ZA200300900B - Novel aminocyclohexane derivatives. - Google Patents
Novel aminocyclohexane derivatives. Download PDFInfo
- Publication number
- ZA200300900B ZA200300900B ZA200300900A ZA200300900A ZA200300900B ZA 200300900 B ZA200300900 B ZA 200300900B ZA 200300900 A ZA200300900 A ZA 200300900A ZA 200300900 A ZA200300900 A ZA 200300900A ZA 200300900 B ZA200300900 B ZA 200300900B
- Authority
- ZA
- South Africa
- Prior art keywords
- methyl
- trans
- cyclohexyl
- amino
- ethyl
- Prior art date
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- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical class NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 92
- -1 aryl-lower-alkyl Chemical group 0.000 claims description 53
- 125000004432 carbon atom Chemical group C* 0.000 claims description 21
- 239000001257 hydrogen Substances 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 238000011282 treatment Methods 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 238000011321 prophylaxis Methods 0.000 claims description 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 11
- 150000002148 esters Chemical class 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 239000000126 substance Substances 0.000 claims description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 239000000460 chlorine Substances 0.000 claims description 8
- 229910052731 fluorine Inorganic materials 0.000 claims description 8
- 239000011737 fluorine Substances 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 6
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- 201000010099 disease Diseases 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical group 0.000 claims description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims description 6
- 230000003463 hyperproliferative effect Effects 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
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- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 5
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- 125000000842 isoxazolyl group Chemical group 0.000 claims description 3
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- VISTZINSMXPVLB-XUTJKUGGSA-N CN([C@H]1CC[C@H](CCCCN2CCCCC2)CC1)C(=O)Oc1ccc(Br)cc1 Chemical compound CN([C@H]1CC[C@H](CCCCN2CCCCC2)CC1)C(=O)Oc1ccc(Br)cc1 VISTZINSMXPVLB-XUTJKUGGSA-N 0.000 claims description 2
- UMFPZRNDIFHBPF-XUTJKUGGSA-N CN([C@H]1CC[C@H](CCCCN2CCCCC2)CC1)S(=O)(=O)c1ccc(cc1)C(F)(F)F Chemical compound CN([C@H]1CC[C@H](CCCCN2CCCCC2)CC1)S(=O)(=O)c1ccc(cc1)C(F)(F)F UMFPZRNDIFHBPF-XUTJKUGGSA-N 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000001041 indolyl group Chemical group 0.000 claims description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
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- ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 239000000556 agonist Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000003529 anticholesteremic agent Substances 0.000 description 1
- 230000036523 atherogenesis Effects 0.000 description 1
- 230000003143 atherosclerotic effect Effects 0.000 description 1
- 229960005370 atorvastatin Drugs 0.000 description 1
- 229940106943 azor Drugs 0.000 description 1
- 239000003613 bile acid Substances 0.000 description 1
- 229920000080 bile acid sequestrant Polymers 0.000 description 1
- 229940096699 bile acid sequestrants Drugs 0.000 description 1
- 210000004204 blood vessel Anatomy 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- MSZJEPVVQWJCIF-UHFFFAOYSA-N butylazanide Chemical compound CCCC[NH-] MSZJEPVVQWJCIF-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- KHIFRQHKENLDSJ-AQYVVDRMSA-N chembl481209 Chemical compound C1C[C@@H](CCCCC(C)(C)N(CC)CC)CC[C@@H]1N(C)S(=O)(=O)C1=CC=C(C(F)(F)F)C=C1 KHIFRQHKENLDSJ-AQYVVDRMSA-N 0.000 description 1
- CMQCZZNYIFRNDR-AQYVVDRMSA-N chembl520926 Chemical compound C([C@@H]1CC[C@H](CC1)N(C)S(=O)(=O)C=1C=CC(=CC=1)C(F)(F)F)CCCC1(N(CC)CC)CC1 CMQCZZNYIFRNDR-AQYVVDRMSA-N 0.000 description 1
- 230000001587 cholestatic effect Effects 0.000 description 1
- 235000019504 cigarettes Nutrition 0.000 description 1
- 125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 description 1
- HWDVTQAXQJQROO-UHFFFAOYSA-N cyclopropylazanide Chemical compound [NH-]C1CC1 HWDVTQAXQJQROO-UHFFFAOYSA-N 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 125000004212 difluorophenyl group Chemical group 0.000 description 1
- QBSJHOGDIUQWTH-UHFFFAOYSA-N dihydrolanosterol Natural products CC(C)CCCC(C)C1CCC2(C)C3=C(CCC12C)C4(C)CCC(C)(O)C(C)(C)C4CC3 QBSJHOGDIUQWTH-UHFFFAOYSA-N 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 230000003828 downregulation Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 150000004675 formic acid derivatives Chemical class 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 230000014509 gene expression Effects 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 230000001965 increasing effect Effects 0.000 description 1
- HCUARRIEZVDMPT-UHFFFAOYSA-N indolyl-2-carboxylic acid Natural products C1=CC=C2NC(C(=O)O)=CC2=C1 HCUARRIEZVDMPT-UHFFFAOYSA-N 0.000 description 1
- 230000007574 infarction Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000033227 intestinal cholesterol absorption Effects 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 208000028867 ischemia Diseases 0.000 description 1
- CAHGCLMLTWQZNJ-RGEKOYMOSA-N lanosterol Chemical compound C([C@]12C)C[C@@H](O)C(C)(C)[C@H]1CCC1=C2CC[C@]2(C)[C@H]([C@H](CCC=C(C)C)C)CC[C@@]21C CAHGCLMLTWQZNJ-RGEKOYMOSA-N 0.000 description 1
- 229940058690 lanosterol Drugs 0.000 description 1
- 208000019423 liver disease Diseases 0.000 description 1
- 208000014018 liver neoplasm Diseases 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 238000010197 meta-analysis Methods 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 230000003228 microsomal effect Effects 0.000 description 1
- 208000010125 myocardial infarction Diseases 0.000 description 1
- NJPKKNHLXHTMLK-UHFFFAOYSA-N n-[4-[5-(diethylamino)pentyl]cyclohexyl]-n-methyl-4-(trifluoromethyl)benzenesulfonamide Chemical compound C1CC(CCCCCN(CC)CC)CCC1N(C)S(=O)(=O)C1=CC=C(C(F)(F)F)C=C1 NJPKKNHLXHTMLK-UHFFFAOYSA-N 0.000 description 1
- KWDTUWVYRBUKHP-UHFFFAOYSA-N n-[4-[5-[bis(2-hydroxyethyl)amino]pentyl]cyclohexyl]-n-methyl-4-(trifluoromethyl)benzenesulfonamide Chemical compound C=1C=C(C(F)(F)F)C=CC=1S(=O)(=O)N(C)C1CCC(CCCCCN(CCO)CCO)CC1 KWDTUWVYRBUKHP-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229960003512 nicotinic acid Drugs 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 108020004017 nuclear receptors Proteins 0.000 description 1
- 235000020824 obesity Nutrition 0.000 description 1
- 230000002018 overexpression Effects 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- JLXXLCJERIYMQG-UHFFFAOYSA-N phenylcyanamide Chemical compound N#CNC1=CC=CC=C1 JLXXLCJERIYMQG-UHFFFAOYSA-N 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000011324 primary prophylaxis Methods 0.000 description 1
- FYPMFJGVHOHGLL-UHFFFAOYSA-N probucol Chemical compound C=1C(C(C)(C)C)=C(O)C(C(C)(C)C)=CC=1SC(C)(C)SC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 FYPMFJGVHOHGLL-UHFFFAOYSA-N 0.000 description 1
- 229960003912 probucol Drugs 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 235000018770 reduced food intake Nutrition 0.000 description 1
- 230000004141 reverse cholesterol transport Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229960002855 simvastatin Drugs 0.000 description 1
- RYMZZMVNJRMUDD-HGQWONQESA-N simvastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)C(C)(C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 RYMZZMVNJRMUDD-HGQWONQESA-N 0.000 description 1
- 208000017520 skin disease Diseases 0.000 description 1
- 230000000391 smoking effect Effects 0.000 description 1
- 238000011301 standard therapy Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 1
- 125000005309 thioalkoxy group Chemical group 0.000 description 1
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- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
‘ Novel Aminocyclohexane Derivatives . The present invention is concerned with novel aminocyclohexanol derivatives, their manufacture and their use as medicaments. In particular, the invention relates to compounds of the formula (I)
I
3 4 Nw-a® 1 A A V
AN > PAN uY (CH) (CH), M
A wherein
U is O or a lone pair, \% is 0, S, -CH»-, -CH=CH-, or -C=C-,
Ww is CO, COO, CONR', CSO, CSNR', SO,, or SO;:NR', mand n independently from each other are 0 to 7 and m+n is 0 to 7, with the proviso thatmisnot0ifVisOorS,
Al is H, lower-alkyl, hydroxy-lower-alkyl, or lower-alkenyl, :
A? is lower-alkyl, cycloalkyl, cycloalkyl-lower-alkyl, or lower-alkenyl, optionally substituted by R?,
A’and A* are hydrogen or lower-alkyl, or
Aland A’ or A' and A’ are bonded to each other to form a ring and - A'- A%- or - A'- A’ are lower-alkylene or lower-alkenylene, optionally substituted by R%, in which one -CH,- group of -A'- A> or -A'-A’- can ) optionally be replaced by NR?, S, or O, or ‘ A’ and A* are bonded to each other to form a ring together with the carbon atom to which they are attached and -A’-A*- is -(CH,)2.s- which can optionally be mono- or multiply-substituted by lower-alkyl,
A® is H, lower-alkyl, lower-alkenyl, or aryl-lower-alkyl,
AS is lower-alkyl, cycloalkyl, aryl, aryl-lower-alkyl, heteroaryl, heteroaryl-lower- , alkyl, lower-alkoxy-carbonyl-lower-alkyl,
R? is hydroxy, hydroxy-lower-alkyl, lower-alkoxy, lower-alkoxycarbonyl, ‘ 5 N(R R?), or thio-lower-alkoxy,
R', R’, R* and R’ independently from each other are hydrogen or lower-alky], and pharmaceutically acceptable salts and/or pharmaceutically acceptable esters thereof.
The compounds of the present invention inhibit 2,3-oxidosqualene-lanosterol cyclase (EC 5.4.99.) which is required for the biosynthesis of cholesterol, ergosterol and other sterols. Causal risk factors that directly promote the development of coronary and peripheral atherosclerosis include elevated low-density lipoprotein cholesterol (LDL-C), low high-density lipoprotein cholesterol (HDL-C), hypertension, cigarette smoking and diabetes mellitus. Other synergistic risk factors include elevated concentrations of triglyceride (TG)-rich lipoproteins, small, dense low-density lipoprotein particles, lipoprotein (a) (Lp(a)), and homocysteine. Predisposing risk factors modify the causal or conditional risk factors and thus affect atherogenesis indirectly. The predisposing risk factors are obesity, physical inactivity, family history of premature CVD, and male sex. The strong connection between coronary heart disease (CHD) and high LDL-C levels in plasma, and the therapeutic advantage of lowering elevated LDL-C levels are now well established (Gotto et al., Circulation 81, 1990, 1721-1733; Stein et al., Nutr. Metab.
Cardiovasc. Dis. 2, 1992, 113-156; Illingworth, Med. Clin. North. Am. 84, 2000, 23-42).
Cholesterol-rich, sometimes unstable, atherosclerotic plaques lead to the occlusion of blood vessels resulting in an ischemia or an infarct. Studies with respect to primary prophylaxis have shown that a lowering of plasma LDL-C levels in plasma reduces the frequency of non-fatal incidences of CHD, while the overall morbidity remains unchanged. The lowering of plasma LDL-C levels in patients with pre-established CHD (secondary intervention) reduces CHD mortality and morbidity; meta-analysis of different studies shows that this decrease is proportional to the reduction of the LDL-C (Ross et al.,
Arch. Intern. Med. 159, 1999, 1793-1802). :
The clinical advantage of cholesterol lowering is greater for patients with pre- : . established CHD than for asymptomatic persons with hypercholesterolemia. According to current guidelines, cholesterol lowering treatment is recommended for patients who had survived a myocardial infarct or patients suffering from angina pectoris or another atherosclerotic disease, with a target LDL-C level of 100 mg/dl.
Preparations such as bile acid sequestrants, fibrates, nicotinic acid, probucol as well as statins, i.e. HMG-Co-A reductase inhibitors such as simvastatin and atorvastatin, are used for usual standard therapies. The best statins reduce plasma LDL-C effectively by at oo least 40%, and also plasma triglycerides, a synergistic risk factor, but less effectively. In contrast, fibrates reduce plasma triglycerides effectively, but not LDL-C. Combination of a ' statin and a fibrate proved to be very efficacious in lowering LDL-C and triglycerides (Ellen and McPherson, J. Cardiol. 81, 1998, 60B-65B), but safety of such a combination remains an issue (Shepherd, Eur. Heart J. 16, 1995, 5-13). A single drug with a mixed profile combining effective lowering of both LDL-C and triglycerides would provide additional clinical benefit to asymptomatic and symptomatic patients.
In humans, statins are well tolerated at standard dosage, but reductions in non-sterol intermediates in the cholesterol synthesis pathway, such as isoprenoids and coenzyme Q, may be associated with adverse clinical events at high doses (Davignon et al., Can. J.
Cardiol. 8, 1992, 843-864; Pederson and Tobert, Drug Safety 14, 1996, 11-24).
This has stimulated the search for, and development of compounds that inhibit cholesterol biosynthesis, yet act distal to the synthesis of these important, non-sterol intermediates. 2,3-oxidosqualene:lanosterol cyclase (OSC), a microsomal enzyme, represents a unique target for a cholesterol-lowering drug (Morand et al,, J. Lipid Res., 38, 1997, 373-390; Mark et al., J. Lipid Res. 37, 1996, 148-158). OSC is downstream of farnesyl-pyrophosphate, beyond the synthesis of isoprenoids and coenzyme Q. In hamsters, pharmacologically active doses of an OSC inhibitor showed no adverse side- effects, in contrast to a statin which reduced food-intake and body weight, and increased plasma bilirubin, liver weight and liver triglyceride content (Morand et al., J. Lipid Res., 38, 1997, 373-390). The compounds described in European Patent Application No. 636 367, which inhibit OSC and which lower the total cholesterol in plasma, belong to these substances.
OSC inhibition does not trigger the overexpression of HMGR because of an indirect, negative feed-back regulatory mechanism involving the production of 24(S),25- epoxycholesterol (Peffley et al., Biochem. Pharmacol. 56, 1998, 439-449; Nelson et al, J.
Biol. Chem. 256, 1981, 1067-1068; Spencer et al., J. Biol. Chem. 260, 1985, 13391-13394; ’ Panini et al., J. Lipid Res. 27, 1986, 1190-1204; Ness et al., Arch. Biochem. Biophys. 308, 1994, 420-425). This negative feed-back regulatory mechanism is fundamental to the . concept of OSC inhibition because (i) it potentiates synergistically the primary inhibitory effect with an indirect down-regulation of HMGR, and (ii) it prevents the massive accumulation of the precursor monooxidosqualene in the liver. In addition, 24(S),25- epoxycholesterol was found to be one of the most potent agonists of the nuclear receptor
LXR (Janowski et al., Proc. Natl. Acad. Sci. USA, 96, 1999, 266-271). Considering that
24(S),25-epoxycholesterol is a by-product of inhibition of OSC it is hypothesized that the
OSC inhibitors of the present invention could also indirectly activate LXR-dependent pathways such as (i) cholesterol-7alpha-hydroxylase to increase the consumption of ) cholesterol via the bile acid route, (ii) expression of ABC proteins with the potential to stimulate reverse cholesterol transport and increase plasma HDL-C levels (Venkateswaran ‘ et al., J. Biol. Chem. 275, 2000, 14700-14707; Costet et al., J. Biol. Chem. June 2000, in press; Ordovas, Nutr Rev 58, 2000, 76-79, Schmitz and Kaminsky, Front Biosci 6, 2001,
D505-D514), and/or inhibit intestinal cholesterol absorption (Mangelsdorf, XIIth
International Symposium on Atherosclerosis, Stockholm, June 2000). In addition, possible cross talks between fatty acid and cholesterol metabolism mediated by liver LXR have been hypothesized (Tobin et al., Mol. Endocrinol. 14, 2000, 741-752).
The present compounds of formula I inhibit OSC and therefore also inhibit the biosynthesis of cholesterol, ergosterol and other sterols, and reduce the plasma cholesterol levels. They can therefore be used in the therapy and prophylaxis of hypercholesterolemia, hyperlipemia, arteriosclerosis and vascular diseases in general. Furthermore, they can be used in the therapy and/or prevention of mycoses, parasite infections, gallstones, cholestatic liver disorders, tumors and hyperproliferative disorders, e.g. hyperproliferative skin and vascular disorders. In addition, it has unexpectedly been found that the compounds of the present invention can also be of therapeutical use to improve glucose tolerance in order to treat and/or prevent related diseases such as diabetes. The compounds of the present invention further exhibit improved pharmacological properties compared to known compounds.
Unless otherwise indicated the following definitions are set forth to illustrate and define the meaning and scope of the various terms used to describe the invention herein.
In this specification the term “lower” is used to mean a group consisting of one to seven, preferably of one to four carbon atom(s).
