RU2012120387A - Замещенные производные 4-аминоциклогексана - Google Patents
Замещенные производные 4-аминоциклогексана Download PDFInfo
- Publication number
- RU2012120387A RU2012120387A RU2012120387/04A RU2012120387A RU2012120387A RU 2012120387 A RU2012120387 A RU 2012120387A RU 2012120387/04 A RU2012120387/04 A RU 2012120387/04A RU 2012120387 A RU2012120387 A RU 2012120387A RU 2012120387 A RU2012120387 A RU 2012120387A
- Authority
- RU
- Russia
- Prior art keywords
- methyl
- cyclohexyl
- polar diastereomer
- dimethyl
- amine
- Prior art date
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- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical class NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 title 1
- 125000003118 aryl group Chemical group 0.000 claims abstract 16
- 150000001875 compounds Chemical class 0.000 claims abstract 15
- 229920006395 saturated elastomer Polymers 0.000 claims abstract 5
- 125000001931 aliphatic group Chemical group 0.000 claims abstract 2
- 229910052799 carbon Inorganic materials 0.000 claims abstract 2
- 229910052717 sulfur Inorganic materials 0.000 claims abstract 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N protonated dimethyl amine Natural products CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims 37
- -1 (4-dimethylamino-1,4-diphenyl-cyclohexyl) -1-methyl-urea Chemical compound 0.000 claims 27
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 11
- 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 11
- 125000001072 heteroaryl group Chemical group 0.000 claims 11
- 150000003839 salts Chemical class 0.000 claims 5
- 125000005842 heteroatom Chemical group 0.000 claims 4
- 239000000203 mixture Substances 0.000 claims 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N mono-methylamine Natural products NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims 4
- 125000001424 substituent group Chemical group 0.000 claims 4
- 238000006467 substitution reaction Methods 0.000 claims 4
- IBNGPIOSWCMJGG-UHFFFAOYSA-N 1-methylindole-2-carbaldehyde Chemical compound C1=CC=C2N(C)C(C=O)=CC2=C1 IBNGPIOSWCMJGG-UHFFFAOYSA-N 0.000 claims 3
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 125000000623 heterocyclic group Chemical group 0.000 claims 3
- 125000001041 indolyl group Chemical group 0.000 claims 3
- 208000011117 substance-related disease Diseases 0.000 claims 3
- 208000007848 Alcoholism Diseases 0.000 claims 2
- 208000024827 Alzheimer disease Diseases 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 206010013654 Drug abuse Diseases 0.000 claims 2
- 208000007271 Substance Withdrawal Syndrome Diseases 0.000 claims 2
- 206010001584 alcohol abuse Diseases 0.000 claims 2
- 208000025746 alcohol use disease Diseases 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 230000003444 anaesthetic effect Effects 0.000 claims 2
- 125000004566 azetidin-1-yl group Chemical group N1(CCC1)* 0.000 claims 2
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 2
- CBOODYUURDDFRY-UHFFFAOYSA-N 1-n,1-n,4-n-trimethyl-1,4-diphenyl-4-n-(pyridin-3-ylmethyl)cyclohexane-1,4-diamine Chemical compound C1CC(N(C)C)(C=2C=CC=CC=2)CCC1(C=1C=CC=CC=1)N(C)CC1=CC=CN=C1 CBOODYUURDDFRY-UHFFFAOYSA-N 0.000 claims 1
- XNDUYJXGSARHSR-UHFFFAOYSA-N 1-n-benzyl-4-n,4-n-dimethyl-1-(3-methyl-1h-indol-2-yl)-4-phenylcyclohexane-1,4-diamine Chemical compound C1CC(N(C)C)(C=2C=CC=CC=2)CCC1(C1=C(C2=CC=CC=C2N1)C)NCC1=CC=CC=C1 XNDUYJXGSARHSR-UHFFFAOYSA-N 0.000 claims 1
- GMTULXZFDHEBJY-UHFFFAOYSA-N 4-[(dimethylamino)methyl]-n,n-dimethyl-1,4-diphenylcyclohexan-1-amine Chemical compound C1CC(CN(C)C)(C=2C=CC=CC=2)CCC1(N(C)C)C1=CC=CC=C1 GMTULXZFDHEBJY-UHFFFAOYSA-N 0.000 claims 1
- WFDROECRMFIKNH-UHFFFAOYSA-N 4-benzyl-4-[(dimethylamino)methyl]-n-methyl-1-phenylcyclohexan-1-amine Chemical compound C1CC(NC)(C=2C=CC=CC=2)CCC1(CN(C)C)CC1=CC=CC=C1 WFDROECRMFIKNH-UHFFFAOYSA-N 0.000 claims 1
- CVKJKMIHXNGOCK-UHFFFAOYSA-N 4-n-[4-(dimethylamino)-1,4-diphenylcyclohexyl]-2-n,4-n-dimethyl-6-piperidin-1-yl-1,3,5-triazine-2,4-diamine Chemical compound N=1C(NC)=NC(N(C)C2(CCC(CC2)(N(C)C)C=2C=CC=CC=2)C=2C=CC=CC=2)=NC=1N1CCCCC1 CVKJKMIHXNGOCK-UHFFFAOYSA-N 0.000 claims 1
- 206010006895 Cachexia Diseases 0.000 claims 1
- 208000024172 Cardiovascular disease Diseases 0.000 claims 1
- 206010011878 Deafness Diseases 0.000 claims 1
- 208000020401 Depressive disease Diseases 0.000 claims 1
- 206010012735 Diarrhoea Diseases 0.000 claims 1
- 208000030814 Eating disease Diseases 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 208000019454 Feeding and Eating disease Diseases 0.000 claims 1
- 206010020772 Hypertension Diseases 0.000 claims 1
- 208000001953 Hypotension Diseases 0.000 claims 1
- 208000019695 Migraine disease Diseases 0.000 claims 1
- 208000008589 Obesity Diseases 0.000 claims 1
- 208000002193 Pain Diseases 0.000 claims 1
- 208000004880 Polyuria Diseases 0.000 claims 1
- 208000003251 Pruritus Diseases 0.000 claims 1
- 206010039966 Senile dementia Diseases 0.000 claims 1
- 201000001880 Sexual dysfunction Diseases 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 208000009205 Tinnitus Diseases 0.000 claims 1
- 206010046543 Urinary incontinence Diseases 0.000 claims 1
- 206010048010 Withdrawal syndrome Diseases 0.000 claims 1
- DLCQYOXVZVHBQJ-UHFFFAOYSA-N [4-(dimethylamino)-1-methyl-4-(4-methylphenyl)cyclohexyl] acetate Chemical compound C=1C=C(C)C=CC=1C1(N(C)C)CCC(C)(OC(C)=O)CC1 DLCQYOXVZVHBQJ-UHFFFAOYSA-N 0.000 claims 1
