CA2566210C - Oxo-substituted cyclohexyl-1,4-diamine derivatives - Google Patents
Oxo-substituted cyclohexyl-1,4-diamine derivatives Download PDFInfo
- Publication number
- CA2566210C CA2566210C CA2566210A CA2566210A CA2566210C CA 2566210 C CA2566210 C CA 2566210C CA 2566210 A CA2566210 A CA 2566210A CA 2566210 A CA2566210 A CA 2566210A CA 2566210 C CA2566210 C CA 2566210C
- Authority
- CA
- Canada
- Prior art keywords
- unsubstituted
- singly
- multiply substituted
- cyclohexyl
- substituted
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
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- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 34
- 150000001875 compounds Chemical class 0.000 claims abstract description 17
- 238000000034 method Methods 0.000 claims abstract description 17
- 238000004519 manufacturing process Methods 0.000 claims abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 68
- 150000003839 salts Chemical class 0.000 claims description 53
- 229920006395 saturated elastomer Polymers 0.000 claims description 51
- -1 benzodioxolanyl Chemical group 0.000 claims description 42
- 239000000203 mixture Substances 0.000 claims description 41
- 125000003118 aryl group Chemical group 0.000 claims description 29
- 208000002193 Pain Diseases 0.000 claims description 28
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 25
- 125000001072 heteroaryl group Chemical group 0.000 claims description 21
- 125000001544 thienyl group Chemical group 0.000 claims description 20
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 19
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 18
- 239000002253 acid Substances 0.000 claims description 16
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 15
- 125000001041 indolyl group Chemical group 0.000 claims description 15
- 125000004076 pyridyl group Chemical group 0.000 claims description 15
- SHKWSBAVRQZYLE-UHFFFAOYSA-N 5-oxo-5-phenylpentanoic acid Chemical compound OC(=O)CCCC(=O)C1=CC=CC=C1 SHKWSBAVRQZYLE-UHFFFAOYSA-N 0.000 claims description 14
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 14
- 125000002541 furyl group Chemical group 0.000 claims description 14
- 238000002360 preparation method Methods 0.000 claims description 14
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 13
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 13
- 239000003814 drug Substances 0.000 claims description 13
- 125000001624 naphthyl group Chemical group 0.000 claims description 13
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 13
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 13
- 150000001768 cations Chemical class 0.000 claims description 12
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 12
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 9
- 208000007271 Substance Withdrawal Syndrome Diseases 0.000 claims description 9
- 230000003444 anaesthetic effect Effects 0.000 claims description 9
- 150000003254 radicals Chemical class 0.000 claims description 9
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- 150000007513 acids Chemical class 0.000 claims description 8
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 8
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 8
- IZOQMUVIDMLRDC-UHFFFAOYSA-N 5-aceto valeric acid Chemical compound CC(=O)CCCCC(O)=O IZOQMUVIDMLRDC-UHFFFAOYSA-N 0.000 claims description 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 7
- 230000008569 process Effects 0.000 claims description 7
