NO317422B1 - Cyklisk amidforbindelse - Google Patents
Cyklisk amidforbindelse Download PDFInfo
- Publication number
- NO317422B1 NO317422B1 NO20004092A NO20004092A NO317422B1 NO 317422 B1 NO317422 B1 NO 317422B1 NO 20004092 A NO20004092 A NO 20004092A NO 20004092 A NO20004092 A NO 20004092A NO 317422 B1 NO317422 B1 NO 317422B1
- Authority
- NO
- Norway
- Prior art keywords
- mmol
- bis
- reduced pressure
- under reduced
- trimethoxyphenyl
- Prior art date
Links
- -1 Cyclic amide compound Chemical class 0.000 title claims description 48
- 150000001875 compounds Chemical class 0.000 claims abstract description 80
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000003814 drug Substances 0.000 claims abstract description 12
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 11
- 229940079593 drug Drugs 0.000 claims abstract description 9
- 238000004519 manufacturing process Methods 0.000 claims abstract description 9
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 3
- 239000000203 mixture Substances 0.000 claims description 83
- 238000002360 preparation method Methods 0.000 claims description 59
- 150000003839 salts Chemical class 0.000 claims description 18
- 230000000172 allergic effect Effects 0.000 claims description 14
- 208000010668 atopic eczema Diseases 0.000 claims description 14
- 239000012453 solvate Substances 0.000 claims description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 9
- 208000026278 immune system disease Diseases 0.000 claims description 9
- 230000002265 prevention Effects 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 239000004480 active ingredient Substances 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 208000006673 asthma Diseases 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 3
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 3
- 206010012438 Dermatitis atopic Diseases 0.000 claims description 3
- 206010012442 Dermatitis contact Diseases 0.000 claims description 3
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 3
- 206010039085 Rhinitis allergic Diseases 0.000 claims description 3
- 201000010105 allergic rhinitis Diseases 0.000 claims description 3
- 201000008937 atopic dermatitis Diseases 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 208000010247 contact dermatitis Diseases 0.000 claims description 3
- 125000005046 dihydronaphthyl group Chemical group 0.000 claims description 3
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 125000005493 quinolyl group Chemical group 0.000 claims description 3
- 125000005277 alkyl imino group Chemical group 0.000 claims description 2
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
- 125000005551 pyridylene group Chemical group 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 239000000043 antiallergic agent Substances 0.000 abstract description 3
- 150000001491 aromatic compounds Chemical class 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 194
- 238000000034 method Methods 0.000 description 156
- 239000000243 solution Substances 0.000 description 86
