CA2692513A1 - Indane-amine derivatives, their preparation and use as medicaments - Google Patents

Indane-amine derivatives, their preparation and use as medicaments Download PDF

Info

Publication number: CA2692513A1
Authority: CA; Canada
Prior art keywords: substituted; mono; optionally; branched; linear
Prior art date: 2007-07-05
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.): Abandoned

Application number

CA 2692513

Other languages

English (en)

French (fr)

Inventor

Monica Garcia-Lopez

Antoni Torrens-Jover

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Esteve Pharmaceuticals SA

Original Assignee

Monica Garcia-Lopez

Antoni Torrens-Jover

Laboratorios Del Dr. Esteve, S.A.

Priority date (The priority date 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 date listed.)

2007-07-05

Filing date

2008-07-04

Publication date

2009-01-08

2008-07-04 Application filed by Monica Garcia-Lopez, Antoni Torrens-Jover, Laboratorios Del Dr. Esteve, S.A. filed Critical Monica Garcia-Lopez

2009-01-08 Publication of CA2692513A1 publication Critical patent/CA2692513A1/en

Status Abandoned legal-status Critical Current

Links

238000002360 preparation method Methods 0.000 title claims abstract description 27
239000003814 drug Substances 0.000 title claims abstract description 22
XJEVHMGJSYVQBQ-UHFFFAOYSA-N 2,3-dihydro-1h-inden-1-amine Chemical class C1=CC=C2C(N)CCC2=C1 XJEVHMGJSYVQBQ-UHFFFAOYSA-N 0.000 title claims abstract description 6
150000001875 compounds Chemical class 0.000 claims abstract description 179
238000000034 method Methods 0.000 claims abstract description 56
238000011282 treatment Methods 0.000 claims abstract description 11
-1 aliphatic radical Chemical class 0.000 claims description 176
229920006395 saturated elastomer Polymers 0.000 claims description 121
229910052801 chlorine Inorganic materials 0.000 claims description 91
229910052731 fluorine Inorganic materials 0.000 claims description 91
229910052794 bromium Inorganic materials 0.000 claims description 90
229910052740 iodine Inorganic materials 0.000 claims description 87
229910052739 hydrogen Inorganic materials 0.000 claims description 71
239000001257 hydrogen Substances 0.000 claims description 63
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 53
150000003839 salts Chemical class 0.000 claims description 51
229910052736 halogen Inorganic materials 0.000 claims description 47
150000002367 halogens Chemical class 0.000 claims description 46
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 39
MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 31
239000000203 mixture Substances 0.000 claims description 28
230000008569 process Effects 0.000 claims description 28
239000012453 solvate Substances 0.000 claims description 24
125000002950 monocyclic group Chemical class 0.000 claims description 20
125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 17
125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 17
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 17
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 17
125000004433 nitrogen atom Chemical group N* 0.000 claims description 16
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 15
238000006243 chemical reaction Methods 0.000 claims description 15