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 6
- 125000002883 imidazolyl group Chemical group 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- OSAHCBHKCKPJGI-UHFFFAOYSA-N 7-keto-n-caprylic acid Chemical compound CC(=O)CCCCCC(O)=O OSAHCBHKCKPJGI-UHFFFAOYSA-N 0.000 claims description 5
- 208000009132 Catalepsy Diseases 0.000 claims description 5
- 206010012735 Diarrhoea Diseases 0.000 claims description 5
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- 206010047853 Waxy flexibility Diseases 0.000 claims description 5
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- 208000022531 anorexia Diseases 0.000 claims description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 5
- 206010061428 decreased appetite Diseases 0.000 claims description 5
- 208000035475 disorder Diseases 0.000 claims description 5
- 230000035619 diuresis Effects 0.000 claims description 5
- 229940079593 drug Drugs 0.000 claims description 5
- 206010015037 epilepsy Diseases 0.000 claims description 5
- 230000008991 intestinal motility Effects 0.000 claims description 5
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 5
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 5
- 230000037023 motor activity Effects 0.000 claims description 5
- 208000004296 neuralgia Diseases 0.000 claims description 5
- 230000004770 neurodegeneration Effects 0.000 claims description 5
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 5
- 230000002981 neuropathic effect Effects 0.000 claims description 5
- 208000021722 neuropathic pain Diseases 0.000 claims description 5
- 230000003957 neurotransmitter release Effects 0.000 claims description 5
- 230000001777 nootropic effect Effects 0.000 claims description 5
- 235000015816 nutrient absorption Nutrition 0.000 claims description 5
- 125000002971 oxazolyl group Chemical group 0.000 claims description 5
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 5
- 125000001425 triazolyl group Chemical group 0.000 claims description 5
- 208000019901 Anxiety disease Diseases 0.000 claims description 4
- 206010006895 Cachexia Diseases 0.000 claims description 4
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 4
- 206010020772 Hypertension Diseases 0.000 claims description 4
- 208000001953 Hypotension Diseases 0.000 claims description 4
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- 208000026139 Memory disease Diseases 0.000 claims description 4
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- 208000026251 Opioid-Related disease Diseases 0.000 claims description 4
- 208000003251 Pruritus Diseases 0.000 claims description 4
- 206010039966 Senile dementia Diseases 0.000 claims description 4
- 201000001880 Sexual dysfunction Diseases 0.000 claims description 4
- 208000009205 Tinnitus Diseases 0.000 claims description 4
- 230000002082 anti-convulsion Effects 0.000 claims description 4
- 230000036506 anxiety Effects 0.000 claims description 4
- 239000012964 benzotriazole Substances 0.000 claims description 4
- 238000011260 co-administration Methods 0.000 claims description 4
- 208000010877 cognitive disease Diseases 0.000 claims description 4
- VKIRRGRTJUUZHS-UHFFFAOYSA-N cyclohexane-1,4-diamine Chemical class NC1CCC(N)CC1 VKIRRGRTJUUZHS-UHFFFAOYSA-N 0.000 claims description 4
- 230000002950 deficient Effects 0.000 claims description 4
- 230000036543 hypotension Effects 0.000 claims description 4
- 230000001771 impaired effect Effects 0.000 claims description 4
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 4