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 74
- 239000011541 reaction mixture Substances 0.000 description 70
- 235000019441 ethanol Nutrition 0.000 description 66
- 239000000843 powder Substances 0.000 description 43
- 238000005160 1H NMR spectroscopy Methods 0.000 description 39
- 239000012230 colorless oil Substances 0.000 description 39
- 239000013078 crystal Substances 0.000 description 39
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 36
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 35
- 238000002844 melting Methods 0.000 description 32
- 230000008018 melting Effects 0.000 description 32
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 24
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 23
- 239000010779 crude oil Substances 0.000 description 22
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
- 150000003863 ammonium salts Chemical class 0.000 description 21
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 21
- 239000012044 organic layer Substances 0.000 description 20
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 238000004440 column chromatography Methods 0.000 description 17
- 239000000741 silica gel Substances 0.000 description 17
- 229910002027 silica gel Inorganic materials 0.000 description 17
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 239000007864 aqueous solution Substances 0.000 description 15
- 238000001816 cooling Methods 0.000 description 15
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 14
- 238000000605 extraction Methods 0.000 description 14
- XWIRYZZSVOHXHS-UHFFFAOYSA-N 4-(3,4,5-trimethoxyphenyl)benzoic acid Chemical compound COC1=C(OC)C(OC)=CC(C=2C=CC(=CC=2)C(O)=O)=C1 XWIRYZZSVOHXHS-UHFFFAOYSA-N 0.000 description 13
- 238000000354 decomposition reaction Methods 0.000 description 12
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 12
- 235000017557 sodium bicarbonate Nutrition 0.000 description 12
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 11
- MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 11
- 238000001914 filtration Methods 0.000 description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 11
- 239000003921 oil Substances 0.000 description 11
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- MVEAAGBEUOMFRX-UHFFFAOYSA-N ethyl acetate;hydrochloride Chemical compound Cl.CCOC(C)=O MVEAAGBEUOMFRX-UHFFFAOYSA-N 0.000 description 9
- 239000012458 free base Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
- 210000004027 cell Anatomy 0.000 description 8
- 150000004985 diamines Chemical class 0.000 description 8
- 229910000027 potassium carbonate Inorganic materials 0.000 description 8
- 229920006395 saturated elastomer Polymers 0.000 description 8
- 239000000706 filtrate Substances 0.000 description 7
- 238000010898 silica gel chromatography Methods 0.000 description 7
- LHHHQPXRGZINLT-UHFFFAOYSA-N 1-(3-piperazin-1-ylpropyl)piperazine;tetrahydrochloride Chemical compound Cl.Cl.Cl.Cl.C1CNCCN1CCCN1CCNCC1 LHHHQPXRGZINLT-UHFFFAOYSA-N 0.000 description 6