- BROMZAHMHRNILO-UHFFFAOYSA-N [4-(dimethylamino)-4-phenyl-1-(4-phenylbutyl)cyclohexyl]methanol Chemical compound C1CC(N(C)C)(C=2C=CC=CC=2)CCC1(CO)CCCCC1=CC=CC=C1 BROMZAHMHRNILO-UHFFFAOYSA-N 0.000 claims 1
- 239000013543 active substance Substances 0.000 claims 1
- 239000000654 additive Substances 0.000 claims 1
- 125000002723 alicyclic group Chemical group 0.000 claims 1
- 125000005037 alkyl phenyl group Chemical group 0.000 claims 1
- 208000022531 anorexia Diseases 0.000 claims 1
- 230000001773 anti-convulsant effect Effects 0.000 claims 1
- 239000001961 anticonvulsive agent Substances 0.000 claims 1
- 229960003965 antiepileptics Drugs 0.000 claims 1
- 239000000427 antigen Substances 0.000 claims 1
- 102000036639 antigens Human genes 0.000 claims 1
- 108091007433 antigens Proteins 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 125000002619 bicyclic group Chemical group 0.000 claims 1
- 235000015165 citric acid Nutrition 0.000 claims 1
- 238000011260 co-administration Methods 0.000 claims 1
- 208000010877 cognitive disease Diseases 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 125000006312 cyclopentyl amino group Chemical group [H]N(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 206010061428 decreased appetite Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 208000035475 disorder Diseases 0.000 claims 1
- 235000014632 disordered eating Nutrition 0.000 claims 1
- 230000035619 diuresis Effects 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 206010013663 drug dependence Diseases 0.000 claims 1
- 206010015037 epilepsy Diseases 0.000 claims 1
- 230000010370 hearing loss Effects 0.000 claims 1
- 231100000888 hearing loss Toxicity 0.000 claims 1
- 208000016354 hearing loss disease Diseases 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 230000036543 hypotension Effects 0.000 claims 1
- 230000000968 intestinal effect Effects 0.000 claims 1
- 230000007803 itching Effects 0.000 claims 1
- 230000003137 locomotive effect Effects 0.000 claims 1
- 229940126601 medicinal product Drugs 0.000 claims 1
- 206010027175 memory impairment Diseases 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 1
- 206010027599 migraine Diseases 0.000 claims 1
- 210000003205 muscle Anatomy 0.000 claims 1
- CCWQWAOMHZZOIO-UHFFFAOYSA-N n-[4-(dimethylamino)-1-(3-methyl-1h-indol-2-yl)-4-phenylcyclohexyl]-n-methylacetamide Chemical compound C1CC(C2=C(C3=CC=CC=C3N2)C)(N(C)C(C)=O)CCC1(N(C)C)C1=CC=CC=C1 CCWQWAOMHZZOIO-UHFFFAOYSA-N 0.000 claims 1
- 230000003533 narcotic effect Effects 0.000 claims 1
- 230000004770 neurodegeneration Effects 0.000 claims 1
- 208000015122 neurodegenerative disease Diseases 0.000 claims 1
- 239000002858 neurotransmitter agent Substances 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 239000002664 nootropic agent Substances 0.000 claims 1
- 230000001777 nootropic effect Effects 0.000 claims 1
- 235000020824 obesity Nutrition 0.000 claims 1
- 239000000014 opioid analgesic Substances 0.000 claims 1
- 229940005483 opioid analgesics Drugs 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 125000003367 polycyclic group Chemical group 0.000 claims 1
- 231100000872 sexual dysfunction Toxicity 0.000 claims 1
- 239000012453 solvate Substances 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- 208000011580 syndromic disease Diseases 0.000 claims 1
- 231100000886 tinnitus Toxicity 0.000 claims 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D209/20—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals substituted additionally by nitrogen atoms, e.g. tryptophane
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- A61K31/136—Amines having aromatic rings, e.g. ketamine, nortriptyline having the amino group directly attached to the aromatic ring, e.g. benzeneamine
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- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
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- A61K31/5375—1,4-Oxazines, e.g. morpholine
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Abstract
1. Соединение общей формулы (1)гдеY, Y', Y, Y', Y, Y', Yи Y' в каждом случае независимо друг от друга выбраны из группы, состоящей из -Н, -F, -Cl, -Br, -I, -CN, -NO, -CHO, -R, -C(=O)R, -C(=O)H, -C(=O)-OH, -C(=O)OR, -C(=O)NH, -C(=O)NHR, C(=O)N(R), -ОН, -OR, -OC(=O)H, -OC(=O)R, -OC(=O)OR, -OC(=O)NHR, -OC(=O)N(R), -SH, -SR, -SOH, -S(=O)-R, -S(=O)NH, -NH, -NHR, N(R), -N(R), -N(R)O, -NHC(=O)R, -NHC(=O)OR, -NHC(=O)NH, NHC(=O)NHRи -NHC(=O)N(R); преимущественно в каждом случае независимо друг от друга выбраны из группы, состоящей из -Н, -F, -Cl, -CN и -С-алифат; или Yи Y', или Yи Y', или Yи Y', или Yи Y' совместно означают =O;Q означает -R, -C(=O)-R, -C(=O)OR, -C(=O)NHR, -C(=O)N(R)или -C(=NH)-R;Rв каждом случае независимо означает -C-алифат, -С-циклоалифат, -арил, -гетероарил, -С-алифат-С-циклоалифат, -C-алифат-арил, -C-алифат-гетероарил, -С-циклоалифат-С-алифат, -С-циклоалифат-арил или -С-циклоалифат-гетероарил;Rи R, независимо друг от друга означают -Н или -R; или Rи Rсовместно образуют кольцо и означают -CHCHOCHCH-, CHCHNRCHCH- или -(СН)-; с указанием, что Rи Rоба одновременно не означают -Н;Rозначает -R;Rв каждом случае независимо означает -Н, -Rили -C(=O)R;n означает целое число от 0 до 12;Х означает -O-, -S- или -NR-;Rозначает -Н, -R, -S(=O)R, -C(=O)R, -C(=O)OR, -C(=O)NH, -C(=O)NHRили -C(=O)N(R);Rозначает -Н, -R, -C(=O)H, -C(=O)R, -C(=O)OH, -C(=O)OR, -C(=O)NH, C(=O)NHR, -C(=O)N(R), -S(=O)-R, -S(=O)-OR, -S(=O)-NH, S(=O)-NHRили -S(=O)-N(R); или Rи Rсовместно образуют кольцо и означают -(СН)-, -CHCHOCHCH- или -CHCHNRCHCH-; с указанием, что если Х означает -О- и одновременно n означает 0, то Rне означает -Н;причем"алифат" в каждом случае представляет собой разветвленный или неразветвленный, насыщенным или моно- или многократно ненасыщенный, незамещенный или моно- или многократно замещенный, алифатический углеводородный остаток;"циклоалифат" в каждом случае представляет собой насыщенный или моно- или многократно ненасыщенный, незамещенный или моно- или многокра�
Claims (10)
1. Соединение общей формулы (1)
где
Y1, Y1', Y2, Y2', Y3, Y3', Y4 и Y4' в каждом случае независимо друг от друга выбраны из группы, состоящей из -Н, -F, -Cl, -Br, -I, -CN, -NO2, -CHO, -R0, -C(=O)R0, -C(=O)H, -C(=O)-OH, -C(=O)OR0, -C(=O)NH2, -C(=O)NHR0, C(=O)N(R0)2, -ОН, -OR0, -OC(=O)H, -OC(=O)R0, -OC(=O)OR0, -OC(=O)NHR0, -OC(=O)N(R0)2, -SH, -SR0, -SO3H, -S(=O)1-2-R0, -S(=O)1-2NH2, -NH2, -NHR0, N(R0)2, -N+(R0)3, -N+(R0)2O-, -NHC(=O)R0, -NHC(=O)OR0, -NHC(=O)NH2, NHC(=O)NHR0 и -NHC(=O)N(R0)2; преимущественно в каждом случае независимо друг от друга выбраны из группы, состоящей из -Н, -F, -Cl, -CN и -С1-8-алифат; или Y1 и Y1', или Y2 и Y2', или Y3 и Y3', или Y4 и Y4' совместно означают =O;
Q означает -R0, -C(=O)-R0, -C(=O)OR0, -C(=O)NHR0, -C(=O)N(R0)2 или -C(=NH)-R0;
R0 в каждом случае независимо означает -C1-8-алифат, -С3-12-циклоалифат, -арил, -гетероарил, -С1-8-алифат-С3-12-циклоалифат, -C1-8-алифат-арил, -C1-8-алифат-гетероарил, -С3-8-циклоалифат-С1-8-алифат, -С3-8-циклоалифат-арил или -С3-8-циклоалифат-гетероарил;
R1 и R2, независимо друг от друга означают -Н или -R0; или R1 и R2 совместно образуют кольцо и означают -CH2CH2OCH2CH2-, CH2CH2NR4CH2CH2- или -(СН2)3-6-; с указанием, что R1 и R2 оба одновременно не означают -Н;
R3 означает -R0;
R4 в каждом случае независимо означает -Н, -R0 или -C(=O)R0;
n означает целое число от 0 до 12;
Х означает -O-, -S- или -NRA-;
RA означает -Н, -R0, -S(=O)0-2R0, -C(=O)R0, -C(=O)OR0, -C(=O)NH2, -C(=O)NHR0 или -C(=O)N(R0)2;
RB означает -Н, -R0, -C(=O)H, -C(=O)R0, -C(=O)OH, -C(=O)OR0, -C(=O)NH2, C(=O)NHR0, -C(=O)N(R0)2, -S(=O)1-2-R0, -S(=O)1-2-OR0, -S(=O)1-2-NH2, S(=O)1-2-NHR0 или -S(=O)1-2-N(R0)2; или RA и RB совместно образуют кольцо и означают -(СН2)2-5-, -CH2CH2OCH2CH2- или -CH2CH2NR4CH2CH2-; с указанием, что если Х означает -О- и одновременно n означает 0, то RB не означает -Н;
причем
"алифат" в каждом случае представляет собой разветвленный или неразветвленный, насыщенным или моно- или многократно ненасыщенный, незамещенный или моно- или многократно замещенный, алифатический углеводородный остаток;
"циклоалифат" в каждом случае представляет собой насыщенный или моно- или многократно ненасыщенный, незамещенный или моно- или многократно замещенный, алициклический, моно- или мультициклический углеводородный остаток, число циклических атомов углерода которого преимущественно находится в указанном диапазоне (т.е. "С3-8-"циклоалифат преимущественно имеет 3, 4, 5, 6, 7 или 8 циклических атомов углерода);
причем относительно "алифат" и "циклоалифат" под "моно- или многократно замещенным" понимается моно- или многократное замещение одного или нескольких атомов водорода, например, однократное, двукратное, трехкратное или полное замещение, заместителями независимо друг от друга выбранными из группы, состоящей из -F, -Cl, -Br, -I, -CN, -NO2, -СНО, =O, -R0, -C(=O)R0, -C(=O)H, C(=O)OH, -C(=O)OR0, -C(=O)NH2, -C(=O)NHR0, -C(=O)N(R0)2, -ОН, -OR0, OC(=O)H, -OC(=O)R0, -OC(=O)OR0, -OC(=O)NHR0, -OC(=O)N(R0)2, -SH, SR0, -SO3H, -S(=O)1-2-R0, -S(=O)1-2NH2, -NH2, -NHR0, -N(R0)2, -N+(R0)3, N+(R0)2O-, -NHC(=O)R0, -NHC(=O)OR0, -NHC(=O)NH2, -NHC(=O)-NHR0, -NH-C(=O)N(R0)2, -Si(R0)3 и -PO(OR0)2;
"арил" в каждом случае независимо означает карбоциклическую кольцевую систему с, по меньшей мере, одним ароматическим кольцом, но без гетероатомов в этом кольце, причем арильные остатки при необходимости могут быть конденсированы с другими насыщенными, (частично) ненасыщенными или ароматическими кольцевыми системами и каждый арильный остаток может быть незамещенным или моно- или многократно замещенным, причем арильные заместители могут быть одинаковыми или различными и в любом и возможном положении арила;
"гетероарил" означает 5-, 6- или 7-членный циклический ароматический остаток, который содержит 1, 2, 3, 4 или 5 гетероатомов, причем гетероатомы одинаково или различно представляют собой азот, кислород или серу, и гетероцикл может быть незамещенным или моно- или многократно замещенным; причем в случае замещения в гетероцикле заместители могут быть одинаковыми или различными и в любом и возможном положении гетероарила; и причем гетероцикл также может быть частью бициклической или полициклической системы;
причем относительно "арил" и "гетероарил" под "моно- или многократно замещенным" понимается моно- или многократное замещение одного или нескольких атомов водорода кольцевой системы заместителями, выбранными из группы, состоящей из -F, -Cl, -Br, -I, -CN, -NO2, -СНО, =O, R0, -C(=O)R0, -С(=O)Н, -С(=O)ОН, -C(=O)OR0, -C(=O)NH2, -C(=O)NHR0, C(=O)-N(R0)2, -ОН, -O(CH2)1-2O-, -OR0, -OC(=O)H, -OC(=O)R0, -OC(=O)OR0, OC(=O)NHR0, -OC(=O)N(R0)2, -SH, -SR0, -SO3H, -S(=O)1-2-R0, -S(=O)1-2NH2, NH2, -NHR0, -N(R0)2, -N+(R0)3, -N+(R0)2O-, -NHC(=O)R0, -NHC(=O)OR0, -NH-C(=O)NH2, -NHC(=O)NHR0, -NHC(=O)N(R0)2, -Si(R0)3 или -PO(OR0)2; причем при необходимости имеющиеся N-кольцевые атомы в каждом случае могут быть окисленными;
в виде отдельного стереоизомера или его смеси, свободных соединений и/или их физиологически совместимых солей;
за исключением 4-(диметиламино)-1-метил-4-р-толилциклогексил ацетата.
