ZA200405452B - Phenylalkynes. - Google Patents
Phenylalkynes. Download PDFInfo
- Publication number
- ZA200405452B ZA200405452B ZA200405452A ZA200405452A ZA200405452B ZA 200405452 B ZA200405452 B ZA 200405452B ZA 200405452 A ZA200405452 A ZA 200405452A ZA 200405452 A ZA200405452 A ZA 200405452A ZA 200405452 B ZA200405452 B ZA 200405452B
- Authority
- ZA
- South Africa
- Prior art keywords
- ynyl
- piperidin
- benzyl
- phenyl
- compound
- Prior art date
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- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 claims description 124
- 150000001875 compounds Chemical class 0.000 claims description 93
- 125000000623 heterocyclic group Chemical group 0.000 claims description 73
- 229960001340 histamine Drugs 0.000 claims description 62
- -1 nitro, hydroxyl Chemical group 0.000 claims description 53
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 48
- 102000005962 receptors Human genes 0.000 claims description 46
- 108020003175 receptors Proteins 0.000 claims description 46
- 239000000203 mixture Substances 0.000 claims description 45
- 125000000217 alkyl group Chemical group 0.000 claims description 44
- 125000002947 alkylene group Chemical group 0.000 claims description 44
- 238000000034 method Methods 0.000 claims description 41
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 39
- 239000000126 substance Substances 0.000 claims description 38
- 125000001424 substituent group Chemical group 0.000 claims description 32
- 208000035475 disorder Diseases 0.000 claims description 24
- 229910052757 nitrogen Inorganic materials 0.000 claims description 18
- 125000002883 imidazolyl group Chemical group 0.000 claims description 17
- 125000003386 piperidinyl group Chemical group 0.000 claims description 17
- 125000003118 aryl group Chemical group 0.000 claims description 16
- 201000010099 disease Diseases 0.000 claims description 15
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 15
- 125000003342 alkenyl group Chemical group 0.000 claims description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 14
- 125000005843 halogen group Chemical group 0.000 claims description 13
- 229940044551 receptor antagonist Drugs 0.000 claims description 13
- 239000002464 receptor antagonist Substances 0.000 claims description 13
- 125000005842 heteroatom Chemical group 0.000 claims description 12
- 206010012289 Dementia Diseases 0.000 claims description 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 125000002757 morpholinyl group Chemical group 0.000 claims description 11
- 125000004452 carbocyclyl group Chemical group 0.000 claims description 10
- 230000000694 effects Effects 0.000 claims description 10
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 9
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 9
- 125000001425 triazolyl group Chemical group 0.000 claims description 9
- 208000026935 allergic disease Diseases 0.000 claims description 8
- 208000010877 cognitive disease Diseases 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- 125000004076 pyridyl group Chemical group 0.000 claims description 8
- 229920006395 saturated elastomer Polymers 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 8
- 208000020925 Bipolar disease Diseases 0.000 claims description 7
- 201000000980 schizophrenia Diseases 0.000 claims description 7