- RVVBNYIXXOJEAD-UHFFFAOYSA-N Cl.Cl.Cl.C1CNCCC1CC(N(C)C)CC1CCNCC1 Chemical compound Cl.Cl.Cl.C1CNCCC1CC(N(C)C)CC1CCNCC1 RVVBNYIXXOJEAD-UHFFFAOYSA-N 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 6
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 6
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 6
- LAONTCVXRKTZNF-FNORWQNLSA-N (e)-5-(3,4,5-trimethoxyphenyl)pent-2-en-4-ynoic acid Chemical compound COC1=CC(C#C\C=C\C(O)=O)=CC(OC)=C1OC LAONTCVXRKTZNF-FNORWQNLSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000001294 propane Substances 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- GOEQRYILPHKWHZ-UHFFFAOYSA-N Cl.Cl.Cl.C1CNCCC1CC(CN(C)C)CC1CCNCC1 Chemical compound Cl.Cl.Cl.C1CNCCC1CC(CN(C)C)CC1CCNCC1 GOEQRYILPHKWHZ-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
- 230000006181 N-acylation Effects 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- 238000005917 acylation reaction Methods 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- QSKWJTXWJJOJFP-UHFFFAOYSA-N chloroform;ethoxyethane Chemical compound ClC(Cl)Cl.CCOCC QSKWJTXWJJOJFP-UHFFFAOYSA-N 0.000 description 4
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- OTSKMPKHMRKHRH-UHFFFAOYSA-N tert-butyl 4-[2-(dimethylamino)-3-[1-[(2-methylpropan-2-yl)oxycarbonyl]piperidin-4-yl]propyl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1CC(N(C)C)CC1CCN(C(=O)OC(C)(C)C)CC1 OTSKMPKHMRKHRH-UHFFFAOYSA-N 0.000 description 4
- HNTKCHNNTDLIGP-UHFFFAOYSA-N tert-butyl 4-[3-methoxy-2-[[1-[(2-methylpropan-2-yl)oxycarbonyl]piperidin-4-yl]methyl]-3-oxopropyl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1CC(C(=O)OC)CC1CCN(C(=O)OC(C)(C)C)CC1 HNTKCHNNTDLIGP-UHFFFAOYSA-N 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- WQIHERMZQSQZPC-YDFGWWAZSA-N (2e,4e)-5-(3,4,5-trimethoxyphenyl)penta-2,4-dienoic acid Chemical compound COC1=CC(\C=C\C=C\C(O)=O)=CC(OC)=C1OC WQIHERMZQSQZPC-YDFGWWAZSA-N 0.000 description 3
- FQUYSHZXSKYCSY-UHFFFAOYSA-N 1,4-diazepane Chemical compound C1CNCCNC1 FQUYSHZXSKYCSY-UHFFFAOYSA-N 0.000 description 3
- UIJWTXNVLRAYEF-UHFFFAOYSA-N 1-[[4-(piperazin-1-ylmethyl)phenyl]methyl]piperazine;tetrahydrochloride Chemical compound Cl.Cl.Cl.Cl.C=1C=C(CN2CCNCC2)C=CC=1CN1CCNCC1 UIJWTXNVLRAYEF-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 3
- 239000013566 allergen Substances 0.000 description 3
- 210000003719 b-lymphocyte Anatomy 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 3
- 210000003630 histaminocyte Anatomy 0.000 description 3
- DXGXHTMGYMBEEU-UHFFFAOYSA-N n,n'-dimethyl-n,n'-di(piperidin-4-yl)ethane-1,2-diamine;tetrahydrochloride Chemical compound Cl.Cl.Cl.Cl.C1CNCCC1N(C)CCN(C)C1CCNCC1 DXGXHTMGYMBEEU-UHFFFAOYSA-N 0.000 description 3
- PCVOMMGITLHDAR-UHFFFAOYSA-N n-methyl-1-piperidin-4-yl-n-(piperidin-4-ylmethyl)methanamine;trihydrochloride Chemical compound Cl.Cl.Cl.C1CNCCC1CN(C)CC1CCNCC1 PCVOMMGITLHDAR-UHFFFAOYSA-N 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- ZEHMXTRWUDLFFB-UHFFFAOYSA-N tert-butyl 4-[2-[(dimethylamino)methyl]-3-[1-[(2-methylpropan-2-yl)oxycarbonyl]piperidin-4-yl]propyl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1CC(CN(C)C)CC1CCN(C(=O)OC(C)(C)C)CC1 ZEHMXTRWUDLFFB-UHFFFAOYSA-N 0.000 description 3