The term "lone pair" refers to an unbound electron pair, in particular to the unbound electron pair of a nitrogen atom in e.g. an amine.
The term “halogen” refers to fluorine, chlorine, bromine and iodine, with chlorine and bromine being preferred. : The term “alkyl”, alone or in combination with other groups, refers to a branched or straight-chain monovalent saturated aliphatic hydrocarbon radical of one to twenty carbon atoms, preferably one to sixteen carbon atoms. Alkyl groups can optionally be substituted e.g. with halogen, CN, NO, carboxy, and/or phenyl. Other, more preferred subsituents are hydroxy, lower-alkoxy, NH,, N(lower-alkyl),, and/or lower-alkoxy-
carbonyl.
The term “lower-alkyl” , alone or in combination with other groups, refers to a . branched or straight-chain monovalent alkyl radical of one to seven carbon atoms, preferably one to four carbon atoms. This term is further exemplified by such radicals as , 5 methyl, ethyl, n-propyl, isopropyl, n-butyl, s-butyl, t-butyl and the like. A lower-alkyl group may have a substitution pattern as described earlier in connection with the term "alkyl".
The term “cycloalkyl” refers to a monovalent carbocyclic radical of 3 to 10 carbon atom(s), preferably 3 to 6 carbon atoms. Cycloalkyl in which one or more -CHS- group is replaced by O, S, NH or N(lower-alkyl) are referred to as "heterocycloalkyl".
The term “alkoxy“ refers to the group R’-O-, wherein R’ is an alkyl. The term "lower- alkoxy" refers to the group R’-O-, wherein R’ is a lower-alkyl. The term “thio-alkoxy“ refers to the group R’-S-, wherein R’ is an alkyl. The term "thio-lower-alkoxy" refers to the group R’-S-, wherein R’ is a lower-alkyl.
The term “alkenyl”, alone or in combination with other groups, stands for a straight- chain or branched hydrocarbon residue comprising an olefinic bond and up to 20, preferably up to 16 carbon atoms. The term "lower-alkenyl" refers to a straight-chain or branched hydrocarbon residue comprising an olefinic bond and up to 7, preferably up to 4 carbon atoms, such as e.g. 2-propenyl. An alkenyl or lower-alkenyl group may have a substitution pattern as described earlier in connection with the term "alkyl".
The term "alkylene" refers to a straight chain or branched divalent saturated aliphatic hydrocarbon group of 1 to 20 carbon atoms, preferably 1 to 16 carbon atoms. The term "lower-alkylene" refers to a straight chain or branched divalent saturated aliphatic hydrocarbon group of 1 to 7, preferably 2 to 4 carbon atoms. An alkylene or lower- alkylene group may have a substitution pattern as described earlier in connection with the term "alkyl".
The term "alkenylene" refers to a straight chain or branched divalent hydrocarbon group comprising an olefinic bond and up to 20 carbon atoms, preferably up to 16.carbon ‘ atoms. The term "lower-alkenylene" refers to a straight chain or branched divalent hydrocarbon group comprising an olefinic bond and up to 7, preferably up to 4 C-atoms. : An alkenylene or lower-alkenylene group may have a substitution pattern as described earlier in connection with the term "alkyl".
The term "aryl" relates to the phenyl or naphthyl group which can optionally be mono- or multiply-substituted by lower-alkyl, lower-alkyl-di-oxo, halogen, hydroxy,
cyano, CFs, NH,, N(lower-alkyl),, aminocarbonyl, carboxy, nitro, lower-alkoxy, lower- alkylcarbonyl, lower-alkylcarbonyloxy, aryl, aryloxy, or lower-alkylcarbonyl-amino, preferably by lower-alkyl, lower-alkyl-di-oxo, halogen, hydroxy, cyano, CFs, NH,, ’ N(lower-alkyl),, aminocarbonyl, carboxy, nitro, lower-alkoxy, lower-alkylcarbonyl, lower- alkylcarbonyloxy, aryl, or aryloxy. Preferred substituents are lower-alkyl, lower alkoxy, ' lower-alkyl-carbonyl, lower-alkoxycarbonyl, fluorine, chlorine, bromine, CN, CFs, NO,
NH,, and/or N(lower-alkyl),. More preferred substituents are fluorine, chlorine, bromine and CFs.
The term "heteroaryl" refers to an aromatic 5- or 6-membered ring which can comprise 1, 2 or 3 atoms selected from nitrogen, oxygen and/or sulphur such as furyl, pyridyl, 1,2-, 1,3- and 1,4-diazinyl, thienyl, isoxazolyl, oxazolyl, imidazolyl, or pyrrolyl.
The term "heteroaryl" further refers to bicyclic aromatic groups comprising two 5- or 6- membered rings, in which one or both rings can contain 1, 2 or 3 atoms selected from nitrogen, oxygen or sulphur such as e,g, indol or chinolin, or partially hydrogenated bicyclic aromatic groups such as e.g. indolinyl. A heteroaryl group may have a substitution pattern as described earlier in connection with the term "aryl".
The term "pharmaceutically acceptable salts" embraces salts of the compounds of formula (I) with inorganic or organic acids such as hydrochloric acid, hydrobromic acid, nitric acid, sulphuric acid, phosphoric acid, citric acid, formic acid, maleic acid, acetic acid, fumaric acid, succinic acid, tartaric acid, methanesulphonic acid, p-toluenesulphonic acid and the like, which are non toxic to living organisms. Preferred salts are formates, hydrochlorides and hydrobromides.
The term "pharmaceutically acceptable esters” embraces esters of the compounds of formula (I), in which hydroxy groups have been converted to the corresponding esters with inorganic or organic acids such as, nitric acid, sulphuric acid, phosphoric acid, citric acid, formic acid, maleic acid, acetic acid, succinic acid, tartaric acid, methanesulphonic acid, p-toluenesulphonic acid and the like, which are non toxic to living organisms.
In detail, the present invention relates to compounds of formula (I)
A” a2 At JO all > A oY, CHI, (Ch 0
A wherein
U is O or a lone pair,
Vv is 0, §, -CH,-, -CH=CH-, or -C=C-, : w is CO, COO, CONR', CSO, CSNR', SO;, or SO,NR', . mandn independently from each other are 0 to 7 and m+n is 0 to 7, with the proviso thatmisnot0ifVisOorS,
Al is H, lower-alkyl, hydroxy-lower-alkyl, or lower-alkenyl,
A? is lower-alkyl, cycloalkyl, cycloalkyl-lower-alkyl, or lower-alkenyl, optionally substituted by R?,
A’and A* are hydrogen or lower-alkyl, or
Aland AZor A! and A’ are bonded to each other to form a ring and - Al- AZ or - A'- A’- are lower-alkylene or lower-alkenylene, optionally substituted by R?, in which one -CH,- group of -A'- A%- or -A'-A’- can optionally be replaced by NR’, S, or O, or
A? and A* are bonded to each other to form a ring together with the carbon atom to which they are attached and ASA is -(CHa);.5- which can optionally be mono- or multiply-substituted by lower-alkyl,
A’ is H, lower-alkyl, lower-alkenyl, or aryl-lower-alkyl,
AS is lower-alkyl, cycloalkyl, aryl, aryl-lower-alkyl, heteroaryl, heteroaryl-lower- alkyl, lower-alkoxy-carbonyl-lower-alkyl,
R? 1s hydroxy, hydroxy-lower-alkyl, lower-alkoxy, lower-alkoxycarbonyl,
N(R*R’), or thio-lower-alkoxy,
RY, R®, R* and R’ independently from each other are hydrogen or lower-alkyl, and pharmaceutically acceptable salts and/or pharmaceutically acceptable esters thereof. : Compounds of formula (I) as defined above, wherein A* and A* are not bonded to each other to form a ring together with the carbon atom to which they are attached, are preferred. In such compounds,
Al is H, lower-alkyl, hydroxy-lower-alkyl, or lower-alkenyl
A? is lower-alkyl, cycloalkyl, cycloalkyl-lower-alkyl, or lower-alkenyl, optionally substituted by R?, . A’and A* are hydrogen or lower-alkyl, or
Aland A? or A! and A’ are bonded to each other to form a ring and - Al- A%- or - Al A’- are lower-alkylene or lower-alkenylene, optionally substituted by R?, in which one -CH,- group of -A’- A%- or -A'-A’- can optionally be replaced by NR, S, or O.
Preferred are compounds of formula (I) and/or pharmaceutically acceptable salts thereof. Another preferred embodiment relates to compounds of formula (I) wherein U is alone pair and a further preferred embodiment relates to compounds of formula (I) wherein U is O.
A further preferred embodiment of the present invention relates to the trans-form of the compounds as defined above characterized by formula (Ia)
A°
AL pt yen
AN. > ~~ Va Si uN, (CH), (Chay (1a)
A wherein U,V, W, m, n, Al, AZ A%, A%, A’ and A® have the significances given above.
Compounds in which V represents O are particularly preferred, as are compounds wherein V is -CH,-. Compounds in which V represents -C=C- are also preferred. Further, compounds in which V represents -C=C- also relate to a preferred embodiment of the present invention.
Of the compounds of the present invention, those in which W represents CO, COO,
CONR!, CSNR, SO, or SO,NR’ and R’ is hydrogen are preferred, with those wherein W represents COO or SO; being particularly and individually preferred. Co
Compounds of the present invention in which n is 0 are preferred, as are those in which n is 1. Another preferred embodiment relates to compounds as defined above, wherein mis 1 to 6. In addition, compounds as defined above, wherein mis 0 and V is -C=C- or -C=C-, are also preferred.
In compounds wherein A' represents lower-alkyl, such a lower-alkyl group can optionally be substituted by fluorine. Other preferred compounds of the present invention are those in which A’ represents H, methyl, ethyl, isopropyl, 2-hydroxy-ethyl or 2- propenyl. Another group of preferred compounds of the present invention are those in which A? represents lower-alkyl, cycloalkyl-lower-alky, or lower-alkenyl, optionally . substituted with R?, wherein R* is hydroxy, methoxy, or ethoxycarbonyl, with those compounds wherein A” represents methyl, ethyl, 2-hydroxy-ethyl, 2-propenyl, propyl or v isopropyl being especially preferred.
Compounds of formula (I), wherein A! and A? are bonded to each other to form a ring and -A'-A’- is lower-alkylene or lower-alkenylene, optionally substituted by
R?, in which one -CH,- group of -A'-A%- can optionally be replaced by NR?, S, or O, wherein R” and R® are as defined above are also preferred, with compounds as defined above, wherein A' and A” are bonded to each other to form a ring and -A'-A%- is lower- alkylene or lower-alkenylene, optionally substituted by R? in which one -CH- group of -
A'-A%- can optionally be replaced by O, wherein R? is hydroxy or 2-hydroxyethyl being particularly preferred. In compounds wherein A' and A” are bonded to each other to form a ring, said ring is preferrably a 4-, 5-, or 6-membered ring such as e.g. piperidinyl or pyrrolidinyl. Preferred compounds as defined above are those wherein A' and A? are bonded to each other to form a ring and SAMA is -(CH;)s-. Such compounds consequently comprise a piperidinyl group.
A further preferred embodiment of the present invention relates to compounds of formula (I), wherein A? and/or A* represent hydrogen. Compounds of formula (I) as defined above, wherein A’ and A* are bonded to each other to form a cyclopropyl-ring together with the carbon atom to which they are attached and -A3-A% is -(CH,),- represent another preferred embodiment of the present invention. The term -(CH,);.5- denotes the groups -(CH;)2-, -(CHz)s-, -(CH,)s- and -(CHa)s-.
Compounds of formula (I), in which A’isH, lower-alkyl, lower-alkenyl, or benzyl optionally substituted with halogen are also preferred, with those wherein A’ represents methyl or ethyl being especially preferred.
Compounds of formula (I), wherein A® is lower-alkyl, cycloalkyl, phenyl, naphthyl, phenyl-lower-alkyl, pyridyl, indolyl, indolinyl, thienyl, thienyl-methylene, furyl- ‘ 30 methylene, benzodioxyl, chinolyl, isoxazolyl, or imidazolyl, optionally substituted by one or more substituents selected from the group consisting of lower-alkyl, lower-alkoxy, ) lower-alkylcarbonyl, lower-alkoxycarbonyl, fluorine, chlorine, bromine, CN, CFs, NO», or
N(R®R”), wherein R® and R’ independently from each other are hydrogen or lower-alkyl are another preferred embodiment of the present invention, with those compounds wherein A® is phenyl optionally substituted by one or more substituents selected from the group consisting of fluorine, chlorine, bromine and CFs, being more preferred, and with those compounds wherein A°® is 4-chloro-phenyl, 4-bromo-phenyl or 4-trifluoromethyl- phenyl being particularly preferred.