- 206010028735 Nasal congestion Diseases 0.000 claims description 6
- 206010039085 Rhinitis allergic Diseases 0.000 claims description 6
- 201000010105 allergic rhinitis Diseases 0.000 claims description 6
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 6
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 230000001404 mediated effect Effects 0.000 claims description 6
- 201000003631 narcolepsy Diseases 0.000 claims description 6
- 125000002971 oxazolyl group Chemical group 0.000 claims description 6
- 125000004193 piperazinyl group Chemical group 0.000 claims description 6
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 6
- HDRIBIYPLKZUDQ-UHFFFAOYSA-N 4-[[3-(4-piperidin-1-ylbut-1-ynyl)phenyl]methyl]morpholine Chemical compound C=1C=CC(CN2CCOCC2)=CC=1C#CCCN1CCCCC1 HDRIBIYPLKZUDQ-UHFFFAOYSA-N 0.000 claims description 5
- 230000037007 arousal Effects 0.000 claims description 5
- 208000006673 asthma Diseases 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- 150000003857 carboxamides Chemical class 0.000 claims description 5
- 125000002541 furyl group Chemical group 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 208000027061 mild cognitive impairment Diseases 0.000 claims description 5
- 125000000335 thiazolyl group Chemical group 0.000 claims description 5
- 208000024827 Alzheimer disease Diseases 0.000 claims description 4
- 208000030814 Eating disease Diseases 0.000 claims description 4
- 208000019454 Feeding and Eating disease Diseases 0.000 claims description 4
- 208000020358 Learning disease Diseases 0.000 claims description 4
- 208000019695 Migraine disease Diseases 0.000 claims description 4
- 208000012886 Vertigo Diseases 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 150000001408 amides Chemical class 0.000 claims description 4
- 235000014632 disordered eating Nutrition 0.000 claims description 4
- 206010015037 epilepsy Diseases 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 230000002401 inhibitory effect Effects 0.000 claims description 4
- 201000003723 learning disability Diseases 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 206010027599 migraine Diseases 0.000 claims description 4
- 201000003152 motion sickness Diseases 0.000 claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 231100000889 vertigo Toxicity 0.000 claims description 4
- GNEXGCZJYUOOFU-UHFFFAOYSA-N 1-methyl-4-[[4-(4-piperidin-1-ylbut-1-ynyl)phenyl]methyl]piperazine Chemical compound C1CN(C)CCN1CC1=CC=C(C#CCCN2CCCCC2)C=C1 GNEXGCZJYUOOFU-UHFFFAOYSA-N 0.000 claims description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
- XNOOLEJPOXDMDY-UHFFFAOYSA-N 3-[1-[[3-(4-piperidin-1-ylbut-1-ynyl)phenyl]methyl]piperidin-4-yl]-1h-benzimidazol-2-one Chemical compound O=C1NC2=CC=CC=C2N1C(CC1)CCN1CC(C=1)=CC=CC=1C#CCCN1CCCCC1 XNOOLEJPOXDMDY-UHFFFAOYSA-N 0.000 claims description 3
- 208000026139 Memory disease Diseases 0.000 claims description 3
- 125000001422 pyrrolinyl group Chemical group 0.000 claims description 3
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 3
- WTCXKVCGOQQVCC-UHFFFAOYSA-N 1-[[4-(4-piperidin-1-ylbut-1-ynyl)phenyl]methyl]piperidine-4-carboxamide Chemical compound C1CC(C(=O)N)CCN1CC1=CC=C(C#CCCN2CCCCC2)C=C1 WTCXKVCGOQQVCC-UHFFFAOYSA-N 0.000 claims description 2
- KJUYUPFAJWJDHB-UHFFFAOYSA-N 1-benzyl-4-[[4-(4-piperidin-1-ylbut-1-ynyl)phenyl]methyl]piperazine Chemical compound C=1C=C(CN2CCN(CC=3C=CC=CC=3)CC2)C=CC=1C#CCCN1CCCCC1 KJUYUPFAJWJDHB-UHFFFAOYSA-N 0.000 claims description 2