- OQRASJGXDJLFGJ-DQVHGGFXSA-N (2e,4e)-5-(3,4,5-trimethoxyphenyl)-1-[4-[2-[4-[(2e,4e)-5-(3,4,5-trimethoxyphenyl)penta-2,4-dienoyl]piperazin-1-yl]ethyl]piperazin-1-yl]penta-2,4-dien-1-one Chemical compound COC1=C(OC)C(OC)=CC(\C=C\C=C\C(=O)N2CCN(CCN3CCN(CC3)C(=O)\C=C\C=C\C=3C=C(OC)C(OC)=C(OC)C=3)CC2)=C1 OQRASJGXDJLFGJ-DQVHGGFXSA-N 0.000 description 2
- AVOJMQQGWGTJII-HJAKVRDMSA-N (2e,4e)-5-(3,4,5-trimethoxyphenyl)-1-[4-[3-[4-[(2e,4e)-5-(3,4,5-trimethoxyphenyl)penta-2,4-dienoyl]piperazin-1-yl]propyl]piperazin-1-yl]penta-2,4-dien-1-one Chemical compound COC1=C(OC)C(OC)=CC(\C=C\C=C\C(=O)N2CCN(CCCN3CCN(CC3)C(=O)\C=C\C=C\C=3C=C(OC)C(OC)=C(OC)C=3)CC2)=C1 AVOJMQQGWGTJII-HJAKVRDMSA-N 0.000 description 2
- HYNNSZLTBDCVCP-YDFGWWAZSA-N (2e,4e)-5-(3,4,5-trimethoxyphenyl)penta-2,4-dienoyl chloride Chemical compound COC1=CC(\C=C\C=C\C(Cl)=O)=CC(OC)=C1OC HYNNSZLTBDCVCP-YDFGWWAZSA-N 0.000 description 2
- CIWNGFZYMANOIV-DQVHGGFXSA-N (2e,4e)-5-(3,4,5-trimethylphenyl)-1-[4-[[4-[[4-[(2e,4e)-5-(3,4,5-trimethylphenyl)penta-2,4-dienoyl]piperazin-1-yl]methyl]phenyl]methyl]piperazin-1-yl]penta-2,4-dien-1-one Chemical compound CC1=C(C)C(C)=CC(\C=C\C=C\C(=O)N2CCN(CC=3C=CC(CN4CCN(CC4)C(=O)\C=C\C=C\C=4C=C(C)C(C)=C(C)C=4)=CC=3)CC2)=C1 CIWNGFZYMANOIV-DQVHGGFXSA-N 0.000 description 2
- YNBRTIPMOZZCIS-DFYQYMBYSA-N (2e,4e)-5-(4-tert-butyl-2-methoxyphenyl)-1-[4-[3-[4-[(2e,4e)-5-(4-tert-butyl-2-methoxyphenyl)penta-2,4-dienoyl]piperazin-1-yl]propyl]piperazin-1-yl]penta-2,4-dien-1-one Chemical compound COC1=CC(C(C)(C)C)=CC=C1\C=C\C=C\C(=O)N1CCN(CCCN2CCN(CC2)C(=O)\C=C\C=C\C=2C(=CC(=CC=2)C(C)(C)C)OC)CC1 YNBRTIPMOZZCIS-DFYQYMBYSA-N 0.000 description 2
- UEFHPLAYIVWGEN-JHTXPFLLSA-N (2e,4e)-5-(4-tert-butylphenyl)-1-[4-[8-[4-[(2e,4e)-5-(4-tert-butylphenyl)penta-2,4-dienoyl]piperazin-1-yl]octyl]piperazin-1-yl]penta-2,4-dien-1-one Chemical compound C1=CC(C(C)(C)C)=CC=C1\C=C\C=C\C(=O)N1CCN(CCCCCCCCN2CCN(CC2)C(=O)\C=C\C=C\C=2C=CC(=CC=2)C(C)(C)C)CC1 UEFHPLAYIVWGEN-JHTXPFLLSA-N 0.000 description 2
- PGXMSCLDDYTKNV-UHHUPYCYSA-N (2e,4e)-5-[4-(trifluoromethyl)phenyl]-1-[4-[3-[4-[(2e,4e)-5-[4-(trifluoromethyl)phenyl]penta-2,4-dienoyl]piperazin-1-yl]propyl]piperazin-1-yl]penta-2,4-dien-1-one Chemical compound C1=CC(C(F)(F)F)=CC=C1\C=C\C=C\C(=O)N1CCN(CCCN2CCN(CC2)C(=O)\C=C\C=C\C=2C=CC(=CC=2)C(F)(F)F)CC1 PGXMSCLDDYTKNV-UHHUPYCYSA-N 0.000 description 2
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 description 2
- KCEGAKABOVLGHS-JOBJLJCHSA-N (e)-1-[4-[2-(dimethylamino)-3-[1-[(e)-5-(3,4,5-trimethoxyphenyl)pent-2-en-4-ynoyl]piperidin-4-yl]propyl]piperidin-1-yl]-5-(3,4,5-trimethoxyphenyl)pent-2-en-4-yn-1-one Chemical compound COC1=C(OC)C(OC)=CC(C#C\C=C\C(=O)N2CCC(CC(CC3CCN(CC3)C(=O)\C=C\C#CC=3C=C(OC)C(OC)=C(OC)C=3)N(C)C)CC2)=C1 KCEGAKABOVLGHS-JOBJLJCHSA-N 0.000 description 2
- FZIKOOIVBDKYOE-AOEKMSOUSA-N (e)-5-(3,4,5-trimethoxyphenyl)-1-[4-[3-[4-[(e)-5-(3,4,5-trimethoxyphenyl)pent-2-en-4-ynoyl]piperazin-1-yl]propyl]piperazin-1-yl]pent-2-en-4-yn-1-one Chemical compound COC1=C(OC)C(OC)=CC(C#C\C=C\C(=O)N2CCN(CCCN3CCN(CC3)C(=O)\C=C\C#CC=3C=C(OC)C(OC)=C(OC)C=3)CC2)=C1 FZIKOOIVBDKYOE-AOEKMSOUSA-N 0.000 description 2
