C1CC(NC(=O)CCC(=O)NCC2OCCC2)CCC1(N(C)C)CC1=CC=CC(Cl)=C1 GKAWYEOBECKPBV-UHFFFAOYSA-N 0.000 claims 1
- YFLCAICXMPAALB-UHFFFAOYSA-N n'-[4-[(3-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]-n-(pyridin-2-ylmethyl)butanediamide Chemical compound C1CC(NC(=O)CCC(=O)NCC=2N=CC=CC=2)CCC1(N(C)C)CC1=CC=CC(Cl)=C1 YFLCAICXMPAALB-UHFFFAOYSA-N 0.000 claims 1
- LYWBEPOOUHOGTD-UHFFFAOYSA-N n'-[4-[(3-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]-n-[(2,4-difluorophenyl)methyl]butanediamide Chemical compound C1CC(NC(=O)CCC(=O)NCC=2C(=CC(F)=CC=2)F)CCC1(N(C)C)CC1=CC=CC(Cl)=C1 LYWBEPOOUHOGTD-UHFFFAOYSA-N 0.000 claims 1
- COCDCMCWKIOYIO-UHFFFAOYSA-N n'-[4-[(3-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]-n-[(2,5-dichlorophenyl)methyl]butanediamide Chemical compound C1CC(NC(=O)CCC(=O)NCC=2C(=CC=C(Cl)C=2)Cl)CCC1(N(C)C)CC1=CC=CC(Cl)=C1 COCDCMCWKIOYIO-UHFFFAOYSA-N 0.000 claims 1
- RPCBVLOMFGMMAD-UHFFFAOYSA-N n'-[4-[(3-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]-n-[(2-methylphenyl)methyl]butanediamide Chemical compound C1CC(NC(=O)CCC(=O)NCC=2C(=CC=CC=2)C)CCC1(N(C)C)CC1=CC=CC(Cl)=C1 RPCBVLOMFGMMAD-UHFFFAOYSA-N 0.000 claims 1
- KABKCDZVCQGDEY-UHFFFAOYSA-N n'-[4-[(3-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]-n-[(3,4-dichlorophenyl)methyl]butanediamide Chemical compound C1CC(NC(=O)CCC(=O)NCC=2C=C(Cl)C(Cl)=CC=2)CCC1(N(C)C)CC1=CC=CC(Cl)=C1 KABKCDZVCQGDEY-UHFFFAOYSA-N 0.000 claims 1
- XHEBVTYAYCEFDS-UHFFFAOYSA-N n'-[4-[(3-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]-n-[(3,5-dichlorophenyl)methyl]butanediamide Chemical compound C1CC(NC(=O)CCC(=O)NCC=2C=C(Cl)C=C(Cl)C=2)CCC1(N(C)C)CC1=CC=CC(Cl)=C1 XHEBVTYAYCEFDS-UHFFFAOYSA-N 0.000 claims 1
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- CXUIBELNWTWBOV-UHFFFAOYSA-N n'-[4-[(3-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]-n-[2-(2,4-dichlorophenyl)ethyl]butanediamide Chemical compound C1CC(NC(=O)CCC(=O)NCCC=2C(=CC(Cl)=CC=2)Cl)CCC1(N(C)C)CC1=CC=CC(Cl)=C1 CXUIBELNWTWBOV-UHFFFAOYSA-N 0.000 claims 1
- LITWINWJYKRBPM-UHFFFAOYSA-N n'-[4-[(3-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]-n-[2-(2-ethoxyphenyl)ethyl]butanediamide Chemical compound CCOC1=CC=CC=C1CCNC(=O)CCC(=O)NC1CCC(CC=2C=C(Cl)C=CC=2)(N(C)C)CC1 LITWINWJYKRBPM-UHFFFAOYSA-N 0.000 claims 1
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- GCZWZOYKRYKNKT-UHFFFAOYSA-N n'-[4-[(3-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]-n-[[3-fluoro-5-(trifluoromethyl)phenyl]methyl]butanediamide Chemical compound C1CC(NC(=O)CCC(=O)NCC=2C=C(C=C(F)C=2)C(F)(F)F)CCC1(N(C)C)CC1=CC=CC(Cl)=C1 GCZWZOYKRYKNKT-UHFFFAOYSA-N 0.000 claims 1
- AMIKNHAYAGDHLB-UHFFFAOYSA-N n'-[4-[(3-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]-n-[[4-fluoro-3-(trifluoromethyl)phenyl]methyl]butanediamide Chemical compound C1CC(NC(=O)CCC(=O)NCC=2C=C(C(F)=CC=2)C(F)(F)F)CCC1(N(C)C)CC1=CC=CC(Cl)=C1 AMIKNHAYAGDHLB-UHFFFAOYSA-N 0.000 claims 1
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- ZMQVZCMFJKCJTJ-UHFFFAOYSA-N n'-benzyl-n-[4-[(3-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]-n'-ethylbutanediamide Chemical compound C1CC(CC=2C=C(Cl)C=CC=2)(N(C)C)CCC1NC(=O)CCC(=O)N(CC)CC1=CC=CC=C1 ZMQVZCMFJKCJTJ-UHFFFAOYSA-N 0.000 claims 1
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- WTWOHPQAHUWSPN-UHFFFAOYSA-N n-(4-benzyl-4-morpholin-4-ylcyclohexyl)-4-oxo-4-[4-(quinolin-2-ylmethyl)piperazin-1-yl]butanamide Chemical compound C1CN(CC=2N=C3C=CC=CC3=CC=2)CCN1C(=O)CCC(=O)NC(CC1)CCC1(N1CCOCC1)CC1=CC=CC=C1 WTWOHPQAHUWSPN-UHFFFAOYSA-N 0.000 claims 1