- GZLFAQOQWQWXSE-UHFFFAOYSA-N 1-phenyl-4-[[4-(4-piperidin-1-ylbut-1-ynyl)phenyl]methyl]piperazine Chemical compound C=1C=C(CN2CCN(CC2)C=2C=CC=CC=2)C=CC=1C#CCCN1CCCCC1 GZLFAQOQWQWXSE-UHFFFAOYSA-N 0.000 claims description 2
- VEKIYFGCEAJDDT-UHFFFAOYSA-N 2-pyridin-3-ylpyridine Chemical group N1=CC=CC=C1C1=CC=CN=C1 VEKIYFGCEAJDDT-UHFFFAOYSA-N 0.000 claims description 2
- FSHOZBSEBOHWPV-UHFFFAOYSA-N 4-[[3-(4-piperidin-1-ylbut-1-ynyl)phenyl]methyl]thiomorpholine Chemical compound C=1C=CC(CN2CCSCC2)=CC=1C#CCCN1CCCCC1 FSHOZBSEBOHWPV-UHFFFAOYSA-N 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000004450 alkenylene group Chemical group 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000004914 dipropylamino group Chemical group C(CC)N(CCC)* 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- HKQISMPAKKLRTM-UHFFFAOYSA-N n,n-diethyl-1-[[3-(4-piperidin-1-ylbut-1-ynyl)phenyl]methyl]piperidine-3-carboxamide Chemical compound C1C(C(=O)N(CC)CC)CCCN1CC1=CC=CC(C#CCCN2CCCCC2)=C1 HKQISMPAKKLRTM-UHFFFAOYSA-N 0.000 claims description 2
- XDQMOBHJYLWFRT-UHFFFAOYSA-N n-methyl-n-[[3-(4-piperidin-1-ylbut-1-ynyl)phenyl]methyl]-2-pyridin-2-ylethanamine Chemical compound C=1C=CC(C#CCCN2CCCCC2)=CC=1CN(C)CCC1=CC=CC=N1 XDQMOBHJYLWFRT-UHFFFAOYSA-N 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 238000002560 therapeutic procedure Methods 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 11
- 238000002600 positron emission tomography Methods 0.000 claims 6
- 239000003068 molecular probe Substances 0.000 claims 5
- 239000002552 dosage form Substances 0.000 claims 4
- UIDQQTHLSRGAPO-UHFFFAOYSA-N 1-[[3-(4-piperidin-1-ylbut-1-ynyl)phenyl]methyl]piperidine Chemical compound C=1C=CC(CN2CCCCC2)=CC=1C#CCCN1CCCCC1 UIDQQTHLSRGAPO-UHFFFAOYSA-N 0.000 claims 3
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 claims 3
- RFPKAGSDFZFKNX-UHFFFAOYSA-N 1-[[3-(4-morpholin-4-ylbut-1-ynyl)phenyl]methyl]piperidin-4-ol Chemical compound C1CC(O)CCN1CC1=CC=CC(C#CCCN2CCOCC2)=C1 RFPKAGSDFZFKNX-UHFFFAOYSA-N 0.000 claims 2
- KCDNDVYRBIJQQP-UHFFFAOYSA-N 1-[[3-(4-thiomorpholin-4-ylbut-1-ynyl)phenyl]methyl]piperidin-4-ol Chemical compound C1CC(O)CCN1CC1=CC=CC(C#CCCN2CCSCC2)=C1 KCDNDVYRBIJQQP-UHFFFAOYSA-N 0.000 claims 2
- NVYKUZPOGWHWQN-UHFFFAOYSA-N 1-methyl-4-[[3-(4-piperidin-1-ylbut-1-ynyl)phenyl]methyl]piperazine Chemical compound C1CN(C)CCN1CC1=CC=CC(C#CCCN2CCCCC2)=C1 NVYKUZPOGWHWQN-UHFFFAOYSA-N 0.000 claims 2
- DYDQDHCNGTXGJV-UHFFFAOYSA-N 2-[4-[[3-(4-piperidin-1-ylbut-1-ynyl)phenyl]methyl]piperazin-1-yl]pyrimidine Chemical compound C=1C=CC(CN2CCN(CC2)C=2N=CC=CN=2)=CC=1C#CCCN1CCCCC1 DYDQDHCNGTXGJV-UHFFFAOYSA-N 0.000 claims 2
- PAQHERKZFLOHCA-UHFFFAOYSA-N 4-[[3-(4-piperidin-1-ylbut-1-ynyl)phenyl]methyl]morpholine;dihydrochloride Chemical compound Cl.Cl.C=1C=CC(CN2CCOCC2)=CC=1C#CCCN1CCCCC1 PAQHERKZFLOHCA-UHFFFAOYSA-N 0.000 claims 2
- 229940119240 Histamine H4 receptor antagonist Drugs 0.000 claims 2
- 239000003396 histamine H4 receptor antagonist Substances 0.000 claims 2
- 230000014759 maintenance of location Effects 0.000 claims 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 2
- OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 claims 1
- QNSRHBOZQLXYNV-UHFFFAOYSA-N 1,4,7-trioxa-10-azacyclododecane Chemical compound C1COCCOCCOCCN1 QNSRHBOZQLXYNV-UHFFFAOYSA-N 0.000 claims 1