Preferred compounds of general formula (I) are those selected from the group . 5 consisting of trans-{4-[6-(Allyl-methyl-amino)-hexyloxy}-cyclohexyl}-methyl-carbamic acid 4-nitro- phenyl ester, trans-{4-[6-(Allyl-methyl-amino)-hexyloxy] -cyclohexyl}-methyl-carbamic acid naphthalen-2-yl ester, trans-{4-[6-(Allyl-methyl-amino)-hexyloxy]-cyclohexyl}-methyl-carbamic acid pentafluorophenylmethyl ester, trans-{4-{6-(Allyl-methyl-amino)-hexyloxy]-cyclohexyl}-methyl-carbamic acid benzyl ester, trans-{4-[6-(Allyl-methyl-amino)-hexyloxy] -cyclohexyl}-methyl-carbamic acid phenyl ester, ‘trans-{4-[6-(Allyl-methyl-amino)-hexyloxy]-cyclohexyl}-methyl-carbamic acid p-tolyl ester, trans-{4-[6-(Allyl-methyl-amino)-hexyloxy]-cyclohexyl}-methyl-carbamic acid 4-bromo- phenyl ester, trans-{4-[6-(Allyl-methyl-amino)-hexyloxy]-cyclohexyl}-methyl-carbamic acid 4-fluoro- phenyl ester, trans-{4-[6-(Allyl-methyl-amino)-hexyloxy]-cyclohexyl}-methyl-carbamic acid 4-chloro- phenyl ester, trans-{4-[6-(Allyl-methyl-amino)-hexyloxy]-cyclohexyl}-methyl-carbamic acid hexyl ester, trans-{4-[6-(Allyl-methyl-amino)-hexyloxy]-cyclohexyl}-methyl-carbamic acid 4- methoxy-phenyl ester, trans-{4-[6-(Allyl-methyl-amino)-hexyloxy]-cyclohexyl}-methyl-carbamic acid isobutyl ester, trans-{4-[6-(Allyl-methyl-amino)-hexyloxy]-cyclohexyl}-methyl-carbamic acid 4- trifluoromethyl-phenyl ester, : . trans- {4-[7-(Allyl-methyl-amino)-heptyloxy]-cyclohexyl}-methyl-carbamic acid 4-bromo- phenyl ester, } trans-{4- [5-(Allyl-methyl-amino)-pentyloxy]-cyclohexyl}-methyl-carbamic acid 4-bromo- phenyl ester, trans-{4-[4-(Allyl-methyl-amino)-butoxy]-cyclohexyl}-methyl-carbamic acid 4-bromo- phenyl ester, trans-{4-[7-(Allyl-methyl-amino)-heptyloxy]-cyclohexyl}-methyl-carbamic acid 4-fluoro-
phenyl ester, trans-{4-[5-(Allyl-methyl-amino)-pentyloxy]-cyclohexyl} -methyl-carbamic acid 4-fluoro- phenyl ester, - trans-{4-[5-(Allyl-methyl-amino)-pentyloxy]-cyclohexyl}-methyl-carbamic acid 4- trifluoromethyl-phenyl ester,
: trans-{4-[{4-(Allyl-methyl-amino)-butoxy]-cyclohexyl}-methyl-carbamic acid 4- trifluoromethyl-phenyl ester, {4-trans-[4-(Allyl-methyl-amino)-butoxy]-cyclohexyl}-methyl-carbamic acid 4-chloro- phenyl ester,
{4-trans-[4-(Allyl-methyl-amino)-butoxy]-cyclohexyl}-methyl-carbamic acid isobutyl ester,
{4-trans-[4-(Allyl-methyl-amino)-butoxy]-cyclohexyl}-methyl-carbamic acid phenyl ester, 4-({4-trans-[4-(Allyl-methyl-amino)-butoxy] -cyclohexyl} -methyl-carbamoyloxy)-benzoic acid methyl ester,
{4-trans-[4-(Allyl-methyl-amino)-butoxy]-cyclohexyl}-methyl-carbamic acid 4-methoxy- phenyl ester,
{4-trans-[4-(Allyl-methyl-amino)-butoxy]-cyclohexyl}-methyl-carbamic acid p-tolyl ester, trans-(4-{4-[Ethyl-(2-hydroxy-ethyl)-amino]-butoxy}-cyclohexyl)-methyl-carbamic acid 4-trifluoromethyl-phenyl ester,
trans-{4-(4-Diethylamino-butoxy)-cyclohexyl]-methyl-carbamic acid 4-trifluoromethyl- phenyl ester, trans- [4-(4-Dimethylamino-butoxy)-cyclohexyl]-methyl-carbamic acid 4-triflnoromethyl- phenyl ester, trans-(4-{4-[Bis-(2-hydroxy-ethyl)-amino]-butoxy}-cyclohexyl)-methyl-carbamic acid 4-
trifluoromethyl-phenyl ester, {4-trans-[3-(Allyl-methyl-amino)-propoxy]-cyclohexyl}-methyl-carbamic acid 4-fluoro- phenyl ester,
{4-trans-[3-(Allyl-methyl-amino)-propoxy] -cyclohexyl}-methyl-carbamic acid 4-bromo- phenyl ester,
trans{4-[6-(Allyl-methyl-amino)-hexyloxy]-cyclohexyl}-methyl-carbamic acid 2,4- difluoro-phenyl ester, [4-[Trans-4-(Allyl-methyl-amino)-butoxy]-cyclohexyl}-methyl-carbamic acid 3,4- : difluoro-phenyl ester,
[trans-4-(4-Dimethylamino-butoxy)-cyclohexyl]-methyl-carbamic acid 3,4-difluoro-
: 35 phenyl ester, (trans-4-{4-[Ethyl-(2-hydroxy-ethyl)-amino]-butoxy}-cyclohexyl)-methyl-carbamic acid 3,4-difluoro-phenyl ester, [trans-4-(4-Diethylamino-butoxy)-cyclohexyl]-methyl-carbamic acid 3,4-difluoro-phenyl ester,
ethyl-|trans-4-(4-piperidin-1-yl-butoxy)-cyclohexyl] -carbamic acid 3,4-difluoro-phenyl ester, [trans-4-(4-Azetidin-1-yl-butoxy)-cyclohexyl]-methyl-carbamic acid 3,4-difluoro-phenyl . ester,
Methyl-[trans-4-(4-morpholin-4-yl-butoxy)-cyclohexyl] -carbamic acid 3,4-difluoro- . phenyl ester,
Methyl-[trans-4-(4-pyrrolidin- 1-yl-butoxy)-cyclohexyl]-carbamic acid 3,4-difluoro- phenyl ester, (4-{trans-4-[Ethyl-(2-methoxy-ethyl)-amino]-butoxy}-cyclohexyl)-methyl-carbamic acid 3,4-difluoro-phenyl ester, trans-5-Chloro-thiophene-2-sulfonic acid {4-[6-(allyl-methyl-amino)-hexyloxy]- cyclohexyl}-methyl-amide, trans-N-{4-[6-(Allyl-methyl-amino)-hexyloxy]-cyclohexyl}-4,N-dimethyl- benzenesulfonamide, trans-Naphthalene-2-sulfonic acid {4-[6-(allyl-methyl-amino)-hexyloxy]-cyclohexyl}- methyl-amide, trans-N-{4-{6-(Allyl-methyl-amino)-hexyloxyl-cyclohexyl}-N-methyl- methanesulfonamide, trans-Quinoline-8-sulfonic acid {4-[6-(allyl-methyl-amino)-hexyloxy]-cyclohexyl}- methyl-amide, trans-N-{4-[6-(Allyl-methyl-amino)-hexyloxy]-cyclohexyl}-N-methyl-C-phenyl- methanesulfonamide, trans-3,5-Dimethyl-isoxazole-4-sulfonic acid {4-[6-(allyl-methyl-amino)-hexyloxy]- cyclohexyl}-methyl-amide, trans-Naphthalene-1-sulfonic acid {4-[6-(allyl-methyl-amino)-hexyloxy]-cyclohexyl}- methyl-amide, trans-N-{4-[6-(Allyl-methyl-amino)-hexyloxy]-cyclohexyl}-4-methoxy-N-methyl- benzenesulfonamide, trans-N-{4-[6-(Allyl-methyl-amino)-hexyloxy]-cyclohexyl}-N-methyl- benzenesulfonamide, trans-N-{4-[6-(Allyl-methyl-amino)-hexyloxy]-cyclohexyl}-4-fluoro-N-methyl- benzenesulfonamide, oo : trans-Thiophene-2-sulfonic acid {4-[6-(allyl-methyl-amino)-hexyloxy]-cyclohexyl}- methyl-amide, . 35 trans-N-{4-[6-(Allyl-methyl-amino)-hexyloxy]-cyclohexyl}-2-fluoro-N-methyl- benzenesulfonamide, trans-1-Methyl-1H-imidazole-4-sulfonic acid {4-[6-(allyl-methyl-amino)-hexyloxy]- cyclohexyl}-methyl-amide, trans-N-{4-[6-(Allyl-methyl-amino)-hexyloxy]-cyclohexyl}-4-tert-butyl-N-methyl-
benzenesulfonamide, trans-N-{4-[6-(Allyl-methyl-amino)-hexyloxy]-cyclohexyl}-4-butoxy-N-methyl- benzenesulfonamide, : trans-N-{4-[6-(Allyl-methyl-amino)-hexyloxy]-cyclohexyl}-4-chloro-N-methyl- benzenesulfonamide,
’ trans-N-{4-[6-(Allyl-methyl-amino)-hexyloxy]-cyclohexyl}-N-methyl-4-trifluoromethyl- benzenesulfonamide, trans-N-{4-[6-(Allyl-methyl-amino)-hexyloxy]-cyclohexyl}-4-bromo-N-methyl- benzenesulfonamide,
© 10 trans-N-{4-[6-(Allyl-methyl-amino)-hexyloxy]-cyclohexyl}-N-methyl-4-nitro- benzenesulfonamide, trans-4-Bromo-N-(4-{6-[(2-methoxy-ethyl)-methyl-amino]-hexyloxy}-cyclohexyl)-N- methyl-benzenesulfonamide, trans-N-(4-{6-[ (2-Methoxy-ethyl)-methyl-amino]-hexyloxy}-cyclohexyl)-N-methyl-4-
trifluoromethyl-benzenesulfonamide, trans-4-Bromo-N-methyl-N-[4-(6-morpholin-4-yl-hexyloxy)-cyclohexyl]- benzenesulfonamide, trans-N-[4-(6-Azetidin-1-yl-hexyloxy)-cyclohexyl]-4-bromo-N-methyl- benzenesulfonamide,
trans-4-Bromo-N-{4-[6-(butyl-methyl-amino)-hexyloxy]-cyclohexyl}-N-methyl- benzenesulfonamide, trans-4-Bromo-N-methyl-N-[4-(6-piperidin-1-yl-hexyloxy)-cyclohexyl}- benzenesulfonamide, trans-4-Bromo-N-{4-[6-(3,6-dihydro-2H-pyridin-1-yl)-hexyloxy]-cyclohexyl}-N-methyl-
benzenesulfonamide, trans-4-Bromo-N-(4-{6-[ethyl-(2-hydroxy-ethyl)-amino]-hexyloxy}-cyclohexyl)-N- methyl-benzenesulfonamide, trans-4-Bromo-N-{4-[6-(3-hydroxy-pyrrolidin-1-yl)-hexyloxy]-cyclohexyl}-N-methyl- benzenesulfonamide,
trans-4-Bromo-N-methyl-N-{4-[6-(methyl-propyl-amino)-hexyloxy]-cyclohexyl}- benzenesulfonamide, trans-4-Bromo-N-[4-(6-diallylamino-hexyloxy)-cyclohexyl]-N-methyl- o
: benzenesulfonamide, trans-4-Bromo-N-{4-[6-(4-hydroxymethyl-piperidin-1-yl)-hexyloxy]-cyclohexyl}-N-
: 35 methyl-benzenesulfonamide, trans-4-Bromo-N-(4-{6-[(2-hydroxy-ethyl)-methyl-amino]-hexyloxy}-cyclohexyl)-N- methyl-benzenesulfonamide, trans-4-Bromo-N-methyl-N-{4-[6-(4-methyl-piperidin-1-yl)-hexyloxy]-cyclohexyl}- benzenesulfonamide,
trans-4-Bromo-N-{4-[6-(4-hydroxy-piperidin-1-yl)-hexyloxy] -cyclohexyl}-N-methyl-
benzenesulfonamide,
trans-4-Bromo-N-{4-[6-(cyclopropylmethyl-methyl-amino)-hexyloxy]-cyclohexyl}-N- : methyl-benzenesulfonamide,
trans-[(6-{4-](4-Bromo-benzenesulfonyl)-methyl-amino]-cyclohexyloxy}-hexyl)-methyl-
’ amino] -acetic acid ethyl ester,
trans-N-[4-(6-Allylamino-hexyloxy)-cyclohexyl]-4-bromo-N-methyl-
benzenesulfonamide,
trans-4-Bromo-N-{4-[6-(2-hydroxy-ethylamino)-hexyloxy]-cyclohexyl}-N-methyl-
benzenesulfonamide, trans-4-Bromo-N-{4-(6-ethylamino-hexyloxy)-cyclohexyl]-N-methyl- benzenesulfonamide, trans-N-Methyl-N-{4-(6-morpholin-4-yl-hexyloxy)-cyclohexyl]-4-trifluoromethyl- benzenesulfonamide,
trans-N-[4-(6-Azetidin-1-yl-hexyloxy)-cyclohexyl]-N-methyl-4-trifluoromethyl- benzenesulfonamide, trans-N-{4-[6-(Butyl-methyl-amino)-hexyloxy]-cyclohexyl}-N-methyl-4-trifluoromethyl- - benzenesulfonamide, trans-N-Methyl-N-[4-(6-piperidin- 1-yl-hexyloxy)-cyclohexyl] -4-trifluoromethyl-
benzenesulfonamide, trans-N-{4-[{6-(3,6-Dihydro-2H-pyridin-1-yl1)-hexyloxy]-cyclohexyl}-N-methyl-4- trifluoromethyl-benzenesulfonamide, trans-N-(4-{6-[ Ethyl-(2-hydroxy-ethyl)-amino]-hexyloxy}-cyclohexyl)-N-methyl-4- trifluoromethyl-benzenesulfonamide,
trans-N-{4-[6-(3-Hydroxy-pyrrolidin-1-yl)-hexyloxy]-cyclohexyl}-N-methyl-4- trifluoromethyl-benzenesulfonamide, trans-N-Methyl-N-{4-[6-(methyl-propyl-amino)-hexyloxy]-cyclohexyl}-4- trifluoromethyl-benzenesulfonamide, trans-N-[4-(6-Diallylamino-hexyloxy)-cyclohexyl]-N-methyl-4-trifluoromethyl-
benzenesulfonamide, trans-N-{4-[6-(4-Hydroxymethyl-piperidin- 1-yl)-hexyloxy]-cyclohexyl}-N-methyl-4- trifluoromethyl-benzenesulfonamide, :
’ trans-N-(4-{6-[(2-Hydroxy-ethyl)-methyl-amino] -hexyloxy}-cyclohexyl)-N-methyl-4- trifluoromethyl-benzenesulfonamide,
: 35 trans-N-{4-[6-(4-Hydroxy-piperidin-1-yi)-hexyloxy]-cyclohexyl}-N-methyi-4- trifluoromethyl-benzenesulfonamide, trans-N-{4-{6-(Cyclopropylmethyl-methyl-amino)-hexyloxy]-cyclohexyl}-N-methyl-4- trifiuoromethyl-benzenesulfonamide, trans-[Methyl- (6-{4-[methyl-(4-trifluoromethyl-benzenesulfonyl)-amino} -
cyclohexyloxy}-hexyl)-amino]-acetic acid ethyl ester, trans-[ Methyl-(6-{4- [methyl-(4-trifluoromethyl-benzenesulfonyl)-amino]- cyclohexyloxy}-hexyl)-amino]-acetic acid, ’ trans-N-[4-(6-Allylamino-hexyloxy)- cyclohexyl] -N-methyl-4-trifluoromethyl- benzenesulfonamide, ’ N-{4-trans-[6-(Allyl-methyl-amino)-hexyloxy]-cyclohexyl}-3-chloro-N-methyl- benzenesulfonamide,
N-{4-trans-[6-(Allyl-methyl-amino)-hexyloxy]-cyclohexyl}-2,4-difluoro-N-methyl- benzenesulfonamide,
N-{4-trans-[6-(Allyl-methyl-amino)-hexyloxy]-cyclohexyl}-2-bromo-N-methyl- benzenesulfonamide,
N-{4-trans-[6-(Allyl-methyl-amino)-hexyloxy]-cyclohexyl}-3-bromo-N-methyl- benzenesulfonamide,
N-{4-trans-[6-(Allyl-methyl-amino)-hexyloxy]-cyclohexyl}-2,4-dichloro-N-methyl- benzenesulfonamide,
N-{4-trans-[6- (Allyl-methyl-amino)-hexyloxy]-cyclohexyl}-3-fluoro-N-methyl- benzenesulfonamide,
N-{4-trans-[6-(Allyl-methyl-amino)-hexyloxy]-cyclohexyl}-3,4-dichloro-N-methyl- benzenesulfonamide,
N-{4-trans-[6-(Allyl-methyl-amino)-hexyloxy]-cyclohexyl}-2-chloro-N-methyl- benzenesulfonamide,
N-{4-trans-{6-(Allyl-methyl-amino)-hexyloxy]-cyclohexyl}-3,4-difluoro-N-methyl- benzenesulfonamide, trans-N-[4-(3-Allylamino-propoxy)-cyclohexyl] -N-methyl-4-trifluoromethyl- benzenesulfonamide, trans-N-{4-[3-(Allyl-methyl-amino)-propoxy]-cyclohexyl}N-methyl4-trifluoromethyl- benzenesulfonamide, trans-N-(4-{3-[Ethyl-(2-hydroxy-ethyl)-amino]-propoxy}-cyclohexyl) N-methyl-4- trifluoromethyl-benzenesulfonamide, trans-N-[4-(3-Diethylamino-propoxy)-cyclohexyl]-N-methyl-4-trifluoromethyl- benzenesulfonamide, trans-N-(4-{3-[(2-Hydroxy-ethyl)-methyl-amino]-propoxy} -cyclohexyl)-N-methyl-4- ’ trifluoromethyl-benzenesulfonamide, trans-N-(4-{3-[Bis-(2-hydroxy-ethyl)-amino]-propoxy}-cyclohexyl) N-methyl-4- . 35 trifluoromethyl-benzenesulfonamide, trans-N-{4-[3-(Cyclopropylmethyl-methyl-amino)-propoxy]-cyclohexyl}-N-methyl-4- trifluoromethyl-benzenesulfonamide, trans-N-Methyl-N-{4-(3-pyrrolidin-1-yl-propoxy)- cyclohexyl] -4-trifluoromethyl- benzenesulfonamide,