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 15
239000012429 reaction media Substances 0.000 claims description 15
QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims description 14
239000002253 acid Substances 0.000 claims description 13
239000003054 catalyst Substances 0.000 claims description 13
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 13
229910052760 oxygen Inorganic materials 0.000 claims description 13
229910052717 sulfur Inorganic materials 0.000 claims description 12
238000002156 mixing Methods 0.000 claims description 10
208000002193 Pain Diseases 0.000 claims description 9
201000010099 disease Diseases 0.000 claims description 9
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 9
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
239000003446 ligand Substances 0.000 claims description 9
IHSBTIJZJJXCJQ-MRXNPFEDSA-N (1r)-n,n-dimethyl-6-(1,3,5-trimethylpyrazol-4-yl)-2,3-dihydro-1h-inden-1-amine Chemical compound C([C@H](C1=C2)N(C)C)CC1=CC=C2C=1C(C)=NN(C)C=1C IHSBTIJZJJXCJQ-MRXNPFEDSA-N 0.000 claims description 8
208000019695 Migraine disease Diseases 0.000 claims description 8
208000002551 irritable bowel syndrome Diseases 0.000 claims description 8
206010027599 migraine Diseases 0.000 claims description 8
IHSBTIJZJJXCJQ-UHFFFAOYSA-N n,n-dimethyl-6-(1,3,5-trimethylpyrazol-4-yl)-2,3-dihydro-1h-inden-1-amine Chemical compound C1=C2C(N(C)C)CCC2=CC=C1C=1C(C)=NN(C)C=1C IHSBTIJZJJXCJQ-UHFFFAOYSA-N 0.000 claims description 7
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 description 6
208000004454 Hyperalgesia Diseases 0.000 claims description 6
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical group [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 6
208000004296 neuralgia Diseases 0.000 claims description 6
208000021722 neuropathic pain Diseases 0.000 claims description 6
208000019888 Circadian rhythm sleep disease Diseases 0.000 claims description 4
208000001456 Jet Lag Syndrome Diseases 0.000 claims description 4
206010046543 Urinary incontinence Diseases 0.000 claims description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
150000007529 inorganic bases Chemical class 0.000 claims description 4
208000033915 jet lag type circadian rhythm sleep disease Diseases 0.000 claims description 4
230000001404 mediated effect Effects 0.000 claims description 4
150000007530 organic bases Chemical class 0.000 claims description 4
208000012672 seasonal affective disease Diseases 0.000 claims description 4
208000019116 sleep disease Diseases 0.000 claims description 4
208000011580 syndromic disease Diseases 0.000 claims description 4
208000019901 Anxiety disease Diseases 0.000 claims description 3
206010058019 Cancer Pain Diseases 0.000 claims description 3
208000024172 Cardiovascular disease Diseases 0.000 claims description 3
208000000094 Chronic Pain Diseases 0.000 claims description 3
208000035154 Hyperesthesia Diseases 0.000 claims description 3
206010020772 Hypertension Diseases 0.000 claims description 3
208000022559 Inflammatory bowel disease Diseases 0.000 claims description 3
208000026139 Memory disease Diseases 0.000 claims description 3
208000028017 Psychotic disease Diseases 0.000 claims description 3
208000005298 acute pain Diseases 0.000 claims description 3