- MRBFGEHILMYPTF-UHFFFAOYSA-N 1-(2-Pyrimidyl)piperazine Chemical compound C1CNCCN1C1=NC=CC=N1 MRBFGEHILMYPTF-UHFFFAOYSA-N 0.000 claims 1
- KKIMDKMETPPURN-UHFFFAOYSA-N 1-(3-(trifluoromethyl)phenyl)piperazine Chemical compound FC(F)(F)C1=CC=CC(N2CCNCC2)=C1 KKIMDKMETPPURN-UHFFFAOYSA-N 0.000 claims 1
- AFLLBHCLMHXGNC-UHFFFAOYSA-N 1-[4-[4-(pyrrolidin-1-ylmethyl)phenyl]but-3-ynyl]piperidine Chemical compound C=1C=C(CN2CCCC2)C=CC=1C#CCCN1CCCCC1 AFLLBHCLMHXGNC-UHFFFAOYSA-N 0.000 claims 1
- MEMJPSSYGARVOB-UHFFFAOYSA-N 1-[[3-(4-piperidin-1-ylbut-1-ynyl)phenyl]methyl]piperidine-4-carboxamide Chemical compound C1CC(C(=O)N)CCN1CC1=CC=CC(C#CCCN2CCCCC2)=C1 MEMJPSSYGARVOB-UHFFFAOYSA-N 0.000 claims 1
- XAKYFXRPZKRNIZ-UHFFFAOYSA-N 1-[[4-(4-piperidin-1-ylbut-1-ynyl)phenyl]methyl]-3,4,4a,5,6,7,8,8a-octahydro-2h-quinoline Chemical compound C=1C=C(CN2C3CCCCC3CCC2)C=CC=1C#CCCN1CCCCC1 XAKYFXRPZKRNIZ-UHFFFAOYSA-N 0.000 claims 1
- YISLPZXINLTTCO-UHFFFAOYSA-N 1-[[4-(4-piperidin-1-ylbut-1-ynyl)phenyl]methyl]-4-propan-2-ylpiperazine Chemical compound C1CN(C(C)C)CCN1CC1=CC=C(C#CCCN2CCCCC2)C=C1 YISLPZXINLTTCO-UHFFFAOYSA-N 0.000 claims 1
- TWJSDUFYUPMDGD-UHFFFAOYSA-N 1-[[4-(4-piperidin-1-ylbut-1-ynyl)phenyl]methyl]piperidine Chemical compound C=1C=C(CN2CCCCC2)C=CC=1C#CCCN1CCCCC1 TWJSDUFYUPMDGD-UHFFFAOYSA-N 0.000 claims 1
- HTQWGIHCFPWKAS-UHFFFAOYSA-N 1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one Chemical compound C1CNCCC11C(=O)NCN1C1=CC=CC=C1 HTQWGIHCFPWKAS-UHFFFAOYSA-N 0.000 claims 1
- NKAGQGFDMMBLEC-UHFFFAOYSA-N 1-phenyl-8-[[3-(4-piperidin-1-ylbut-1-ynyl)phenyl]methyl]-1,3,8-triazaspiro[4.5]decan-4-one Chemical compound C1CN(CC=2C=C(C=CC=2)C#CCCN2CCCCC2)CCC11C(=O)NCN1C1=CC=CC=C1 NKAGQGFDMMBLEC-UHFFFAOYSA-N 0.000 claims 1
- DQVLWFYATHVBOZ-UHFFFAOYSA-N 2-(1h-indol-3-yl)-n-methyl-n-[[3-(4-piperidin-1-ylbut-1-ynyl)phenyl]methyl]ethanamine Chemical compound C=1NC2=CC=CC=C2C=1CCN(C)CC(C=1)=CC=CC=1C#CCCN1CCCCC1 DQVLWFYATHVBOZ-UHFFFAOYSA-N 0.000 claims 1
- MAUNJNQYQQHKDB-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-n-methyl-n-[[3-(4-piperidin-1-ylbut-1-ynyl)phenyl]methyl]ethanamine Chemical compound C1=C(OC)C(OC)=CC=C1CCN(C)CC1=CC=CC(C#CCCN2CCCCC2)=C1 MAUNJNQYQQHKDB-UHFFFAOYSA-N 0.000 claims 1
- BZOIPHABEDFJAI-UHFFFAOYSA-N 2-[1-[[4-(4-piperidin-1-ylbut-1-ynyl)phenyl]methyl]piperidin-2-yl]ethanol Chemical compound OCCC1CCCCN1CC1=CC=C(C#CCCN2CCCCC2)C=C1 BZOIPHABEDFJAI-UHFFFAOYSA-N 0.000 claims 1
- IAFUZCLDORRBJY-UHFFFAOYSA-N 2-piperidin-4-yloxypyrimidine Chemical compound C1CNCCC1OC1=NC=CC=N1 IAFUZCLDORRBJY-UHFFFAOYSA-N 0.000 claims 1
- HRGXROVFENCVIO-UHFFFAOYSA-N 3-[[3-(4-piperidin-1-ylbut-1-ynyl)phenyl]methyl]-1,3-thiazolidine Chemical compound C=1C=CC(CN2CSCC2)=CC=1C#CCCN1CCCCC1 HRGXROVFENCVIO-UHFFFAOYSA-N 0.000 claims 1
- 125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 claims 1
- DPBWFNDFMCCGGJ-UHFFFAOYSA-N 4-Piperidine carboxamide Chemical compound NC(=O)C1CCNCC1 DPBWFNDFMCCGGJ-UHFFFAOYSA-N 0.000 claims 1
- PAFPCBPHDUAMIX-UHFFFAOYSA-N 4-[4-[3-(thiomorpholin-4-ylmethyl)phenyl]but-3-ynyl]morpholine Chemical compound C=1C=CC(CN2CCSCC2)=CC=1C#CCCN1CCOCC1 PAFPCBPHDUAMIX-UHFFFAOYSA-N 0.000 claims 1
- CLDUIGXUVKXZHW-UHFFFAOYSA-N 4-[4-[3-[(4-methoxypiperidin-1-yl)methyl]phenyl]but-3-ynyl]morpholine Chemical compound C1CC(OC)CCN1CC1=CC=CC(C#CCCN2CCOCC2)=C1 CLDUIGXUVKXZHW-UHFFFAOYSA-N 0.000 claims 1