trans-N-[4-(3-Ethylamino-propoxy)-cyclohexyl]-N-methyl-4-trifluoromethyl- benzenesulfonamide, trans-N-Methyl-N-[4-(3-morpholin-4-yl-propoxy)-cyclohexyl]- 4-trifluoromethyl- benzenesulfonamide, trans-N-{4-[3-(2-Hydroxy-ethylamino)-propoxy]-cyclohexyl}-N-methyl-4- . trifluoromethyl-benzenesulfonamide, trans-N-(4-{3-[Ethyl-(2-methoxy-ethyl)-amino] -propoxy}-cyclohexyl)-N-methyl-4- trifluoromethyl-benzenesulfonamide, trans-N-{4-[3-(3,6-Dihydro-2H-pyridin-1-yl)-propoxy]- cyclohexyl}-N-methyl-4- trifluoromethyl-benzenesulfonamide, trans-N-Methyl-N-{4-[3-(methyl-propyl-amino)-propoxy]- cyclohexyl}-4- trifluoromethyl-benzenesulfonamide, trans-N-{4-(4-Allylamino-butoxy)-cyclohexyl] -N-methyl-4-trifluoromethyl- benzenesulfonamide,
N-{4-trans-[4-(Allyl-methyl-amino)-butoxy]-cyclohexyl}-N-methyl-4-trifluoromethyl- benzenesulfonamide, trans-N-(4-{4-[Ethyl-(2-hydroxy-ethyl)-amino]-butoxy}-cyclohexyl)-N-methyl-4- trifluoromethyl-benzenesulfonamide, trans-N-[4-(4-Diethylamino-butoxy)-cyclohexyl] -N-methyl-4-triftuoromethyl- benzenesulfonamide, trans-N-[4-(4-Dimethylamino-butoxy)-cyclohexyl]-N-methyl-4-trifluoromethyl- benzenesulfonamide, trans-N-(4-{4-[(2-Methoxy-ethyl)-methyl-amino]-butoxy}-cyclohexyl)-N-methyl-4- trifluoromethyl-benzenesulfonamide, trans-N-(4-{4-[(2-Hydroxy-ethyl)-methyl-amino]-butoxy}-cyclohexyl)-N-methyl-4- trifluoromethyl-benzenesulfonamide, trans-N-(4-{4-[Bis-(2-hydroxy-ethyl)-amino]-butoxy}-cyclohexyl)-N-methyl-4- trifluoromethyl-benzenesulfonamide, trans-N-{4-[4-(Cyclopropylmethyl-methyl-amino)-butoxy]- cyclohexyl}-N-methyl-4- trifluoromethyl-benzenesulfonamide, trans-N-[4-(4-Ethylamino-butoxy)-cyclohexyl]-N-methyl-4-trifluoromethyl- benzenesulfonamide, : trans-N-Methyl-N-[4-(4-morpholin-4-yl-butoxy)-cyclohexyl]-4-trifluoromethyl- benzenesulfonamide, . 35 trans-N-{4-[4-(2-Hydroxy-ethylamino)-butoxy}-cyclohexyl}-N-methyl-4- trifluoromethyl-benzenesulfonamide, trans-N-{4-[4-(3,6-Dihydro-2H-pyridin-1-yl)-butoxy]- cyclohexyl}-N-methyl-4- trifluoromethyl-benzenesulfonamide, trans-N-Methyl-N-{4-[4-(methyl-propyl-amino)-butoxy]- cyclohexyl}-4-trifluoromethyl-
benzenesulfonamide, trans-N-(4-{4-[Ethyl-(2-methoxy-ethyl)-amino]-butoxy}-cyclohexyl)-N-methyl-4- trifluoromethyl-benzenesulfonamide, . trans-N-(4-{3-](2-Methoxy-ethyl)-methyl-amino]-propoxy}-cyclohexyl)-N-methyl-4- trifluoromethyl-benzenesulfonamide, ‘ N-{4-trans-[3-( Allyl-methyl-amino)-propoxy] -cyclohexyl}-4-chloro-N-methyl- benzenesulfonamide,
N-{4-trans-[4-(Allyl-methyl-amino)-butoxy]-cyclohexyl}-4-chloro-N-methyl- benzenesulfonamide,
N-{4-trans-{4-(Allyl-methyl-amino)-butoxy]-cyclohexyl}-4-bromo-N-methyl- benzenesulfonamide,
N-{4-trans-[4-(Allyl-methyl-amino)-butoxy]-cyclohexyl}-N-methyl-C-phenyl- methanesulfonamide,
N-{4-trans-[4-(Allyl-methyl-amino)-butoxy] -cyclohexyl}-4-fluoro-N-methyl- benzenesulfonamide,
N-{4-trans-[4-(Allyl-methyl-amino)-butoxy]-cyclohexyl}-2-fluoro-N-methyl- benzenesulfonamide,
N-{4-trans-[4- (Allyl-methyl-amino)-butoxy]-cyclohexyl}-N-methyl-benzenesulfonamide, 5-Chloro-thiophene-2-sulfonic acid {4-trans-[4-(allyl-methyl-amino)-butoxy]- cyclohexyll-methyl-amide, trans-Pyridine-2-carboxylic acid {4-[6-(allyl-methyl-amino)-hexyloxy]-cyclohexyl}- methyl-amide, trans- 1H-Indole-2-carboxylic acid {4-[6-(allyl-methyl-amino)-hexyloxy]-cyclohexyl}- methyl-amide, trans-N-{4-[6-(Allyl-methyl-amino)-hexyloxy]-cyclohexyl}-N-methyl-benzamide, trans-N-{4-[6-(Allyl-methyl-amino)-hexyloxy]-cyclohexyl}-4-chloro-N-methyl- benzamide, trans-N-{4-[6-(Allyl-methyl-amino)-hexyloxy]-cyclohexyl}-4-fluoro-N-methyl- benzamide, trans-N-{4-[6-(Allyl-methyl-amino)-hexyloxy]-cyclohexyl}-4-bromo-N-methyl- benzamide, trans-N-{4-[6-(Allyl-methyl-amino)-hexyloxy]-cyclohexyl}-N-methyl-4-trifluoromethyl- - benzamide, trans-Thiophene-3-carboxylic acid {4-[6-(allyl-methyl-amino)-hexyloxy]-cyclohexyl}- . 35 methyl-amide, trans-5-Bromo-thiophene-2-carboxylic acid {4-[6-(allyl-methyl-amino)-hexyloxy]- cyclohexyl}-methyl-amide, trans-N-{4-({6-(Allyl-methyl-amino)-hexyloxy]-cyclohexyl}-N-methyl-2-thiophen-3-yi- acetamide,
trans-N-{4-[6-(Allyl-methyl-amino)-hexyloxy] -cyclohexyl}-2-(2,4-difluoro-phenyl)-N- methyl-acetamide, trans-5-Fluoro-1H-indole-2-carboxylic acid {4-[6-(allyl-methyl-amino)-hexyloxy]- ' cyclohexyl}-methyl-amide, trans-N-{4-[6-(Allyl-methyl-amino)-hexyloxy]-cyclohexyl}-2-(4-fluoro-phenyl)-N- . methyl-acetamide, trans-1H-Indole-5-carboxylic acid {4-[6-(allyl-methyl-amino)-hexyloxy]-cyclohexyl}- methyl-amide, trans-N-{4-[6-(Allyl-methyl-amino)-hexyloxy] -cyclohexyl}-3-chloro-N-methyl-
benzamide, trans-N-{4-[6-(Allyl-methyl-amino)-hexyloxy]-cyclohexyl}-4-fluoro-3,N-dimethyl- benzamide, trans-N-{4-[6-(Allyl-methyl-amino)-hexyloxy]-cyclohexyl}-N-methyl-4-nitro-benzamide, trans-N-{4-[6-(Allyl-methyl-amino)-hexyloxy] -cyclohexyl}-4,N-dimethyl-benzamide,
trans-N-{4-[6-(Allyl-methyl-amino)-hexyloxy] -cyclohexyl}-3-cyano-N-methyl- benzamide, trans-N-{4-[6-(Allyl-methyl-amino)-hexyloxy]-cyclohexyl}-3,N-dimethyl-benzamide, trans-N-{4-[6-(Allyl-methyl-amino)-hexyloxy]-cyclohexyl}-3,4-dimethoxy-N-methyl- benzamide,
trans-N-{4-[6-(Allyl-methyl-amino)-hexyloxy]-cyclohexyl}-4-methoxy-N-methyl- benzamide, trans-N-{4-[6-(Allyl-methyl-amino)-hexyloxy]-cyclohexyl}-4-fluoro-N-methyl-3-nitro- benzamide, trans-4-Acetyl-N-{4-[6-(allyl-methyl-amino)-hexyloxy]-cyclohexyl}-N-methyl-
benzamide, trans-N-{4-({7-(Allyl-methyl-amino)-heptyloxy]-cyclohexyl}-N-methyl-4-trifluoromethyl- benzamide, trans-N-{4-[5-(Allyl-methyl-amino)-pentyloxy]-cyclohexyl}-N-methyl-4-trifluoromethyl- benzamide,
trans-N-{4-[4-(Allyl-methyl-amino)-butoxy]-cyclohexyl}-3-cyano-N-methyl-benzamide, trans-N-{4-[5-(Allyl-methyl-amino)-pentyloxy]-cyclohexyl}-4-bromo-N-methyl- benzamide, :
: trans-N-{4-[4-(Allyl-methyl-amino)-butoxy]-cyclohexyl}-4-bromo-N-methyl-benzamide, trans-5-Bromo-thiophene-2-carboxylic acid {4-[4-(allyl-methyl-amino)-butoxy]-
. 35 cyclohexyl}-methyl-amide, trans-N-{4-[5-(Allyl-methyl-amino)-pentyloxyl-cyclohexyl}-4-fluoro-N-methyl- benzamide, trans-N-{4-[4-(Allyl-methyl-amino)-butoxy]-cyclohexyl}-4-fluoro-N-methyl-benzamide, trans-1-{4-[6-(Allyl-methyl-amino)-hexyloxy]-cyclohexyl}-3-(2,4-difluoro-phenyl)-1-
methyl-urea, trans-1-{4-[6-(Allyl-methyl-amino)-hexyloxy] -cyclohexyl}-3-(2,4-dimethoxy-phenyl)-1- methyl-urea, : trans-1-{4-[6-(Allyl-methyl-amino)-hexyloxy] -cyclohexyl}-3-(4-fluoro-phenyl)-1-methyl- urea, ‘ trans-1-{4-[6-(Allyl-methyl-amino)-hexyloxy]-cyclohexyl}-3-(4-methoxy-phenyl)-1- methyl-urea, trans-1-{4-][6-(Allyl-methyl-amino)-hexyloxy] -cyclohexyl}-1-methyl-3-p-tolyl-urea, trans-1-{4-[6-(Allyl-methyl-amino)-hexyloxy]-cyclohexyl}-3- (4-methoxy-2-methyl-
phenyl)-1-methyl-urea, trans-1-{4-[6-(Allyl-methyl-amino)-hexyloxy]-cyclohexyl}-3-(2,4-dimethyl-phenyl)-1- methyl-urea, trans-1-{4-[6-(Allyl-methyl-amino)-hexyloxy]-cyclohexyl}-1-methyl-3-(3,4,5-trimethoxy- phenyl)-urea,
trans-1-{4-[6-(Allyl-methyl-amino)-hexyloxy]-cyclohexyl}-3-(3,4-dimethyl-phenyl)-1- methyl-urea, trans-3-(4-Acetyl-phenyl)-1-{4-[6- (allyl-methyl-amino)-hexyloxy]-cyclohexyl}-1-methyl- urea, trans-1-{4-[6-(Allyl-methyl-amino)-hexyloxy]-cyclohexyl}-3-(4-chloro-phenyl)-1-
methyl-urea, trans-1-{4-[6-(Allyl-methyl-amino)-hexyloxy]-cyclohexyl}-1-methyl-3-phenyl-urea, trans-1-{4-[6-(Allyl-methyl-amino)-hexyloxy]-cyclohexyl}-1-methyl-3-(4- trifluoromethyl-phenyl)-urea, trans-1-{4-[6-(Allyl-methyl-amino)-hexyloxy]-cyclohexyl}-3-(3,4-dichloro-phenyl)-1-
methyl-urea, trans-1-{4-[6-(Allyl-methyl-amino)-hexyloxy]-cyclohexyl}-3-(4-bromo-phenyl)-1- methyl-urea, trans-1-{4-[6-(Allyl-methyl-amino)-hexyloxy]-cyclohexyl}-1-methyl-3-naphthalen-2-yl- urea,
trans-1-{4-[6-(allyl-methyl-amino)-hexyloxy]-cyclohexyl}-1 -methyl-3- (4-nitro-phenyl)- urea, trans-1-{4-[6-(Allyl-methyl-amino)-hexyloxy] -cyclohexyl}-3- (4-dimethylamino-phenyl)-
: 1-methyl-urea, trans-1-{4-[7-(Allyl-methyl-amino)-heptyloxy]-cyclohexyl}-1-methyl-3-p-tolyl-urea,
trans-1-{4-[7-(Allyl-methyl-amino)-heptyloxy]-cyclohexyl}-3-(4-fluoro-phenyl)-1- methylurea, trans-1-{4-[7-(Allyl-methyl-amino)-heptyloxy]-cyclohexyl}-3-(4-bromo-phenyl)-1- methylurea, trans-1-{4-[7-(Allyl-methyl-amino)-heptyloxy]-cyclohexyl}-3-(4-butyl-phenyl)-1-
methylurea, trans-1-{4-[5-(Allyl-methyl-amino)-pentyloxy]-cyclohexyl}- 1-methyl-3-p-tolyl-urea, trans-1-{4-[5-(Allyl-methyl-amino)-pentyloxy]-cyclohexyl}-3-(4-fluoro-phenyl)-1- methylurea, trans-1-{4-[5-(Allyl-methyl-amino)-pentyloxy]-cyclohexyl}-3-(4-bromo-phenyl)-1- ’ methylurea, trans-1-{4-[4-(Allyl-methyl-amino)-butoxy] -cyclohexyl}-1-methyl-3-p-tolyl-urea, trans-1-{4-[4-(Allyl-methyl-amino)-butoxy]-cyclohexyl}-3-(4-fluoro-phenyl)-1-methyl- urea,
trans-1-{4-[4-(Allyl-methyl-amino)-butoxy]-cyclohexyl}-3-(4-bromo-phenyl)-1-methyl- urea, trans-1-{4-[4-(Allyl-methyl-amino)-butoxy]-cyclohexyl}-3-(4-butyl-phenyl)-1-methyl- urea, trans-Methyl-{4-[4-(methyl-propyl-amino)-butoxy}-cyclohexyl}-carbamic acid 4-
trifluoromethyl-phenyl ester, trans-N-(4-[6-(Allyl-methyl-amino)-hexyloxy]-cyclohexyl)-4-bromo-N-methyl- benzenesulfonamide, trans-4-Bromo-N-[4-(6-dimethylamino-hexyloxy)-cyclohexyl]-N-methyl- benzenesulfonamide,
trans-4-Bromo-N-(4-{6-[(2-methoxy-ethyl)-methyl-amino]-hexyloxy}-cyclohexyl)-N- methyl-benzenesulfonamide, trans-N-(4-[6-(Allyl-methyl-amino)-hexyloxy]-cyclohexyl)-N-methyl-4-trifluoromethyl- benzenesulfonamide, trans-N-[4-(6-Dimethylamino-hexyloxy)-cyclohexyl]-N-methyl-4-trifluoromethyl-
benzenesulfonamide, trans-N-(4-{6-[(2-Methoxy-ethyl)-methyl-amino]-hexyloxy}-cyclohexyl)-N-methyl-4- trifluoromethyl-benzenesulfonamide, trans-4-Bromo-N-[4-(6-diethylamino-hexyloxy)-cyclohexyl]-N-methyl- benzenesulfonamide,
trans-4-Bromo-N-{4-[6-(isopropyl-methyl-amino)-hexyloxy]-cyclohexyl}-N-methyl- benzenesulfonamide, trans-4-Bromo-N-methyl-N-[4-(6-pyrrolidin- 1-yl-hexyloxy)-cyclohexyl]-
’ benzenesulfonamide, trans-N-[4-(6-Diethylamino-hexyloxy)-cyclohexyl]-N-methyl-4-trifluoromethyl-
: 35 benzenesulfonamide, trans-N-{4-[6-(Isopropyl-methyl-amino)-hexyloxy]-cyclohexyl}-N-methyl-4- trifluoromethyl-benzenesulfonamide, trans-N-Methyl-N-[4-(6-pyrrolidin-1-yl-hexyloxy)-cyclohexyl]-4-trifluoromethyl- benzenesulfonamide,
trans-4-Chloro-N-(4-{6-[(2-methoxy-ethyl)-methyl-amino]-hexyloxy}-cyclohexyl)-N- methyl-benzenesulfonamide, trans-(4-{6-[(2-Methoxy-ethyl)-methyl-amino]-hexyloxy}-cyclohexyl)-methyl-carbamic : acid 4-chloro-phenyl ester, trans-4-Chloro-N-(4-{6-[(2-methoxy-ethyl)-methyl-amino]-hexyloxy}-cyclohexyl)-
: benzenesulfonamide, trans-4-Bromo-N-(4-{6-[(2-methoxy-ethyl)-methyl-amino]-hexyloxy}-cyclohexyl)- benzenesulfonamide, trans-4-Chloro-N-(4-{6-[ (2-methoxy-ethyl)-methyl-amino]-hexyloxy}-cyclohexyl)-N-
propyl-benzenesulfonamide, trans-4-Bromo-N-(4-{6-[(2-methoxy-ethyl)-methyl-amino]-hexyloxy}-cyclohexyl)-N- propyl-benzenesulfonamide, trans-4-Chloro-N-(4-{6-[(2-methoxy-ethyl)-methyl-amino]-hexyloxy}-cyclohexyl)-N- (2,4,5-trifluoro-benzyl)-benzenesulfonamide,
trans-4-Bromo-N-(4-{6-[(2-methoxy-ethyl)-methyl-amino]}-hexyloxy}-cyclohexyl)-N- (2,4,5-trifluoro-benzyl)-benzenesulfonamide, trans-(4-{6-[(2-Methoxy-ethyl)-methyl-amino]-hexyloxy}-cyclohexyl)-carbamic acid 4- - chloro-phenyl ester, trans-Ethyl-(4-{6-[(2-methoxy-ethyl)-methyl-amino]-hexyloxy}-cyclohexyl)-carbamic acid 4-chloro-phenyl ester, trans-(4-{6-[(2-Methoxy-ethyl)-methyl-amino]-hexyloxy}-cyclohexyl)-propyl-carbamic acid 4-chloro-phenyl ester, trans-(4-{6-[(2-Methoxy-ethyl)-methyl-amino]-hexyloxy}-cyclohexyl)-(2,4,5-trifluoro- benzyl)-carbamic acid 4-chloro-phenyl ester,
trans-Ethyl-(4-{6-[ethyl-(2-hydroxy-ethyl)-amino]-hexyloxy}-cyclohexyl)-carbamic acid benzyl ester, trans-Benzyl-(4-{6-[ethyl-(2-hydroxy-ethyl)-amino]-hexyloxy}-cyclohexyl)-carbamic acid benzyl ester, trans-(4-{6-[Ethyl-(2-hydroxy-ethyl)-amino]-hexyloxy}-cyclohexyl)-methyl-carbamic
530 acid benzyl ester, trans-Allyl-(4-{6- [ethyl-(2-hydroxy-ethyl)-amino]-hexyloxy}-cyclohexyl)-carbamic acid benzyl ester,