239000002671 adjuvant Substances 0.000 claims description 3
206010053552 allodynia Diseases 0.000 claims description 3
230000036506 anxiety Effects 0.000 claims description 3
230000019771 cognition Effects 0.000 claims description 3
208000010877 cognitive disease Diseases 0.000 claims description 3
230000000302 ischemic effect Effects 0.000 claims description 3
230000004770 neurodegeneration Effects 0.000 claims description 3
229910052763 palladium Inorganic materials 0.000 claims description 3
201000000980 schizophrenia Diseases 0.000 claims description 3
208000020685 sleep-wake disease Diseases 0.000 claims description 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
208000009935 visceral pain Diseases 0.000 claims description 3
CMJAEJACNGQGQB-OAHLLOKOSA-N (1r)-n-methyl-6-(1,3,5-trimethylpyrazol-4-yl)-2,3-dihydro-1h-inden-1-amine Chemical compound C([C@H](C1=C2)NC)CC1=CC=C2C=1C(C)=NN(C)C=1C CMJAEJACNGQGQB-OAHLLOKOSA-N 0.000 claims description 2
CMJAEJACNGQGQB-HNNXBMFYSA-N (1s)-n-methyl-6-(1,3,5-trimethylpyrazol-4-yl)-2,3-dihydro-1h-inden-1-amine Chemical compound C([C@@H](C1=C2)NC)CC1=CC=C2C=1C(C)=NN(C)C=1C CMJAEJACNGQGQB-HNNXBMFYSA-N 0.000 claims description 2
VLEAYEDIGNNUNW-UHFFFAOYSA-N 6-(1,3,5-trimethylpyrazol-4-yl)-2,3-dihydro-1h-inden-1-amine Chemical compound CC1=NN(C)C(C)=C1C1=CC=C(CCC2N)C2=C1 VLEAYEDIGNNUNW-UHFFFAOYSA-N 0.000 claims description 2
LPGVMYMKZYZHEL-UHFFFAOYSA-N 6-(1-ethyl-3,5-dimethylpyrazol-4-yl)-n-methyl-2,3-dihydro-1h-inden-1-amine Chemical compound CCN1N=C(C)C(C=2C=C3C(NC)CCC3=CC=2)=C1C LPGVMYMKZYZHEL-UHFFFAOYSA-N 0.000 claims description 2
CKGDSJGCZOJIAU-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-n,n-dimethyl-2,3-dihydro-1h-inden-1-amine Chemical compound C1=C2C(N(C)C)CCC2=CC=C1C1=C(Cl)C=CC=C1Cl CKGDSJGCZOJIAU-UHFFFAOYSA-N 0.000 claims description 2
RKDSAENZICXMKO-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-n-methyl-2,3-dihydro-1h-inden-1-amine Chemical compound C1=C2C(NC)CCC2=CC=C1C1=C(Cl)C=CC=C1Cl RKDSAENZICXMKO-UHFFFAOYSA-N 0.000 claims description 2
CHAIPOURHRIZNF-UHFFFAOYSA-N 6-(2,6-difluorophenyl)-n,n-dimethyl-2,3-dihydro-1h-inden-1-amine Chemical compound C1=C2C(N(C)C)CCC2=CC=C1C1=C(F)C=CC=C1F CHAIPOURHRIZNF-UHFFFAOYSA-N 0.000 claims description 2
QXAJQTHHTMRURJ-UHFFFAOYSA-N 6-(2,6-difluorophenyl)-n-methyl-2,3-dihydro-1h-inden-1-amine Chemical compound C1=C2C(NC)CCC2=CC=C1C1=C(F)C=CC=C1F QXAJQTHHTMRURJ-UHFFFAOYSA-N 0.000 claims description 2
SUGYDDYCZCHNPF-UHFFFAOYSA-N 6-(2,6-dimethoxyphenyl)-n-methyl-2,3-dihydro-1h-inden-1-amine Chemical compound C1=C2C(NC)CCC2=CC=C1C1=C(OC)C=CC=C1OC SUGYDDYCZCHNPF-UHFFFAOYSA-N 0.000 claims description 2
JATZJNPVVYAZEG-UHFFFAOYSA-N 6-(2,6-dimethylphenyl)-n,n-dimethyl-2,3-dihydro-1h-inden-1-amine Chemical compound C1=C2C(N(C)C)CCC2=CC=C1C1=C(C)C=CC=C1C JATZJNPVVYAZEG-UHFFFAOYSA-N 0.000 claims description 2
HIPKHAZXPXHSED-UHFFFAOYSA-N 6-(2,6-dimethylphenyl)-n-methyl-2,3-dihydro-1h-inden-1-amine Chemical compound C1=C2C(NC)CCC2=CC=C1C1=C(C)C=CC=C1C HIPKHAZXPXHSED-UHFFFAOYSA-N 0.000 claims description 2
ZCXZUKWOSUVQPY-UHFFFAOYSA-N 6-(2-chloro-6-methoxyphenyl)-n,n-dimethyl-2,3-dihydro-1h-inden-1-amine Chemical compound COC1=CC=CC(Cl)=C1C1=CC=C(CCC2N(C)C)C2=C1 ZCXZUKWOSUVQPY-UHFFFAOYSA-N 0.000 claims description 2