- ANDUWBDYYCFMSZ-UHFFFAOYSA-N 4-[4-[3-[(4-methylpiperazin-1-yl)methyl]phenyl]but-3-ynyl]morpholine Chemical compound C1CN(C)CCN1CC1=CC=CC(C#CCCN2CCOCC2)=C1 ANDUWBDYYCFMSZ-UHFFFAOYSA-N 0.000 claims 1
- NGJBPOOMWRYCPF-UHFFFAOYSA-N 4-[4-[3-[(4-methylpiperazin-1-yl)methyl]phenyl]but-3-ynyl]thiomorpholine Chemical compound C1CN(C)CCN1CC1=CC=CC(C#CCCN2CCSCC2)=C1 NGJBPOOMWRYCPF-UHFFFAOYSA-N 0.000 claims 1
- UTXBZYNRYPXBIF-UHFFFAOYSA-N 4-[[3-(4-thiomorpholin-4-ylbut-1-ynyl)phenyl]methyl]thiomorpholine Chemical compound C=1C=CC(CN2CCSCC2)=CC=1C#CCCN1CCSCC1 UTXBZYNRYPXBIF-UHFFFAOYSA-N 0.000 claims 1
- QTHFIFDZWPIKFW-UHFFFAOYSA-N 4-[[4-(4-piperidin-1-ylbut-1-ynyl)phenyl]methyl]morpholine Chemical compound C=1C=C(CN2CCOCC2)C=CC=1C#CCCN1CCCCC1 QTHFIFDZWPIKFW-UHFFFAOYSA-N 0.000 claims 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims 1
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 claims 1
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Natural products C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- UZBQIPPOMKBLAS-UHFFFAOYSA-N diethylazanide Chemical compound CC[N-]CC UZBQIPPOMKBLAS-UHFFFAOYSA-N 0.000 claims 1
- GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 1
- ZXQKYQVJDRTTLZ-UHFFFAOYSA-N n,n-diethylpiperidine-3-carboxamide Chemical compound CCN(CC)C(=O)C1CCCNC1 ZXQKYQVJDRTTLZ-UHFFFAOYSA-N 0.000 claims 1
- NAEMSSPGTTWGRL-UHFFFAOYSA-N n-[1-[[3-(4-piperidin-1-ylbut-1-ynyl)phenyl]methyl]piperidin-4-yl]pyridin-2-amine Chemical compound C=1C=CC(CN2CCC(CC2)NC=2N=CC=CC=2)=CC=1C#CCCN1CCCCC1 NAEMSSPGTTWGRL-UHFFFAOYSA-N 0.000 claims 1
- SWAPONVCAWDMOV-UHFFFAOYSA-N n-[[3-(4-piperidin-1-ylbut-1-ynyl)phenyl]methyl]aniline Chemical compound C=1C=CC(CNC=2C=CC=CC=2)=CC=1C#CCCN1CCCCC1 SWAPONVCAWDMOV-UHFFFAOYSA-N 0.000 claims 1
- UTXXQPKHMURRBG-UHFFFAOYSA-N n-ethyl-n-[[4-(4-piperidin-1-ylbut-1-ynyl)phenyl]methyl]ethanamine Chemical compound C1=CC(CN(CC)CC)=CC=C1C#CCCN1CCCCC1 UTXXQPKHMURRBG-UHFFFAOYSA-N 0.000 claims 1
- NCIKQJBVUNUXLW-UHFFFAOYSA-N n-omega-methyltryptamine Natural products C1=CC=C2C(CCNC)=CNC2=C1 NCIKQJBVUNUXLW-UHFFFAOYSA-N 0.000 claims 1
- CTSIKBGUCQWRIM-UHFFFAOYSA-N n-prop-2-enylcyclopentanamine Chemical compound C=CCNC1CCCC1 CTSIKBGUCQWRIM-UHFFFAOYSA-N 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 238000002603 single-photon emission computed tomography Methods 0.000 claims 1
- HLDJRFVSQVBMKH-UHFFFAOYSA-N tert-butyl 4-[[4-(4-piperidin-1-ylbut-1-ynyl)phenyl]methyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1CC1=CC=C(C#CCCN2CCCCC2)C=C1 HLDJRFVSQVBMKH-UHFFFAOYSA-N 0.000 claims 1
- 239000005557 antagonist Substances 0.000 description 10
- 229940079593 drug Drugs 0.000 description 7
- 239000003814 drug Substances 0.000 description 7
- 239000000556 agonist Substances 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 102000000543 Histamine Receptors Human genes 0.000 description 4
- 108010002059 Histamine Receptors Proteins 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 239000003446 ligand Substances 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- 102000004190 Enzymes Human genes 0.000 description 3
- 108090000790 Enzymes Proteins 0.000 description 3
- 230000009471 action Effects 0.000 description 3
- 210000004556 brain Anatomy 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 238000002648 combination therapy Methods 0.000 description 3
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- 210000001519 tissue Anatomy 0.000 description 3