- trans-(4-{6-[Ethyl-(2-hydroxy-ethyl)-amino]-hexyloxy}-cyclohexyl)-(2,4,5-trifluoro- benzyl)-carbamic acid benzyl ester,
: 35 trans-[4-(6-Azetidin-1-yl-hexyloxy)-cyclohexyl]-ethyl-carbamic acid benzyl ester, trans-[4-(6-Azetidin-1-yl-hexyloxy)-cyclohexyl]-benzyl-carbamic acid benzyl ester, trans-[4-(6-Azetidin-1-yl-hexyloxy)-cyclohexyl] -methyl-carbamic acid benzyl ester, trans-Ethyl-(4-{6-[(2-hydroxy-ethyl)-methyl-amino]-hexyloxy}-cyclohexyl)-carbamic acid benzyl ester,
trans-Benzyl-(4-{6-[(2-hydroxy-ethyl)-methyl-amino]-hexyloxy}-cyclohexyl)-carbamic acid benzyl ester, trans-(4-{6-[(2-Hydroxy-ethyl)-methyl-amino]-hexyloxy}-cyclohexyl)-methyl-carbamic ‘ acid benzyl ester, trans-Allyl-(4-{6-[(2-hydroxy-ethyl)-methyl-amino]-hexyloxy}-cyclohexyl)-carbamic acid : benzyl ester, trans-(4-{6-[(2-Hydroxy-ethyl)-methyl-amino]-hexyloxy}-cyclohexyl)-(2,4,5-trifluoro- benzyl)-carbamic acid benzyl ester, trans-Ethyl-(4-{6-[(2-methoxy-ethyl)-methyl-amino]-hexyloxy}-cyclohexyl)-carbamic acid benzyl ester, trans-Benzyl-(4-{6-[(2-methoxy-ethyl)-methyl-amino]-hexyloxy}-cyclohexyl)-carbamic acid benzyl ester, trans-(4-{6-{(2-Methoxy-ethyl)-methyl-amino]-hexyloxy}-cyclohexyl)-methyl-carbamic acid benzyl ester,
trans-(4-{6-[(2-Methoxy-ethyl)-methyl-amino]-hexyloxy}-cyclohexyl)-(2,4,5-trifluoro- benzyl)-carbamic acid benzyl ester, trans-Ethyl-[4-(6-morpholin-4-yl-hexyloxy)-cyclohexyl] -carbamic acid benzyl ester, trans-Benzyl-[4-(6-morpholin-4-yl-hexyloxy)-cyclohexyl] -carbamic acid benzyl ester, trans-Methyl-[4-(6-morpholin-4-yl-hexyloxy)-cyclohexyl]-carbamic acid benzyl ester,
trans-Allyl-[4-(6-morpholin-4-yl-hexyloxy)-cyclohexyl] -carbamic acid benzyl ester, trans-[4-(6-Morpholin-4-yl-hexyloxy)-cyclohexyl]-(2,4,5-trifluoro-benzyl)-carbamic acid benzyl ester, trans-Ethyl-[4-(6-pyrrolidin- 1-yl-hexyloxy)-cyclohexyl]-carbamic acid benzyl ester, trans-Benzyl-[4-(6-pyrrolidin-1-yl-hexyloxy)-cyclohexyl]-carbamic acid benzyl ester,
trans-Methyl-[4-(6-pyrrolidin-1-yl-hexyloxy)-cyclohexyl]-carbamic acid benzyl ester, trans-Allyl-[4-(6-pyrrolidin-1-yl-hexyloxy)-cyclohexyl]-carbamic acid benzyl ester, trans-[4-(6-Pyrrolidin- 1-yl-hexyloxy)-cyclohexyl]-(2,4,5-trifluoro-benzyl)-carbamic acid benzyl ester, trans-{4-[6-(Allyl-methyl-amino)-hexyloxy]-cyclohexyl}-methyl-carbamic acid benzyl ester, trans-{4-[6-(Allyl-methyl-amino)-hexyloxy]-cyclohexyl}-ethyl-carbamic acid benzyl ester, trans-Allyl-{4-[6-(allyl-methyl-amino)-hexyloxy] -cyclohexyl}-carbamic acid benzyl ester,
- trans-{4-[6-(Allyl-methyl-amino)-hexyloxy] -cyclohexyl}-benzyl-carbamic acid benzyl ester,
trans-{4-[6-(Allyl-methyl-amino)-hexyloxy]-cyclohexyl}-(2,4,5-trifluoro-benzyl)- carbamic acid benzyl ester, trans-[4-(6-Dimethylamino-hexyloxy)-cyclohexyl]-methyl-carbamic acid benzyl ester, trans- [4-(6-Dimethylamino-hexyloxy)-cyclohexyl]-ethyl-carbamic acid benzyl ester, trans-Allyl-[4- (6-dimethylamino-hexyloxy)-cyclohexyl]-carbamic acid benzyl ester,
trans-Benzyl-[4-(6-dimethylamino-hexyloxy)-cyclohexyl]-carbamic acid benzyl ester, trans-[4-(6-Dimethylamino-hexyloxy)-cyclohexyl]-(2,4,5-trifluoro-benzyl)-carbamic acid benzyl ester, : trans-(4-[5-(Allyl-methyl-amino)-pentyloxy]-cyclohexyl)-methyl-carbamic acid tert-butyl ester, ‘ trans-(4-[3-(Allyl-methyl-amino)-propoxy]-cyclohexyl)-methyl-carbamic acid tert-butyl ester, trans-(4-[4-(Allyl-methyl-amino)-butoxy]-cyclohexyl)-methyl-carbamic acid tert-butyl ester,
trans-(4-[7-(Allyl-methyl-amino)-heptyloxy]-cyclohexyl)-methyl-carbamic acid tert-butyl ester, trans-4-Chloro-N-ethyl-N-(4-{6-[ (2-methoxy-ethyl)-methyl-amino]-hexyloxy}- cyclohexyl)-benzenesulfonamide, trans-4-Bromo-N-ethyl-N-(4-{6-[(2-methoxy-ethyl)-methyl-amino]-hexyloxy}-
cyclohexyl)-benzenesulfonamide, trans-{4-[4-(Allyl-methyl-amino)-butoxy]-cyclohexyl}-methyl-carbamic acid 4-chloro- phenyl ester, trans-{4-[5-(Allyl-methyl-amino)-pentyloxy]-cyclohexyl}-methyl-carbamic acid 4-chloro- phenyl ester,
trans-(4-{6-[Ethyl-(2-hydroxy-ethyl)-amino]-hexyloxy}-cyclohexyl)-methyl-carbamic acid 4-chloro-phenyl ester, trans-(4-{4-[Ethyl-(2-hydroxy-ethyl)-amino]-butoxy}-cyclohexyl)-methyl-carbamic acid 4-chloro-phenyl ester, trans-(4-{5-[Ethyl-(2-hydroxy-ethyl)-amino]-pentyloxy}-cyclohexyl)-methyl-carbamic acid 4-chloro-phenyl ester, trans-[4-(6-Dimethylamino-hexyloxy)-cyclohexyl]-methyl-carbamic acid 4-chloro-phenyl ester, trans-[4-(4-Dimethylamino-butoxy)-cyclohexyl]-methyl-carbamic acid 4-chloro-phenyl ester,
trans-[4-(5-Dimethylamino-pentyloxy)-cyclohexyl]-methyl-carbamic acid 4-chloro- phenyl ester, trans-(4-{6-[Ethyl-(2-methoxy-ethyl)-amino]-hexyloxy}-cyclohexyl)-methyl-carbamic
’ acid 4-chloro-phenyl ester, trans-(4-{4-[Ethyl-(2-methoxy-ethyl)-amino]-butoxy}-cyclohexyl)-methyl-carbamic acid
: 35 4-chloro-phenyl ester, trans-{4-[3-(Allyl-methyl-amino)-propoxy]-cyclohexyl}-methyl-carbamic acid 4-chloro- phenyl ester, trans-(4-{3-[Ethyl-(2-methoxy-ethyl)-amino]-propoxy}-cyclohexyl)-methyl-carbamic acid 4-chloro-phenyl ester,
trans-(4-{5-[Ethyl-(2-methoxy-ethyl)-amino]-pentyloxy}-cyclohexyl)-methyl-carbamic acid 4-chloro-phenyl ester, trans-[4-(3-Dimethylamino-propoxy)- cyclohexyl] -methyl-carbamic acid 4-chloro-phenyl ’ ester, trans-(4-{3-[Ethyl-(2-hydroxy-ethyl)-amino]-propoxy}-cyclohexyl)-methyl-carbamic acid ’ 4-chloro-phenyl ester, trans-Methyl-[4-(3-piperidin-1-yl-propoxy)-cyclohexyl] -carbamic acid 4-chloro-phenyl ester, trans-Methyl-[4-(4-piperidin-1-yl-butoxy)-cyclohexyl]-carbamic acid 4-chloro-phenyl ester, trans-Methyl-[4-(6-piperidin-1-yl-hexyloxy)-cyclohexyl] -carbamic acid 4-chloro-phenyl ester, trans-Methyl-[4-(5-piperidin- 1-yl-pentyloxy)-cyclohexyl]-carbamic acid 4-chloro-phenyl ester,
trans-{4-(3-Diethylamino-propoxy)-cyclohexyl]-methyl-carbamic acid 4-chloro-phenyl ester, trans-{4-(6-Diethylamino-hexyloxy)-cyclohexyl]-methyl-carbamic acid 4-chloro-phenyl ester, trans-[4-(4-Diethylamino-butoxy)-cyclohexyl]-methyl-carbamic acid 4-chloro-phenyl ester, trans-[4-(5-Diethylamino-pentyloxy)-cyclohexyl]-methyl-carbamic acid 4-chloro-phenyl ester, trans-Methyl-[4-(3-pyrrolidin-1-yl-propoxy)-cyclohexyl]-carbamic acid 4-chloro-phenyl ester,
trans-Methyl-(4-(6-pyrrolidin-1-yl-hexyloxy)-cyclohexyl]-carbamic acid 4-chloro-phenyl ester, trans-(4-{6-[(2-Hydroxy-ethyl)-methyl-amino]-hexyloxy}-cyclohexyl)-methyl-carbamic acid 4-chloro-phenyl ester, trans-(4-{4-[(2-Hydroxy-ethyl)-methyl-amino] -butoxy}- cyclohexyl)-methyl-carbamic acid 4-chloro-phenyl ester, trans-(4-{5-[(2-Hydroxy-ethyl)-methyl-amino] -pentyloxy}-cyclohexyl)-methyl-carbamic acid 4-chloro-phenyl ester,
‘ trans-Methyl- [4-(4-pyrrolidin-1-yl-butoxy)-cyclohexyl] - carbamic acid 4-chloro-phenyl ester,
: 35 trans-Methyl-[4-(5-pyrrolidin-1-yl-pentyloxy)-cyclohexyl]-carbamic acid 4-chloro-phenyl ester, trans-(4-{3-[(2-Hydroxy-ethyl)-methyl-amino]-propoxy}-cyclohexyl)-methyl-carbamic acid 4-chloro-phenyl ester, trans-[4-(5-Dimethylamino-pentyloxy)-cyclohexyl]-methyl-carbamic acid 4-chloro-
phenyl ester N-oxide, trans-{4-[5-(Allyl-methyl-amino)-pentyl]-cyclohexyl}-methyl-carbamic acid 4- trifluoromethyl-phenyl ester, ’ trans-(4-{5-] Ethyl-(2-hydroxy-ethyl)-amino] -pentyl}-cyclohexyl)-methyl-carbamic acid 4-trifluoromethyl-phenyl ester, : trans-{4-[5-(Allyl-methyl-amino)-pentyl]-cyclohexyl}-methyl-carbamic acid 4-bromo- phenyl ester, trans-(4-{5- [Ethyl-(2-hydroxy-ethyl)-amino]-pentyl}-cyclohexyl)-methyl-carbamic acid 4-bromo-phenyl ester,
trans-{4-[5-(Allyl-methyl-amino)-pentyl]-cyclohexyl}-methyl-carbamic acid 3,4-difluoro- phenyl ester, trans-(4-{5-[Ethyl-(2-hydroxy-ethyl)-amino]-pentyl}-cyclohexyl)-methyl-carbamic acid 3,4-difluoro-phenyl ester, trans-{4-[5-(Allyl-methyl-amino)-pentyl]-cyclohexyl}-methyl-carbamic acid 4-chloro-
phenyl ester, trans-{4-[3-(Allyl-methyl-amino)-propoxymethyl] -cyclohexyl}-methyl-carbamic acid 4- chloro-phenyl ester, trans-(4-{3-[Ethyl-(2-hydroxy-ethyl)-amino]-propoxymethyl}-cyclohexyl)-methyl- carbamic acid 4-chloro-phenyl ester,
trans-[4-(3-Azetidin-1-yl-propoxymethyl)-cyclohexyl]-methyl-carbamic acid 4-chloro- phenyl ester, trans-Methyl-[4-(3-piperidin-1-yl-propoxymethyl)-cyclohexyl] -carbamic acid 4-chloro- phenyl ester, trans-(4-{3-[Ethyl-(2-methoxy-ethyl)-amino]-propoxymethyl}-cyclohexyl)-methyl-
carbamic acid 4-chloro-phenyl ester, trans-{4-[4-(Allyl-methyl-amino)-butoxymethyl]-cyclohexyl}-methyl-carbamic acid 4- chloro-phenyl ester, trans-{4-[2-(Allyl-methyl-amino)-ethoxymethyl}-cyclohexyl}-methyl-carbamic acid 4- chloro-phenyl ester,
trans-N-{4-[3-(Allyl-methyl-amino)-propoxymethyl]-cyclohexyl}-N-methyl-4- triftuoromethyl-benzenesulfonamide, (trans)-N-(4-{3-[Ethyl- (2-hydroxy-ethyl)-amino]-propoxymethyl}-cyclohexyl)-N-
’ methyl-4-trifluoromethyl-benzenesulfonamide, trans-N-[4-(3-Azetidin-1-yl-propoxymethyl)-cyclohexyl]-N-methyl-4-trifluoromethyl-
: 35 benzenesulfonamide, trans-N-Methyl-N-[4-(3-piperidin-1-yl-propoxymethyl)-cyclohexyl]-4-trifluoromethyl- benzenesulfonamide, (trans)-N-[4-(2-Dimethylamino-ethylsulfanylmethyl)-cyclohexyl]-N-methyl-4- trifluoromethyl-benzenesulfonamide,
trans-N-[4-(2-Diethylamino-ethylsulfanylmethyl)-cyclohexyl] -N-methyl-4- trifluoromethyl-benzenesulfonamide, trans-N-{4-[2-(Allyl-methyl-amino)-ethylsulfanylmethyl]-cyclohexyl}-N-methyl-4~ ‘ trifluoromethyl-benzenesulfonamide, trans-[4-(2-Diethylamino-ethylsulfanylmethyl)-cyclohexyl]-methyl-carbamic acid 4- chloro-phenyl ester, trans-{4-[2-(Allyl-methyl-amino)-ethylsulfanylmethyl]-cyclohexyl}-methyl-carbamic acid 4-chloro-phenyl ester, trans-{4-[3-(Allyl-methyl-amino)-propylsulfanylmethyl]-cyclohexyl}-methyl-carbamic acid 4-chloro-phenyl ester, trans-[4-(2-Dimethylamino-ethylsulfanylmethyl)-cyclohexyl]-methyl-carbamic acid 4- chloro-phenyl ester, trans-(4-{2-[Ethyl-(2-hydroxy-ethyl)-amino]-ethylsulfanylmethyl}-cyclohexyl)-methyl- carbamic acid 4-chloro-phenyl ester,
trans-Methyl-{4-[2-(methyl-propyl-amino)-ethylsulfanylmethyl]-cyclohexyl}-carbamic acid 4-chloro-phenyl ester, trans-{4-[3-(Allyl-methyl-amino)-prop-1-ynyl]-cyclohexyl}-methyl-carbamic acid 4- chloro-phenyl ester, trans-(4-{3- [Ethyl-(2-hydroxy-ethyl)-amino] -prop-1-ynyl}-cyclohexyl)-methyl-carbamic acid 4-chloro-phenyl ester, trans-(4-{3-[Ethyl-(2-hydroxy-ethyl)-amino]-propyl}-cyclohexyl)-methyl-carbamic acid 4-chloro-phenyl ester, trans-Methyl- {4-[4-(methyl-propyl-amino)-butoxy]-cyclohexyl}-carbamic acid 3,4- difluoro-phenyl ester,
trans-[4-[6-(Allyl-methyl-amino)-hexyloxy]-cyclohexyl]-methyl-sulfamic acid benzyl amide, trans-{4-[6-(Allyl-methyl-amino)-hexyloxy]-cyclohexyl}-methyl-sulfamic acid phenyl amide, trans-4-[({4-[6-(Allyl-methyl-amino)-hexyloxy]-cyclohexyl}-methyl-sulfamoyloxy)-
methyl]-benzoic acid methyl ester, trans-{4-[6-(Allyl-methyl-amino)-hexyloxy]-cyclohexyl}-methyl-sulfamic acid butyl amide, Fy
: trans-{4-[6-(Allyl-methyl-amino)-hexyloxy]-cyclohexyl}-methyl-sulfamic acid phenethyl amide,
‘ 35 trans-{4-[6-(Allyl-methyl-amino)-hexyloxy]-cyclohexyl}-methyl-sulfamic acid furan-2- ylmethyl amide, trans-({4-[6-(Allyl-methyl-amino)-hexyloxy]-cyclohexyl}-methyl-sulfonylamino)-acetic acid ethyl ester, trans-{4-[6-(Allyl-methyl-amino)-hexyloxy]-cyclohexyl}-methyl-sulfamic acid cyclopropyl amide, trans-{4-[6-(Allyl-methyl-amino)-hexyloxy]-cyclohexyl}-methyl-sulfamic acid 2,2,2- trifluoro-ethyl amide, trans-{4-[6-(Allyl-methyl-amino)-hexyloxy]-cyclohexyl}-methyl-sulfamic acid benzo[1,3]dioxol-5-ylmethyl amide,
‘ trans-{4-[6-(Allyl-methyl-amino)-hexyloxy]-cyclohexyl}-methyl-sulfamic acid 4- fluorobenzyl amide, trans-{4-[6-(Allyl-methyl-amino)-hexyloxy]-cyclohexyl}-methyl-sulfamic acid (4-chloro- phenyl)-amide,
trans-{4-[6-(Allyl-methyl-amino)-hexyloxy]-cyclohexyl}-methyl-sulfamic acid (4-fluoro- phenyl)-amide, trans-{4-[6-(Allyl-methyl-amino)-hexyloxy]-cyclohexyl}-methyl-sulfamic acid (4-bromo- phenyl)-amide, trans-{4-[6-(Allyl-methyl-amino)-hexyloxy]-cyclohexyl}-methyl-sulfamic acid (p-tolyl)-