FZWIKZGONKCEME-UHFFFAOYSA-N 6-(2-chloro-6-methoxyphenyl)-n-methyl-2,3-dihydro-1h-inden-1-amine Chemical compound C1=C2C(NC)CCC2=CC=C1C1=C(Cl)C=CC=C1OC FZWIKZGONKCEME-UHFFFAOYSA-N 0.000 claims description 2
JWLCDEUYMMJNNX-UHFFFAOYSA-N 6-(2-methoxyphenyl)-n-methyl-2,3-dihydro-1h-inden-1-amine Chemical compound C1=C2C(NC)CCC2=CC=C1C1=CC=CC=C1OC JWLCDEUYMMJNNX-UHFFFAOYSA-N 0.000 claims description 2
ZDEJJSKBRSXYRU-UHFFFAOYSA-N 6-(2-methoxypyridin-3-yl)-n-methyl-2,3-dihydro-1h-inden-1-amine Chemical compound C1=C2C(NC)CCC2=CC=C1C1=CC=CN=C1OC ZDEJJSKBRSXYRU-UHFFFAOYSA-N 0.000 claims description 2
DCODOSAMXPDUBW-UHFFFAOYSA-N 6-(3,5-dimethyl-1,2-oxazol-4-yl)-n,n-dimethyl-2,3-dihydro-1h-inden-1-amine Chemical compound C1=C2C(N(C)C)CCC2=CC=C1C=1C(C)=NOC=1C DCODOSAMXPDUBW-UHFFFAOYSA-N 0.000 claims description 2
KRCGZBLMQMIFMF-UHFFFAOYSA-N 6-(3,5-dimethyl-1,2-oxazol-4-yl)-n-methyl-2,3-dihydro-1h-inden-1-amine Chemical compound C1=C2C(NC)CCC2=CC=C1C=1C(C)=NOC=1C KRCGZBLMQMIFMF-UHFFFAOYSA-N 0.000 claims description 2
GUZKCLJPUXLBTE-UHFFFAOYSA-N 6-(3,5-dimethyl-1-propan-2-ylpyrazol-4-yl)-n,n-dimethyl-2,3-dihydro-1h-inden-1-amine Chemical compound CC(C)N1N=C(C)C(C=2C=C3C(N(C)C)CCC3=CC=2)=C1C GUZKCLJPUXLBTE-UHFFFAOYSA-N 0.000 claims description 2
PQNSALZBXCFIGU-UHFFFAOYSA-N 6-(3,5-dimethyl-1-propan-2-ylpyrazol-4-yl)-n-methyl-2,3-dihydro-1h-inden-1-amine Chemical compound C1=C2C(NC)CCC2=CC=C1C=1C(C)=NN(C(C)C)C=1C PQNSALZBXCFIGU-UHFFFAOYSA-N 0.000 claims description 2
LZTXPEUQOANFCH-UHFFFAOYSA-N 6-(3,5-dimethyl-1-propylpyrazol-4-yl)-n,n-dimethyl-2,3-dihydro-1h-inden-1-amine Chemical compound CCCN1N=C(C)C(C=2C=C3C(N(C)C)CCC3=CC=2)=C1C LZTXPEUQOANFCH-UHFFFAOYSA-N 0.000 claims description 2
GNENGMYMMMELAC-UHFFFAOYSA-N 6-(3,5-dimethyl-1-propylpyrazol-4-yl)-n-methyl-2,3-dihydro-1h-inden-1-amine Chemical compound CCCN1N=C(C)C(C=2C=C3C(NC)CCC3=CC=2)=C1C GNENGMYMMMELAC-UHFFFAOYSA-N 0.000 claims description 2
HXTUBSFEYJBQMB-UHFFFAOYSA-N 6-(3,5-dimethyl-1h-pyrazol-4-yl)-n,n-dimethyl-2,3-dihydro-1h-inden-1-amine Chemical compound C1=C2C(N(C)C)CCC2=CC=C1C=1C(C)=NNC=1C HXTUBSFEYJBQMB-UHFFFAOYSA-N 0.000 claims description 2
GXTLSVIFEHDOMC-UHFFFAOYSA-N 6-(3,5-dimethyl-1h-pyrazol-4-yl)-n-methyl-2,3-dihydro-1h-inden-1-amine Chemical compound C1=C2C(NC)CCC2=CC=C1C=1C(C)=NNC=1C GXTLSVIFEHDOMC-UHFFFAOYSA-N 0.000 claims description 2
GGJIPOJDSNMSMG-UHFFFAOYSA-N 6-[1-(methoxymethyl)-3,5-dimethylpyrazol-4-yl]-n,n-dimethyl-2,3-dihydro-1h-inden-1-amine Chemical compound COCN1N=C(C)C(C=2C=C3C(N(C)C)CCC3=CC=2)=C1C GGJIPOJDSNMSMG-UHFFFAOYSA-N 0.000 claims description 2
FVBURPCLODXARJ-UHFFFAOYSA-N 6-[1-(methoxymethyl)-3,5-dimethylpyrazol-4-yl]-n-methyl-2,3-dihydro-1h-inden-1-amine Chemical compound C1=C2C(NC)CCC2=CC=C1C=1C(C)=NN(COC)C=1C FVBURPCLODXARJ-UHFFFAOYSA-N 0.000 claims description 2
RZJNNNOPIJBABZ-UHFFFAOYSA-N 6-[2,6-bis(trifluoromethyl)phenyl]-n,n-dimethyl-2,3-dihydro-1h-inden-1-amine Chemical compound C1=C2C(N(C)C)CCC2=CC=C1C1=C(C(F)(F)F)C=CC=C1C(F)(F)F RZJNNNOPIJBABZ-UHFFFAOYSA-N 0.000 claims description 2
MWGWXWCRBQXUJS-UHFFFAOYSA-N 6-[2,6-bis(trifluoromethyl)phenyl]-n-methyl-2,3-dihydro-1h-inden-1-amine Chemical compound C1=C2C(NC)CCC2=CC=C1C1=C(C(F)(F)F)C=CC=C1C(F)(F)F MWGWXWCRBQXUJS-UHFFFAOYSA-N 0.000 claims description 2
