AU2009228637B2 - (Hetero-)aryl cyclohexane derivatives - Google Patents
(Hetero-)aryl cyclohexane derivatives Download PDFInfo
- Publication number
- AU2009228637B2 AU2009228637B2 AU2009228637A AU2009228637A AU2009228637B2 AU 2009228637 B2 AU2009228637 B2 AU 2009228637B2 AU 2009228637 A AU2009228637 A AU 2009228637A AU 2009228637 A AU2009228637 A AU 2009228637A AU 2009228637 B2 AU2009228637 B2 AU 2009228637B2
- Authority
- AU
- Australia
- Prior art keywords
- indol
- aliphatic
- methyl
- nhc
- dimethyl
- 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.)
- Ceased
Links
- -1 aryl cyclohexane derivatives Chemical class 0.000 title claims description 36
- 150000001875 compounds Chemical class 0.000 claims abstract description 167
- 229940079593 drug Drugs 0.000 claims abstract description 28
- 239000003814 drug Substances 0.000 claims abstract description 28
- 238000000034 method Methods 0.000 claims abstract description 17
- 125000003118 aryl group Chemical group 0.000 claims description 80
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 claims description 68
- 239000000203 mixture Substances 0.000 claims description 68
- 125000001424 substituent group Chemical group 0.000 claims description 53
- 229920006395 saturated elastomer Polymers 0.000 claims description 36
- 125000001072 heteroaryl group Chemical group 0.000 claims description 31
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 30
- 125000001931 aliphatic group Chemical group 0.000 claims description 28
- 150000003839 salts Chemical class 0.000 claims description 28
- 125000005842 heteroatom Chemical group 0.000 claims description 23
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims description 19
- 208000002193 Pain Diseases 0.000 claims description 19
- 229910052757 nitrogen Inorganic materials 0.000 claims description 17
- 230000000694 effects Effects 0.000 claims description 14
- 125000000623 heterocyclic group Chemical group 0.000 claims description 12
- 229910052717 sulfur Inorganic materials 0.000 claims description 12
- 229940005483 opioid analgesics Drugs 0.000 claims description 11
- 230000036407 pain Effects 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 239000001301 oxygen Substances 0.000 claims description 10
- 238000006467 substitution reaction Methods 0.000 claims description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 230000003444 anaesthetic effect Effects 0.000 claims description 7
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- 206010012335 Dependence Diseases 0.000 claims description 6
- 208000007271 Substance Withdrawal Syndrome Diseases 0.000 claims description 6
- 239000013543 active substance Substances 0.000 claims description 6
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 6
- 239000012453 solvate Substances 0.000 claims description 6
- 208000004880 Polyuria Diseases 0.000 claims description 5
- 230000035619 diuresis Effects 0.000 claims description 5