- 201000003723 learning disability Diseases 0.000 claims description 4
- 230000003137 locomotive effect Effects 0.000 claims description 4
- 206010027599 migraine Diseases 0.000 claims description 4
- 239000003158 myorelaxant agent Substances 0.000 claims description 4
- 235000020824 obesity Nutrition 0.000 claims description 4
- 239000000014 opioid analgesic Substances 0.000 claims description 4
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 4
- 231100000872 sexual dysfunction Toxicity 0.000 claims description 4
- 125000003107 substituted aryl group Chemical group 0.000 claims description 4
- 208000011580 syndromic disease Diseases 0.000 claims description 4
- 231100000886 tinnitus Toxicity 0.000 claims description 4
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 3
- UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Natural products C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 3
- 239000000654 additive Substances 0.000 claims description 3
- 125000003354 benzotriazolyl group Chemical class N1N=NC2=C1C=CC=C2* 0.000 claims description 3
- 238000010168 coupling process Methods 0.000 claims description 3
- 238000005859 coupling reaction Methods 0.000 claims description 3
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 3
- SCHWABGSWZDREQ-UHFFFAOYSA-N n-[4-(dimethylamino)-4-phenylcyclohexyl]-5-oxo-5-phenylpentanamide;hydrochloride Chemical compound Cl.C1CC(N(C)C)(C=2C=CC=CC=2)CCC1NC(=O)CCCC(=O)C1=CC=CC=C1 SCHWABGSWZDREQ-UHFFFAOYSA-N 0.000 claims description 3
- 125000004306 triazinyl group Chemical group 0.000 claims description 3
- 125000006704 (C5-C6) cycloalkyl group Chemical group 0.000 claims description 2
- PDQRQJVPEFGVRK-UHFFFAOYSA-N 2,1,3-benzothiadiazole Chemical class C1=CC=CC2=NSN=C21 PDQRQJVPEFGVRK-UHFFFAOYSA-N 0.000 claims description 2
- 125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000004847 2-fluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000006179 2-methyl benzyl group Chemical group [H]C1=C([H])C(=C(C([H])=C1[H])C([H])([H])*)C([H])([H])[H] 0.000 claims description 2
- 125000003852 3-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])* 0.000 claims description 2
- 125000006284 3-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(F)=C1[H])C([H])([H])* 0.000 claims description 2
- 125000006180 3-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1[H])C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims description 2
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims description 2
- 125000006181 4-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 2
- XSCHRSMBECNVNS-UHFFFAOYSA-N benzopyrazine Natural products N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims description 2
- 125000000609 carbazolyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 2
- 239000003153 chemical reaction reagent Substances 0.000 claims description 2
- 230000008878 coupling Effects 0.000 claims description 2
- ZSBRUECKKQYGSW-UHFFFAOYSA-N n-[4-(dimethylamino)-4-(2-phenylethyl)cyclohexyl]-4-oxo-4-phenylbutanamide Chemical compound C1CC(NC(=O)CCC(=O)C=2C=CC=CC=2)CCC1(N(C)C)CCC1=CC=CC=C1 ZSBRUECKKQYGSW-UHFFFAOYSA-N 0.000 claims description 2
- OGWCCMHJLPUJGR-UHFFFAOYSA-N n-[4-(dimethylamino)-4-(2-phenylethyl)cyclohexyl]-5-oxo-5-phenylpentanamide Chemical compound C1CC(NC(=O)CCCC(=O)C=2C=CC=CC=2)CCC1(N(C)C)CCC1=CC=CC=C1 OGWCCMHJLPUJGR-UHFFFAOYSA-N 0.000 claims description 2
- KVBXMQNDDNSVRA-UHFFFAOYSA-N n-[4-(dimethylamino)-4-phenylcyclohexyl]-5-oxo-5-phenylpentanamide Chemical compound C1CC(N(C)C)(C=2C=CC=CC=2)CCC1NC(=O)CCCC(=O)C1=CC=CC=C1 KVBXMQNDDNSVRA-UHFFFAOYSA-N 0.000 claims description 2