amide, trans-{4-[6-(Allyl-methyl-amino)-hexyloxy]-cyclohexyl}-methyl-sulfamic acid (3,4- difluoro-phenyl)-amide, trans-{4-[6-(Allyl-methyl-amino)-hexyloxy]-cyclohexyl}-methyl-sulfamic acid (4- trifluoromethyl-phenyl)-amide,
trans-{4-[6-(Allyl-methyl-amino)-hexyloxy]-cyclohexyl}-methyl-sulfamic acid (3-fluoro- phenyl)-amide, trans-{4-[{6-(Allyl-methyl-amino)-hexyloxy]-cyclohexyl}-methyl-sulfamic acid (4-cyano- phenyl)-amide, trans-{4-[6-(Allyl-methyl-amino)-hexyloxy]-cyclohexyl}-methyl-sulfamic acid (2,4-
difluoro-phenyl)-amide, trans-{4-[6-(Allyl-methyl-amino)-hexyloxy]-cyclohexyl}-methyl-sulfamic acid (4- methoxy-phenyl)-amide, trans-{4-[6-(Allyl-methyl-amino)-hexyloxy]-cyclohexyl}-methyl-sulfamic acid (2,5- difluoro-phenyl)-amide,
trans-{4-[5-(Allyl-methyl-amino)-pentyloxy]-cyclohexyl}-methyl-sulfamic acid benzyl amide, trans-{4-[5-(Allyl-methyl-amino)-pentyloxy]-cyclohexyl}-methyl-sulfamic acid phenyl
- amide, trans-{4-[5-(Allyl-methyl-amino)-pentyloxy]-cyclohexyl}-methyl-sulfamic acid p-
. 35 chlorophenyl amide, trans-{4-[5-(Allyl-methyl-amino)-pentyloxy]-cyclohexyl}-methyl-sulfamic acid p- bromophenyl amide, trans-{4-[5-(Allyl-methyl-amino)-pentyloxy]-cyclohexyl}-methyl-sulfamic acid p- methylphenyl amide,
trans-{4-[5-(Allyl-methyl-amino)-pentyloxy]-cyclobexyl}-methyl-sulfamic acid p- triftuoromethylphenyl amide, trans-{4-[5-(Allyl-methyl-amino)-pentyloxy]-cyclohexyl}-methyl-sulfamic acid p- ’ cyanophenyl amide, trans-{4-[5-(Allyl-methyl-amino)-pentyloxy]-cyclohexyl}-methyl-sulfamic acid p- methoxyphenyl amide, trans-{4-[5-(Allyl-methyl-amino)-pentyloxy]-cyclohexyl}-methyl-sulfamic acid 3,4~ difluorophenyl amide, trans-{4-[5-(Allyl-methyl-amino)-pentyloxy]-cyclohexyl}-methyl-sulfamic acid 3-
fluorophenyl amide, trans-{4-[5-(Allyl-methyl-amino)-pentyloxy]-cyclohexyl}-methyl-sulfamic acid 2,4- difluorophenyl amide, trans-{4-[5-(Allyl-methyl-amino)-pentyloxy] -cyclohexyl}-methyl-sulfamic acid 2,5- difluorophenyl amide,
trans-{4-[3-(Allyl-methyl-amino)-propoxy]-cyclohexyl}-methyl-sulfamic acid phenyl amide, trans-{4-[3-(Allyl-methyl-amino)-propoxy]-cyclohexyl}-methyl-sulfamic acid 3,4- difluorophenyl amide, trans-{4-[3-(Allyl-methyl-amino)-propoxy]-cyclohexyl}-methyl-sulfamic acid 4-
chlorophenyl amide, trans-{4-[3-(Allyl-methyl-amino)-propoxy}-cyclohexyl}-methyl-sulfamic acid benzyl amide, trans-{4-[4-(Allyl-methyl-amino)-butoxy]-cyclohexyl}-methyl-sulfamic acid phenyl amide,
trans-{4-[4-(Allyl-methyl-amino)-butoxy]-cyclohexyl}-methyl-sulfamic acid 3-fluoro phenyl amide, trans-{4-[4-(Allyl-methyl-amino)-butoxy]-cyclohexyl}-methyl-sulfamic acid 3,4-difluoro phenyl amide, trans-{4-[4-(Allyl-methyl-amino)-butoxy] -cyclohexyl}-methyl-sulfamic acid 4-chloro phenyl amide, trans-{4-[4-(Allyl-methyl-amino)-butoxy]-cyclohexyl}-methyl-sulfamic acid benzyl amide,
’ trans-({4-[4-(Allyl-methyl-amino)-butoxy]-cyclohexyl}-methyl-sulfamoylamino)-acetic acid ethyl ester,
: 35 trans-{4-[7-(Allyl-methyl-amino)-heptyloxy]-cyclohexyl}-methyl-sulfamic acid phenyl amide, trans-{4-[7-(Allyl-methyl-amino)-heptyloxy] -cyclohexyl}-methyl-sulfamic acid 3-fluoro- phenyl amide, trans-{4-[7-(Allyl-methyl-amino)-heptyloxy]-cyclohexyl}-methyl-sulfamic acid 3,4-
difluoro-phenyl amide, trans-{4-[7-(Allyl-methyl-amino)-heptyloxy]-cyclohexyl}-methyl-sulfamic acid 4-chloro- phenyl amide, : trans-{4-(7-(Allyl-methyl-amino)-heptyloxy]-cyclohexyl}-methyl-sulfamic acid furan-2- ylmethyl amide, trans-{4-{7-(Allyl-methyl-amino)-heptyloxy]-cyclohexyl}-methyl-sulfamic acid benzyl amide, trans-({4-[7-(Allyl-methyl-amino)-heptyloxy]-cyclohexyl}-methyl-sulfamoyloxy)-acetic acid ethyl amide,
trans-1-{4-[6-(Allyl-methyl-amino)-hexyloxy]-cyclohexyl}-3-(2-bromo-4-fluoro-phenyl)- 1-methyl-thiourea, trans-1-{4-[6-(Allyl-methyl-amino)-hexyloxy]-cyclohexyl}-3-(4-bromo-2-methyl- phenyl)-1-methyl-thiourea, trans-1-{4-[6-( Allyl-methyl-amino)-hexyloxy]-cyclohexyl}-1-methyl-3-(4-
trifluoromethyl-phenyl)-thiourea, trans1-{4-[6- (Allyl-methyl-amino)-hexyloxy) -cyclohexyl}-3-(4-chloro-phenyl)-1-methyl- thiourea, trans1-{4-[6-(Allyl-methyl-amino)-hexyloxy]-cyclohexyl}-3-(4-methoxy-phenyl)-1- methyl-thiourea,
trans-1-{4-[6-(Allyl-methyl-amino)-hexyloxy]-cyclohexyl}-3-(4-cyano-phenyl)-1-methyl- thiourea, trans-1-{4-[6-(Allyl-methyl-amino)-hexyloxy]-cyclohexyl}- 1-methyl-3-(3-methyl-butyl)- thiourea, trans-1-{4-[6-(Allyl-methyl-amino)-hexyloxy]-cyclohexyl}-3-sec-butyl-1-methyl-thiourea,
trans-1-{4-[4-(Allyl-methyl-amino)-butoxy]-cyclohexyl}-1-methyl-3-(4-trifluoromethyl- phenyl)-thiourea, trans-1-{4-[4-(Allyl-methyl-amino)-butoxy]-cyclohexyl}-3-(4-cyano-phenyl)- 1-methyl- thiourea, trans-1-{4-[{4- (Allyl-methyl-amino)-butoxy]- cyclohexyl}-1-methyl-3-(3-methyl-butyl)-
thiourea, trans-1-{4-[7-(Allyl-methyl-amino)-heptyloxy]-cyclohexyl}-1-methyl-3-(4- trifluoromethyl-phenyl)-thiourea,
: trans-1-{4-[7-(Allyl-methyl-amino)-heptyloxy]-cyclohexyl}-3-(4-cyano-phenyl)-1- methyl-thiourea,
. 35 trans-1-{4-[7-(Allyl-methyl-amino)-heptyloxy]-cyclohexyl}-1-methyl-3-(3-methyl-butyl)- thiourea, trans-1-{4-[3-(Allyl-methyl-amino)-propoxy]-cyclohexyl}-1-methyl-3-(4-trifluoromethyl- phenyl)-thiourea, trans-[4-(6-Dimethylamino-hexyloxy)-cyclohexyl]-carbamic acid benzyl ester,
trans-[4-(5-Dimethylamino-pentyloxy)-cyclohexyl]-carbamic acid benzyl ester, trans-{4-[6-(Allyl-methyl-amino)-hexyloxy]-cyclohexyl}-carbamic acid benzyl ester, trans-N-{4-[5-(Allyl-methyl-amino)-pentyl]-cyclohexyl}-N-methyl-4-trifluoromethyl- ‘ benzenesulfonamide, trans-N-(4-{5-[Ethyl-(2-hydroxy-ethyl)-amino|-pentyl}-cyclohexyl) -N-methyl-4- ’ trifluoromethyl-benzenesulfonamide, and trans-{4-[4-(Allyl-methyl-amino)-butyl]-cyclohexyl}-methyl-carbamic acid 4-chloro- phenyl ester, and pharmaceutically acceptable salts thereof.
Other preferred compounds of general formula (I) are those selected from the group consisting of trans-N-[4-(3-Allylamino-propoxy)-cyclohexyl]-N-methyl-4-trifluoromethyl- benzenesulfonamide, trans-N-{4-[4-(Allyl-methyl-amino)-butoxy]-cyclohexyl}-N-ethyl-4-trifluoromethyl- benzenesulfonamide, trans-N-[4-(4-Dimethylamino-butoxy)-cyclohexyl]-N-ethyl-4-trifluoromethyl- benzenesulfonamide, trans-N-Ethyl-N-(4-{4-[(2-hydroxy-ethyl)-methyl-amino]-butoxy}-cyclohexyl)-4- trifluoromethyl-benzenesulfonamide, trans-N-Ethyl-N-(4-{4-[(2-methoxy-ethyl)-methyl-amino]-butoxy}-cyclohexyl)-4- trifluoromethyl-benzenesulfonamide, trans-N-Ethyl-N-(4-{4- [ethyl-(2-hydroxy-ethyl)-amino]-butoxy}-cyclohexyl)-4- trifluoromethyl-benzenesulfonamide, trans-N-Ethyl-N-(4-{4-[ethyl-(2-methoxy-ethyl)-amino]-butoxy}-cyclohexyl)-4- trifluoromethyl-benzenesulfonamide, trans-N-(4-{4-[Bis-(2-hydroxy-ethyl)-amino]-butoxy}- cyclohexyl) -N-ethyl-4- trifluoromethyl-benzenesulfonamide, trans-N- [4-(4-Diethylamino-butoxy)-cyclohexyl]-N-ethyl-4-trifluoromethyl- benzenesulfonamide, trans-N-{[4-(4-Allylamino-butoxy)-cyclohexyl]-N-ethyl-4-trifluoromethyl- benzenesulfonamide, - . trans-N-Ethyl-N-{4-(4-piperidin- 1-yl-butoxy)-cyclohexyl]-4-trifluoromethyl- benzenesulfonamide, . trans-N-Ethyl-N-{4-[4-(4-methyl-piperazin-1-yl)-butoxy]-cyclohexyl}-4-trifluoromethyl- benzenesulfonamide, trans-[4-(6-Dimethylamino-hexyloxy)-cyclohexyl]-carbamic acid benzyl ester, trans-[4-(5-Dimethylamino-pentyloxy)-cyclohexyl]-carbamic acid benzyl ester,
Trans-N-{4-[4-(2-Hydroxy-ethylamino)-butyl]-cyclohexyl}-N-methyl-4-trifluoromethyl-
benzenesulfonamide,
Trans-N-[4-(5-Ethylamino-pentyl)-cyclohexyl]-N-methyl-4-trifluoromethyl- benzenesulfonamide, trans- N-(4-{5-[Ethyl-(2-hydroxy-ethyl)-amino] -pentyl}-cyclohexyl)-N-methyl-4- trifluoromethyl-benzenesulfonamide N-oxide, : trans-N-(4-{5-[Ethyl-(2-fluoro-ethyl)-amino]-pentyl}-cyclohexyl)-N-methyl-4- trifluoromethyl-benzenesulfonamide, trans-4-Bromo-N-[4-(2-diisopropylamino-ethoxy)-cyclohexyl]-N-methyl- benzenesulfonamide,
Trans-4-Bromo-N-methyl-N-[4-(2-piperidin-1-yl-ethoxy)-cyclohexyl]- benzenesulfonamide,
Trans-4-Bromo-N-[4-(2-diethylamino-ethoxy)-cyclohexyl]-N-methyl- benzenesulfonamide, trans-4-Bromo-N-methyl-N-[4-(2-morpholin-4-yl-ethoxy)-cyclohexyl]- benzenesulfonamide, trans-4-Bromo-N-methyl-N-{4-(2-pyrrolidin- 1-yl-ethoxy)-cyclohexyl]- benzenesulfonamide,
Trans-N-[4-(3-Dimethylamino-3-methyl-butoxy)-cyclohexyl]-N-methyl-4- trifluoromethyl-benzenesulfonamide,
Trans-N-{4-[2-(1-Dimethylamino-cyclopropyl)-ethoxy]-cyclohexyl}-N-methyl-4- trifluoromethyl-benzenesulfonamide,
Trans-N-[4-(5-Diethylamino-5-methyl-hexyl)-cyclohexyl] -N-methyl-4-trifluoromethyl- benzenesulfonamide,
Trans-N-{4-[4-(1-Diethylamino-cyclopropyl)-butyl]-cyclohexyl}-N-methyl-4- trifluoromethyl-benzenesulfonamide, trans-N-[4-(4-Dimethylamino-pentyloxy)-cyclohexyl]-N-methyl-4-trifluoromethyl- benzenesulfonamide, trans-N-[4-(2-Diethylamino-ethoxy)-cyclohexyl]-N-methyl-4-trifluoromethyl- benzenesulfonamide, trans-N-Methyl-N-[4-(2-piperidin-1-yl-ethoxy)-cyclohexyl]-4-trifluoromethyl- benzenesulfonamide, trans-N- [4-(2-Diisopropylamino-ethoxy)-cyclohexyl]-N-methyl-4-trifluoromethyl- ’ benzenesulfonamide, trans-N-Methyl-N-[4-(2-pyrrolidin-1-yl-ethoxy)-cyclohexyl]-4-trifluoromethyl- : 35 benzenesulfonamide, trans-N-Methyl-N-[4-(2-morpholin-4-yl-ethoxy)-cyclohexyl]-4-trifluoromethyl- benzenesulfonamide, trans-N-Methyl-N-[4-(4-piperidin- 1-yl-pentyloxy)-cyclohexyl]-4-trifluoromethyl- benzenesulfonamide,
Trans-[4-(3-Dimethylamino-3-methyl-but-1-ynyl)-cyclohexyl] -methyl-carbamic acid tert-butyl ester, cis- N-(4-{5-[Ethyl-(2-hydroxy-ethyl)-amino]-pentyl}-cyclohexyl)-N-methyl-4- trifftuoromethyl-benzenesulfonamide, trans-(4-{4-[Ethyl-(2-hydroxy-ethyl)-amino]-butyl}-cyclohexyl)-methyl-carbamic acid 4-
chloro-phenyl ester, trans-{4- [4-(Allyl-methyl-amino)-butyl]-cyclohexyl}-methyl-carbamic acid 4- trifluoromethyl-phenyl ester, trans-(4-{4-[Ethyl-(2-hydroxy-ethyl)-amino]-butyl}-cyclohexyl)-methyl-carbamic acid 4-
trifluoromethyl-phenyl ester, trans-{4-[4-(Allyl-methyl-amino)-butyl]-cyclohexyl}-methyl-carbamic acid 4-bromo- phenyl ester, trans-(4-{4-[Ethyl- (2-hydroxy-ethyl)-amino]-butyl}-cyclohexyl)-methyl-carbamic acid 4- bromo-phenyl ester,
trans-Methyl-{4-[4-(methyl-propyl-amino)-butyl]-cyclohexyl}-carbamic acid 4-bromo- phenyl ester, trans-[4-(4-Diethylamino-butyl)-cyclohexyl}-methyl-carbamic acid 4-bromo-phenyl ester, trans-[4-(4-Dimethylamino-butyl)-cyclohexyl}-methyl-carbamic acid 4-bromo-phenyl ester, trans-Methyl-[4-(4-piperidin-1-yl-butyl)-cyclohexyl]-carbamic acid 4-bromo-phenyl ester, trans-Methyl-{4-[4-(4-methyl-piperazin-1-yl)-butyl}-cyclohexyl}-carbamic acid 4-bromo- phenyl ester,
trans-Methyl-[4-(4-morpholin-4-yl-butyl)-cyclohexyl]- carbamic acid 4-bromo-phenyl ester, trans-Methyl- [4-(4-thiomorpholin-4-yl-butyl)-cyclohexyl]-carbamic acid 4-bromo- phenyl ester, trans-Methyl-[4-(4-piperidin-1-yl-butyl)-cyclohexyl]-carbamic acid 4-trifluoromethyl-
phenyl ester, trans-[4-(4-Dimethylamino-butyl)-cyclohexyl]-methyl-carbamic acid 4-trifluoromethyi- phenyl ester,
: trans-Methyl- [4-(4-thiomorpholin-4-yl-butyl)-cyclohexyl]-carbamic acid 4- trifluoromethyl-phenyl ester,
, 35 trans-Methyl-{4-[4-(methyl-propyl-amino)-butyl]-cyclohexyl}-carbamic acid 4- trifluoromethyl-phenyl ester, trans-N-{4-[4-(Allyl-methyl-amino)-butyl]-cyclohexyl}-N-methyl-4-trifluoromethyl- benzenesulfonamide, trans-N-(4-{4-[Ethyl-(2-hydroxy-ethyl)-amino]-butyl}-cyclohexyl)-N-methyl-4-