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- XGZYGTDWHUCLNT-UHFFFAOYSA-N n-(4-benzyl-4-morpholin-4-ylcyclohexyl)-n'-methyl-n'-[1-[(2-phenylmethoxyphenyl)methyl]pyrrolidin-3-yl]butanediamide Chemical compound C1CC(CC=2C=CC=CC=2)(N2CCOCC2)CCC1NC(=O)CCC(=O)N(C)C(C1)CCN1CC1=CC=CC=C1OCC1=CC=CC=C1 XGZYGTDWHUCLNT-UHFFFAOYSA-N 0.000 claims 1
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- BPQFIGNSTMDQGQ-UHFFFAOYSA-N n-[(3-bromophenyl)methyl]-n'-[4-[(4-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]butanediamide Chemical compound C1CC(NC(=O)CCC(=O)NCC=2C=C(Br)C=CC=2)CCC1(N(C)C)CC1=CC=C(Cl)C=C1 BPQFIGNSTMDQGQ-UHFFFAOYSA-N 0.000 claims 1
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- AXXPFGASLSWKMY-UHFFFAOYSA-N n-[(4-bromo-2-fluorophenyl)methyl]-n'-[4-[(3-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]butanediamide Chemical compound C1CC(NC(=O)CCC(=O)NCC=2C(=CC(Br)=CC=2)F)CCC1(N(C)C)CC1=CC=CC(Cl)=C1 AXXPFGASLSWKMY-UHFFFAOYSA-N 0.000 claims 1
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- UPHYLOOFXHFYFQ-UHFFFAOYSA-N n-[2-(2,4-dichlorophenyl)ethyl]-n'-[4-(dimethylamino)-4-[(3-methylphenyl)methyl]cyclohexyl]butanediamide Chemical compound C1CC(NC(=O)CCC(=O)NCCC=2C(=CC(Cl)=CC=2)Cl)CCC1(N(C)C)CC1=CC=CC(C)=C1 UPHYLOOFXHFYFQ-UHFFFAOYSA-N 0.000 claims 1
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- UQKHCPNCHRMVCP-UHFFFAOYSA-N n-[2-(2,6-dichlorophenyl)ethyl]-n'-[4-(dimethylamino)-4-thiophen-2-ylcyclohexyl]butanediamide Chemical compound C1CC(N(C)C)(C=2SC=CC=2)CCC1NC(=O)CCC(=O)NCCC1=C(Cl)C=CC=C1Cl UQKHCPNCHRMVCP-UHFFFAOYSA-N 0.000 claims 1
- QQGBSOLXWJLGJR-UHFFFAOYSA-N n-[2-(2-chlorophenyl)ethyl]-n'-[4-(dimethylamino)-4-[(3-methylphenyl)methyl]cyclohexyl]butanediamide Chemical compound C1CC(NC(=O)CCC(=O)NCCC=2C(=CC=CC=2)Cl)CCC1(N(C)C)CC1=CC=CC(C)=C1 QQGBSOLXWJLGJR-UHFFFAOYSA-N 0.000 claims 1
- RNQCYFKTGQCZSQ-UHFFFAOYSA-N n-[2-(2-chlorophenyl)ethyl]-n'-[4-(dimethylamino)-4-[(4-methylphenyl)methyl]cyclohexyl]butanediamide Chemical compound C1CC(NC(=O)CCC(=O)NCCC=2C(=CC=CC=2)Cl)CCC1(N(C)C)CC1=CC=C(C)C=C1 RNQCYFKTGQCZSQ-UHFFFAOYSA-N 0.000 claims 1
- QCANYWZUCDEULE-UHFFFAOYSA-N n-[2-(2-chlorophenyl)ethyl]-n'-[4-[(3-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]butanediamide Chemical compound C1CC(NC(=O)CCC(=O)NCCC=2C(=CC=CC=2)Cl)CCC1(N(C)C)CC1=CC=CC(Cl)=C1 QCANYWZUCDEULE-UHFFFAOYSA-N 0.000 claims 1
- YPZNHWILUFTWPR-UHFFFAOYSA-N n-[2-(3,4-dichlorophenyl)ethyl]-n'-[4-(dimethylamino)-4-phenylcyclohexyl]butanediamide Chemical compound C1CC(N(C)C)(C=2C=CC=CC=2)CCC1NC(=O)CCC(=O)NCCC1=CC=C(Cl)C(Cl)=C1 YPZNHWILUFTWPR-UHFFFAOYSA-N 0.000 claims 1
- QXRKYIYTEWOVCO-UHFFFAOYSA-N n-[2-(3-chlorophenyl)ethyl]-n'-[4-(dimethylamino)-4-[(3-methylphenyl)methyl]cyclohexyl]butanediamide Chemical compound C1CC(NC(=O)CCC(=O)NCCC=2C=C(Cl)C=CC=2)CCC1(N(C)C)CC1=CC=CC(C)=C1 QXRKYIYTEWOVCO-UHFFFAOYSA-N 0.000 claims 1
- KXSAXLILVPCYHA-UHFFFAOYSA-N n-[2-(3-chlorophenyl)ethyl]-n'-[4-(dimethylamino)-4-phenylcyclohexyl]butanediamide Chemical compound C1CC(N(C)C)(C=2C=CC=CC=2)CCC1NC(=O)CCC(=O)NCCC1=CC=CC(Cl)=C1 KXSAXLILVPCYHA-UHFFFAOYSA-N 0.000 claims 1
- BPXMBHRFROTJIV-UHFFFAOYSA-N n-[2-(3-chlorophenyl)ethyl]-n'-[4-(dimethylamino)-4-thiophen-2-ylcyclohexyl]butanediamide Chemical compound C1CC(N(C)C)(C=2SC=CC=2)CCC1NC(=O)CCC(=O)NCCC1=CC=CC(Cl)=C1 BPXMBHRFROTJIV-UHFFFAOYSA-N 0.000 claims 1