- 125000004607 1,2,3,4-tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
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- 210000002460 smooth muscle Anatomy 0.000 description 1
- 201000009032 substance abuse Diseases 0.000 description 1
- 231100000736 substance abuse Toxicity 0.000 description 1
- 208000011117 substance-related disease Diseases 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 230000005062 synaptic transmission Effects 0.000 description 1
- 210000003568 synaptosome Anatomy 0.000 description 1
- UOUFRTFWWBCVPV-UHFFFAOYSA-N tert-butyl 4-(2,4-dioxo-1H-thieno[3,2-d]pyrimidin-3-yl)piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(CC1)n1c(=O)[nH]c2ccsc2c1=O UOUFRTFWWBCVPV-UHFFFAOYSA-N 0.000 description 1
- 125000006092 tetrahydro-1,1-dioxothienyl group Chemical group 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000004595 tetrahydroindoazolyl group Chemical group 0.000 description 1
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000004627 thianthrenyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3SC12)* 0.000 description 1
- 125000004640 thiazaolyl group Chemical group S1C(=NC=C1)* 0.000 description 1
- 125000001984 thiazolidinyl group Chemical group 0.000 description 1
- 125000004589 thienofuryl group Chemical group O1C(=CC2=C1C=CS2)* 0.000 description 1
- 125000004588 thienopyridyl group Chemical group S1C(=CC2=C1C=CC=N2)* 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
- WCNFFKHKJLERFM-UHFFFAOYSA-N thiomorpholinyl sulfone group Chemical group N1(CCSCC1)S(=O)(=O)N1CCSCC1 WCNFFKHKJLERFM-UHFFFAOYSA-N 0.000 description 1
- ZCAGUOCUDGWENZ-UHFFFAOYSA-N thiomorpholinyl sulfoxide group Chemical group N1(CCSCC1)S(=O)N1CCSCC1 ZCAGUOCUDGWENZ-UHFFFAOYSA-N 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000006168 tricyclic group Chemical group 0.000 description 1
- 210000005166 vasculature Anatomy 0.000 description 1
Classifications
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom
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- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/444—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring heteroatom, e.g. amrinone
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- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4453—Non condensed piperidines, e.g. piperocaine only substituted in position 1, e.g. propipocaine, diperodon
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- C07D203/12—Radicals substituted by nitrogen atoms not forming part of a nitro radical
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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
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
- C07D209/16—Tryptamines
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- 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
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- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
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- C07D211/22—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms
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- C07D211/40—Oxygen atoms
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- C07D211/44—Oxygen atoms attached in position 4
- C07D211/46—Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4