- IPKZARMWLZBCQJ-UTLPMFLDSA-N (e)-5-(3,4,5-trimethoxyphenyl)-1-[4-[[4-[[4-[(e)-5-(3,4,5-trimethoxyphenyl)pent-2-en-4-ynoyl]piperazin-1-yl]methyl]phenyl]methyl]piperazin-1-yl]pent-2-en-4-yn-1-one Chemical compound COC1=C(OC)C(OC)=CC(C#C\C=C\C(=O)N2CCN(CC=3C=CC(CN4CCN(CC4)C(=O)\C=C\C#CC=4C=C(OC)C(OC)=C(OC)C=4)=CC=3)CC2)=C1 IPKZARMWLZBCQJ-UTLPMFLDSA-N 0.000 description 2
- DEFCFMXORSSQOZ-UHFFFAOYSA-N 1-(4-piperazin-1-ylphenyl)piperazine Chemical compound C1CNCCN1C1=CC=C(N2CCNCC2)C=C1 DEFCFMXORSSQOZ-UHFFFAOYSA-N 0.000 description 2
- DMSAAJLTEQKUOX-UHFFFAOYSA-N 1-(8-piperazin-1-yloctyl)piperazine;tetrahydrochloride Chemical compound Cl.Cl.Cl.Cl.C1CNCCN1CCCCCCCCN1CCNCC1 DMSAAJLTEQKUOX-UHFFFAOYSA-N 0.000 description 2
- SUJMREDOOVESCO-UHFFFAOYSA-N 1-[[4-(piperazin-1-ylmethyl)cyclohexyl]methyl]piperazine;tetrahydrochloride Chemical compound Cl.Cl.Cl.Cl.C1CNCCN1CC(CC1)CCC1CN1CCNCC1 SUJMREDOOVESCO-UHFFFAOYSA-N 0.000 description 2
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- KLKBCNDBOVRQIJ-UHFFFAOYSA-N tert-butyl 4-(aminomethyl)piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(CN)CC1 KLKBCNDBOVRQIJ-UHFFFAOYSA-N 0.000 description 1
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- OEEPZAXERCKOQL-UHFFFAOYSA-N tert-butyl 4-[2-amino-3-[1-[(2-methylpropan-2-yl)oxycarbonyl]piperidin-4-yl]propyl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1CC(N)CC1CCN(C(=O)OC(C)(C)C)CC1 OEEPZAXERCKOQL-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/70—Sulfur atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/14—Decongestants or antiallergics
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- 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]
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- 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
- C07D211/08—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
- C07D211/18—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
- C07D211/26—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 nitrogen atoms
-
- 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
- C07D211/08—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
- C07D211/18—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
- C07D211/34—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 carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- 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
- C07D211/56—Nitrogen atoms
- C07D211/58—Nitrogen atoms attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
- C07D213/82—Amides; Imides in position 3
-
- 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
- C07D295/18—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 carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
-
- 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
- C07D295/18—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 carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/192—Radicals derived from carboxylic acids from aromatic carboxylic acids