- ZKVQHXRCKNFUAB-UHFFFAOYSA-N n-[2-(4-bromophenyl)ethyl]-n'-[4-(dimethylamino)-4-thiophen-2-ylcyclohexyl]butanediamide Chemical compound C1CC(N(C)C)(C=2SC=CC=2)CCC1NC(=O)CCC(=O)NCCC1=CC=C(Br)C=C1 ZKVQHXRCKNFUAB-UHFFFAOYSA-N 0.000 claims 1
- XFHOPGDZLYEBBH-UHFFFAOYSA-N n-[2-(4-chlorophenyl)ethyl]-n'-[4-(dimethylamino)-4-[(3-methylphenyl)methyl]cyclohexyl]butanediamide Chemical compound C1CC(NC(=O)CCC(=O)NCCC=2C=CC(Cl)=CC=2)CCC1(N(C)C)CC1=CC=CC(C)=C1 XFHOPGDZLYEBBH-UHFFFAOYSA-N 0.000 claims 1
- RGVDJYGFXPUIFC-UHFFFAOYSA-N n-[2-(4-chlorophenyl)ethyl]-n'-[4-(dimethylamino)-4-[(4-methylphenyl)methyl]cyclohexyl]butanediamide Chemical compound C1CC(NC(=O)CCC(=O)NCCC=2C=CC(Cl)=CC=2)CCC1(N(C)C)CC1=CC=C(C)C=C1 RGVDJYGFXPUIFC-UHFFFAOYSA-N 0.000 claims 1
- VQSWPPBVRXENTN-UHFFFAOYSA-N n-[2-(4-chlorophenyl)ethyl]-n'-[4-(dimethylamino)-4-phenylcyclohexyl]butanediamide Chemical compound C1CC(N(C)C)(C=2C=CC=CC=2)CCC1NC(=O)CCC(=O)NCCC1=CC=C(Cl)C=C1 VQSWPPBVRXENTN-UHFFFAOYSA-N 0.000 claims 1
- JFUCKBOGAKIEOI-UHFFFAOYSA-N n-[2-(4-chlorophenyl)ethyl]-n'-[4-[(3-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]butanediamide Chemical compound C1CC(NC(=O)CCC(=O)NCCC=2C=CC(Cl)=CC=2)CCC1(N(C)C)CC1=CC=CC(Cl)=C1 JFUCKBOGAKIEOI-UHFFFAOYSA-N 0.000 claims 1
- YYUKHBKPJQBLCQ-UHFFFAOYSA-N n-[2-(4-chlorophenyl)propyl]-n'-[4-(dimethylamino)-4-[(3-methylphenyl)methyl]cyclohexyl]butanediamide Chemical compound C=1C=C(Cl)C=CC=1C(C)CNC(=O)CCC(=O)NC(CC1)CCC1(N(C)C)CC1=CC=CC(C)=C1 YYUKHBKPJQBLCQ-UHFFFAOYSA-N 0.000 claims 1
- NIMBYGLLYRLCRP-UHFFFAOYSA-N n-[2-[(2,6-dichlorophenyl)methylsulfanyl]ethyl]-n'-[4-(dimethylamino)-4-thiophen-2-ylcyclohexyl]butanediamide Chemical compound C1CC(N(C)C)(C=2SC=CC=2)CCC1NC(=O)CCC(=O)NCCSCC1=C(Cl)C=CC=C1Cl NIMBYGLLYRLCRP-UHFFFAOYSA-N 0.000 claims 1
- GRKGHBZDNKJMQP-UHFFFAOYSA-N n-[4-(azepan-1-yl)-4-benzylcyclohexyl]-4-(2,3-dihydroindol-1-yl)-4-oxobutanamide Chemical compound C1CC2=CC=CC=C2N1C(=O)CCC(=O)NC(CC1)CCC1(N1CCCCCC1)CC1=CC=CC=C1 GRKGHBZDNKJMQP-UHFFFAOYSA-N 0.000 claims 1
- ZCYCAJHNNUEBGI-UHFFFAOYSA-N n-[4-(dimethylamino)-4-[(3-methylphenyl)methyl]cyclohexyl]-4-[4-(3-methoxyphenyl)piperazin-1-yl]-4-oxobutanamide Chemical compound COC1=CC=CC(N2CCN(CC2)C(=O)CCC(=O)NC2CCC(CC=3C=C(C)C=CC=3)(CC2)N(C)C)=C1 ZCYCAJHNNUEBGI-UHFFFAOYSA-N 0.000 claims 1
- NQWPQPRQWJEUPY-UHFFFAOYSA-N n-[4-(dimethylamino)-4-[(3-methylphenyl)methyl]cyclohexyl]-n'-(1,2,3,4-tetrahydronaphthalen-1-yl)butanediamide Chemical compound C1CC(NC(=O)CCC(=O)NC2C3=CC=CC=C3CCC2)CCC1(N(C)C)CC1=CC=CC(C)=C1 NQWPQPRQWJEUPY-UHFFFAOYSA-N 0.000 claims 1
- FYBLINSTOBKPHZ-UHFFFAOYSA-N n-[4-(dimethylamino)-4-[(3-methylphenyl)methyl]cyclohexyl]-n'-(1-naphthalen-1-ylethyl)butanediamide Chemical compound C=1C=CC2=CC=CC=C2C=1C(C)NC(=O)CCC(=O)NC(CC1)CCC1(N(C)C)CC1=CC=CC(C)=C1 FYBLINSTOBKPHZ-UHFFFAOYSA-N 0.000 claims 1
- IJIJCROPTXRFHS-UHFFFAOYSA-N n-[4-(dimethylamino)-4-[(3-methylphenyl)methyl]cyclohexyl]-n'-(1-naphthalen-2-ylethyl)butanediamide Chemical compound C=1C=C2C=CC=CC2=CC=1C(C)NC(=O)CCC(=O)NC(CC1)CCC1(N(C)C)CC1=CC=CC(C)=C1 IJIJCROPTXRFHS-UHFFFAOYSA-N 0.000 claims 1
- OWOWMDKBOKQLHE-UHFFFAOYSA-N n-[4-(dimethylamino)-4-[(3-methylphenyl)methyl]cyclohexyl]-n'-(4-methoxyphenyl)butanediamide Chemical compound C1=CC(OC)=CC=C1NC(=O)CCC(=O)NC1CCC(CC=2C=C(C)C=CC=2)(N(C)C)CC1 OWOWMDKBOKQLHE-UHFFFAOYSA-N 0.000 claims 1