ROCBXKRXYBYUJU-UHFFFAOYSA-N 6-[3,5-dimethyl-1-(2-methylpropyl)pyrazol-4-yl]-n,n-dimethyl-2,3-dihydro-1h-inden-1-amine Chemical compound CC(C)CN1N=C(C)C(C=2C=C3C(N(C)C)CCC3=CC=2)=C1C ROCBXKRXYBYUJU-UHFFFAOYSA-N 0.000 claims description 2
VDQZKQACTOLIBE-UHFFFAOYSA-N 6-[3,5-dimethyl-1-(2-methylpropyl)pyrazol-4-yl]-n-methyl-2,3-dihydro-1h-inden-1-amine Chemical compound C1=C2C(NC)CCC2=CC=C1C=1C(C)=NN(CC(C)C)C=1C VDQZKQACTOLIBE-UHFFFAOYSA-N 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims description 2
SRPOINZXVOEHTD-UHFFFAOYSA-N n,n-dimethyl-6-pyrrolidin-1-yl-2,3-dihydro-1h-inden-1-amine Chemical compound C1=C2C(N(C)C)CCC2=CC=C1N1CCCC1 SRPOINZXVOEHTD-UHFFFAOYSA-N 0.000 claims description 2
OSQYVQDDYPFRHH-UHFFFAOYSA-N n,n-dipropyl-6-(1,3,5-trimethylpyrazol-4-yl)-2,3-dihydro-1h-inden-1-amine Chemical compound C1=C2C(N(CCC)CCC)CCC2=CC=C1C=1C(C)=NN(C)C=1C OSQYVQDDYPFRHH-UHFFFAOYSA-N 0.000 claims description 2
CMJAEJACNGQGQB-UHFFFAOYSA-N n-methyl-6-(1,3,5-trimethylpyrazol-4-yl)-2,3-dihydro-1h-inden-1-amine Chemical compound C1=C2C(NC)CCC2=CC=C1C=1C(C)=NN(C)C=1C CMJAEJACNGQGQB-UHFFFAOYSA-N 0.000 claims description 2
NQCSVMDTUOZUMO-UHFFFAOYSA-M trimethyl-[6-(1,3,5-trimethylpyrazol-4-yl)-2,3-dihydro-1h-inden-1-yl]azanium;iodide Chemical compound [I-].CC1=NN(C)C(C)=C1C1=CC=C(CCC2[N+](C)(C)C)C2=C1 NQCSVMDTUOZUMO-UHFFFAOYSA-M 0.000 claims description 2
IHSBTIJZJJXCJQ-INIZCTEOSA-N (1s)-n,n-dimethyl-6-(1,3,5-trimethylpyrazol-4-yl)-2,3-dihydro-1h-inden-1-amine Chemical compound C([C@@H](C1=C2)N(C)C)CC1=CC=C2C=1C(C)=NN(C)C=1C IHSBTIJZJJXCJQ-INIZCTEOSA-N 0.000 claims 1
MJPPKUDCNMXQIL-UHFFFAOYSA-N 6-(1-ethyl-3,5-dimethylpyrazol-4-yl)-n,n-dimethyl-2,3-dihydro-1h-inden-1-amine Chemical compound CCN1N=C(C)C(C=2C=C3C(N(C)C)CCC3=CC=2)=C1C MJPPKUDCNMXQIL-UHFFFAOYSA-N 0.000 claims 1
SXIJHAUDJJPKBS-UHFFFAOYSA-N 6-(2,6-dimethoxyphenyl)-n,n-dimethyl-2,3-dihydro-1h-inden-1-amine Chemical compound COC1=CC=CC(OC)=C1C1=CC=C(CCC2N(C)C)C2=C1 SXIJHAUDJJPKBS-UHFFFAOYSA-N 0.000 claims 1
RAHSDTADCRVMOD-UHFFFAOYSA-N 6-(2-methoxyphenyl)-n,n-dimethyl-2,3-dihydro-1h-inden-1-amine Chemical compound COC1=CC=CC=C1C1=CC=C(CCC2N(C)C)C2=C1 RAHSDTADCRVMOD-UHFFFAOYSA-N 0.000 claims 1
POMMDXVZELAEAZ-UHFFFAOYSA-N 6-(2-methoxypyridin-3-yl)-n,n-dimethyl-2,3-dihydro-1h-inden-1-amine Chemical compound COC1=NC=CC=C1C1=CC=C(CCC2N(C)C)C2=C1 POMMDXVZELAEAZ-UHFFFAOYSA-N 0.000 claims 1
125000005843 halogen group Chemical group 0.000 claims 1
HTVPUOMMICYRHS-UHFFFAOYSA-N n,n-diethyl-6-(1,3,5-trimethylpyrazol-4-yl)-2,3-dihydro-1h-inden-1-amine Chemical compound C1=C2C(N(CC)CC)CCC2=CC=C1C=1C(C)=NN(C)C=1C HTVPUOMMICYRHS-UHFFFAOYSA-N 0.000 claims 1
LRGSUTGOKWAGOG-UHFFFAOYSA-N n,n-dimethyl-6-piperidin-1-yl-2,3-dihydro-1h-inden-1-amine Chemical compound C1=C2C(N(C)C)CCC2=CC=C1N1CCCCC1 LRGSUTGOKWAGOG-UHFFFAOYSA-N 0.000 claims 1
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims 1
241001465754 Metazoa Species 0.000 abstract description 5
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
125000004129 indan-1-yl group Chemical group [H]C1=C([H])C([H])=C2C(=C1[H])C([H])([H])C([H])([H])C2([H])* 0.000 description 29
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 28
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 27
239000000047 product Substances 0.000 description 24