-
- 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
- C07D401/14—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 three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (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)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pulmonology (AREA)
- Dermatology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Ophthalmology & Optometry (AREA)
- Immunology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP3765098 | 1998-02-19 | ||
PCT/JP1999/000659 WO1999042446A1 (fr) | 1998-02-19 | 1999-02-16 | Composes cycliques d'amide |
Publications (3)
Publication Number | Publication Date |
---|---|
NO20004092L NO20004092L (no) | 2000-08-16 |
NO20004092D0 NO20004092D0 (no) | 2000-08-16 |
NO317422B1 true NO317422B1 (no) | 2004-10-25 |
Family
ID=12503531
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO20004092A NO317422B1 (no) | 1998-02-19 | 2000-08-16 | Cyklisk amidforbindelse |
Country Status (15)
Country | Link |
---|---|
US (2) | US6448242B1 (fr) |
EP (1) | EP1057815B1 (fr) |
JP (1) | JP4388228B2 (fr) |
CN (1) | CN1114591C (fr) |
AT (1) | ATE372320T1 (fr) |
AU (1) | AU747815B2 (fr) |
BR (1) | BR9908105A (fr) |
CA (1) | CA2320971A1 (fr) |
DE (1) | DE69937045T2 (fr) |
HU (1) | HUP0104432A3 (fr) |
NO (1) | NO317422B1 (fr) |
NZ (1) | NZ505912A (fr) |
RU (1) | RU2220140C2 (fr) |
TW (1) | TW587077B (fr) |
WO (1) | WO1999042446A1 (fr) |
Families Citing this family (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
NZ514021A (en) | 1999-04-26 | 2001-09-28 | Neurosearch As | Heteroaryl diazacycloalkanes, their preparation and use |
DE10005150A1 (de) | 2000-02-07 | 2001-08-09 | Merck Patent Gmbh | Verfahren zur Herstellung von 5-Arylnicotinaldehyden |
MY131890A (en) * | 2001-03-13 | 2007-09-28 | Schering Corp | Piperidine compounds |
US6632810B2 (en) * | 2001-06-29 | 2003-10-14 | Kowa Co., Ltd. | Cyclic diamine compound with condensed-ring groups |
US6706703B2 (en) | 2001-06-29 | 2004-03-16 | Kowa Co., Ltd. | Bis(5-aryl-2-pyridyl) derivatives |
US6432957B1 (en) * | 2001-06-29 | 2002-08-13 | Kowa Co., Ltd. | Piperazine derivative |
US6890940B2 (en) | 2001-06-29 | 2005-05-10 | Kowa Co., Ltd. | Bis(2-aryl-5-pyridyl) derivatives |
US6787653B2 (en) | 2002-06-06 | 2004-09-07 | Kowa Co., Ltd. | Preparation process of biphenylcarboxylic acid amide derivatives |
US7504401B2 (en) | 2003-08-29 | 2009-03-17 | Locus Pharmaceuticals, Inc. | Anti-cancer agents and uses thereof |
US20060258691A1 (en) * | 2005-05-13 | 2006-11-16 | Joseph Barbosa | Methods and compositions for improving cognition |
WO2006124748A2 (fr) | 2005-05-13 | 2006-11-23 | Lexicon Genetics Incorporated | Composes polycycliques et procedes pour les utiliser |
WO2007115805A2 (fr) * | 2006-04-05 | 2007-10-18 | European Molecular Biology Laboratory (Embl) | Inhibiteurs de la kinase aurora |
TW200827345A (en) * | 2006-11-07 | 2008-07-01 | Lexicon Pharmaceuticals Inc | (R)-phenyl(heterocycle)methanol-based compounds, compositions comprising them and methods of their use |