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical class C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- 239000012453 solvate Substances 0.000 claims 17
- 208000007848 Alcoholism Diseases 0.000 claims 3
- 206010013654 Drug abuse Diseases 0.000 claims 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 3
- 206010001584 alcohol abuse Diseases 0.000 claims 3
- 208000025746 alcohol use disease Diseases 0.000 claims 3
- 201000009032 substance abuse Diseases 0.000 claims 3
- 208000011117 substance-related disease Diseases 0.000 claims 3
- VCUSYDGPHVVMDW-UHFFFAOYSA-N 4-(4-chlorophenyl)-n-[4-(dimethylamino)-4-phenylcyclohexyl]-4-oxobutanamide;hydrochloride Chemical compound Cl.C1CC(N(C)C)(C=2C=CC=CC=2)CCC1NC(=O)CCC(=O)C1=CC=C(Cl)C=C1 VCUSYDGPHVVMDW-UHFFFAOYSA-N 0.000 claims 2
- 230000004913 activation Effects 0.000 claims 2
- RCGCUAYSBSTLBF-UHFFFAOYSA-N 2-(3-acetyl-2,2-dimethylcyclobutyl)-n-[4-(dimethylamino)-4-[(4-methylphenyl)methyl]cyclohexyl]acetamide Chemical compound C1CC(NC(=O)CC2C(C(C(C)=O)C2)(C)C)CCC1(N(C)C)CC1=CC=C(C)C=C1 RCGCUAYSBSTLBF-UHFFFAOYSA-N 0.000 claims 1
- CGMPDBZLLYKFHT-UHFFFAOYSA-N 2-(3-acetyl-2,2-dimethylcyclobutyl)-n-[4-[(3-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]acetamide Chemical compound C1CC(NC(=O)CC2C(C(C(C)=O)C2)(C)C)CCC1(N(C)C)CC1=CC=CC(Cl)=C1 CGMPDBZLLYKFHT-UHFFFAOYSA-N 0.000 claims 1
- LBUGDZKZSTZSPU-UHFFFAOYSA-N 2-(3-benzoylphenyl)-n-(4-benzyl-4-pyrrolidin-1-ylcyclohexyl)propanamide Chemical compound C=1C=CC(C(=O)C=2C=CC=CC=2)=CC=1C(C)C(=O)NC(CC1)CCC1(N1CCCC1)CC1=CC=CC=C1 LBUGDZKZSTZSPU-UHFFFAOYSA-N 0.000 claims 1
- AGNBRSNIQDMPLT-UHFFFAOYSA-N 2-(3-benzoylphenyl)-n-(4-phenyl-4-piperidin-1-ylcyclohexyl)propanamide Chemical compound C=1C=CC(C(=O)C=2C=CC=CC=2)=CC=1C(C)C(=O)NC(CC1)CCC1(C=1C=CC=CC=1)N1CCCCC1 AGNBRSNIQDMPLT-UHFFFAOYSA-N 0.000 claims 1
- VYAKFVOLVPXKOM-UHFFFAOYSA-N 2-(3-benzoylphenyl)-n-[4-(dimethylamino)-4-[(2-methylphenyl)methyl]cyclohexyl]propanamide Chemical compound C=1C=CC(C(=O)C=2C=CC=CC=2)=CC=1C(C)C(=O)NC(CC1)CCC1(N(C)C)CC1=CC=CC=C1C VYAKFVOLVPXKOM-UHFFFAOYSA-N 0.000 claims 1
- NZXXHDHXPVJQQD-UHFFFAOYSA-N 2-(3-benzoylphenyl)-n-[4-(dimethylamino)-4-[(3-methylphenyl)methyl]cyclohexyl]propanamide Chemical compound C=1C=CC(C(=O)C=2C=CC=CC=2)=CC=1C(C)C(=O)NC(CC1)CCC1(N(C)C)CC1=CC=CC(C)=C1 NZXXHDHXPVJQQD-UHFFFAOYSA-N 0.000 claims 1
- YTOGHMWQACIDSK-UHFFFAOYSA-N 2-(3-benzoylphenyl)-n-[4-(dimethylamino)-4-[(4-methylphenyl)methyl]cyclohexyl]propanamide Chemical compound C=1C=CC(C(=O)C=2C=CC=CC=2)=CC=1C(C)C(=O)NC(CC1)CCC1(N(C)C)CC1=CC=C(C)C=C1 YTOGHMWQACIDSK-UHFFFAOYSA-N 0.000 claims 1
- VRMJHEJJIQXHJX-UHFFFAOYSA-N 2-(3-benzoylphenyl)-n-[4-[(3-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]propanamide Chemical compound C=1C=CC(C(=O)C=2C=CC=CC=2)=CC=1C(C)C(=O)NC(CC1)CCC1(N(C)C)CC1=CC=CC(Cl)=C1 VRMJHEJJIQXHJX-UHFFFAOYSA-N 0.000 claims 1
- QXDKUFHYJVHZBL-UHFFFAOYSA-N 2-(3-benzoylphenyl)-n-[4-benzyl-4-(dimethylamino)cyclohexyl]propanamide Chemical compound C=1C=CC(C(=O)C=2C=CC=CC=2)=CC=1C(C)C(=O)NC(CC1)CCC1(N(C)C)CC1=CC=CC=C1 QXDKUFHYJVHZBL-UHFFFAOYSA-N 0.000 claims 1
- BBIQSUZHBCIUSG-UHFFFAOYSA-N 2-[2-(1-benzofuran-3-yl)phenyl]-n-[4-(dimethylamino)-4-(2-phenylethyl)cyclohexyl]propanamide Chemical compound C=1C=CC=C(C=2C3=CC=CC=C3OC=2)C=1C(C)C(=O)NC(CC1)CCC1(N(C)C)CCC1=CC=CC=C1 BBIQSUZHBCIUSG-UHFFFAOYSA-N 0.000 claims 1