2. Соединение по п.1, где n=0 и Х означает -NRA-.
3. Соединение по п.1 или 2, которое имеет общую формулу (2)
где
(гетеро-)арил означает гетероарил или арил, в каждом случае незамещенный или моно- или многократно замещенным, причем заместители независимо друг от друга выбраны из группы, состоящей из F, -Cl, -Br, -I, -CN, -NO2, -СНО, -R0, -C(=O)R0, -C(=O)H, -C(=O)OH, C(=O)OR0, -C(=O)NH2, -С(=O)NH-R0, -C(=O)-N(R0)2, -ОН, -O(CH2)1-2O-, -OR0, -OC(=O)H, -OC(=O)R0, -OC(=O)OR0, -OC(=O)NHR0, -OC(=O)N(R0)2, -SH, SR0, -SO3H, -S(=O)1-2-R0, -S(=O)1-2NH2, -NH2, -NHR0, -N(R0)2, -N+(R0)3, N+(R0)2O-, -NHC(=O)R0, -NHC(=O)-OR0, -NH-C(=O)NH2, -NHC(=O)NHR0 и NHC(=O)N(R0)2.
5. Соединение по одному из пп.1, 3 или 4, где
Q означает -C1-8-алифат, -арил, -C1-8-алифат-арил, -гетероарил, -С(=O)-гетероарил или -С(=NH)-гетероарил;
R1 означает -СН3;
R2 означает -H или -СН3; или
R1 и R2 совместно образуют кольцо и означают -(СН2)3-4-;
Х означает -О- или -NRA-;
RA означает -H или -С1-8-алифат;
RB означает -H, -C1-8-алифат, -C1-8-алифат-арил, -C1-8-алифат-гетероарил, -С(=O)-С1-8-алифат, -С(=O)-С1-8-алифат-арил, -С(=O)-С1-8-алифат-гетероарил, -С(=O)-С3-8-циклоалифат-арил, -С(=O)-С3-8-циклоалифат-гетероарил, -C(=O)NH-C1-8-алифат, -S(=O)1-2-С1-8-алифат, -S(=O)1-2-арил, S(=O)1-2-гетероарил, -S(=O)1-2-С1-8-алифат-арил, -S(=O)1-2-С1-8-алифат-гетероарил, -S(=O)1-2-С3-8-циклоалифат-арил или -S(=O)1-2-С3-8-циклоалифат-гетероарил; или RA и RB совместно образуют кольцо и означают -(СН2)3-4-; с указанием, что если Х означает -О- и одновременно n означает 0, то RB не означает -H;
RC означает -H, -F, -Cl, -Br, -I, -CN, -NO2, -CF3, -ОН или -ОСН3; и
n означает 0, 1, 2, 3 или 4;
причем алифат, арил и гетероарил в каждом случае являются незамещенными или моно- или многократно замещенными.
6. Соединение по п.5, где
Q означает -C1-8-алкил, -фенил, -C1-8-алкил-фенил, -индолил, -С(=O)-индолил или -С(=NH)-индолил;
R1 означает -СН3;
R2 означает -Н или -СН3; или
R1 и R2 совместно образуют кольцо и означают -(СН2)3-4-;
Х означает -О- или -NRA-;
RA означает -Н или -C1-8-алкил;
RB означает -Н, -C1-8-алкил, -C1-8-алкил-фенил, -C1-3-алкил-индолил, С(=O)-C1-8-алкил, -С(=O)-С1-8-алкил-арил, -С(=O)-С1-8-алкил-гетероарил, С(=O)-Сциклопропил-арил, -С(=O)-циклопропил-гетероарил, -С(=O)NH-С1-8-алкил, -S(=O)2-С1-8-алкил, -S(=O)2-С1-8-алкил-арил, -S(=O)2-С1-8-алкил-гетероарил, -S(=O)2-циклопропил-арил, -S(=O)2-циклопропил-гетероарил S(=O)2-фенил; или RA и RB совместно образуют кольцо и означают -(СН2)3-4-; с указанием, что если Х означает -О- и одновременно n означает 0, то RB не означает -Н;
RC означает -Н, -F, -Cl, -Br, -I, -CN, -NO2, -CF3, -ОН или -ОСН3; и
n означает 0, 1, 2, 3 или 4;
причем алифат, арил и гетероарил в каждом случае являются незамещенными или моно- или многократно замещенными.