- MYCMSFYLBALJSR-UHFFFAOYSA-N 1-benzyl-n,n-dimethyl-4,4-bis[3-(2-pyridin-4-ylethyl)-1h-indol-2-yl]cyclohexan-1-amine Chemical compound C1CC(C2=C(C3=CC=CC=C3N2)CCC=2C=CN=CC=2)(C2=C(C3=CC=CC=C3N2)CCC=2C=CN=CC=2)CCC1(N(C)C)CC1=CC=CC=C1 MYCMSFYLBALJSR-UHFFFAOYSA-N 0.000 claims description 4
- IKMCGLBRZOQHPZ-UHFFFAOYSA-N 1-butyl-4,4-bis(5-fluoro-3-methyl-1h-indol-2-yl)-n,n-dimethylcyclohexan-1-amine Chemical compound C1CC(CCCC)(N(C)C)CCC1(C1=C(C2=CC(F)=CC=C2N1)C)C1=C(C)C2=CC(F)=CC=C2N1 IKMCGLBRZOQHPZ-UHFFFAOYSA-N 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 239000005864 Sulphur Substances 0.000 claims description 4
- 239000002671 adjuvant Substances 0.000 claims description 4
- 125000004122 cyclic group Chemical group 0.000 claims description 4
- 125000003367 polycyclic group Chemical group 0.000 claims description 4
- LUBJCRLGQSPQNN-UHFFFAOYSA-N 1-Phenylurea Chemical compound NC(=O)NC1=CC=CC=C1 LUBJCRLGQSPQNN-UHFFFAOYSA-N 0.000 claims description 3
- KDQMUHLWMMPREV-UHFFFAOYSA-N 1-butyl-4,4-bis[3-[2-(3,4-dihydro-1h-isoquinolin-2-yl)ethyl]-1h-indol-2-yl]-n,n-dimethylcyclohexan-1-amine Chemical compound C1CC(CCCC)(N(C)C)CCC1(C1=C(C2=CC=CC=C2N1)CCN1CC2=CC=CC=C2CC1)C1=C(CCN2CC3=CC=CC=C3CC2)C2=CC=CC=C2N1 KDQMUHLWMMPREV-UHFFFAOYSA-N 0.000 claims description 3
- WSCQZQRYQBQGLM-UHFFFAOYSA-N 1-butyl-n,n-dimethyl-4,4-bis(3-methyl-1h-indol-2-yl)cyclohexan-1-amine Chemical compound C1CC(CCCC)(N(C)C)CCC1(C1=C(C2=CC=CC=C2N1)C)C1=C(C)C2=CC=CC=C2N1 WSCQZQRYQBQGLM-UHFFFAOYSA-N 0.000 claims description 3
- IZWDLGKGBTTWEK-UHFFFAOYSA-N 2-[2-[2-[4-butyl-4-(dimethylamino)-1-(3-methyl-1h-indol-2-yl)cyclohexyl]-1h-indol-3-yl]ethyl]isoindole-1,3-dione Chemical compound C1CC(CCCC)(N(C)C)CCC1(C1=C(C2=CC=CC=C2N1)CCN1C(C2=CC=CC=C2C1=O)=O)C1=C(C)C2=CC=CC=C2N1 IZWDLGKGBTTWEK-UHFFFAOYSA-N 0.000 claims description 3
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- 208000020401 Depressive disease Diseases 0.000 claims description 3
- 206010012735 Diarrhoea Diseases 0.000 claims description 3
- 208000030814 Eating disease Diseases 0.000 claims description 3
- 208000019454 Feeding and Eating disease Diseases 0.000 claims description 3
- 206010020772 Hypertension Diseases 0.000 claims description 3
- 208000001953 Hypotension Diseases 0.000 claims description 3
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- 206010046543 Urinary incontinence Diseases 0.000 claims description 3
- 239000000654 additive Substances 0.000 claims description 3
- 125000002723 alicyclic group Chemical group 0.000 claims description 3
- 208000022531 anorexia Diseases 0.000 claims description 3
- 230000002082 anti-convulsion Effects 0.000 claims description 3
- 230000036506 anxiety Effects 0.000 claims description 3
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- 229910052731 fluorine Inorganic materials 0.000 claims description 3
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- 230000008991 intestinal motility Effects 0.000 claims description 3
- 206010027599 migraine Diseases 0.000 claims description 3
- 239000003158 myorelaxant agent Substances 0.000 claims description 3
- 230000003957 neurotransmitter release Effects 0.000 claims description 3
- 230000001777 nootropic effect Effects 0.000 claims description 3