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- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
- C07D295/027—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring
- C07D295/03—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring with the ring nitrogen atoms directly attached to acyclic carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/06—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by halogen atoms or nitro radicals
- C07D295/073—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by halogen atoms or nitro radicals with the ring nitrogen atoms and the substituents separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/096—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/10—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms
- C07D295/112—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/135—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/20—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof
- C07D295/205—Radicals derived from carbonic acid
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
- C07D401/04—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 directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
- C07D401/12—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 chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/10—Spiro-condensed systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/10—Spiro-condensed systems
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- Immunology (AREA)
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- Psychology (AREA)
- Ophthalmology & Optometry (AREA)
- Otolaryngology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
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- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Indole Compounds (AREA)
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ZA200405452A ZA200405452B (en) | 2001-12-10 | 2004-07-08 | Phenylalkynes. |
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EP (1) | EP1451167B1 (ru) |
JP (1) | JP2005511740A (ru) |
KR (1) | KR20040068202A (ru) |
CN (1) | CN1617865A (ru) |
AR (1) | AR037757A1 (ru) |
AT (1) | ATE319694T1 (ru) |
AU (1) | AU2002357775A1 (ru) |
BR (1) | BR0214886A (ru) |
CA (1) | CA2469893A1 (ru) |
CO (1) | CO5590900A2 (ru) |
CY (1) | CY1105345T1 (ru) |
DE (1) | DE60209794T2 (ru) |
DK (1) | DK1451167T3 (ru) |
EA (1) | EA200400661A1 (ru) |
ES (1) | ES2259728T3 (ru) |
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MX (1) | MXPA04005562A (ru) |
NO (1) | NO20042919L (ru) |
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PT (1) | PT1451167E (ru) |
TW (1) | TWI281471B (ru) |
WO (1) | WO2003050099A1 (ru) |
ZA (1) | ZA200405452B (ru) |
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US20040002604A1 (en) | 2001-12-10 | 2004-01-01 | Richard Apodaca | Phenylalkynes |
ME00334B (me) | 2002-10-23 | 2011-05-10 | Janssen Pharmaceutica Nv | Piperazinil i diazapanil benzamidi i benzotioamidi |
JP2006505590A (ja) | 2002-10-23 | 2006-02-16 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | ヒスタミンh3受容体調節物質としてのフェニルピペリジンおよびフェニルピロリジン |
MXPA05005830A (es) * | 2002-12-02 | 2006-02-08 | Johnson & Johnson | Metodos para preparar derivados de fenilalquino. |
EP1707203A1 (en) * | 2005-04-01 | 2006-10-04 | Bioprojet | Treatment of parkinson's disease obstructive sleep apnea, dementia with lewy bodies, vascular dementia with non-imidazole alkylamines histamine H3- receptor ligands |
