NO327074B1 - Cyklisk aminforbindelse, slike forbindelser for bruk som medikament, farmasoytiske blandinger inneholdende slike samt anvendelse av disse for fremstilling av medisin for behandling av sykdommer. - Google Patents
Cyklisk aminforbindelse, slike forbindelser for bruk som medikament, farmasoytiske blandinger inneholdende slike samt anvendelse av disse for fremstilling av medisin for behandling av sykdommer. Download PDFInfo
- Publication number
- NO327074B1 NO327074B1 NO20040877A NO20040877A NO327074B1 NO 327074 B1 NO327074 B1 NO 327074B1 NO 20040877 A NO20040877 A NO 20040877A NO 20040877 A NO20040877 A NO 20040877A NO 327074 B1 NO327074 B1 NO 327074B1
- Authority
- NO
- Norway
- Prior art keywords
- trimethoxyphenyl
- methyl
- piperidine
- pyridin
- synthesis
- Prior art date
Links
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- -1 Cyclic amine compound Chemical class 0.000 title claims description 98
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims description 7
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- 238000002360 preparation method Methods 0.000 claims description 39
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- 230000008595 infiltration Effects 0.000 claims description 19
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- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 125000003342 alkenyl group Chemical group 0.000 claims description 11
- 125000000304 alkynyl group Chemical group 0.000 claims description 11
- 208000021386 Sjogren Syndrome Diseases 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
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- 229910052736 halogen Inorganic materials 0.000 claims description 7
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- 206010020751 Hypersensitivity Diseases 0.000 claims description 6
- 208000026935 allergic disease Diseases 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000004414 alkyl thio group Chemical group 0.000 claims description 5
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- 125000001424 substituent group Chemical group 0.000 claims description 2
- 239000000543 intermediate Substances 0.000 description 343
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- 238000003786 synthesis reaction Methods 0.000 description 259
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 209
- 238000005160 1H NMR spectroscopy Methods 0.000 description 179
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- 239000012458 free base Substances 0.000 description 90
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- 150000003840 hydrochlorides Chemical class 0.000 description 17
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- 150000001805 chlorine compounds Chemical class 0.000 description 16
- 238000004440 column chromatography Methods 0.000 description 16
- UPMRLMOBRSDTLI-UHFFFAOYSA-N 3-(chloromethyl)-5-(3,4,5-trimethoxyphenyl)pyridine Chemical compound COC1=C(OC)C(OC)=CC(C=2C=C(CCl)C=NC=2)=C1 UPMRLMOBRSDTLI-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 150000001412 amines Chemical class 0.000 description 15
- 210000004027 cell Anatomy 0.000 description 15
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 14