- 239000000014 opioid analgesic Substances 0.000 claims description 3
- 231100000872 sexual dysfunction Toxicity 0.000 claims description 3
- 208000011580 syndromic disease Diseases 0.000 claims description 3
- UIWRWOAJDRHUIH-UHFFFAOYSA-N 1-[2-[2-[4-butyl-4-(dimethylamino)-1-(3-methyl-1h-indol-2-yl)cyclohexyl]-1h-indol-3-yl]ethyl]-3-phenylurea Chemical compound C1CC(CCCC)(N(C)C)CCC1(C1=C(C2=CC=CC=C2N1)CCNC(=O)NC=1C=CC=CC=1)C1=C(C)C2=CC=CC=C2N1 UIWRWOAJDRHUIH-UHFFFAOYSA-N 0.000 claims description 2
- HIIRPBXAWXPDIH-UHFFFAOYSA-N 1-[2-[2-[4-butyl-4-(dimethylamino)-1-(5-fluoro-3-methyl-1h-indol-2-yl)cyclohexyl]-1h-indol-3-yl]ethyl]-3-phenylurea Chemical compound C1CC(CCCC)(N(C)C)CCC1(C1=C(C2=CC=CC=C2N1)CCNC(=O)NC=1C=CC=CC=1)C1=C(C)C2=CC(F)=CC=C2N1 HIIRPBXAWXPDIH-UHFFFAOYSA-N 0.000 claims description 2
- YFXBMXXXKCCOIV-UHFFFAOYSA-N 1-butyl-4,4-bis(1,3-dimethylindol-2-yl)-n,n-dimethylcyclohexan-1-amine Chemical compound C1CC(CCCC)(N(C)C)CCC1(C=1N(C2=CC=CC=C2C=1C)C)C1=C(C)C2=CC=CC=C2N1C YFXBMXXXKCCOIV-UHFFFAOYSA-N 0.000 claims description 2
- APIOHNCKCJAMAP-UHFFFAOYSA-N 1-butyl-n,n-dimethyl-4,4-bis[3-methyl-5-(trifluoromethyl)-1h-indol-2-yl]cyclohexan-1-amine;2-hydroxypropane-1,2,3-tricarboxylic acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O.C1CC(CCCC)(N(C)C)CCC1(C1=C(C2=CC(=CC=C2N1)C(F)(F)F)C)C1=C(C)C2=CC(C(F)(F)F)=CC=C2N1 APIOHNCKCJAMAP-UHFFFAOYSA-N 0.000 claims description 2
- CBISQFFYOFELJO-UHFFFAOYSA-N 2-[4-butyl-1-[3-(2-pyridin-4-ylethyl)-1h-indol-2-yl]-4-pyrrolidin-1-ylcyclohexyl]-3-(2-pyridin-4-ylethyl)-1h-indole Chemical compound C1CC(CCCC)(N2CCCC2)CCC1(C1=C(C2=CC=CC=C2N1)CCC=1C=CN=CC=1)C=1NC2=CC=CC=C2C=1CCC1=CC=NC=C1 CBISQFFYOFELJO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- IPOCNSUALLUPCK-UHFFFAOYSA-N n,n-dimethyl-4,4-bis[3-(2-pyridin-4-ylethyl)-1h-indol-2-yl]-1-thiophen-2-ylcyclohexan-1-amine Chemical compound C1CC(N(C)C)(C=2SC=CC=2)CCC1(C1=C(C2=CC=CC=C2N1)CCC=1C=CN=CC=1)C=1NC2=CC=CC=C2C=1CCC1=CC=NC=C1 IPOCNSUALLUPCK-UHFFFAOYSA-N 0.000 claims description 2
- BIUVCUNDWHNGFO-UHFFFAOYSA-N n-[2-[2-[4-butyl-4-(dimethylamino)-1-(3-methyl-1h-indol-2-yl)cyclohexyl]-1h-indol-3-yl]ethyl]cyclopentanesulfonamide Chemical compound C1CC(CCCC)(N(C)C)CCC1(C1=C(C2=CC=CC=C2N1)CCNS(=O)(=O)C1CCCC1)C1=C(C)C2=CC=CC=C2N1 BIUVCUNDWHNGFO-UHFFFAOYSA-N 0.000 claims description 2
- 230000004770 neurodegeneration Effects 0.000 claims description 2
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 2
- LKTYBGSDBHRPMR-UHFFFAOYSA-N 1-butyl-n,n-dimethyl-4,4-bis[3-(2-pyridin-4-ylethyl)-1h-indol-2-yl]cyclohexan-1-amine Chemical compound C1CC(CCCC)(N(C)C)CCC1(C1=C(C2=CC=CC=C2N1)CCC=1C=CN=CC=1)C1=C(CCC=2C=CN=CC=2)C2=CC=CC=C2N1 LKTYBGSDBHRPMR-UHFFFAOYSA-N 0.000 claims 1
- BTWGTJPUJWBWPE-UHFFFAOYSA-N 2-[2-[2-[4-butyl-4-(dimethylamino)-1-[3-[2-(1,3-dioxoisoindol-2-yl)ethyl]-1h-indol-2-yl]cyclohexyl]-1h-indol-3-yl]ethyl]isoindole-1,3-dione Chemical compound C1CC(CCCC)(N(C)C)CCC1(C1=C(C2=CC=CC=C2N1)CCN1C(C2=CC=CC=C2C1=O)=O)C1=C(CCN2C(C3=CC=CC=C3C2=O)=O)C2=CC=CC=C2N1 BTWGTJPUJWBWPE-UHFFFAOYSA-N 0.000 claims 1