- SUYMQMIXCPOTRL-UHFFFAOYSA-N n-[4-(dimethylamino)-4-[(3-methylphenyl)methyl]cyclohexyl]-n'-[1-(4-fluorophenyl)ethyl]butanediamide Chemical compound C=1C=C(F)C=CC=1C(C)NC(=O)CCC(=O)NC(CC1)CCC1(N(C)C)CC1=CC=CC(C)=C1 SUYMQMIXCPOTRL-UHFFFAOYSA-N 0.000 claims 1
- UPMCMWPLLUDWJL-UHFFFAOYSA-N n-[4-(dimethylamino)-4-[(3-methylphenyl)methyl]cyclohexyl]-n'-[2-(1h-indol-3-yl)ethyl]-n'-methylbutanediamide Chemical compound C1CC(NC(=O)CCC(=O)N(C)CCC=2C3=CC=CC=C3NC=2)CCC1(N(C)C)CC1=CC=CC(C)=C1 UPMCMWPLLUDWJL-UHFFFAOYSA-N 0.000 claims 1
- KGWQYPSJCIXTTN-UHFFFAOYSA-N n-[4-(dimethylamino)-4-[(4-methylphenyl)methyl]cyclohexyl]-4-[4-(2,3-dimethylphenyl)piperazin-1-yl]-4-oxobutanamide Chemical compound C1CC(NC(=O)CCC(=O)N2CCN(CC2)C=2C(=C(C)C=CC=2)C)CCC1(N(C)C)CC1=CC=C(C)C=C1 KGWQYPSJCIXTTN-UHFFFAOYSA-N 0.000 claims 1
- RRELSIGJFHWMFA-UHFFFAOYSA-N n-[4-(dimethylamino)-4-[(4-methylphenyl)methyl]cyclohexyl]-4-[4-(2-methylphenyl)piperazin-1-yl]-4-oxobutanamide Chemical compound C1CC(NC(=O)CCC(=O)N2CCN(CC2)C=2C(=CC=CC=2)C)CCC1(N(C)C)CC1=CC=C(C)C=C1 RRELSIGJFHWMFA-UHFFFAOYSA-N 0.000 claims 1
- KJHYQVFHFSAZRE-UHFFFAOYSA-N n-[4-(dimethylamino)-4-[(4-methylphenyl)methyl]cyclohexyl]-4-[4-(3-methylphenyl)piperazin-1-yl]-4-oxobutanamide Chemical compound C1CC(NC(=O)CCC(=O)N2CCN(CC2)C=2C=C(C)C=CC=2)CCC1(N(C)C)CC1=CC=C(C)C=C1 KJHYQVFHFSAZRE-UHFFFAOYSA-N 0.000 claims 1
- ZVPHTLLLBPIRAH-UHFFFAOYSA-N n-[4-(dimethylamino)-4-[(4-methylphenyl)methyl]cyclohexyl]-4-oxo-4-(4-pyridin-2-ylpiperazin-1-yl)butanamide Chemical compound C1CC(NC(=O)CCC(=O)N2CCN(CC2)C=2N=CC=CC=2)CCC1(N(C)C)CC1=CC=C(C)C=C1 ZVPHTLLLBPIRAH-UHFFFAOYSA-N 0.000 claims 1
- BPKRYZTUVGRRGG-UHFFFAOYSA-N n-[4-(dimethylamino)-4-[(4-methylphenyl)methyl]cyclohexyl]-n'-(1,2,3,4-tetrahydronaphthalen-1-yl)butanediamide Chemical compound C1CC(NC(=O)CCC(=O)NC2C3=CC=CC=C3CCC2)CCC1(N(C)C)CC1=CC=C(C)C=C1 BPKRYZTUVGRRGG-UHFFFAOYSA-N 0.000 claims 1
- CTPPVBPHXJBWGX-UHFFFAOYSA-N n-[4-(dimethylamino)-4-[(4-methylphenyl)methyl]cyclohexyl]-n'-(4-phenylmethoxyphenyl)butanediamide Chemical compound C1CC(NC(=O)CCC(=O)NC=2C=CC(OCC=3C=CC=CC=3)=CC=2)CCC1(N(C)C)CC1=CC=C(C)C=C1 CTPPVBPHXJBWGX-UHFFFAOYSA-N 0.000 claims 1
- LATYAWSALCFQEK-UHFFFAOYSA-N n-[4-(dimethylamino)-4-[(4-methylphenyl)methyl]cyclohexyl]-n'-methyl-n'-(2-pyridin-2-ylethyl)butanediamide Chemical compound C1CC(NC(=O)CCC(=O)N(C)CCC=2N=CC=CC=2)CCC1(N(C)C)CC1=CC=C(C)C=C1 LATYAWSALCFQEK-UHFFFAOYSA-N 0.000 claims 1
- XLQNYWWRWDBQIB-UHFFFAOYSA-N n-[4-(dimethylamino)-4-phenylcyclohexyl]-4-[4-hydroxy-4-[3-(trifluoromethyl)phenyl]piperidin-1-yl]-4-oxobutanamide Chemical compound C1CC(N(C)C)(C=2C=CC=CC=2)CCC1NC(=O)CCC(=O)N(CC1)CCC1(O)C1=CC=CC(C(F)(F)F)=C1 XLQNYWWRWDBQIB-UHFFFAOYSA-N 0.000 claims 1
- PBLGUXFNSUZNQD-UHFFFAOYSA-N n-[4-(dimethylamino)-4-phenylcyclohexyl]-n'-[2-(1h-indol-3-yl)ethyl]-n'-methylbutanediamide Chemical compound C1CC(NC(=O)CCC(=O)N(C)CCC=2C3=CC=CC=C3NC=2)CCC1(N(C)C)C1=CC=CC=C1 PBLGUXFNSUZNQD-UHFFFAOYSA-N 0.000 claims 1
- SWBTZALKAUHCJE-UHFFFAOYSA-N n-[4-(dimethylamino)-4-thiophen-2-ylcyclohexyl]-4-[4-hydroxy-4-[3-(trifluoromethyl)phenyl]piperidin-1-yl]-4-oxobutanamide Chemical compound C1CC(N(C)C)(C=2SC=CC=2)CCC1NC(=O)CCC(=O)N(CC1)CCC1(O)C1=CC=CC(C(F)(F)F)=C1 SWBTZALKAUHCJE-UHFFFAOYSA-N 0.000 claims 1