- 239000003795 chemical substances by application Substances 0.000 description 14
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- 239000003921 oil Substances 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000003480 eluent Substances 0.000 description 12
- 230000002401 inhibitory effect Effects 0.000 description 12
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 12
- 229920006395 saturated elastomer Polymers 0.000 description 12
- 125000004938 5-pyridyl group Chemical group N1=CC=CC(=C1)* 0.000 description 11
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 11
- 210000000265 leukocyte Anatomy 0.000 description 11
- 235000002639 sodium chloride Nutrition 0.000 description 11
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 10
- ZSUFBKHEFBKBDJ-UHFFFAOYSA-N tert-butyl 4-(4-methoxyanilino)piperidine-1-carboxylate Chemical compound C1=CC(OC)=CC=C1NC1CCN(C(=O)OC(C)(C)C)CC1 ZSUFBKHEFBKBDJ-UHFFFAOYSA-N 0.000 description 10
- ROUYFJUVMYHXFJ-UHFFFAOYSA-N tert-butyl 4-oxopiperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(=O)CC1 ROUYFJUVMYHXFJ-UHFFFAOYSA-N 0.000 description 10
- 238000012360 testing method Methods 0.000 description 10
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 10
- 239000012467 final product Substances 0.000 description 9
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- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 9
- 235000017557 sodium bicarbonate Nutrition 0.000 description 9
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- 125000003710 aryl alkyl group Chemical group 0.000 description 8
- 230000002757 inflammatory effect Effects 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- WPHUUIODWRNJLO-UHFFFAOYSA-N 2-nitrobenzenesulfonyl chloride Chemical compound [O-][N+](=O)C1=CC=CC=C1S(Cl)(=O)=O WPHUUIODWRNJLO-UHFFFAOYSA-N 0.000 description 7
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- LWMPFIOTEAXAGV-UHFFFAOYSA-N piperidin-1-amine Chemical class NN1CCCCC1 LWMPFIOTEAXAGV-UHFFFAOYSA-N 0.000 description 7
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- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 7
- RULQUTYJXDLRFL-UHFFFAOYSA-N (3,4,5-trimethoxyphenyl)boronic acid Chemical compound COC1=CC(B(O)O)=CC(OC)=C1OC RULQUTYJXDLRFL-UHFFFAOYSA-N 0.000 description 6
- GNUTYFLMOHIJKQ-UHFFFAOYSA-N 5-[2-(chloromethyl)phenyl]-1,2,3-trimethoxybenzene Chemical compound COC1=C(OC)C(OC)=CC(C=2C(=CC=CC=2)CCl)=C1 GNUTYFLMOHIJKQ-UHFFFAOYSA-N 0.000 description 6
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- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
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- 239000010410 layer Substances 0.000 description 6
- CUPNTLOAPAPLPS-UHFFFAOYSA-N n-benzyl-1-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]piperidin-4-amine Chemical compound COC1=C(OC)C(OC)=CC(C=2N=CC=C(CN3CCC(CC3)NCC=3C=CC=CC=3)C=2)=C1 CUPNTLOAPAPLPS-UHFFFAOYSA-N 0.000 description 6
- 238000000746 purification Methods 0.000 description 6
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- FLBYXCQUWKHXHB-UHFFFAOYSA-N 1-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]piperidin-4-one Chemical compound COC1=C(OC)C(OC)=CC(C=2N=CC=C(CN3CCC(=O)CC3)C=2)=C1 FLBYXCQUWKHXHB-UHFFFAOYSA-N 0.000 description 5