trifluoromethyl-benzenesulfonamide, trans-N-Methyl-N- [4-(4-piperidin-1-yl-butyl)- cyclohexyl] -4-trifluoromethyl- benzenesulfonamide, ‘ trans-N-[4-(4-Dimethylamino-butyl)-cyclohexyl]-N-methyl-4-trifluoromethyl- benzenesulfonamide, : trans-N-Methyl-N-{4-[4-(methyl-propyl-amino)-butyl] -cyclohexyl}-4-trifluoromethyl- benzenesulfonamide, trans-N-(4-{4-[Bis-(2-hydroxy-ethyl)-amino] -butyl}-cyclohexyl)-N-methyl-4- trifluoromethyl-benzenesulfonamide, trans-{4-[5-(Allyl-methyl-amino)-pentyl]-cyclohexyl}-methyl-carbamic acid 2,4-difluoro- phenyl ester, trans-(4-{5-{Ethyl-(2-hydroxy-ethyl)-amino]-pentyl}-cyclohexyl)-methyl-carbamic acid 2,4-difluoro-phenyl ester, trans-(4-{5-[Ethyl-(2-hydroxy-ethyl)-amino]-pentyl}-cyclohexyl)-methyl-carbamic acid 4-chloro-phenyl ester, trans-Methyl-{4-[5-(methyl-propyl-amino)-pentyl]-cyclohexyl}-carbamic acid 4-chloro- phenyl ester, trans-{4-(5-Dimethylamino-pentyl)-cyclohexyl]-methyl-carbamic acid 4-chloro-phenyl ester, trans-Methyl-[4-(5-piperidin- 1-yl-pentyl)-cyclohexyl]-carbamic acid 4-chloro-phenyl ester, trans-Methyl-{4-[5-(4-methyl-piperazin-1-yl)-pentyl]-cyclohexyl}-carbamic acid 4- chloro-phenyl ester, trans-{4-[5-(Cyclopropyl-methyl-amino)-pentyl]-cyclohexyl}-methyl-carbamic acid 4- chloro-phenyl ester, trans-N- [4-(5-Diethylamino-pentyl)-cyclohexyl]-N-methyl-4-trifluoromethyl- benzenesulfonamide, trans-N-(4-{5-[Bis-(2-hydroxy-ethyl)-amino]-pentyl}-cyclohexyl)-N-methyl-4- trifluoromethyl-benzenesulfonamide, (cis){4-[5-(Allyl-methyl-amino)-pentyl]-cyclohexyl}-methyl-carbamic acid 4- trifluoromethyl-phenyl ester, trans-{4-{5-(Allylamino)-pentyl]-cyclohexyl}-methyl-carbamic acid 4-trifluoromethyl- . phenyl ester,
Trans-Methyl-[4-(5-methylamino-pentyl)-cyclohexyl]-carbamic acid 4-trifluoromethyl- . 35 phenyl ester, trans-N-[4-(5-Allylamino-pentyl)-cyclohexyl]-N-methyl-4-trifluoromethyl- benzenesulfonamide, trans-N-{4-[5-(2-Hydroxy-1,1-dimethyl-ethylamino)-pentyl]-cyclohexyl}-N-methyl-4- trifluoromethyl-benzenesulfonamide,
trans-N-Methyl-N-[4-(5-methylamino-pentyl)-cyclohexyl]-4-trifluoromethyl- benzenesulfonamide, (trans)-[4-(5-Dimethylamino-pent-1-ynyl)-cyclohexyl]-methyl-carbamic acid 4-chloro- phenyl ester,
Trans-Methyl-{4-[5-(methyl-propyl-amino)-pent-1-ynyl}-cyclohexyl}-carbamic acid 4- : chloro-phenyl ester,
Trans-(4-{5-[Ethyl-(2-hydroxy-ethyl)-amino]-pent- 1-ynyl}-cyclohexyl)-methyl-carbamic acid 4-chloro-phentyl ester,
Trans-N-(4-{3-[Bis-(2-hydroxy-ethyl)-amino]-prop-1-ynyl}-cyclohexyl)-N-methyl-4- trifluoromethyl-benzenesulfonamide,
Trans-N-(4-{3-[Ethyl-(2-hydroxy-ethyl)-amino]-prop-1-ynyl}-cyclohexyl)-N-methyl-4- trifluoromethyl-benzenesulfonamide, trans-[4-(4-Dimethylamino-butoxy)-cyclohexyl]-methyl-carbamic acid isobutyl ester, trans-(4-{4-{Ethyl-(2-hydroxy-ethyl)-amino}-butoxy}-cyclohexyl)-methyl-carbamic acid isobutyl ester, trans-[4-(4-Diethylamino-butoxy)-cyclohexyl] -methyl-carbamic acid isobutyl ester, trans-[4-(4-Azetidin-1-yl-butoxy)-cyclohexyl]-methyl-carbamic acid isobutyl ester, trans-Methyl-[4-(4-morpholin-4-yl-butoxy)-cyclohexyl] -carbamic acid isobutyl ester, trans-Methyl-[4-(4-pyrrolidin-1-yl-butoxy)-cyclohexyl]-carbamic acid isobutyl ester, trans-(4-{4-[Ethyl-(2-methoxy-ethyl)-amino]-butoxy}-cyclohexyl)-methyl-carbamic acid isobutyl ester, trans-Methyl-{4-[4-(methyl-propyl-amino)-butoxy]-cyclohexyl}-carbamic acid isobutyl ester, trans-(4-{4-[Bis-(2-hydroxy-ethyl)-amino}-butoxy}-cyclohexyl)-methyl-carbamic acid isobutyl ester, trans-{4-[4-(Cyclopropylmethyl-methyl-amino)-butoxy]-cyclohexyl}-methyl-carbamic acid isobutyl ester,
Trans-N-(4-{3-[Bis-(2-hydroxy-ethyl)-amino]-propyl}-cyclohexyl)-N-methyl-4- trifluoromethyl-benzenesulfonamide,
Trans-N-(4-{3-[Ethyl-(2-hydroxy-ethyl)-amino]-propyl}-cyclohexyl)-N-methyl-4- trifluoromethyl-benzenesulfonamide,
Trans-[4-(3-Dimethylamino-prop-1-ynyl)-cyclohexyl]-methyl-carbamic acid 4-chloro- ’ phenyl ester,
Trans-(4-{3-[Bis-(2-hydroxy-ethyl)-amino]-prop-1-ynyl}-cyclohexyl)-methyl-carbamic : 35 acid 4-trifluoromethyl-phenyl ester,
Trans-Methyl-[4-(3-piperidin-1-yl-prop-1-ynyl)-cyclohexyl]-carbamic acid 4-chloro- phenyl ester,
Trans-[4-(3-Dimethylamino-prop- 1-ynyl)-cyclohexyl]-methyl-carbamic acid 4- trifluoromethyl-phenyl ester,
Trans-Methyl- {4-[3-(methyl-propyl-amino)-prop-1-ynyl]-cyclohexyl}-carbamic acid 4- trifluoromethyl-phenyl ester,
Trans-Methyl- [4~(3-piperidin-1-yl-prop- 1-ynyl)-cyclohexyl] -carbamic acid 4- ) trifluoromethyl-pheny] ester, trans-{4-[4-(Allyl-methyl-amino)-butoxy]-cyclohexyl}-methyl-carbamic acid 2,4- ’ difluoro-phenyl ester, trans-[4-(4-Dimethylamino-butoxy)-cyclohexyl}-methyl-carbamic acid 2,4-difluoro- phenyl ester, trans-(4-{4-[Ethyl-(2-hydroxy-ethyl)-amino]-butoxy}-cyclohexyl) -methyl-carbamic acid 2,4-difluoro-phenyl ester, trans-Methyl-[4-(4-morpholin-4-yl-butoxy)-cyclohexyl]-carbamic acid 2,4-difluoro- phenyl ester, trans-(4-{4-[Ethyl-(2-methoxy-ethyl)-amino]-butoxy}-cyclohexyl)-methyl-carbamic acid 2,4-difluoro-phenyl ester, trans-Methyl-{4-[4-(methyl-propyl-amino)-butoxy]-cyclohexyl}-carbamic acid 2,4- difluoro-phenyl ester, trans-3,4-Difluoro-N-methyl-N-{4-[4-(methyl-propyl-amino)-butoxy] -cyclohexyl}- : benzenesulfonamide, trans-N-(4-{4-[Ethyl-(2-hydroxy-ethyl)-amino]-butoxy}-cyclohexyl)-3,4-difluoro-N- methyl-benzenesulfonamide, trans-2,4-Difluoro-N-methyl-N-{4-{4-(methyl-propyl-amino)-butoxy]-cyclohexyl}- benzenesulfonamide, trans-N-(4-{4-[Ethyl-(2-hydroxy-ethyl)-amino]-butoxy}-cyclohexyl)-2,4-difluoro-N- methyl-benzenesulfonamide,
Trans-4-Dimethylamino-N-[4-(4-dimethylamino-butoxy)-cyclohexyl]-3-fluoro-N- methyl-benzenesulfonamide,
Trans-4-Dimethylamino-N-[4-(4-dimethylamino-butoxy)-cyclohexyl]-2-fluoro-N- methyl-benzenesulfonamide,
Trans-Methyl-{4-[3-(methyl-propyl-amino)-prop-1-ynyl}-cyclohexyl}-carbamic acid 4- chloro-phenyl ester,
Trans-Methyl-{4-[3-(methyl-propyl-amino)-prop-1-ynyl]-cyclohexyl}-carbamic acid 4- chloro-phenyl ester, : Trans-[4-(3-Dimethylamino-propyl)-cyclohexyl]-methyl-carbamic acid 4-chloro-phenyl ester, : 35 Trans-(4-{3-[Ethyl-(2-hydroxy-ethyl)-amino]-propyl}-cyclohexyl)-methyl-carbamic acid 4-trifluoromethyl-phenyl ester,
Trans-(4-{3-[Bis-(2-hydroxy-ethyl)-amino]-propyl}-cyclohexyl)-methyl-carbamic acid 4- trifluoromethyl-phenyl ester,
Trans-Methyl-{4-(3-(methyl-propyl-amino)-propyl]-cyclohexyl}-carbamic acid 4-chloro-
phenyl ester,
Trans-(4-{4-[Ethyl-(2-hydroxy-ethyl)-amino]-but- 1-ynyl}-cyclohexyl)-methyl- carbamic acid 4-chloro-phenyl ester, ’ Trans-N-(4-{5-[Ethyl-(2-hydroxy-ethyl)-amino]-pent- 1-ynyl}-cyclohexyl)-N-methyl-4- trifluoromethyl-benzenesulfonamide, : ' Trans-N-Methyl-N-{4-[5-(methyl-propyl-amino)-pent-1-ynyl]-cyclohexyl}-4- trifluoromethyl-benzenesulfonamide,
Trans-N-[4-(4-Dimethylamino-but-1-ynyl)-cyclohexyl]-N-methyl-4-trifluoromethyl- benzenesulfonamide,
Trans-N-Methyl-N-{4-[4-(methyl-propyl-amino)-but-1-ynyl] -cyclohexyl}-4- trifluoromethyl-benzenesulfonamide,
Trans-N-(4-{4-[Ethyl-(2-hydroxy-ethyl)-amino]-but-1-ynyl}-cyclohexyl)-N-methyl-4- trifluoromethyl-benzenesulfonamide,
Trans-Methyl-{4-[3-(methyl-propyl-amino)-prop-1-ynyl]-cyclohexyl}-carbamic acid 4- methoxy-phenyl ester,
Trans-Methyl-{4-[3-(methyl-propyl-amino)-prop-1-ynyl]-cyclohexyl}-carbamic acid p- tolyl ester,
Trans-(4-{3-[Ethyl-(2-methoxy-ethyl)-amino]-prop- 1-ynyl}-cyclohexyl)-methyl-carbamic acid 4-chloro-phenyl ester, trans-{4-[5-(Allyl-methyl-amino)-pentyl]-cyclohexyl}-methyl-carbamic acid 4- trifluoromethyl-phenyl ester N-oxide,
Trans-N-Methyl-N-{4-[3-(methyl-propyl-amino)-prop-1-ynyl}-cyclohexyl}-4- trifluoromethyl-benzenesulfonamide,
Trans-N-[4-(3-Dimethylamino-prop-1-ynyl)-cyclohexyl]-N-methyl-4-trifluoromethyl- benzenesulfonamide,
Trans-N-(4-{3-[Ethyl-(2-methoxy-ethyl)-amino]-prop-1-ynyl}-cyclohexyl)-N-methyl-4- trifluoromethyl-benzenesulfonamide,
Trans-Methyl-{4-[4-(methyl-propyl-amino)-but-1-ynyl]-cyclohexyl}-carbamic acid 4- trifluoromethyl-phenyl ester, Trans-[4-(4-Dimethylamino-but-1-ynyl)-cyclohexyl]-methyl-carbamic acid 4- trifluoromethyl-phenyl ester,
Trans-{4-[4-(Allyl-methyl-amino)-but-1-ynyl]-cyclohexyl}-methyl-carbamic acid 4- ’ trifluoromethyl-phenyl ester,
Trans-(4-{4-[Ethyl-(2-hydroxy-ethyl)-amino]-but-1-ynyl}-cyclohexyl)-methyl-carbamic acid 4-trifluoromethyl-phenyl ester,
Trans-Methyl-{4-[4-(methyl-propyl-amino)-but- 1-ynyl]-cyclohexyl}-carbamic acid 4- chloro-phenyl ester,
Trans-[4-(4-Dimethylamino-but-1-ynyl)-cyclohexyl]-methyl-carbamic acid 4-chloro- phenyl ester,
Trans-{4-[4-(Allyl-methyl-amino)-but-1-ynyl]-cyclohexyl}-methyl-carbamic acid 4- chloro-phenyl ester, trans-(1E)-N-Methyl-N-{4-[3-(methyl-propyl-amino)-propenyl]-cyclohexyl}-4- : trifluoromethyl-benzenesulfonamide, trans-(1E)-N-[4-(3-Dimethylamino-propenyl)-cyclohexyl]-N-methyl-4-trifluoromethyl- : benzenesulfonamide, trans-(1E)-N-{4-[3-(Allyl-methyl-amino)-propenyl]-cyclohexyl}-N-methyl-4- trifluoromethyl-benzenesulfonamide, trans-(1E)-N-(4-{3-[Ethyl-(2-hydroxy-ethyl)-amino]-propenyl}-cyclohexyl)-N-methyl-4- trifluoromethyl-benzenesulfonamide, trans-N-Methyl-4-nitro-N-[4-(4-piperidin-1-yl-butoxy)-cyclohexyl]- benzenesulfonamide, trans-N-(4-{4-[Ethyl-(2-methoxy-ethyl)-amino]-butoxy}-cyclohexyl)-N-methyl-4-nitro- benzenesulfonamide, trans-N-[4-(4-Dimethylamino-butoxy)-cyclohexyl]-N-methyl-4-nitro- benzenesulfonamide, trans-N-{4-[4-(Allyl-methyl-amino)-butoxy]-cyclohexyl}-N-methyl-4-nitro- benzenesulfonamide, trans-N-(4-{4-[Ethyl-(2-hydroxy-ethyl)-amino]-butoxy}-cyclohexyl)-N-methyl-4-nitro- benzenesulfonamide, trans-N-{4-[4-(4-Hydroxy-piperidin-1-yl)-butoxy]-cyclohexyl}-N-methyl-4-nitro- benzenesulfonamide,
Trans-Methyl-{4-[3-(methyl-propyl-amino)-propyl]-cyclohexyl}-carbamic acid p-tolyl ester,
Trans-4-Amino-N-methyl-N-{4-[3-(methyl-propyl-amino)-prop-1-ynyl] -cyclohexyl}- benzenesulfonamide,
Trans-Methyl-{4-[3-(methyl-propyl-amino)-propenyl]-cyclohexyl}-carbamic acid 4- trifluoromethyl-phenyl ester,
Trans-Methyl-{4-[3-(methyl-propyl-amino)-propenyl]-cyclohexyl}-carbamic acid 4- chloro-phenyl ester, trans-(1E)-(4-{3- [Ethyl-(2-methoxy-ethyl)-amino]-propenyl}-cyclohexyl)-methyl- carbamic acid 4-chloro-phenyl ester, Co ) trans-(1E)-(4-{3-[Ethyl-(2-hydroxy-ethyl)-amino]-propenyl}-cyclohexyl)-methyl- carbamic acid 4-chloro-phenyl ester, ; 35 Trans-4-Chloro-N-methyl-N-{4-[3-(methyl-propyl-amino)-prop-1-ynyl]-cyclohexyl}- benzamide,
Trans-3-(4-Chloro-phenyl)- 1-methyl- 1-{4-3-(methyl-propyl-amino)-prop-1-ynyl]- cyclohexyl}-urea,
Trans-4-Chloro-N-(4-{3-[ethyl- (2-hydroxy-ethyl)-amino]-prop-1-ynyl}-cyclohexyl)-N-
Claims (1)
- Claims1. Compounds of formula (I) A°N. A A w-a" AND OPN oY. (CH), (CF © A wherein U is O or a lone pair, Vv 1s O, §, -CH,-, -CH=CH-, or -C=C-, Ww is CO, COO, CONR', CSO, CSNR', SO, or SO.NR', mandn independently from each other are 0 to 7 and m+n is 0 to 7, with the proviso thatmisnot0if VisOorS, A is H, lower-alkyl, hydroxy-lower-alkyl, or lower-alkenyl, A? is lower-alkyl, cycloalkyl, cycloalkyl-lower-alkyl, or lower-alkenyl, optionally substituted by R, A’and A* are hydrogen or lower-alkyl, or A'and A? or A! and A’ are bonded to each other to form a ring and - A'- A% or - Al- A3- are lower-alkylene or lower-alkenylene, optionally substituted by R?, in which one -CH- group of -A'- A> or -A'-A’- can optionally be replaced by NR?, S, or O, or A’ and A* are bonded to each other to form a ring together with the carbon atom to which they are attached and AAs -(CHy_);-5- which can optionally be mono- or multiply-substituted by lower-alkyl, A® is H, lower-alkyl, lower-alkenyl, or aryl-lower-alkyl, ’ AS is lower-alkyl, cycloalkyl, aryl, aryl-lower-alkyl, heteroaryl, heteroaryl-lower- alkyl, lower-alkoxy-carbonyl-lower-alkyl, R? is hydroxy, hydroxy-lower-alkyl, lower-alkoxy, lower-alkoxycarbonyl, N(R*R?), or thio-lower-alkoxy,R', R?, R* and R’® independently from each other are hydrogen or lower-alkyl, and pharmaceutically acceptable salts and/or pharmaceutically acceptable esters thereof.) 