- QEYOBKOCZIIXTJ-UHFFFAOYSA-N n-[4-(dimethylamino)-4-thiophen-2-ylcyclohexyl]-4-oxo-4-[4-[5-(trifluoromethyl)pyridin-2-yl]piperazin-1-yl]butanamide Chemical compound C1CC(N(C)C)(C=2SC=CC=2)CCC1NC(=O)CCC(=O)N(CC1)CCN1C1=CC=C(C(F)(F)F)C=N1 QEYOBKOCZIIXTJ-UHFFFAOYSA-N 0.000 claims 1
- LDWPZOOQXNRHJD-UHFFFAOYSA-N n-[4-(dimethylamino)-4-thiophen-2-ylcyclohexyl]-5-[4-(4-fluorophenyl)-3,6-dihydro-2h-pyridin-1-yl]-5-oxopentanamide Chemical compound C1CC(N(C)C)(C=2SC=CC=2)CCC1NC(=O)CCCC(=O)N(CC=1)CCC=1C1=CC=C(F)C=C1 LDWPZOOQXNRHJD-UHFFFAOYSA-N 0.000 claims 1
- KFFICUUZFLVAFB-UHFFFAOYSA-N n-[4-(dimethylamino)-4-thiophen-2-ylcyclohexyl]-5-[4-[(2-methoxynaphthalen-1-yl)methyl]piperazin-1-yl]-5-oxopentanamide Chemical compound COC1=CC=C2C=CC=CC2=C1CN(CC1)CCN1C(=O)CCCC(=O)NC(CC1)CCC1(N(C)C)C1=CC=CS1 KFFICUUZFLVAFB-UHFFFAOYSA-N 0.000 claims 1
- OOTSNPHFURUMBY-UHFFFAOYSA-N n-[4-(dimethylamino)-4-thiophen-2-ylcyclohexyl]-n'-(4-phenoxyphenyl)butanediamide Chemical compound C1CC(N(C)C)(C=2SC=CC=2)CCC1NC(=O)CCC(=O)NC(C=C1)=CC=C1OC1=CC=CC=C1 OOTSNPHFURUMBY-UHFFFAOYSA-N 0.000 claims 1
- ZALJFRYCPUSAMQ-UHFFFAOYSA-N n-[4-(dimethylamino)-4-thiophen-2-ylcyclohexyl]-n'-(4-phenylbutan-2-yl)butanediamide Chemical compound C1CC(C=2SC=CC=2)(N(C)C)CCC1NC(=O)CCC(=O)NC(C)CCC1=CC=CC=C1 ZALJFRYCPUSAMQ-UHFFFAOYSA-N 0.000 claims 1
- UMLUFUOUFZXQEZ-UHFFFAOYSA-N n-[4-(dimethylamino)-4-thiophen-2-ylcyclohexyl]-n'-[(2-ethoxyphenyl)methyl]-n'-(furan-2-ylmethyl)butanediamide Chemical compound CCOC1=CC=CC=C1CN(C(=O)CCC(=O)NC1CCC(CC1)(N(C)C)C=1SC=CC=1)CC1=CC=CO1 UMLUFUOUFZXQEZ-UHFFFAOYSA-N 0.000 claims 1
- ZBEVJBQAQNKFGI-UHFFFAOYSA-N n-[4-(dimethylamino)-4-thiophen-2-ylcyclohexyl]-n'-[2-(1h-indol-3-yl)ethyl]-n'-methylbutanediamide Chemical compound C1CC(NC(=O)CCC(=O)N(C)CCC=2C3=CC=CC=C3NC=2)CCC1(N(C)C)C1=CC=CS1 ZBEVJBQAQNKFGI-UHFFFAOYSA-N 0.000 claims 1
- VMGIUTXLKOWTFX-UHFFFAOYSA-N n-[4-(dimethylamino)-4-thiophen-2-ylcyclohexyl]-n'-methyl-n'-[1-[(4-phenylphenyl)methyl]pyrrolidin-3-yl]butanediamide Chemical compound C1CC(N(C)C)(C=2SC=CC=2)CCC1NC(=O)CCC(=O)N(C)C(C1)CCN1CC(C=C1)=CC=C1C1=CC=CC=C1 VMGIUTXLKOWTFX-UHFFFAOYSA-N 0.000 claims 1
- GFVASFORBFLJFI-UHFFFAOYSA-N n-[4-[(3-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]-4-(3,5-dimethylpiperidin-1-yl)-4-oxobutanamide Chemical compound C1C(C)CC(C)CN1C(=O)CCC(=O)NC1CCC(CC=2C=C(Cl)C=CC=2)(N(C)C)CC1 GFVASFORBFLJFI-UHFFFAOYSA-N 0.000 claims 1
- AIYBZINDJZZCMF-UHFFFAOYSA-N n-[4-[(3-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]-4-(3,6-dihydro-2h-pyridin-1-yl)-4-oxobutanamide Chemical compound C1CC(NC(=O)CCC(=O)N2CC=CCC2)CCC1(N(C)C)CC1=CC=CC(Cl)=C1 AIYBZINDJZZCMF-UHFFFAOYSA-N 0.000 claims 1
- OUWKCWRKOKBYGR-UHFFFAOYSA-N n-[4-[(3-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]-4-oxo-4-(4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-8-yl)butanamide Chemical compound C1CC(NC(=O)CCC(=O)N2CCC3(CC2)C(NCN3C=2C=CC=CC=2)=O)CCC1(N(C)C)CC1=CC=CC(Cl)=C1 OUWKCWRKOKBYGR-UHFFFAOYSA-N 0.000 claims 1
- IZRDYCBZFRSLAB-UHFFFAOYSA-N n-[4-[(3-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]-4-oxo-4-thiomorpholin-4-ylbutanamide Chemical compound C1CC(NC(=O)CCC(=O)N2CCSCC2)CCC1(N(C)C)CC1=CC=CC(Cl)=C1 IZRDYCBZFRSLAB-UHFFFAOYSA-N 0.000 claims 1
- RDQLKSINALNSLM-UHFFFAOYSA-N n-[4-[(3-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]-n'-(1,2,3,4-tetrahydronaphthalen-1-yl)butanediamide Chemical compound C1CC(NC(=O)CCC(=O)NC2C3=CC=CC=C3CCC2)CCC1(N(C)C)CC1=CC=CC(Cl)=C1 RDQLKSINALNSLM-UHFFFAOYSA-N 0.000 claims 1