- OKWNDHFPWXJEHM-UHFFFAOYSA-N 2-(3,4,5-trimethoxyphenyl)pyridine Chemical compound COC1=C(OC)C(OC)=CC(C=2N=CC=CC=2)=C1 OKWNDHFPWXJEHM-UHFFFAOYSA-N 0.000 description 5
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 5
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- 101150041968 CDC13 gene Proteins 0.000 description 5
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- IXAFYHFNZFZYDI-UHFFFAOYSA-N n-(3-methylsulfanylphenyl)-1-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]piperidin-4-amine Chemical compound COC1=C(OC)C(OC)=CC(C=2N=CC=C(CN3CCC(CC3)NC=3C=C(SC)C=CC=3)C=2)=C1 IXAFYHFNZFZYDI-UHFFFAOYSA-N 0.000 description 5
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- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 4
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- 239000012280 lithium aluminium hydride Substances 0.000 description 4
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 4
- 238000010172 mouse model Methods 0.000 description 4
- VOWJPYFFGLZMRS-UHFFFAOYSA-N n-(4-butylphenyl)-1-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]piperidin-4-amine Chemical compound C1=CC(CCCC)=CC=C1NC1CCN(CC=2C=C(N=CC=2)C=2C=C(OC)C(OC)=C(OC)C=2)CC1 VOWJPYFFGLZMRS-UHFFFAOYSA-N 0.000 description 4
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 4
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical class C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000012453 solvate Substances 0.000 description 4
- CSRZQMIRAZTJOY-UHFFFAOYSA-N trimethylsilyl iodide Chemical compound C[Si](C)(C)I CSRZQMIRAZTJOY-UHFFFAOYSA-N 0.000 description 4
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 3
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
- 125000005809 3,4,5-trimethoxyphenyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 3
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- AMBAUMZEGSXEMH-UHFFFAOYSA-N tert-butyl 4-(3,4-difluoroanilino)-2-oxopiperidine-1-carboxylate Chemical compound C1C(=O)N(C(=O)OC(C)(C)C)CCC1NC1=CC=C(F)C(F)=C1 AMBAUMZEGSXEMH-UHFFFAOYSA-N 0.000 description 1
- CSNCRRGPAWIBOE-UHFFFAOYSA-N tert-butyl 4-(4-butoxyanilino)piperidine-1-carboxylate Chemical compound C1=CC(OCCCC)=CC=C1NC1CCN(C(=O)OC(C)(C)C)CC1 CSNCRRGPAWIBOE-UHFFFAOYSA-N 0.000 description 1
- JSLCGLDYCFQAPJ-UHFFFAOYSA-N tert-butyl 4-(4-chloroanilino)piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1NC1=CC=C(Cl)C=C1 JSLCGLDYCFQAPJ-UHFFFAOYSA-N 0.000 description 1
- WQRRYURNCWSHJE-UHFFFAOYSA-N tert-butyl 4-(4-ethoxyanilino)piperidine-1-carboxylate Chemical compound C1=CC(OCC)=CC=C1NC1CCN(C(=O)OC(C)(C)C)CC1 WQRRYURNCWSHJE-UHFFFAOYSA-N 0.000 description 1
- TUYSUNKDSSHKHM-UHFFFAOYSA-N tert-butyl 4-(4-fluoroanilino)piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1NC1=CC=C(F)C=C1 TUYSUNKDSSHKHM-UHFFFAOYSA-N 0.000 description 1
- DNIYLSKPGSXPON-UHFFFAOYSA-N tert-butyl 4-[2-methoxy-n-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]anilino]piperidine-1-carboxylate Chemical compound COC1=CC=CC=C1N(C1CCN(CC1)C(=O)OC(C)(C)C)CC1=CC=NC(C=2C=C(OC)C(OC)=C(OC)C=2)=C1 DNIYLSKPGSXPON-UHFFFAOYSA-N 0.000 description 1