DE602006013501D1 (de) | 2005-09-16 | 2010-05-20 | Janssen Pharmaceutica Nv | Cyclopropylamine als modulatoren des histamin-h3-rezeptors |
CA2690229C (en) * | 2007-06-29 | 2013-10-29 | Acucela, Inc. | Alkynyl phenyl derivative compounds for treating ophthalmic diseases and disorders |
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US5352707A (en) | 1992-03-26 | 1994-10-04 | Harbor Branch Oceanographic Institution, Inc. | Method for treating airway congestion |
US5217986A (en) | 1992-03-26 | 1993-06-08 | Harbor Branch Oceanographic Institution, Inc. | Anti-allergy agent |
US5869479A (en) | 1997-08-14 | 1999-02-09 | Schering Corporation | Treatment of upper airway allergic responses |
GB9803536D0 (en) | 1998-02-19 | 1998-04-15 | Black James Foundation | Histamine H,receptor ligands |
AU3894299A (en) | 1998-05-15 | 1999-12-06 | American Home Products Corporation | Compositions comprising 2-phenyl-indole compounds and estrogen formulations |
EP0978512A1 (en) | 1998-07-29 | 2000-02-09 | Societe Civile Bioprojet | Non-imidazole aryloxy (or arylthio) alkylamines as histamine H3-receptor antagonists and their therapeutic applications |
WO2001066534A2 (en) * | 2000-03-09 | 2001-09-13 | Abbott Laboratories | Cyclic and bicyclic diamino histamine-3 receptor antagonists |
SE0002419D0 (sv) | 2000-06-27 | 2000-06-27 | Ericsson Telefon Ab L M | Telekommunikationsförfarande och anordning |
EP1379493A2 (en) | 2001-03-23 | 2004-01-14 | Eli Lilly and Company | Non-imidazole aryl alkylamines compounds as histamine h3 receptor antagonists, preparation and therapeutic uses |
AU2003202949A1 (en) | 2002-01-11 | 2003-07-30 | Ali Alwattari | Methods and apparatus for spinning spider silk protein |
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2002
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- 2002-12-02 MX MXPA04005562A patent/MXPA04005562A/es unknown
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- 2002-12-02 PT PT02792315T patent/PT1451167E/pt unknown
- 2002-12-02 JP JP2003551124A patent/JP2005511740A/ja not_active Withdrawn
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- 2002-12-02 EA EA200400661A patent/EA200400661A1/ru unknown
- 2002-12-02 CN CNA028278194A patent/CN1617865A/zh active Pending
- 2002-12-09 AR ARP020104760A patent/AR037757A1/es unknown
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2004
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TW200400952A (en) | 2004-01-16 |
EP1451167A1 (en) | 2004-09-01 |
EA200400661A1 (ru) | 2004-12-30 |
ES2259728T3 (es) | 2006-10-16 |
ATE319694T1 (de) | 2006-03-15 |
JP2005511740A (ja) | 2005-04-28 |
US20030144323A1 (en) | 2003-07-31 |
DE60209794T2 (de) | 2006-11-09 |
CY1105345T1 (el) | 2010-03-03 |
NZ533990A (en) | 2006-04-28 |
NO20042919L (no) | 2004-09-02 |
EP1451167B1 (en) | 2006-03-08 |
US6884803B2 (en) | 2005-04-26 |
CN1617865A (zh) | 2005-05-18 |
TWI281471B (en) | 2007-05-21 |
KR20040068202A (ko) | 2004-07-30 |
DK1451167T3 (da) | 2006-07-03 |
IL162309A0 (en) | 2005-11-20 |
DE60209794D1 (de) | 2006-05-04 |
CO5590900A2 (es) | 2005-12-30 |
WO2003050099A1 (en) | 2003-06-19 |
AR037757A1 (es) | 2004-12-01 |
BR0214886A (pt) | 2004-12-07 |
MXPA04005562A (es) | 2005-04-19 |
PT1451167E (pt) | 2006-07-31 |
CA2469893A1 (en) | 2003-06-19 |
AU2002357775A1 (en) | 2003-06-23 |
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