- KRGYCWGSJDRDPU-UHFFFAOYSA-N 2-[3-acetyl-2,2-bis(methylamino)cyclobutyl]-n-(4-benzyl-4-piperidin-1-ylcyclohexyl)acetamide Chemical compound C1C(C(C)=O)C(NC)(NC)C1CC(=O)NC1CCC(CC=2C=CC=CC=2)(N2CCCCC2)CC1 KRGYCWGSJDRDPU-UHFFFAOYSA-N 0.000 claims 1
- ZCLNIXLPZIHBQK-UHFFFAOYSA-N 2-[3-acetyl-2,2-bis(methylamino)cyclobutyl]-n-[4-(dimethylamino)-4-[(2-fluorophenyl)methyl]cyclohexyl]acetamide Chemical compound C1C(C(C)=O)C(NC)(NC)C1CC(=O)NC1CCC(CC=2C(=CC=CC=2)F)(N(C)C)CC1 ZCLNIXLPZIHBQK-UHFFFAOYSA-N 0.000 claims 1
- ZRHBADTWVNQLEW-UHFFFAOYSA-N 2-[3-acetyl-2,2-bis(methylamino)cyclobutyl]-n-[4-(dimethylamino)-4-[(3-methylphenyl)methyl]cyclohexyl]acetamide Chemical compound C1C(C(C)=O)C(NC)(NC)C1CC(=O)NC1CCC(CC=2C=C(C)C=CC=2)(N(C)C)CC1 ZRHBADTWVNQLEW-UHFFFAOYSA-N 0.000 claims 1
- GPJMBUQXRHPVHZ-UHFFFAOYSA-N 2-[3-acetyl-2,2-bis(methylamino)cyclobutyl]-n-[4-[(4-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]acetamide Chemical compound C1C(C(C)=O)C(NC)(NC)C1CC(=O)NC1CCC(CC=2C=CC(Cl)=CC=2)(N(C)C)CC1 GPJMBUQXRHPVHZ-UHFFFAOYSA-N 0.000 claims 1
- OAZNKACQOGTEHO-UHFFFAOYSA-N 2-[3-acetyl-2,2-bis(methylamino)cyclobutyl]-n-[4-benzyl-4-(dimethylamino)cyclohexyl]acetamide Chemical compound C1C(C(C)=O)C(NC)(NC)C1CC(=O)NC1CCC(CC=2C=CC=CC=2)(N(C)C)CC1 OAZNKACQOGTEHO-UHFFFAOYSA-N 0.000 claims 1
- MBJMGSOAYZIFRE-UHFFFAOYSA-N 4-(4-chlorophenyl)-n-[4-(dimethylamino)-4-[(4-methylphenyl)methyl]cyclohexyl]-4-oxobutanamide Chemical compound C1CC(NC(=O)CCC(=O)C=2C=CC(Cl)=CC=2)CCC1(N(C)C)CC1=CC=C(C)C=C1 MBJMGSOAYZIFRE-UHFFFAOYSA-N 0.000 claims 1
- OFXTXOFRRFIADV-UHFFFAOYSA-N 4-(4-chlorophenyl)-n-[4-[(2-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]-4-oxobutanamide Chemical compound C1CC(NC(=O)CCC(=O)C=2C=CC(Cl)=CC=2)CCC1(N(C)C)CC1=CC=CC=C1Cl OFXTXOFRRFIADV-UHFFFAOYSA-N 0.000 claims 1
- IHAGUOIXHBTIPF-UHFFFAOYSA-N 4-(4-fluorophenyl)-4-oxo-n-(4-phenyl-4-piperidin-1-ylcyclohexyl)butanamide Chemical compound C1=CC(F)=CC=C1C(=O)CCC(=O)NC1CCC(C=2C=CC=CC=2)(N2CCCCC2)CC1 IHAGUOIXHBTIPF-UHFFFAOYSA-N 0.000 claims 1
- LHFMEGFSMVFTKA-UHFFFAOYSA-N 4-oxo-4-phenyl-2-(4-phenyl-4-piperidin-1-ylcyclohexyl)butanamide Chemical compound C1CC(C=2C=CC=CC=2)(N2CCCCC2)CCC1C(C(=O)N)CC(=O)C1=CC=CC=C1 LHFMEGFSMVFTKA-UHFFFAOYSA-N 0.000 claims 1
- XZMUZXDJQRRMOL-UHFFFAOYSA-N 5-oxo-5-phenyl-n-(4-phenyl-4-piperidin-1-ylcyclohexyl)pentanamide Chemical compound C1CC(C=2C=CC=CC=2)(N2CCCCC2)CCC1NC(=O)CCCC(=O)C1=CC=CC=C1 XZMUZXDJQRRMOL-UHFFFAOYSA-N 0.000 claims 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims 1
- 230000000996 additive effect Effects 0.000 claims 1
- LUMJDZUCCQIHEG-UHFFFAOYSA-N n-(4-benzyl-4-piperidin-1-ylcyclohexyl)-4-(4-fluorophenyl)-4-oxobutanamide Chemical compound C1=CC(F)=CC=C1C(=O)CCC(=O)NC1CCC(CC=2C=CC=CC=2)(N2CCCCC2)CC1 LUMJDZUCCQIHEG-UHFFFAOYSA-N 0.000 claims 1
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102004023501A DE102004023501A1 (de) | 2004-05-10 | 2004-05-10 | Oxosubstituierte Cyclohexyl-1,4-diamin-Derivate |
| DE102004023501.5 | 2004-05-10 | ||
| PCT/EP2005/004907 WO2005110970A1 (de) | 2004-05-10 | 2005-05-06 | Oxosubstituierte cyclohexyl-1,4-diamin-derivate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2566210A1 CA2566210A1 (en) | 2005-11-24 |
| CA2566210C true CA2566210C (en) | 2013-08-27 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2566210A Expired - Fee Related CA2566210C (en) | 2004-05-10 | 2005-05-06 | Oxo-substituted cyclohexyl-1,4-diamine derivatives |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US7476763B2 (https=) |
| EP (1) | EP1751088B1 (https=) |