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 18
239000002585 base Substances 0.000 description 18
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 17
239000000243 solution Substances 0.000 description 16
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ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 15
238000005481 NMR spectroscopy Methods 0.000 description 15
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
150000001412 amines Chemical class 0.000 description 15
239000011541 reaction mixture Substances 0.000 description 15
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ZZYXNRREDYWPLN-UHFFFAOYSA-N pyridine-2,3-diamine Chemical compound NC1=CC=CN=C1N ZZYXNRREDYWPLN-UHFFFAOYSA-N 0.000 description 1
JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
238000003653 radioligand binding assay Methods 0.000 description 1
239000000018 receptor agonist Substances 0.000 description 1
229940044601 receptor agonist Drugs 0.000 description 1
239000002464 receptor antagonist Substances 0.000 description 1
229940044551 receptor antagonist Drugs 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000011514 reflex Effects 0.000 description 1
238000011160 research Methods 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
230000004044 response Effects 0.000 description 1
238000010517 secondary reaction Methods 0.000 description 1
229940076279 serotonin Drugs 0.000 description 1
HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 description 1
235000019254 sodium formate Nutrition 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
238000007614 solvation Methods 0.000 description 1
241000894007 species Species 0.000 description 1
238000002798 spectrophotometry method Methods 0.000 description 1
210000000952 spleen Anatomy 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000011593 sulfur Chemical group 0.000 description 1
229940032330 sulfuric acid Drugs 0.000 description 1
239000001117 sulphuric acid Substances 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
238000010189 synthetic method Methods 0.000 description 1
239000007916 tablet composition Substances 0.000 description 1
230000008685 targeting Effects 0.000 description 1
UBCKGWBNUIFUST-YHYXMXQVSA-N tetrachlorvinphos Chemical compound COP(=O)(OC)O\C(=C/Cl)C1=CC(Cl)=C(Cl)C=C1Cl UBCKGWBNUIFUST-YHYXMXQVSA-N 0.000 description 1
125000005329 tetralinyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
210000001103 thalamus Anatomy 0.000 description 1
229930192474 thiophene Natural products 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
239000003029 tricyclic antidepressant agent Substances 0.000 description 1
IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
229910052722 tritium Inorganic materials 0.000 description 1
125000004417 unsaturated alkyl group Chemical group 0.000 description 1
230000024883 vasodilation Effects 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
150000003751 zinc Chemical class 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/06—Antimigraine agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/40—Oxygen atoms
- C07D211/42—Oxygen atoms attached in position 3 or 5
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/08—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms

Landscapes

Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Chemical Kinetics & Catalysis (AREA)
Animal Behavior & Ethology (AREA)
Medicinal Chemistry (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Neurosurgery (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Pain & Pain Management (AREA)
Psychiatry (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Hospice & Palliative Care (AREA)
Anesthesiology (AREA)
Rheumatology (AREA)
Urology & Nephrology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pyridine Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

CA 2692513 2007-07-05 2008-07-04 Indane-amine derivatives, their preparation and use as medicaments Abandoned CA2692513A1 (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
EP07384028A EP2011786A1 (en)	2007-07-05	2007-07-05	Indane-amine derivatives, their preparation and use as medicaments
EP07384028.2		2007-07-05
PCT/EP2008/005500 WO2009003719A2 (en)	2007-07-05	2008-07-04	Indane-amine derivatives, their preparation and use as medicaments

Publications (1)

Publication Number	Publication Date
CA2692513A1 true CA2692513A1 (en)	2009-01-08

Family

ID=38961113

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA 2692513 Abandoned CA2692513A1 (en)	2007-07-05	2008-07-04	Indane-amine derivatives, their preparation and use as medicaments

Country Status (8)

Country	Link
US (1)	US8232307B2 (es)
EP (2)	EP2011786A1 (es)
JP (1)	JP2010532326A (es)
CN (1)	CN101730683A (es)
AR (1)	AR067454A1 (es)
CA (1)	CA2692513A1 (es)
TW (1)	TW200918506A (es)
WO (1)	WO2009003719A2 (es)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP2308849A1 (en) *	2009-10-06	2011-04-13	Laboratorios Del. Dr. Esteve, S.A.	Indane-amine derivatives, their preparation and use as medicaments
JP2014502765A (ja) *	2011-01-07	2014-02-03	アクセスビジネスグループインターナショナルリミテッドライアビリティカンパニー	製品情報を有する郵送可能な品目
PT2861604T (pt)	2012-06-08	2017-05-05	Gilead Sciences Inc	Inibidores macrocíclicos de vírus flaviridae
IN2014MN02658A (es)	2012-06-08	2015-08-21	Gilead Sciences Inc
EP2676954A1 (en) *	2012-06-19	2013-12-25	Laboratorios del Dr. Esteve S.A.	Heterocyclyl-substituted-phenyl derivatives as vasodilators
CN105037168A (zh) *	2015-08-31	2015-11-11	吴玲	利用d-酒石酸拆分制备s-5-溴-1-氨基茚满
WO2017070229A1 (en)	2015-10-19	2017-04-27	Board Of Regents, The University Of Texas System	Piperazinyl norbenzomorphan compounds and methods for using the same
CA3022432A1 (en) *	2016-04-29	2017-11-02	Board Of Regents, The University Of Texas System	Sigma receptor binders
WO2017190109A1 (en)	2016-04-29	2017-11-02	Board Of Regents, The University Of Texas System	Sigma receptor binders

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AT294090B (de) *	1969-04-22	1971-11-10	Degussa	Verfahren zur Herstellung von neuen Aminopyridinen, von deren optisch aktiven bzw. diastereomeren Formen, deren Salzen und deren quartären Verbindungen
DE3623944A1 (de) *	1986-07-16	1988-02-11	Thomae Gmbh Dr K	Neue benzolsulfonamido-indanylverbindungen, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung
JP4782252B2 (ja) *	1994-01-10	2011-09-28	テバファーマシューティカルインダストリーズリミテッド	１−アミノインダン及びこれらの組成物
GB9509156D0 (en) *	1995-05-05	1995-06-28	Sandoz Ltd	Organic compounds
TWI242011B (en) *	1997-03-31	2005-10-21	Eisai Co Ltd	1,4-substituted cyclic amine derivatives
US7135575B2 (en) *	2003-03-03	2006-11-14	Array Biopharma, Inc.	P38 inhibitors and methods of use thereof
JP2008500383A (ja) *	2004-05-21	2008-01-10	ファイザー・プロダクツ・インク	５−ｈｔ１ｂアンタゴニスト、インバースアゴニストおよび部分アゴニストとしてのテトラヒドロナフチルピペラジン類
EP1956006A1 (en) *	2007-02-06	2008-08-13	Laboratorios del Dr. Esteve S.A.	Heterocyclyl-substituted-tetrahydro-naphthalen derivatives as 5-HT7 receptor ligands