TW200823193A (en) * | 2006-11-07 | 2008-06-01 | Lexicon Pharmaceuticals Inc | (S)-phenyl(heterocycle)methanol-based compounds, compositions comprising them and methods of their use |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GR81827B (fr) * | 1983-03-21 | 1984-12-12 | Boehringer Ingelheim Ltd | |
US4692448A (en) * | 1984-11-20 | 1987-09-08 | Boehringer Ingelheim Pharmaceuticals, Inc. | Bis(arylpiperazinyl)sulfur compounds |
JPH01106818A (ja) | 1987-10-20 | 1989-04-24 | Teijin Ltd | 抗アレルギー剤 |
JPH04129790A (ja) * | 1990-09-20 | 1992-04-30 | Ricoh Co Ltd | 多色感熱記録材料 |
JP2991897B2 (ja) | 1993-06-30 | 1999-12-20 | ハウス食品株式会社 | ガゼットタイプの食品充填用包装袋 |
JPH08109177A (ja) | 1994-08-18 | 1996-04-30 | Asahi Chem Ind Co Ltd | シクロアルキルアルキルアミン誘導体およびその用途 |
JP3265134B2 (ja) | 1994-09-20 | 2002-03-11 | 帝人株式会社 | 含窒素二環性複素環誘導体およびこれを含有する医薬製剤 |
CA2202904C (fr) | 1994-10-17 | 2006-12-19 | Yukio Amano | Composition preventive et remede pour les maladies allergiques de type i |
JP3808921B2 (ja) * | 1995-11-20 | 2006-08-16 | 興和株式会社 | 細胞接着阻害剤 |
-
1999
- 1999-02-16 BR BR9908105-9A patent/BR9908105A/pt not_active IP Right Cessation
- 1999-02-16 US US09/622,586 patent/US6448242B1/en not_active Expired - Fee Related
- 1999-02-16 AT AT99903925T patent/ATE372320T1/de not_active IP Right Cessation
- 1999-02-16 NZ NZ505912A patent/NZ505912A/xx unknown
- 1999-02-16 CA CA002320971A patent/CA2320971A1/fr not_active Abandoned
- 1999-02-16 AU AU24408/99A patent/AU747815B2/en not_active Ceased
- 1999-02-16 DE DE69937045T patent/DE69937045T2/de not_active Expired - Lifetime
- 1999-02-16 HU HU0104432A patent/HUP0104432A3/hu unknown
- 1999-02-16 JP JP2000532398A patent/JP4388228B2/ja not_active Expired - Lifetime
- 1999-02-16 WO PCT/JP1999/000659 patent/WO1999042446A1/fr active IP Right Grant
- 1999-02-16 RU RU2000124097/04A patent/RU2220140C2/ru not_active IP Right Cessation
- 1999-02-16 EP EP99903925A patent/EP1057815B1/fr not_active Expired - Lifetime
- 1999-02-16 CN CN99803094A patent/CN1114591C/zh not_active Expired - Fee Related
- 1999-02-19 TW TW088102504A patent/TW587077B/zh not_active IP Right Cessation
-
2000
- 2000-08-16 NO NO20004092A patent/NO317422B1/no unknown
-
2002
- 2002-06-19 US US10/173,670 patent/US6645957B2/en not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
CA2320971A1 (fr) | 1999-08-26 |
NO20004092L (no) | 2000-08-16 |
CN1291186A (zh) | 2001-04-11 |
HUP0104432A2 (hu) | 2002-04-29 |
HUP0104432A3 (en) | 2003-04-28 |
RU2220140C2 (ru) | 2003-12-27 |
ATE372320T1 (de) | 2007-09-15 |
TW587077B (en) | 2004-05-11 |
WO1999042446A1 (fr) | 1999-08-26 |
EP1057815A4 (fr) | 2004-12-08 |
US20030096828A1 (en) | 2003-05-22 |
US6448242B1 (en) | 2002-09-10 |
NO20004092D0 (no) | 2000-08-16 |
EP1057815A1 (fr) | 2000-12-06 |
JP4388228B2 (ja) | 2009-12-24 |
AU2440899A (en) | 1999-09-06 |
CN1114591C (zh) | 2003-07-16 |
DE69937045D1 (de) | 2007-10-18 |
NZ505912A (en) | 2002-09-27 |
DE69937045T2 (de) | 2008-05-29 |
EP1057815B1 (fr) | 2007-09-05 |
AU747815B2 (en) | 2002-05-23 |
BR9908105A (pt) | 2000-10-17 |
US6645957B2 (en) | 2003-11-11 |
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