- YEJVEANATOIFGL-UHFFFAOYSA-N n-[4-[(3-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]-n'-(1-naphthalen-1-ylethyl)butanediamide Chemical compound C=1C=CC2=CC=CC=C2C=1C(C)NC(=O)CCC(=O)NC(CC1)CCC1(N(C)C)CC1=CC=CC(Cl)=C1 YEJVEANATOIFGL-UHFFFAOYSA-N 0.000 claims 1
- JPJNUCONERTLJL-UHFFFAOYSA-N n-[4-[(3-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]-n'-(1-phenylpropyl)butanediamide Chemical compound C=1C=CC=CC=1C(CC)NC(=O)CCC(=O)NC(CC1)CCC1(N(C)C)CC1=CC=CC(Cl)=C1 JPJNUCONERTLJL-UHFFFAOYSA-N 0.000 claims 1
- VBPTVJHIFWUNDP-UHFFFAOYSA-N n-[4-[(3-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]-n'-(2,3-dihydro-1h-inden-2-yl)butanediamide Chemical compound C1CC(NC(=O)CCC(=O)NC2CC3=CC=CC=C3C2)CCC1(N(C)C)CC1=CC=CC(Cl)=C1 VBPTVJHIFWUNDP-UHFFFAOYSA-N 0.000 claims 1
- OEBJAHCGKOEWOH-UHFFFAOYSA-N n-[4-[(3-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]-n'-(2-oxooxolan-3-yl)butanediamide Chemical compound C1CC(NC(=O)CCC(=O)NC2C(OCC2)=O)CCC1(N(C)C)CC1=CC=CC(Cl)=C1 OEBJAHCGKOEWOH-UHFFFAOYSA-N 0.000 claims 1
- FUWWKBSULKYINE-UHFFFAOYSA-N n-[4-[(3-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]-n'-(4-phenylbutan-2-yl)butanediamide Chemical compound C1CC(CC=2C=C(Cl)C=CC=2)(N(C)C)CCC1NC(=O)CCC(=O)NC(C)CCC1=CC=CC=C1 FUWWKBSULKYINE-UHFFFAOYSA-N 0.000 claims 1
- NTDWNTPUXBDSEC-UHFFFAOYSA-N n-[4-[(3-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]-n'-[(2,5-dimethoxyphenyl)methyl]-n'-(furan-2-ylmethyl)butanediamide Chemical compound COC1=CC=C(OC)C(CN(CC=2OC=CC=2)C(=O)CCC(=O)NC2CCC(CC=3C=C(Cl)C=CC=3)(CC2)N(C)C)=C1 NTDWNTPUXBDSEC-UHFFFAOYSA-N 0.000 claims 1
- ZCYZOXNLESJEKE-UHFFFAOYSA-N n-[4-[(3-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]-n'-[(2-fluorophenyl)methyl]-n'-(furan-2-ylmethyl)butanediamide Chemical compound C1CC(NC(=O)CCC(=O)N(CC=2OC=CC=2)CC=2C(=CC=CC=2)F)CCC1(N(C)C)CC1=CC=CC(Cl)=C1 ZCYZOXNLESJEKE-UHFFFAOYSA-N 0.000 claims 1
- PKXNEDJYEQWIEV-UHFFFAOYSA-N n-[4-[(3-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]-n'-[2-(1h-indol-3-yl)ethyl]-n'-methylbutanediamide Chemical compound C1CC(NC(=O)CCC(=O)N(C)CCC=2C3=CC=CC=C3NC=2)CCC1(N(C)C)CC1=CC=CC(Cl)=C1 PKXNEDJYEQWIEV-UHFFFAOYSA-N 0.000 claims 1
- YHMVEYYCWOYTTA-UHFFFAOYSA-N n-[4-[(3-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]-n'-methyl-n'-(pyridin-3-ylmethyl)butanediamide Chemical compound C1CC(NC(=O)CCC(=O)N(C)CC=2C=NC=CC=2)CCC1(N(C)C)CC1=CC=CC(Cl)=C1 YHMVEYYCWOYTTA-UHFFFAOYSA-N 0.000 claims 1
- KMXNOIWMUFWEKK-UHFFFAOYSA-N n-[4-[(4-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]-4-(1,4-dioxa-8-azaspiro[4.5]decan-8-yl)-4-oxobutanamide Chemical compound C1CC(NC(=O)CCC(=O)N2CCC3(CC2)OCCO3)CCC1(N(C)C)CC1=CC=C(Cl)C=C1 KMXNOIWMUFWEKK-UHFFFAOYSA-N 0.000 claims 1
- QZIKZCAXQJDKEL-UHFFFAOYSA-N n-[4-[(4-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]-4-(2,6-dimethylmorpholin-4-yl)-4-oxobutanamide Chemical compound C1C(C)OC(C)CN1C(=O)CCC(=O)NC1CCC(CC=2C=CC(Cl)=CC=2)(N(C)C)CC1 QZIKZCAXQJDKEL-UHFFFAOYSA-N 0.000 claims 1
- BHHVOKFCQNZHNW-UHFFFAOYSA-N n-[4-[(4-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]-4-(3,6-dihydro-2h-pyridin-1-yl)-4-oxobutanamide Chemical compound C1CC(NC(=O)CCC(=O)N2CC=CCC2)CCC1(N(C)C)CC1=CC=C(Cl)C=C1 BHHVOKFCQNZHNW-UHFFFAOYSA-N 0.000 claims 1
- LAYAVMLBPGUJPH-UHFFFAOYSA-N n-[4-[(4-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]-4-[4-(4-ethoxyphenyl)piperazin-1-yl]-4-oxobutanamide Chemical compound C1=CC(OCC)=CC=C1N1CCN(C(=O)CCC(=O)NC2CCC(CC=3C=CC(Cl)=CC=3)(CC2)N(C)C)CC1 LAYAVMLBPGUJPH-UHFFFAOYSA-N 0.000 claims 1