2007
- 2007-07-05 EP EP07384028A patent/EP2011786A1/en not_active Withdrawn
2008
- 2008-07-04 TW TW097125197A patent/TW200918506A/zh unknown
- 2008-07-04 AR ARP080102908A patent/AR067454A1/es unknown
- 2008-07-04 WO PCT/EP2008/005500 patent/WO2009003719A2/en active Application Filing
- 2008-07-04 EP EP08773876A patent/EP2173712A2/en not_active Withdrawn
- 2008-07-04 CN CN200880023486A patent/CN101730683A/zh active Pending
- 2008-07-04 JP JP2010513794A patent/JP2010532326A/ja active Pending
- 2008-07-04 US US12/667,587 patent/US8232307B2/en not_active Expired - Fee Related
- 2008-07-04 CA CA 2692513 patent/CA2692513A1/en not_active Abandoned

Also Published As

Publication number	Publication date
CN101730683A (zh)	2010-06-09
US8232307B2 (en)	2012-07-31
EP2011786A1 (en)	2009-01-07
AR067454A1 (es)	2009-10-14
JP2010532326A (ja)	2010-10-07
EP2173712A2 (en)	2010-04-14
TW200918506A (en)	2009-05-01
WO2009003719A3 (en)	2009-08-13
WO2009003719A2 (en)	2009-01-08
US20110053980A1 (en)	2011-03-03

Legal Events

Date	Code	Title	Description
2014-08-31	FZDE	Discontinued	Effective date: 20140704

Publication	Publication Date	Title
CA2692513A1 (en)	2009-01-08	Indane-amine derivatives, their preparation and use as medicaments
CA2682163A1 (en)	2008-10-02	Heterocyclyl-substituted-tetrahydro-naphthalen-amine derivatives, their preparation and use as medicaments
CA2471880A1 (en)	2003-07-17	1h-pyrazolyl derivative compounds, for use in diseases associated with the 5-ht2c receptor
JP2005517681A (ja)	2005-06-16	５−ｈｔ２ｃ受容体と関連する疾患における使用のための４−スルフィド／スルホキシド／スルホニル−１ｈ−ピラゾリル誘導体化合物
JP6329961B2 (ja)	2018-05-23	置換ピラゾロ［３，４−ｄ］ピリミジン化合物、その製造及びシグマ受容体リガンドとしての使用
JP6243416B2 (ja)	2017-12-06	インデン誘導体、その製造方法および医薬品としての使用
US8097641B2 (en)	2012-01-17	Heterocyclyl substituted tetrahydronaphthalene derivatives as 5-HT7 receptor ligands
CA2673601A1 (en)	2008-07-03	Heterocyclyl-substituted-ethylamino-phenyl derivatives, their preparation and use as medicaments
MX2008013478A (es)	2008-10-29	Compuestos biciclicos de tetrahidropirrol.
US20120322842A1 (en)	2012-12-20	Heterocycyl-substituted-alkylaminophenyl derivatives, their preparation and use as medicaments
EP1935886A1 (en)	2008-06-25	Heterocyclyl-substituted-ethylamino-phenyl derivatives, their preparation and use as medicaments
CA2675468A1 (en)	2008-08-07	Aryl-substituted sulfonamides for the treatment of cognitive or food ingestion related disorders
US20120264799A1 (en)	2012-10-18	Indane-amine derivatives, their preparation and use as medicaments
EP1997807A1 (en)	2008-12-03	Heterocyclyl-substituted-ethylamino-phenyl derivatives, their preparation and use as medicaments