| JP (1) | JP4896009B2 (https=) |
| CA (1) | CA2566210C (https=) |
| DE (1) | DE102004023501A1 (https=) |
| WO (1) | WO2005110970A1 (https=) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2008110351A2 (en) * | 2007-03-15 | 2008-09-18 | Dompe' Pha.R.Ma S.P.A. | Use of (r) and (s)-2-aryl-propionic acid derivatives as antiseptic agents |
| AU2009228647B2 (en) | 2008-03-27 | 2013-07-04 | Grunenthal Gmbh | Substituted spirocyclic cyclohexane derivatives |
| JP5529843B2 (ja) | 2008-03-27 | 2014-06-25 | グリュネンタール・ゲゼルシャフト・ミト・ベシュレンクテル・ハフツング | 置換シクロヘキシルジアミン |
| EP2280941B1 (de) | 2008-03-27 | 2015-05-06 | Grünenthal GmbH | (hetero-)aryl-cyclohexan-derivate |
| ES2375543T3 (es) | 2008-03-27 | 2012-03-01 | Grünenthal GmbH | Derivados de espiro(5.5)undecano. |
| ES2464102T3 (es) | 2008-03-27 | 2014-05-30 | Grünenthal GmbH | Derivados de 4-aminociclohexano sustituidos |
| CN102046591B (zh) | 2008-03-27 | 2014-12-03 | 格吕伦塔尔有限公司 | 羟甲基环己胺 |
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| US5304479A (en) | 1991-12-06 | 1994-04-19 | Diagnostic Reagents, Inc. | Phencyclidine compounds and assays for its determination |
| CA2373855A1 (en) * | 1999-05-12 | 2000-11-23 | Solvay Pharmaceuticals B.V. | Method of treating psychotic disorders |
| FR2797874B1 (fr) * | 1999-08-27 | 2002-03-29 | Adir | Nouveaux derives de la pyridine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| GB0012240D0 (en) | 2000-05-19 | 2000-07-12 | Merck Sharp & Dohme | Therapeutic agents |
| ES2188344B1 (es) * | 2000-11-29 | 2004-09-16 | Laboratorios Vita, S.A. | Compuestos derivados de benzotiofeno, su procedimiento de obtencion y utilizacion de los mismos. |
| DE10123163A1 (de) * | 2001-05-09 | 2003-01-16 | Gruenenthal Gmbh | Substituierte Cyclohexan-1,4-diaminderivate |
| US6571525B2 (en) | 2001-08-01 | 2003-06-03 | J. David Coleman | Construction block |
| EP1458704A1 (en) * | 2001-12-21 | 2004-09-22 | H. Lundbeck A/S | Aminoindane derivatives as serotonin and norepinephrine uptake inhibitors |
| US6818772B2 (en) * | 2002-02-22 | 2004-11-16 | Abbott Laboratories | Antagonists of melanin concentrating hormone effects on the melanin concentrating hormone receptor |
| DE10252665A1 (de) | 2002-11-11 | 2004-06-03 | Grünenthal GmbH | 4-Aminomethyl-1-aryl-cyclohexylamin-Derivate |
| DE10252650A1 (de) * | 2002-11-11 | 2004-05-27 | Grünenthal GmbH | Cyclohexyl-Harnstoff-Derivate |
| DE102004023522A1 (de) * | 2004-05-10 | 2005-12-01 | Grünenthal GmbH | Substituierte Cyclohexyl-1,4-diamin-Derivate |
-
2004
- 2004-05-10 DE DE102004023501A patent/DE102004023501A1/de not_active Withdrawn
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2005
- 2005-05-06 WO PCT/EP2005/004907 patent/WO2005110970A1/de not_active Ceased
- 2005-05-06 EP EP05738450.5A patent/EP1751088B1/de not_active Expired - Lifetime
- 2005-05-06 CA CA2566210A patent/CA2566210C/en not_active Expired - Fee Related
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2006
- 2006-11-09 US US11/594,952 patent/US7476763B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US20070088034A1 (en) | 2007-04-19 |
| JP4896009B2 (ja) | 2012-03-14 |
| EP1751088B1 (de) | 2014-10-08 |
| EP1751088A1 (de) | 2007-02-14 |
| JP2007536317A (ja) | 2007-12-13 |
| DE102004023501A1 (de) | 2005-12-01 |
| US7476763B2 (en) | 2009-01-13 |
| CA2566210A1 (en) | 2005-11-24 |
| WO2005110970A1 (de) | 2005-11-24 |
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|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
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