7. Соединение по п.1, выбранное из группы, состоящей из
- 1-(имино(1-метил-1Н-индол-2-ил)метил)-N1,N1,N4,N4-тетраметил-4-фенилциклогексан-1,4-диамин бис(2-гидроксипропан-1,2,3-трикарбоксилат);
- 4-(диметиламино)-4-фенил-1-(пирролидин-1-ил)циклогексил)(1-метил-1Н-индол-2-ил)метанон;
- 1-(имино(1-метил-1Н-индол-2-ил)метил)-N1,N1,N4,N4-тетраметил-4-фенилциклогексан-1,4-диамин бис(2-гидроксипропан-1,2,3-трикарбоксилат);
- 1,4-бис(диметиламино)-4-фенилциклогексил)(1-метил-1Н-индол-2-ил)метанон;
- 4-(имино(1-метил-1Н-индол-2-ил)метил)-N,N-диметил-1-фенил-4-(пирролидин-1-ил)циклогексанамин;
- 4-(диметиламино)-4-фенил-1-(пирролидин-1-ил)циклогексил)(1-метил-1 Н-индол-2-ил)метанон;
- N1,N1,N4-триметил-1,4-дифенилциклогексан-1,4-диамин;
- N1,N1,N4,N4-тетраметил-1,4-дифенилциклогексан-1,4-диамин;
- 1-бензил-N1,N1,N4,N4-тетраметил-4-фенилциклогексан-1,4-диамин;
- 4-метокси-4-(3-(метоксиметил)-1Н-индол-2-ил)-N,N-диметил-1-фенилциклогексанамин 2-гидроксипропан-1,2,3-трикарбоксилат;
- 4-(бензилокси)-4-(3-(метоксиметил)-1Н-индол-2-ил)-N,N-диметил-1-фенилциклогексанамин;
- 4-этокси-4-(3-(метоксиметил)-1Н-индол-2-ил)-N,N-диметил-1-фенилциклогексанамин 2-гидроксипропан-1,2,3-трикарбоксилат;
- N-((-4-(диметиламино)-1-метил-4-фенилциклогексил)метил)ацетамид 2-гидроксипропан-1,2,3-трикарбоксилат;
- 4-хлоро-N-((-4-(диметиламино)-1-метил-4-фенилциклогексил)метил)бензолсульфонамид 2-гидроксипропан-1,2,3-трикарбоксилат;
- N-((1-бутил-4-(диметиламино)-4-фенилциклогексил)метил)-4-хлоробензолсульфонамид 2-гидроксипропан-1,2,3-трикарбоксилат;
- N-((-4-(диметиламино)-4-фенил-1-(4-фенилбутил)циклогексил)метанол;
- N(4-((диметиламино)метил)-N,N-диметил-1,4-дифенилциклогексанамин;
- 4-бензил-4-((диметиламино)метил)-N,N-диметил-1-фенилциклогексанамин;
- 4-(((1Н-индол-2-ил)метиламино)метил)-N,N,4-триметил-1-фенилциклогексанамин;
- N1,N1,N4,N4-тетраметил-1-(3-метил-1Н-индол-2-ил)-4-фенилциклогексан-1,4-диамин;
- N-(4-(диметиламино)-1-(3-метил-1Н-индол-2-ил)-4-фенилциклогексил)-N-метилкоричный амид; и
- N-(4-(диметиламино)-1-(3-метил-1Н-индол-2-ил)-4-фенилциклогексил)-N-метилацетамид;
- [4-бензил-4-(диметиламинометил)-1-фенил-циклогексил]-диметил-амин;
- (4-диметиламино-1,4-дифенил-циклогексил)-метил-диметил-амин (неполярный диастереомер);
- (Е)-N-(4-диметиламино-1,4-дифенил-циклогексил)-N-метил-3-фенил-акриламид (неполярный диастереомер);
- N-(4-диметиламино-1,4-дифенил-циклогексил)-N-метил-ацетамид (неполярный диастереомер);
- N-(4-диметиламино-1,4-дифенил-циклогексил)-N-метил-метансульфоновой кислоты амид (полярный диастереомер);
- (Е)-N-(4-диметиламино-1,4-дифенил-циклогексил)-N-метил-3-фенил-акриламид (полярный диастереомер);
- N-(4-диметиламино-1,4-дифенил-циклогексил)-N-метил-ацетамид (полярный диастереомер);
- 3-бензил-1-(4-диметиламино-1,4-дифенил-циклогексил)-1-метил-мочевина (неполярный диастереомер);
- 3-бензил-1-(4-диметиламино-1,4-дифенил-циклогексил)-1-метил-мочевина (полярный диастереомер);
- 1-(4-диметиламино-1,4-дифенил-циклогексил)-3-этил-1-метил-мочевина (неполярный диастереомер);
- 1-(4-диметиламино-1,4-дифенил-циклогексил)-3-этил-1-метил-мочевина (полярный диастереомер);
- (4-бензил-4-((диметиламино)метил)-N-метил-1-фенилциклогексанамин (полярный диастереомер);
- (1-бензил-4-диметиламино-4-фенил-циклогексил)-метил-диметил-амин (полярный диастереомер);
- [4-(диметил-амино)-4-(3-метил-1Н-индол-2-ил)-1-фенил-циклогексил]-диметил-амин (полярный диастереомер);
- [4-диметиламино-4-(3-метил-1Н-индол-2-ил)-1-фенил-циклогексил]-диметил-амин (неполярный диастереомер);
- [4-(диметиламинометил)-1,4-дифенил-циклогексил]-диметил-амин (полярный диастереомер);
- диметил-(4-метиламино-4-фенил-1-тиофен-2-ил-циклогексил)-амин (неполярный диастереомер);
- диметил-(4-метиламино-4-фенил-1-тиофен-2-ил-циклогексил)-амин (полярный диастереомер);
- [4-(диметил-амино)-4-фенил-1-тиофен-2-ил-циклогексил]-диметил-амин (полярный диастереомер);
- (4-диметиламино-4-фенил-1-тиофен-2-ил-циклогексил)-диметил-амин (неполярный диастереомер);
- (Е)-N-[[4-диметиламино-4-(3-фторфенил)-1-метил-циклогексил]-метил]-3-фенил-акриламид (полярный диастереомер);
- (Е)-N-[[4-диметиламино-4-(3-фторфенил)-1-метил-циклогексил]-метил]-3-фенил-акриламид (неполярный диастереомер);
- (Е)-N-[[4-диметиламино-4-(3-фторфенил)-1-метил-циклогексил]-метил]-2-фенил-этенсульфоновой кислоты амид (неполярный диастереомер);
- (Е)-N-[[4-диметиламино-4-(3-фторфенил)-1-метил-циклогексил]-метил]-2-фенил-этенсульфоновой кислоты амид (полярный диастереомер);
- (1-бутил-4-метиламино-4-фенил-циклогексил)-диметил-амин (неполярный диастереомер);
- (1-бутил-4-метиламино-4-фенил-циклогексил)-диметил-амин (полярный диастереомер);
- [4-(бутил-метил-амино)-1,4-дифенил-циклогексил]-диметил-амин (неполярный диастереомер);
- [4-(бутил-метил-амино)-1,4-дифенил-циклогексил]-диметил-амин (полярный диастереомер);
- [4-(бензил-метил-амино)-1,4-дифенил-циклогексил]-диметил-амин (неполярный диастереомер);
- [4-(бензил-метил-амино)-1,4-дифенил-циклогексил]-диметил-амин (полярный диастереомер);