- WEPMQIVSSZPEJA-UHFFFAOYSA-N n-[4-[(4-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]-4-oxo-4-thiomorpholin-4-ylbutanamide Chemical compound C1CC(NC(=O)CCC(=O)N2CCSCC2)CCC1(N(C)C)CC1=CC=C(Cl)C=C1 WEPMQIVSSZPEJA-UHFFFAOYSA-N 0.000 claims 1
- LVCJMEUOXSKIJC-UHFFFAOYSA-N n-[4-[(4-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]-n'-(1-phenylpropyl)butanediamide Chemical compound C=1C=CC=CC=1C(CC)NC(=O)CCC(=O)NC(CC1)CCC1(N(C)C)CC1=CC=C(Cl)C=C1 LVCJMEUOXSKIJC-UHFFFAOYSA-N 0.000 claims 1
- HPGMFQMFFYDEEC-UHFFFAOYSA-N n-[4-[(4-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]-n'-(4-methoxyphenyl)butanediamide Chemical compound C1=CC(OC)=CC=C1NC(=O)CCC(=O)NC1CCC(CC=2C=CC(Cl)=CC=2)(N(C)C)CC1 HPGMFQMFFYDEEC-UHFFFAOYSA-N 0.000 claims 1
- JMNCHLKFSDCOAF-UHFFFAOYSA-N n-[4-[(4-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]-n'-(4-phenylbutan-2-yl)butanediamide Chemical compound C1CC(CC=2C=CC(Cl)=CC=2)(N(C)C)CCC1NC(=O)CCC(=O)NC(C)CCC1=CC=CC=C1 JMNCHLKFSDCOAF-UHFFFAOYSA-N 0.000 claims 1
- YKVKSJDALVSZJP-UHFFFAOYSA-N n-[4-[(4-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]-n'-[2-(1h-indol-3-yl)ethyl]-n'-methylbutanediamide Chemical compound C1CC(NC(=O)CCC(=O)N(C)CCC=2C3=CC=CC=C3NC=2)CCC1(N(C)C)CC1=CC=C(Cl)C=C1 YKVKSJDALVSZJP-UHFFFAOYSA-N 0.000 claims 1
- PADCLMHQSZKQMU-UHFFFAOYSA-N n-[4-[(4-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]-n'-methyl-n'-(pyridin-3-ylmethyl)butanediamide Chemical compound C1CC(NC(=O)CCC(=O)N(C)CC=2C=NC=CC=2)CCC1(N(C)C)CC1=CC=C(Cl)C=C1 PADCLMHQSZKQMU-UHFFFAOYSA-N 0.000 claims 1
- DVMVJMYHWZZDJL-UHFFFAOYSA-N n-[4-benzyl-4-(dimethylamino)cyclohexyl]-5-(4-cycloheptylpiperazin-1-yl)-5-oxopentanamide Chemical compound C1CC(NC(=O)CCCC(=O)N2CCN(CC2)C2CCCCCC2)CCC1(N(C)C)CC1=CC=CC=C1 DVMVJMYHWZZDJL-UHFFFAOYSA-N 0.000 claims 1
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102004023522A DE102004023522A1 (de) | 2004-05-10 | 2004-05-10 | Substituierte Cyclohexyl-1,4-diamin-Derivate |
| DE102004023522.8 | 2004-05-10 | ||
| PCT/EP2005/004913 WO2005110974A1 (de) | 2004-05-10 | 2005-05-06 | Substituierte cyclohexyl-1,4-diamin-derivate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2566297A1 CA2566297A1 (en) | 2005-11-24 |
| CA2566297C true CA2566297C (en) | 2012-10-30 |
Family
ID=34967002
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2566297A Expired - Fee Related CA2566297C (en) | 2004-05-10 | 2005-05-06 | Substituted cyclohexyl-1,4-diamine derivatives |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US8088763B2 (https=) |
| EP (1) | EP1745010B1 (https=) |
| JP (1) | JP5037337B2 (https=) |
| AT (1) | ATE438617T1 (https=) |
| CA (1) | CA2566297C (https=) |
| CY (1) | CY1109569T1 (https=) |
| DE (2) | DE102004023522A1 (https=) |
| DK (1) | DK1745010T3 (https=) |
| ES (1) | ES2333026T3 (https=) |
| PL (1) | PL1745010T3 (https=) |
| PT (1) | PT1745010E (https=) |
| SI (1) | SI1745010T1 (https=) |
| WO (1) | WO2005110974A1 (https=) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102004023501A1 (de) * | 2004-05-10 | 2005-12-01 | Grünenthal GmbH | Oxosubstituierte Cyclohexyl-1,4-diamin-Derivate |
| MX2009004314A (es) * | 2006-11-13 | 2009-05-05 | Pfizer Prod Inc | Diaril, dipiridinil y arilpiridinilderivados y usos de los mismos. |
| AU2009228647B2 (en) | 2008-03-27 | 2013-07-04 | Grunenthal Gmbh | Substituted spirocyclic cyclohexane derivatives |