- HUZILLSKENSLEU-UHFFFAOYSA-N 4-(1,3-benzodioxol-5-yl)-n,n-dimethyl-4-(3-methyl-1h-indol-2-yl)-1-phenylcyclohexan-1-amine Chemical compound C1CC(C=2C=C3OCOC3=CC=2)(C2=C(C3=CC=CC=C3N2)C)CCC1(N(C)C)C1=CC=CC=C1 HUZILLSKENSLEU-UHFFFAOYSA-N 0.000 claims 1
- FIQQPFFLTHVIBR-UHFFFAOYSA-N 4-(4-methoxyphenyl)-n,n-dimethyl-4-(3-methyl-1h-indol-2-yl)-1-phenylcyclohexan-1-amine Chemical compound C1=CC(OC)=CC=C1C1(C2=C(C3=CC=CC=C3N2)C)CCC(C=2C=CC=CC=2)(N(C)C)CC1 FIQQPFFLTHVIBR-UHFFFAOYSA-N 0.000 claims 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims 1
- WZNNQOWCJYPQPU-UHFFFAOYSA-N [2-[2-[4-butyl-4-(dimethylamino)-1-(5-fluoro-3-methyl-1h-indol-2-yl)cyclohexyl]-1h-indol-3-yl]-2-phenylethyl] carbamate Chemical compound C1CC(CCCC)(N(C)C)CCC1(C1=C(C2=CC=CC=C2N1)C(COC(N)=O)C=1C=CC=CC=1)C1=C(C)C2=CC(F)=CC=C2N1 WZNNQOWCJYPQPU-UHFFFAOYSA-N 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- CAMHUNYKDAFKQJ-UHFFFAOYSA-N n,n-dimethyl-4,4-bis(3-methyl-1h-indol-2-yl)-1-phenylcyclohexan-1-amine;2-hydroxypropane-1,2,3-tricarboxylic acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O.C1CC(C2=C(C3=CC=CC=C3N2)C)(C2=C(C3=CC=CC=C3N2)C)CCC1(N(C)C)C1=CC=CC=C1 CAMHUNYKDAFKQJ-UHFFFAOYSA-N 0.000 claims 1
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- UUEYCHLWAOBOHG-UHFFFAOYSA-N 3-(2-pyridin-4-ylethyl)-1h-indole Chemical compound C=1NC2=CC=CC=C2C=1CCC1=CC=NC=C1 UUEYCHLWAOBOHG-UHFFFAOYSA-N 0.000 description 5
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- 238000004848 nephelometry Methods 0.000 description 1
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- 239000008363 phosphate buffer Substances 0.000 description 1
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- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
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- 235000020357 syrup Nutrition 0.000 description 1
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- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 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
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- UWYZHKAOTLEWKK-UHFFFAOYSA-N tetrahydro-isoquinoline Natural products C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 description 1
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- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/08—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing alicyclic rings
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Neurology (AREA)
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- Addiction (AREA)
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- Cardiology (AREA)
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- Hematology (AREA)
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- Heart & Thoracic Surgery (AREA)
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- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Dermatology (AREA)
- Gynecology & Obstetrics (AREA)
- Endocrinology (AREA)
- Obesity (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP08005797 | 2008-03-27 | ||
| EP08005797.9 | 2008-03-27 | ||