- N-[4-(диметил-амино)-1,4-дифенил-циклогексил]-N-метил-2,2-дифенил-ацетамид (полярный диастереомер);
- диметил-[4-(3-метил-1Н-индол-2-ил)-1-фенил-4-пирролидин-1-ил-циклогексил]-аминдигидрохлорид (полярный диастереомер);
- диметил-[4-(3-метил-1Н-индол-2-ил)-1-фенил-4-пирролидин-1-ил-циклогексил]-амин;
- [4-(азетидин-1-ил)-4-(3-метил-1Н-индол-2-ил)-1-фенил-циклогексил]-диметил-амин (неполярный диастереомер);
- N-(4-диметиламино-1,4-дифенил-циклогексил)-N-метил-метансульфоновой кислоты амид (неполярный диастереомер);
- (4-бутил-4-диметиламино-1-фенил-циклогексил)-диметил-амин (неполярный диастереомер);
- (4-бутил-4-диметиламино-1-фенил-циклогексил)-диметил-амин (полярный диастереомер);
- [4-(циклопентил-метил)-4-диметиламино-1-фенил-циклогексил]-метил-амин (неполярный диастереомер);
- [4-(циклопентил-метил)-4-диметиламино-1-фенил-циклогексил]-метил-амин (полярный диастереомер);
- [4-(циклопентил-метил)-4-диметиламино-1-фенил-циклогексил]-диметил-амин (неполярный диастереомер);
- [4-(циклопентил-метил)-4-диметиламино-1-фенил-циклогексил]-диметил-амин (полярный диастереомер);
- (Е)-N-[4-(циклопентил-метил)-4-диметиламино-1-фенил-циклогексил]-N-метил-3-фенил-акриламид (неполярный диастереомер);
- (Е)-N-[4-(циклопентил-метил)-4-диметиламино-1-фенил-циклогексил]-N-метил-3-фенил-акриламид (полярный диастереомер);
- 2-[(4-диметиламино-1,4-дифенил-циклогексил)-метил-амино]-уксусная кислота (полярный диастереомер);
- 2-[(4-диметиламино-1,4-дифенил-циклогексил)-метил-амино]-уксусная кислота (неполярный диастереомер);
- [1-(4-метоксифенил)-4-метиламино-4-фенил-циклогексил]-диметил-амин (неполярный диастереомер);
- [1-(4-метоксифенил)-4-метиламино-4-фенил-циклогексил]-диметил-амин (полярный диастереомер);
- диметил-[4-метиламино-4-фенил-1-[4-(трифторметил)-фенил]-циклогексил]-амин (неполярный диастереомер);
- диметил-[4-метиламино-4-фенил-1-[4-(трифторметил)-фенил]-циклогексил]-амин (полярный диастереомер);
- [4-(диметил-амино)-4-фенил-1-[4-(трифторметил)-фенил]-циклогексил]-диметил-амин (полярный диастереомер);
- [4-диметиламино-4-фенил-1-[4-(трифторметил)-фенил]-циклогексил]-диметил-амин (неполярный диастереомер);
- [4-(диметил-амино)-1-(4-метоксифенил)-4-фенил-циклогексил]-диметил-амин (полярный диастереомер);
- [4-диметиламино-1-(4-метоксифенил)-4-фенил-циклогексил]-диметил-амин (неполярный диастереомер);
- [4-[(1Н-индол-3-ил-метиламино)-метил]-4-метил-1-фенил-циклогексил]-диметил-амин (неполярный диастереомер);
- [4-[(1Н-индол-3-ил-метиламино)-метил]-4-метил-1-фенил-циклогексил]-диметил-амин (полярный диастереомер);
- [4-[(1Н-индол-3-ил-метил-метил-амино)-метил]-4-метил-1-фенил-циклогексил]-диметил-амин (неполярный диастереомер);
- [4-[(1Н-индол-3-ил-метил-метил-амино)-метил]-4-метил-1-фенил-циклогексил]-диметил-амин (полярный диастереомер);
- [3-[[[4-(диметил-амино)-1-метил-4-фенил-циклогексил]-метил-метил-амино]-метил]-1Н-индол-1-ил]-метанол (полярный диастереомер);
- (Е)-N-[4-диметиламино-1-(3-метил-1Н-индол-2-ил)-4-фенил-циклогексил]-N-метил-3-фенил-акриламид (полярный диастереомер);
- [4-диметиламино-1-(3-метил-1Н-индол-2-ил)-4-фенил-циклогексил]-метил-амин (полярный диастереомер);
- [4-диметиламино-1-(3-метил-1Н-индол-2-ил)-4-фенил-циклогексил]-метил-амин (неполярный диастереомер);
- бензил-[4-диметиламино-1-(3-метил-1Н-индол-2-ил)-4-фенил-циклогексил]-амин; 2-гидрокси-пропан-1,2,3-трикарбоновой кислоты;
- диметил-[4-[метил-(пиридин-3-ил-метил)-амино]-1,4-дифенил-циклогексил]-амин (полярный диастереомер);
- [4-[[4,6-бис(метиламино)-[1,3,5]триазин-2-ил]-метил-амино]-1,4-дифенил-циклогексил]-диметил-амин (неполярный диастереомер);
- [4-[[4-(4-метокси-фенокси)-6-метиламино-[1,3,5]триазин-2-ил]-метил-амино]-1,4-дифенил-цикпогексил]-диметил-амин (неполярный диастереомер);
- N-[4-(диметил-амино)-1,4-дифенил-циклогексил]-N-метил-пиридин-3-карбоновой кислоты амид (неполярный диастереомер);
- диметил-[4-[метил-(пиридин-3-ил-метил)-амино]-1,4-дифенил-циклогексил]-амин (неполярный диастереомер);
- [4-[[4,6-бис(метиламино)-[1,3,5]триазин-2-ил]-метил-амино]-1,4-дифенил-циклогексил]-диметил-амин (полярный диастереомер);
- [4-[[4-(4-метокси-фенокси)-6-метиламино-[1,3,5]триазин-2-ил]-метил-амино]-1,4-дифенил-циклогексил]-диметил-амин (полярный диастереомер);
- N-[4-(диметил-амино)-1,4-дифенил-циклогексил]-N,1-диметил-1Н-пиразол-3-карбоновой кислоты амид (полярный диастереомер);
- N-[4-(диметил-амино)-1,4-дифенил-циклогексил]-N,1-диметил-1Н-пиразол-3-карбоновой кислоты амид (неполярный диастереомер);
- [4-(диметил-амино)-1-(3-фторфенил)-4-(3-метил-1Н-индол-2-ил)-циклогексил]-диметил-амин (полярный диастереомер);
- 4-(азетидин-1-ил)-1-(3-фторофенил)-N,N-диметил-4-(3-метил-1Н-индол-2-ил)циклогексанамин (неполярный диастереомер);
- 4-(азетидин-1-ил)-1-(3-фторофенил)-N,N-диметил-4-(3-метил-1Н-индол-2-ил)циклогексанамин (полярный диастереомер);
- [4-диметиламино-1-(3-фторфенил)-4-(3-метил-1Н-индол-2-ил)-циклогексил]-диметил-амин (неполярный диастереомер);