2. Compounds according to claim 1, wherein A> and A* are not bonded to each other to form a ring together with the carbon atom to which they are attached.3. Compounds according to any of claims 1 to 2, characterised by formula (Ia) A°N. 3 4 W-A° A A Vv R AN pe INA ul (CH), (CHa; (Ta) A wherein U, V, W, m,n, A, A%, A%, A*, A’ and A’ have the significances given in any of claims 1 to 2.4. Compounds according to any of claims 1 to 3, wherein U is a lone pair.5. Compounds according to any of claims 1 to 4, wherein V is O.6. Compounds according to any of claims 1 to 4, wherein V is-CH-.7. Compounds according to any of claims 1 to 4, wherein V is -C=C-.8. Compounds according to any of claims 1 to 4, wherein V is -C=C-.9. Compounds according to any of claims 1 to 8, wherein W is CO, COO, CONR', CSNR', SO; or SO,NR' and R' is hydrogen.10. Compounds according to any of claims 1 to 9, wherein W is COO or SO,.11. Compounds according to any of claims 1 to 10, wherein n is 0.12. Compounds according to any of claims 1 to 10, wherein n is 1.13. Compounds according to any of claims 1 to 12, wherein mis 1 to 6.14. Compounds according to any of claims 1 to 12, wherein m is 0 and V is -C=C- or -C=C-15. Compounds according to any of claims 1 to 14, wherein Al is H, methyl, ethyl, isopropyl, 2-hydroxy-ethyl, or 2-propenyl. . 16. Compounds according to any of claims 1 to 15, wherein A? is lower-alky], cycloalkyl-lower-alkyl, or lower-alkenyl, optionally substituted with R%, wherein R is hydroxy, methoxy, or ethoxycarbonyl.17. Compounds according to any of claims 1 to 16, wherein A? is methyl, ethyl, 2- hydroxy-ethyl, 2-propenyl, propyl or isopropyl.18. Compounds according to any of claims 1 to 14, wherein A' and A? are bonded to each other to form a ring and -A'-A%- is lower-alkylene or lower-alkenylene, optionally substituted by R?, in which one -CH,- group of -A'-A’- can optionally be replaced by NR?, S, or O, wherein R? and R® are as defined in claim 1.19. Compounds according to claim 18, wherein Al and A? are bonded to each other to form a ring and -A'-A’- is lower-alkylene or lower-alkenylene, optionally substituted by R?, in which one -CHa- group of -A'-A’- can optionally be replaced by O, wherein R? is hydroxy or 2-hydroxyethyl.20. Compounds according to claim 19, wherein A' and A? are bonded to each other to form a ring and -AL-A% is -(CH,)s-.21. Compounds according to any of claims 1 to 20, wherein A? is hydrogen.22. Compounds according to any of claims 1 to 21, wherein A* is hydrogen.23. Compounds according to any of claims 1 to 19, wherein A® and A* are bonded to each other to form a cyclopropyl-ring together with the carbon atom to which they are attached and -A>-A*%- is -(CH,),-.24. Compounds according to any of claims 1 to 23, wherein A® is H, lower-alkyl, lower-alkenyl, or benzyl optionally substituted with halogen. : 25 25. Compounds according to any of claims 1 to 24, wherein A® is methyl or ethyl. . 26. Compounds according to any of claims 1 to 25, wherein A® is lower-alkyl, cycloalkyl, phenyl, naphthyl, phenyl-lower-alkyl, pyridyl, indolyl, indolinyl, thienyl, thienyl-methylene, furyl-methylene, benzodioxyl, chinolyl, isoxazolyl, or imidazolyl, optionally substituted by one or more substituents selected from the group consisting of lower-alkyl, lower-alkoxy, lower-alkylcarbonyl, lower-alkoxycarbonyl, fluorine, chlorine,bromine, CN, CFs, NO,, or N(R,R”), wherein R® and R’ independently from each other are hydrogen or lower-alkyl. : 27. Compounds according to any of claims 1 to 26, wherein A® is phenyl optionally substituted by one or more substituents selected from the group consisting of fluorine, chlorine, bromine, and CFs.28. Compounds according to any of claims 1 to 27, wherein A® is 4-chloro-phenyl], 4-bromo-phenyl, or 4-trifluoromethyl-phenyl.29. A compound according to any of claims 1 to 28, selected from the group consisting of trans-{4-[6-(Allyl-methyl-amino)-hexyloxy]-cyclohexyl}-methyl-carbamic acid 4-chloro- phenyl ester, trans-{4-[4-(Allyl-methyl-amino)-butoxy]-cyclohexyl}-methyl-carbamic acid 4- trifluoromethyl-phenyl ester, trans-N- [4-(6-Diethylamino-hexyloxy)-cyclohexyl]-N-methyl-4-trifluoromethyl- benzenesulfonamide, trans-{4-[4-(Allyl-methyl-amino)-butoxy]-cyclohexyl}-methyl-carbamic acid 4-chloro- phenyl ester, trans-{4-[2-(Allyl-methyl-amino)-ethylsulfanylmethyl]-cyclohexyl}-methyl- carbamic acid 4-chloro-phenyl ester, trans-{4-[5-(Allyl-methyl-amino)-pentyl]-cyclohexyl}-methyl-carbamic acid 4-chloro- phenyl ester, trans-(4-{4-[Ethyl-(2-hydroxy-ethyl)-amino}-butoxy}-cyclohexyl)-methyl-carbamic acid 4-trifluoromethyl-phenyl ester, trans-N-[4-(3-Allylamino-propoxy)-cyclohexyl]-N-methyl-4-trifluoromethyl- benzenesulfonamide, trans-{4-[5-(Allyl-methyl-amino)-pentyl]-cyclohexyl}-methyl-carbamic acid 4- trifluoromethyl-phenyl ester, trans-(4-{5-[ Ethyl-(2-hydroxy-ethyl)-amino]-pentyl}-cyclohexyl)-methyl-carbamic acid. 4-trifluoromethyl-phenyl ester, trans-(4-{5-[Ethyl-(2-hydroxy-ethyl)-amino]-pentyl}-cyclohexyl)-methyl-carbamic acid 3 4-bromo-phenyl ester, trans-N-(4-{5-[Ethyl-(2-hydroxy-ethyl)-amino]-pentyl}-cyclohexyl)-N-methyl-4- trifluoromethyl-benzenesulfonamide, trans-[4-(4-Dimethylamino-butoxy)-cyclohexyl]-methyl-carbamic acid 4-trifluoromethyl- phenyl ester,trans-{4-[5-(Allyl-methyl-amino)-pentyl]-cyclohexyl}-methyl-carbamic acid 4-bromo- phenyl ester, trans-{4-[3-(Allyl-methyl-amino)-prop-1-ynyl]-cyclohexyl}-methyl-carbamic acid 4- ) chloro-phenyl ester, trans-N-{4-[5-(Allyl-methyl-amino)-pentyl]-cyclohexyl}-N-methyl-4-trifluoromethyl- benzenesulfonamide, trans-(4-{3-[Ethyl-(2-hydroxy-ethyl)-amino]-propyl}-cyclohexyl)-methyl-carbamic acid 4-chloro-phenyl ester, and trans- {4-[4-(Allyl-methyl-amino)-butyl]-cyclohexyl}-methyl-carbamic acid 4-chloro- phenyl ester, and pharmaceutically acceptable salts thereof.30. A compound according to any of claims 1 to 29, selected from the group consisting of Trans-N-[4-(4-Dimethylamino-but-1-ynyl)-cyclohexyl]-N-methyl-4-trifluoromethyl- benzenesulfonamide, trans-Methyl-[4-(5-piperidin-1-yl-pentyl)-cyclohexyl]-carbamic acid 4-chloro-phenyl ester. Trans-Methyl-[4-(5-methylamino-pentyl)-cyclohexyl]-carbamic acid 4-trifluoromethyl- phenyl ester, Trans-(4-{5-[Ethyl-(2-hydroxy-ethyl)-amino]-pent-1-ynyl}-cyclohexyl)-methyl-carbamic acid 4-chloro-pheny! ester, trans-N-Ethyl-N-(4-{4-[(2-hydroxy-ethyl)-methyl-amino]-butoxy}-cyclohexyl)-4- trifluoromethyl-benzenesulfonamide, trans-(1E)-N-(4-{3-[Ethyl-(2-hydroxy-ethyl)-amino]-propenyl}-cyclohexyl)-N-methyl-4- trifluoromethyl-benzenesulfonamide, Trans-4-Bromo-N-[4-(2-diisopropylamino-ethoxy)-cyclohexyl}-N-methyl- benzenesulfonamide, trans-Methyl-[4-(4-piperidin- 1-yl-butyl)-cyclohexyl]- carbamic acid 4-bromo-phenyl ester, trans-N-Methyl-N-[4-(4-piperidin-1-yl-butyl)-cyclohexyl]-4-trifluoromethyl- benzenesulfonamide, - trans-N-(4-{4-[Bis-(2-hydroxy-ethyl)-amino]-butoxy}-cyclohexyl)-N-ethyl-4- trifluoromethyl-benzenesulfonamide, Trans-4-Bromo-N-methyl-N-{4-(2-piperidin-1-yl-ethoxy)-cyclohexyl]- benzenesulfonamide, trans-N-[4-(4-Dimethylamino-butoxy)-cyclohexyl] -N-ethyl-4-trifluoromethyl-benzenesulfonamide, Trans-Methyl-{4-[3-(methyl-propyl-amino)-prop-1-ynyl]-cyclohexyl}-carbamic acid 4- chloro-phenyl ester, : trans-(1E)-N-Methyl-N-{4-[3-(methy!l-propyl-amino)-propenyl]-cyclohexyl}-4- trifluoromethyl-benzenesulfonamide, ’ Trans-N-(4-{4-[Ethyl-(2-hydroxy-ethyl)-amino]-but-1-ynyl}-cyclohexyl)-N-methyl-4- trifluoromethyl-benzenesulfonamide, Trans-N-Methyl-N-{4-[4-(methyl-propyl-amino)-but-1-ynyl]-cyclohexyl}-4- trifluoromethyl-benzenesulfonamide, and Trans-N-{4-[2-(1-Dimethylamino-cyclopropyl)-ethoxy]-cyclohexyl}-N-methyl-4- trifluoromethyl-benzenesulfonamide, and pharmaceutically acceptable salts thereof.31. A process for the manufacture of compounds according to any of claims 1 to 30, which process comprises reacting a compound of formula (II) A° yA (IT) wherein A’ has the significance given in claim 1, ya is a group (A',A%)N-C(A%AY)-(CH2)m-V-(CHa), or HO-(CHy),,, wherein A', AZ, A’ A* V, m and n have the significances given in claim 1, with CISO,-A%, CICOO-A®, CICSO-A®, OCN-A®, SCN-A®, HOOC-A®, or CISO:NR'-A®, wherein A® has the significance given in claim 1.32. Compounds according to any of claims 1 to 30 when manufactured by a process according to claim 31.33. Pharmaceutical compositions comprising a compound according to any of . 25 claims 1 to 30 and a pharmaceutically acceptable carrier and/or adjuvant.34. Compounds according to any of claims 1 to 30 for use as therapeutic active substances.-218- PCT/EP01/09174 : 35. Compounds according to any of claims 1 to 30 for use as active substances in a method for the treatment and/or prophylaxis of diseases which are associated with OSC.36. A method for the prophylaxis of diseases which are associated with OSC such as hypercholesterolemia, hyperlipemia, arteriosclerosis, vascular diseases, mycoses, parasite infections, gallstones, tumors and/or hyperproliferative disorders, and/or prophylaxis of impaired glucose tolerance and diabetes, which method comprises administering a compound according to any of claims 1 to 30 to a human being or animal.37. The use of compounds according to any of claims 1 to 30 for the treatment and/or prophylaxis of diseases which are associated with OSC.38. The use of compounds according to any of claims 1 to 30 for the treatment and/or prophylaxis of hypercholesterolemia, hyperlipemia, arteriosclerosis, vascular diseases, mycoses, parasite infections, gallstones, tumors and/or hyperproliferative disorders, and/or treatment and/or prophylaxis of impaired glucose tolerance, and diabetes.39. The use of compounds according to any of claims 1 to 30 for the preparation of medicaments for the treatment and/or prophylaxis of diseases which are associated with OSC.40. The use of compounds according to any of claims 1 to 30 for the preparation of medicaments for the treatment and/or prophylaxis of hypercholesterolemia, hyperlipemia, arteriosclerosis, vascular diseases, mycoses, parasite infections, gallstones, tumors and/or hyperproliferative disorders, and/or treatment and/or prophylaxis of impaired glucose tolerance and diabetes.41. Use of a compound according to any of claims 1 to 30 in the manufacture of a preparation for use in treating the human or animal body. AMENDED SHEET219- PCT/EP01/09174 : 42. A substance or composition for use in a method of treatment, said substance or composition comprising a compound according to any of claims 1 to 30, and said method comprising administering said substance or composition.43. A substance or composition for use in a method for the treatment and/or prophylaxis of hypercholesterolemia, hyperlipemia, arteriosclerosis, vascular diseases, mycoses, parasite infections, gallstones, tumors and/or hyperproliferative disorders, and/or treatment and/or prophylaxis of impaired glucose tolerance and diabetes, said substance or composition comprising a compound according to any of claims 1 to 30, and said method comprising administering said substance or composition to a human being or animal.44. The novel compounds, processes and methods as well as the use of such compounds substantially as described hereinbefore.45. A compound according to any one of claims 1 to 30, 32, 34 or 35, substantially as herein described and illustrated.46. A process according to claim 31, substantially as herein described and illustrated.47. A composition according to claim 33, substantially as herein described and illustrated.48. Use according to any one of claims 37 to 41, substantially as herein described and illustrated.49. A method according to claim 36, substantially as herein described and illustrated.50. A substance or composition for use in a method of treatment or prevention according to any one of claims 35, 42, or 43, substantially as herein described and illustrated. AMENDED SHEET-220- PCT/EP01/09174 N 51. A new compound, a new process for preparing a compound, a new composition, a new use of a compound as claimed in any one of claims 1 to 30, a new non-therapeutic method of treatment, or a substance or composition for a new use in a method of treatment or prevention, substantially as herein described.AMENDED SHEET
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