| PCT/EP2009/002172 WO2009118163A1 (de) | 2008-03-27 | 2009-03-25 | (hetero-)aryl-cyclohexan-derivate |
Publications (2)
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| AU2009228637A1 AU2009228637A1 (en) | 2009-10-01 |
| AU2009228637B2 true AU2009228637B2 (en) | 2013-12-19 |
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|---|---|---|---|
| AU2009228637A Ceased AU2009228637B2 (en) | 2008-03-27 | 2009-03-25 | (Hetero-)aryl cyclohexane derivatives |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US7977370B2 (enExample) |
| EP (1) | EP2280941B1 (enExample) |
| JP (1) | JP5650637B2 (enExample) |
| CN (1) | CN102046597B (enExample) |
| AR (1) | AR071066A1 (enExample) |
| AU (1) | AU2009228637B2 (enExample) |
| CA (1) | CA2718209A1 (enExample) |
| CL (1) | CL2009000733A1 (enExample) |
| ES (1) | ES2544488T3 (enExample) |
| HU (1) | HUE026184T2 (enExample) |
| IL (1) | IL208137A (enExample) |
| MX (1) | MX2010010446A (enExample) |
| PE (1) | PE20091657A1 (enExample) |
| PL (1) | PL2280941T3 (enExample) |
| RU (1) | RU2502733C2 (enExample) |
| WO (1) | WO2009118163A1 (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8288430B2 (en) * | 2008-03-27 | 2012-10-16 | Grunenthal Gmbh | Spiro(5.5)undecane derivatives |
| RU2532545C2 (ru) | 2008-03-27 | 2014-11-10 | Грюненталь Гмбх | Замещенные производные 4-аминоциклогексана |
| TWI450899B (zh) | 2008-03-27 | 2014-09-01 | 被取代之螺環環已烷衍生物 | |
| SI2271613T1 (sl) | 2008-03-27 | 2014-08-29 | Grunenthal Gmbh | Hidroksimetilcikloheksilamini |
| CA2719743A1 (en) | 2008-03-27 | 2009-10-01 | Gruenenthal Gmbh | Substituted cyclohexyldiamines |
| AR071066A1 (es) | 2008-03-27 | 2010-05-26 | Gruenenthal Chemie | Derivados de (hetero) aril-ciclohexano |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4239780A (en) * | 1979-10-11 | 1980-12-16 | The Upjohn Company | Phospholipase A2 inhibition |
| WO2000025770A1 (en) * | 1998-10-30 | 2000-05-11 | Merck & Co., Inc. | Carbocyclic potassium channel inhibitors |
| WO2001074844A2 (en) * | 2000-04-04 | 2001-10-11 | F. Hoffmann-La Roche Ag | Selective linear peptides with melanocortin-4 receptor (mc4-r) agonist activity |
| WO2002018437A2 (en) * | 2000-08-30 | 2002-03-07 | F. Hoffmann-La Roche Ag | Cyclic peptides having melanocortin-4 receptor agonist activity |
| WO2008009416A1 (de) * | 2006-07-18 | 2008-01-24 | Grünenthal GmbH | Spirocyclische azaindol-derivate |
| WO2008009415A2 (de) * | 2006-07-18 | 2008-01-24 | Grünenthal GmbH | 4-heteroaryl-substituierte 1-aminocyclohexan-1- und cyclohexen-1-derivate mit wirkung auf das opiod rezeptor system |
| WO2008077597A1 (en) * | 2006-12-22 | 2008-07-03 | Novartis Ag | 1-aminomethyl- l- phenyl- cyclohexane derivatives as ddp-iv inhibitors |
Family Cites Families (40)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4065573A (en) | 1976-06-03 | 1977-12-27 | The Upjohn Company | 4-Amino-4-phenylcyclohexanone ketal compositions and process of use |
| US4115589A (en) | 1977-05-17 | 1978-09-19 | The Upjohn Company | Compounds, compositions and method of use |
| US4366172A (en) | 1977-09-29 | 1982-12-28 | The Upjohn Company | 4-Amino-cyclohexanols, their pharmaceutical compositions and methods of use |