- N-(4-диметиламино-1,4-Дифенил-циклогексил)-N-метил-3-(трифторметил)-бензамид (неполярный диастереомер);
- N-(4-диметиламино-1,4-дифенил-циклогексил)-N-метил-3-(трифторметил)-бензамид (полярный диастереомер);
- [4-[[4,6-бис(4-метокси-фенокси)-[1,3,5]триазин-2-ил]-метил-амино]-1,4-дифенил-циклогексил]-диметил-амин (полярный диастереомер);
- (4-диметиламино-1,4-дифенил-циклогексил)-метил-[(1-метил-1Н-пиразол-3-ил)-метил]-амин (полярный диастереомер);
- (4-диметиламино-1,4-дифенил-циклогексил)-метил-[(1-метил-1Н-пиразол-3-ил)-метил]-амин (неполярный диастереомер);
- [4-[[4,6-бис(4-метокси-фенокси)-[1,3,5]триазин-2-ил]-метил-амино]-1,4-дифенил-циклогексил]-диметил-амин (неполярный диастереомер);
- N-(4-диметиламино-1,4-дифенил-циклогексил)-4-метокси-N-метил-бензамид (неполярный диастереомер);
- N-(4-диметиламино-1,4-дифенил-циклогексил)-4-метокси-N-метил-бензамид (полярный диастереомер);
- (4-диметиламино-1,4-дифенил-циклогексил)-[(4-метоксифенил)-метил]-метил-амин (полярный диастереомер);
- (4-диметиламино-1,4-дифенил-циклогексил)-[(4-метоксифенил)-метил]-метил-амин (неполярный диастереомер);
- [1-(3-фторфенил)-4-(3-метил-1Н-индол-2-ил)-4-пирролидин-1-ил-циклогексил]-диметил-амин (неполярный диастереомер);
- [1-(3-фторфенил)-4-(3-метил-1Н-индол-2-ил)-4-пирролидин-1-ил-циклогексил]-диметил-амин (полярный диастереомер);
- [1-(3-фторфенил)-4-метиламино-4-(3-метил-1Н-индол-2-ил)-циклогексил]-диметил-амин;
- диметил-[4-(3-метил-1Н-индол-2-ил)-1-фенил-4-пиперидин-1-ил-циклогексил]-амин (неполярный диастереомер);
- [1-(3-фторфенил)-4-(3-метил-1Н-индол-2-ил)-4-пиперидин-1-ил-циклогексил]-диметил-амин (полярный диастереомер);
- [4-(диметил-амино)-4-(5-фтор-3-метил-1Н-индол-2-ил)-1-фенил-циклогексил]-диметил-амин (полярный диастереомер);
- (4-диметиламино-1,4-дифенил-циклогексил)-метил-[[3-(трифторметил)фенил]-метил]-амин (полярный диастереомер);
- (4-диметиламино-1,4-дифенил-циклогексил)-метил-[[3-(трифторметил)фенил]-метил]-амин (неполярный диастереомер);
- N-(4-диметиламино-1,4-дифенил-циклогексил)-3-фтор-N-метил-бензамид (неполярный диастереомер);
- N-(4-диметиламино-1,4-дифенил-циклогексил)-3-фтор-N-метил-бензамид (полярный диастереомер);
- (4-диметиламино-1,4-дифенил-циклогексил)-[(3-фторфенил)-метил]-метил-амин (неполярный диастереомер);
- (4-диметиламино-1,4-дифенил-циклогексил)-[(3-фторфенил)-метил]-метил-амин (полярный диастереомер);
- 2-[(4-диметиламино-1,4-дифенил-циклогексил)-метил-амино]-этанол (полярный диастереомер);
- 2-[(4-диметиламино-1,4-дифенил-циклогексил)-метил-амино]-N,N-диметил-ацетамид (полярный диастереомер);
- 2-[(4-диметиламино-1,4-дифенил-циклогексил)-метил-амино]-N-метил-ацетамид (полярный диастереомер);
- 2-[(4-диметиламино-1,4-дифенил-циклогексил)-метил-амино]-N,N-диметил-ацетамид (неполярный диастереомер);
- 2-[(4-диметиламино-1,4-дифенил-циклогексил)-метил-амино]-N-метил-ацетамид (неполярный диастереомер);
- [4-диметиламино-4-(5-фтор-3-метил-1Н-индол-2-ил)-1-фенил-циклогексил]-диметил-амин (неполярный диастереомер);
- [4-(5-фтор-3-метил-1Н-индол-2-ил)-1-фенил-4-пирролидин-1-ил-циклогексил]-диметил-амин (неполярный диастереомер);
- 2-[[4-(диметил-амино)-1,4-дифенил-циклогексил]-метил-амино]-этанол (неполярный диастереомер);
- [4-[[4,6-бис(диметиламино)-[1,3,5]триазин-2-ил]-метил-амино]-1,4-дифенил-циклогексил]-диметил-амин (неполярный диастереомер);
- диметил-[4-[метил-(4-метиламино-6-пиперидин-1-ил-[1,3,5]триазин-2-ил)-амино]-1,4-дифенил-циклогексил]-амин (полярный диастереомер);
- 4-[[4-(диметил-амино)-1,4-дифенил-циклогексил]-метил-амино]-бутан-1-ол (полярный диастереомер);
- 3-[[4-(диметил-амино)-1,4-дифенил-циклогексил]-метил-карбамоил]-пропионовая кислота (полярный диастереомер);
- [4-(5-фтор-3-метил-1Н-индол-2-ил)-1-фенил-4-пирролидин-1-ил-циклогексил]-диметил-амин (полярный диастереомер);
- [1-(3-фторфенил)-4-(3-метил-1Н-индол-2-ил)-4-пиперидин-1-ил-циклогексил]-диметил-амин (неполярный диастереомер);
- [4-(азетидин-1-ил)-4-(5-фтор-3-метил-1Н-индол-2-ил)-1-(3-фторфенил)циклогексил]-диметил-амин (неполярный диастереомер);
- [4-(азетидин-1-ил)-4-(5-фтор-3-метил-1Н-индол-2-ил)-1-(3-фторфенил)-циклогексил]-диметил-амин (полярный диастереомер);
- [4-(5-фтор-3-метил-1Н-индол-2-ил)-4-морфолин-4-ил-1-фенил-циклогексил]-диметил-амин (полярный диастереомер);
- [4-(5-фтор-3-метил-1Н-индол-2-ил)-4-метиламино-1-фенил-циклогексил]-диметил-амин (неполярный диастереомер);
- [4-(5-фтор-3-метил-1Н-индол-2-ил)-4-метиламино-1-фенил-циклогексил]-диметил-амин (полярный диастереомер);
- диметил-[4-метиламино-4-(3-метил-1Н-индол-2-ил)-1-тиофен-2-ил-циклогексил]-амин (полярный диастереомер);
- [4-(5-фтор-3-метил-1Н-индол-2-ил)-4-морфолин-4-ил-1-фенил-циклогексил]-диметил-амин (неполярный диастереомер);
- [4-[(4-анилино-6-метиламино-[1,3,5]триазин-2-ил)-метил-амино]-1,4-дифенил-циклогексил]-диметил-амин (неполярный диастереомер);
- [4-[[4-(изопропил-метил-амино)-6-метиламино-[1,3,5]триазин-2-ил]-метил-амино]-1,4-дифенил-циклогексил]-диметил-амин (полярный диастереомер);