| JP5529843B2 (ja) | 2008-03-27 | 2014-06-25 | グリュネンタール・ゲゼルシャフト・ミト・ベシュレンクテル・ハフツング | 置換シクロヘキシルジアミン |
| EP2280941B1 (de) | 2008-03-27 | 2015-05-06 | Grünenthal GmbH | (hetero-)aryl-cyclohexan-derivate |
| ES2375543T3 (es) | 2008-03-27 | 2012-03-01 | Grünenthal GmbH | Derivados de espiro(5.5)undecano. |
| ES2464102T3 (es) | 2008-03-27 | 2014-05-30 | Grünenthal GmbH | Derivados de 4-aminociclohexano sustituidos |
| CN102046591B (zh) * | 2008-03-27 | 2014-12-03 | 格吕伦塔尔有限公司 | 羟甲基环己胺 |
| CN116554127B (zh) * | 2022-01-28 | 2025-03-21 | 成都麻沸散医药科技有限公司 | 哌嗪取代苯酚类衍生物及其用途 |
| CN117430522A (zh) * | 2022-07-14 | 2024-01-23 | 浙江友宁生物医药科技有限公司 | 一种gpr139受体激动剂及其制备方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2373855A1 (en) * | 1999-05-12 | 2000-11-23 | Solvay Pharmaceuticals B.V. | Method of treating psychotic disorders |
| ES2188344B1 (es) * | 2000-11-29 | 2004-09-16 | Laboratorios Vita, S.A. | Compuestos derivados de benzotiofeno, su procedimiento de obtencion y utilizacion de los mismos. |
| DE10123163A1 (de) * | 2001-05-09 | 2003-01-16 | Gruenenthal Gmbh | Substituierte Cyclohexan-1,4-diaminderivate |
| EP1458704A1 (en) * | 2001-12-21 | 2004-09-22 | H. Lundbeck A/S | Aminoindane derivatives as serotonin and norepinephrine uptake inhibitors |
| US6818772B2 (en) * | 2002-02-22 | 2004-11-16 | Abbott Laboratories | Antagonists of melanin concentrating hormone effects on the melanin concentrating hormone receptor |
| DE10252650A1 (de) * | 2002-11-11 | 2004-05-27 | Grünenthal GmbH | Cyclohexyl-Harnstoff-Derivate |
| DE10252666A1 (de) * | 2002-11-11 | 2004-08-05 | Grünenthal GmbH | N-Piperidyl-cyclohexan-Derivate |
-
2004
- 2004-05-10 DE DE102004023522A patent/DE102004023522A1/de not_active Withdrawn
-
2005
- 2005-05-06 CA CA2566297A patent/CA2566297C/en not_active Expired - Fee Related
- 2005-05-06 JP JP2007512033A patent/JP5037337B2/ja not_active Expired - Fee Related
- 2005-05-06 DE DE502005007850T patent/DE502005007850D1/de not_active Expired - Lifetime
- 2005-05-06 DK DK05739598T patent/DK1745010T3/da active
- 2005-05-06 WO PCT/EP2005/004913 patent/WO2005110974A1/de not_active Ceased
- 2005-05-06 US US11/594,963 patent/US8088763B2/en not_active Expired - Fee Related
- 2005-05-06 PT PT05739598T patent/PT1745010E/pt unknown
- 2005-05-06 AT AT05739598T patent/ATE438617T1/de active
- 2005-05-06 PL PL05739598T patent/PL1745010T3/pl unknown
- 2005-05-06 SI SI200530825T patent/SI1745010T1/sl unknown
- 2005-05-06 ES ES05739598T patent/ES2333026T3/es not_active Expired - Lifetime
- 2005-05-06 EP EP05739598A patent/EP1745010B1/de not_active Expired - Lifetime
-
2009
- 2009-11-05 CY CY20091101145T patent/CY1109569T1/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| WO2005110974A1 (de) | 2005-11-24 |
| PT1745010E (pt) | 2009-11-10 |
| ATE438617T1 (de) | 2009-08-15 |
| PL1745010T3 (pl) | 2010-01-29 |
| EP1745010A1 (de) | 2007-01-24 |
| US20070112007A1 (en) | 2007-05-17 |
| SI1745010T1 (sl) | 2010-01-29 |
| DK1745010T3 (da) | 2009-12-07 |
| ES2333026T3 (es) | 2010-02-16 |
| DE502005007850D1 (de) | 2009-09-17 |
| JP5037337B2 (ja) | 2012-09-26 |
| DE102004023522A1 (de) | 2005-12-01 |
| US8088763B2 (en) | 2012-01-03 |
| CY1109569T1 (el) | 2014-08-13 |
| CA2566297A1 (en) | 2005-11-24 |
| EP1745010B1 (de) | 2009-08-05 |
| JP2007536323A (ja) | 2007-12-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20170510 |