| DE19830105C1 (de) * | 1998-07-06 | 2000-02-17 | Gruenenthal Gmbh | Acridinderivate |
| GB0012240D0 (en) | 2000-05-19 | 2000-07-12 | Merck Sharp & Dohme | Therapeutic agents |
| DE10123163A1 (de) | 2001-05-09 | 2003-01-16 | Gruenenthal Gmbh | Substituierte Cyclohexan-1,4-diaminderivate |
| PE20030320A1 (es) * | 2001-07-17 | 2003-04-03 | Gruenenthal Chemie | Derivados sustituidos de 4-aminociclohexanol |
| DE10135636A1 (de) | 2001-07-17 | 2003-02-06 | Gruenenthal Gmbh | Substituierte 4-Aminocyclohexanole |
| WO2003008731A1 (en) | 2001-07-18 | 2003-01-30 | Dipiemme Dies And Plastic Machinery S.R.L. | A corrugated/undulated sheet having protuberances in the grooves defined by the corrugations; process and apparatus |
| DE10213051B4 (de) | 2002-03-23 | 2013-03-07 | Grünenthal GmbH | Substituierte 4-Aminocyclohexanole |
| DE10252667A1 (de) | 2002-11-11 | 2004-05-27 | Grünenthal GmbH | Spirocyclische Cyclohexan-Derivate |
| DE10252666A1 (de) | 2002-11-11 | 2004-08-05 | Grünenthal GmbH | N-Piperidyl-cyclohexan-Derivate |
| 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 |
| AU2003287995A1 (en) | 2002-11-12 | 2004-06-03 | Grunenthal Gmbh | 4-alkyl/4-alkenyl/4-alkynyl methyl/-1-arylcyclohexylamine derivatives |
| AU2003296564A1 (en) | 2002-11-12 | 2004-06-03 | Grunenthal Gmbh | 4-hydroxymethyl-1-aryl-cyclohexylamine derivatives |
| DE10360793A1 (de) | 2003-12-23 | 2005-07-28 | Grünenthal GmbH | Spirocyclische Cyclohexan-Derivate |
| DE10360792A1 (de) | 2003-12-23 | 2005-07-28 | Grünenthal GmbH | Spirocyclische Cyclohexan-Derivate |
| DE102004023508A1 (de) | 2004-05-10 | 2005-12-08 | Grünenthal GmbH | Säurederivate substituierter Cyclohexyl-1,4-diamine |
| DE102004023632A1 (de) | 2004-05-10 | 2005-12-08 | Grünenthal GmbH | Substituierte Cyclohexylcarbonsäure-Derivate |
| DE102004023522A1 (de) | 2004-05-10 | 2005-12-01 | Grünenthal GmbH | Substituierte Cyclohexyl-1,4-diamin-Derivate |
| DE102004023501A1 (de) | 2004-05-10 | 2005-12-01 | Grünenthal GmbH | Oxosubstituierte Cyclohexyl-1,4-diamin-Derivate |
| DE102004023635A1 (de) | 2004-05-10 | 2006-04-13 | Grünenthal GmbH | Heteroarylsubstituierte Cyclohexyl-1,4-diamin-Derivate |
| DE102004023506A1 (de) | 2004-05-10 | 2005-12-01 | Grünenthal GmbH | Kettenverlängerte substituierte Cyclohexyl-1,4-diamin-Derivate |
| DE102004023507A1 (de) | 2004-05-10 | 2005-12-01 | Grünenthal GmbH | Substituierte Cyclohexylessigsäure-Derivate |
| DE102004039382A1 (de) | 2004-08-13 | 2006-02-23 | Grünenthal GmbH | Spirocyclische Cyclohexan-Derivate |
| DE102005016460A1 (de) | 2005-04-11 | 2006-10-19 | Grünenthal GmbH | Spriocyclische Cyclohexanderivate zur Behandlung von Substanzabhängigkeit |
| DE102005061428A1 (de) | 2005-12-22 | 2007-08-16 | Grünenthal GmbH | Substituierte Cyclohexylmethyl-Derivate |
| DE102005061429A1 (de) | 2005-12-22 | 2007-06-28 | Grünenthal GmbH | Substituierte Oxazol-Derivate |
| DE102005061427A1 (de) | 2005-12-22 | 2007-06-28 | Grünenthal GmbH | Substituierte Oxadiazol-Derivate |