- [4-[(4-анилино-6-метиламино-[1,3,5]триазин-2-ил)-метил-амино]-1,4-дифенил-циклогексил]-диметил-амин (полярный диастереомер);
- [4-[[4-(бензиламино)-6-метиламино-[1,3,5]триазин-2-ил]-метил-амино]-1,4-дифенил-циклогексил]-диметил-амин (полярный диастереомер);
- [4-[(4-бутиламино-6-метиламино-[1,3,5]триазин-2-ил)-метил-амино]-1,4-дифенил-циклогексил]-диметил-амин (полярный диастереомер);
- [4-[[4-(4-метокси-фенокси)-[1,3,5]триазин-2-ил]-метил-амино]-1,4-дифенил-циклогексил]-диметил-амин (полярный диастереомер);
- (1,4-дифенил-4-пирролидин-1-ил-циклогексил)-метил-амин (полярный диастереомер);
- (1,4-дифенил-4-пирролидин-1-ил-циклогексил)-метил-амин (неполярный диастереомер);
- [4-[(бензил-метил-амино)-метил]-1,4-дифенил-циклогексил]-диметил-амин;
- [4-диметиламино-1-(3-метил-1Н-индол-2-ил)-4-тиофен-2-ил-циклогексил]-метил-амин (неполярный диастереомер);
- (1,4-дифенил-4-пирролидин-1-ил-циклогексил)-диметил-амин (полярный диастереомер);
- (1,4-дифенил-4-пирролидин-1-ил-циклогексил)-диметил-амин (неполярный диастереомер);
- [4-[[4-(бензиламино)-[1,3,5]триазин-2-ил]-метил-амино]-1,4-дифенил-циклогексил]-диметил-амин (полярный диастереомер);
- диметил-[4-[метил-(4-пиперидин-1-ил-[1,3,5]триазин-2-ил)-амино]-1,4-дифенил-циклогексил]-амин (полярный диастереомер);
- [4-[(4-бутиламино-[1,3,5]триазин-2-ил)-метил-амино]-1,4-дифенил-циклогексил]-диметил-амин (полярный диастереомер);
- [4-[(4-анилино-[1,3,5]триазин-2-ил)-метил-амино]-1,4-дифенил-циклогексил]-диметил-амин (полярный диастереомер);
- [4-[[4-(изопропил-метил-амино)-[1,3,5]триазин-2-ил]-метил-амино]-1,4-дифенил-циклогексил]-диметил-амин (полярный диастереомер);
- [4-[[4-(трет-бутиламино)-[1,3,5]триазин-2-ил]-метил-амино]-1,4-дифенил-циклогексил]-диметил-амин (полярный диастереомер);
- [4-(циклогексил-метиламино)-1-(3-фторфенил)-4-(3-метил-1Н-индол-2-ил)-циклогексил]-диметил-амин (неполярный диастереомер);
- [4-(циклопентиламино)-1-(3-фторфенил)-4-(3-метил-1Н-индол-2-ил)-циклогексил]-диметил-амин (неполярный диастереомер);
- [4-анилино-1-(3-фторфенил)-4-(3-метил-1Н-индол-2-ил)-циклогексил]-диметил-амин;
- [1-(3-фторфенил)-4-(3-метил-1Н-индол-2-ил)-4-(пиридин-4-иламино)-циклогексил]-диметил-амин;
- [4-[(бутил-метил-амино)-метил]-1,4-дифенил-циклогексил]-диметил-амин (неполярный диастереомер);
- [4-[(бутил-метил-амино)-метил]-1,4-дифенил-циклогексил]-диметил-амин (полярный диастереомер);
- N-(4-диметиламино-1,4-дифенил-циклогексил)-N-метил-циклогексанкарбоновой кислоты амид (полярный диастереомер);
- N-(4-диметиламино-1,4-дифенил-циклогексил)-N-метил-тетрагидро-пиран-4-карбоновой кислоты амид (полярный диастереомер);
- циклогексил-метил-(4-диметиламино-1,4-дифенил-циклогексил)-метил-амин (полярный диастереомер);
- (4-диметиламино-1,4-дифенил-циклогексил)-метил-(тетрагидро-пиран-4-ил-метил)-амин (полярный диастереомер);
- N-(4-диметиламино-1,4-дифенил-циклогексил)-N,1-диметил-пиперидин-4-карбоновой кислоты амид (полярный диастереомер);
- (4-диметиламино-1,4-дифенил-циклогексил)-метил-[(1-метил-пиперидин-4-ил)-метил]-амин (полярный диастереомер);
и их физиологически совместимые соли.
8. Лекарственное средство, содержащее по меньшей мере одно соединение по одному из пп.1-7 в виде отдельного стереоизомера или его смеси, свободных соединений и/или их физиологически совместимых солей, а также при необходимости пригодные добавки и/или вспомогательные вещества и/или при необходимости другие действующие вещества.
9. Применение соединения по одному из пп.1-7 в виде отдельного стереоизомера или его смеси, свободного соединения и/или их физиологически совместимых солей, для получения лекарственного средства для лечения боли.
10. Применение соединения по одному из пп.1-7 в виде отдельного стереоизомера или его смеси, свободных соединений и/или их физиологически совместимых солей и/или сольватов для получения лекарственного средства для лечения состояний страха, стресса и связанных со стрессом синдромов, депрессий, эпилепсии, болезни Альцгеймера, старческого слабоумия, общих познавательных дисфункций, нарушений обучения и памяти (как ноотроп), синдромов отмены, злоупотребления алкоголем и/или наркотиками и/или злоупотребления медикаментами и/или алкогольной, наркотической, медикаментозной зависимости, сексуальных дисфункций, сердечно-сосудистых заболеваний, гипотонии, гипертензии, тиннитуса, зуда, мигрени, тугоухости, недостаточной подвижности кишечника, нарушений приема пищи, анорексии, ожирения, локомоторных расстройств, диареи, кахексии, недержания мочи соответственно как мышечный релаксант, противосудорожное средство или анестетик соответственно для совместного приема при лечении с опиоидным анальгетиком или с анестетиком, для диуреза или антинатрийуреза, анксиолизиса, для модуляции двигательной активности, для модуляции распределения нейромедиаторов и лечения связанных с этим нейродегенеративных заболеваний, для лечения синдромов отмены и/или для снижения наркотического потенциала опиоидов.
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