| DE102005061430A1 (de) | 2005-12-22 | 2007-07-05 | Grünenthal GmbH | Substituierte Imidazolin-Derivate |
| DE102006019597A1 (de) | 2006-04-27 | 2007-10-31 | Grünenthal GmbH | Spirocyclische Cyclohexan-Derivate |
| FR2902695B1 (fr) * | 2006-06-26 | 2009-11-20 | Packaging Partner | Etiquette d'information inviolable |
| WO2009011813A2 (en) | 2007-07-13 | 2009-01-22 | Tinnerman Palnut Engineered Products | Seam clip having thermal barrier |
| RU2532545C2 (ru) | 2008-03-27 | 2014-11-10 | Грюненталь Гмбх | Замещенные производные 4-аминоциклогексана |
| AR071066A1 (es) | 2008-03-27 | 2010-05-26 | Gruenenthal Chemie | Derivados de (hetero) aril-ciclohexano |
| CA2719743A1 (en) | 2008-03-27 | 2009-10-01 | Gruenenthal Gmbh | Substituted cyclohexyldiamines |
| SI2271613T1 (sl) | 2008-03-27 | 2014-08-29 | Grunenthal Gmbh | Hidroksimetilcikloheksilamini |
| TWI450899B (zh) | 2008-03-27 | 2014-09-01 | 被取代之螺環環已烷衍生物 | |
| US8288430B2 (en) | 2008-03-27 | 2012-10-16 | Grunenthal Gmbh | Spiro(5.5)undecane derivatives |
-
2009
- 2009-03-25 AR ARP090101056A patent/AR071066A1/es unknown
- 2009-03-25 CL CL2009000733A patent/CL2009000733A1/es unknown
- 2009-03-25 HU HUE09725704A patent/HUE026184T2/en unknown
- 2009-03-25 MX MX2010010446A patent/MX2010010446A/es active IP Right Grant
- 2009-03-25 EP EP20090725704 patent/EP2280941B1/de not_active Not-in-force
- 2009-03-25 CA CA2718209A patent/CA2718209A1/en not_active Abandoned
- 2009-03-25 PE PE2009000444A patent/PE20091657A1/es not_active Application Discontinuation
- 2009-03-25 US US12/410,692 patent/US7977370B2/en not_active Expired - Fee Related
- 2009-03-25 CN CN2009801201880A patent/CN102046597B/zh not_active Expired - Fee Related
- 2009-03-25 RU RU2010143451/04A patent/RU2502733C2/ru not_active IP Right Cessation
- 2009-03-25 AU AU2009228637A patent/AU2009228637B2/en not_active Ceased
- 2009-03-25 PL PL09725704T patent/PL2280941T3/pl unknown
- 2009-03-25 WO PCT/EP2009/002172 patent/WO2009118163A1/de not_active Ceased
- 2009-03-25 ES ES09725704.2T patent/ES2544488T3/es active Active
- 2009-03-25 JP JP2011501139A patent/JP5650637B2/ja not_active Expired - Fee Related
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Also Published As
| Publication number | Publication date |
|---|---|
| MX2010010446A (es) | 2010-11-05 |
| CN102046597A (zh) | 2011-05-04 |
| IL208137A0 (en) | 2010-12-30 |
| CA2718209A1 (en) | 2009-10-01 |
| CL2009000733A1 (es) | 2009-05-15 |
| RU2010143451A (ru) | 2012-05-10 |
| PE20091657A1 (es) | 2009-11-07 |
| AR071066A1 (es) | 2010-05-26 |
| EP2280941A1 (de) | 2011-02-09 |
| CN102046597B (zh) | 2013-09-11 |
| WO2009118163A1 (de) | 2009-10-01 |
| PL2280941T3 (pl) | 2015-10-30 |
| HUE026184T2 (en) | 2016-05-30 |
| HK1153744A1 (zh) | 2012-04-05 |
| US20090247573A1 (en) | 2009-10-01 |
| EP2280941B1 (de) | 2015-05-06 |
| ES2544488T3 (es) | 2015-08-31 |
| RU2502733C2 (ru) | 2013-12-27 |
| JP2011515429A (ja) | 2011-05-19 |
| US7977370B2 (en) | 2011-07-12 |
| IL208137A (en) | 2015-10-29 |
| JP5650637B2 (ja) | 2015-01-07 |
| AU2009228637A1 (en) | 2009-10-01 |
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