- CPBDXRXCDRFOEY-UHFFFAOYSA-N tert-butyl 4-[2-methoxy-n-[[3-(3,4,5-trimethoxyphenyl)phenyl]methyl]anilino]piperidine-1-carboxylate Chemical compound COC1=CC=CC=C1N(C1CCN(CC1)C(=O)OC(C)(C)C)CC1=CC=CC(C=2C=C(OC)C(OC)=C(OC)C=2)=C1 CPBDXRXCDRFOEY-UHFFFAOYSA-N 0.000 description 1
- LTUPGDHQPJSDIA-UHFFFAOYSA-N tert-butyl 4-[2-methoxy-n-[[5-(3,4,5-trimethoxyphenyl)pyridin-3-yl]methyl]anilino]piperidine-1-carboxylate Chemical compound COC1=CC=CC=C1N(C1CCN(CC1)C(=O)OC(C)(C)C)CC1=CN=CC(C=2C=C(OC)C(OC)=C(OC)C=2)=C1 LTUPGDHQPJSDIA-UHFFFAOYSA-N 0.000 description 1
- SDVXCBBIPWQXQE-UHFFFAOYSA-N tert-butyl 4-[3,4-difluoro-n-[[3-(3,4,5-trimethoxyphenyl)phenyl]methyl]anilino]piperidine-1-carboxylate Chemical compound COC1=C(OC)C(OC)=CC(C=2C=C(CN(C3CCN(CC3)C(=O)OC(C)(C)C)C=3C=C(F)C(F)=CC=3)C=CC=2)=C1 SDVXCBBIPWQXQE-UHFFFAOYSA-N 0.000 description 1
- GSYRYOFVGBBHON-UHFFFAOYSA-N tert-butyl 4-[3-methoxy-n-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]anilino]piperidine-1-carboxylate Chemical compound COC1=CC=CC(N(CC=2C=C(N=CC=2)C=2C=C(OC)C(OC)=C(OC)C=2)C2CCN(CC2)C(=O)OC(C)(C)C)=C1 GSYRYOFVGBBHON-UHFFFAOYSA-N 0.000 description 1
- AESCETLYESRMKJ-UHFFFAOYSA-N tert-butyl 4-[3-methoxy-n-[[5-(3,4,5-trimethoxyphenyl)pyridin-3-yl]methyl]anilino]piperidine-1-carboxylate Chemical compound COC1=CC=CC(N(CC=2C=C(C=NC=2)C=2C=C(OC)C(OC)=C(OC)C=2)C2CCN(CC2)C(=O)OC(C)(C)C)=C1 AESCETLYESRMKJ-UHFFFAOYSA-N 0.000 description 1
- JDJNNXICMZCXNQ-UHFFFAOYSA-N tert-butyl 4-[4-(trifluoromethoxy)-n-[[2-[3,4,5-tris(fluoromethoxy)phenyl]pyridin-4-yl]methyl]anilino]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1N(C=1C=CC(OC(F)(F)F)=CC=1)CC1=CC=NC(C=2C=C(OCF)C(OCF)=C(OCF)C=2)=C1 JDJNNXICMZCXNQ-UHFFFAOYSA-N 0.000 description 1
- FNPBBBAMBSBMIN-UHFFFAOYSA-N tert-butyl 4-[4-(trifluoromethoxy)-n-[[5-(3,4,5-trimethoxyphenyl)pyridin-3-yl]methyl]anilino]piperidine-1-carboxylate Chemical compound COC1=C(OC)C(OC)=CC(C=2C=C(CN(C3CCN(CC3)C(=O)OC(C)(C)C)C=3C=CC(OC(F)(F)F)=CC=3)C=NC=2)=C1 FNPBBBAMBSBMIN-UHFFFAOYSA-N 0.000 description 1
- FWNMCPIBSVPQHW-UHFFFAOYSA-N tert-butyl 4-[4-(trifluoromethyl)-n-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]anilino]piperidine-1-carboxylate Chemical compound COC1=C(OC)C(OC)=CC(C=2N=CC=C(CN(C3CCN(CC3)C(=O)OC(C)(C)C)C=3C=CC(=CC=3)C(F)(F)F)C=2)=C1 FWNMCPIBSVPQHW-UHFFFAOYSA-N 0.000 description 1
- SQVQLBKTRAIVIY-UHFFFAOYSA-N tert-butyl 4-[4-(trifluoromethyl)-n-[[3-(3,4,5-trimethoxyphenyl)phenyl]methyl]anilino]piperidine-1-carboxylate Chemical compound COC1=C(OC)C(OC)=CC(C=2C=C(CN(C3CCN(CC3)C(=O)OC(C)(C)C)C=3C=CC(=CC=3)C(F)(F)F)C=CC=2)=C1 SQVQLBKTRAIVIY-UHFFFAOYSA-N 0.000 description 1
- GLZPYGZMEFJROR-UHFFFAOYSA-N tert-butyl 4-[4-bromo-n-[[5-(3,4,5-trimethoxyphenyl)pyridin-3-yl]methyl]anilino]piperidine-1-carboxylate Chemical compound COC1=C(OC)C(OC)=CC(C=2C=C(CN(C3CCN(CC3)C(=O)OC(C)(C)C)C=3C=CC(Br)=CC=3)C=NC=2)=C1 GLZPYGZMEFJROR-UHFFFAOYSA-N 0.000 description 1
- VJVKFAXWJUWYHX-UHFFFAOYSA-N tert-butyl 4-[4-butoxy-n-[[3-(3,4,5-trimethoxyphenyl)phenyl]methyl]anilino]piperidine-1-carboxylate Chemical compound C1=CC(OCCCC)=CC=C1N(C1CCN(CC1)C(=O)OC(C)(C)C)CC1=CC=CC(C=2C=C(OC)C(OC)=C(OC)C=2)=C1 VJVKFAXWJUWYHX-UHFFFAOYSA-N 0.000 description 1
- OXXDZXJPPCJQEW-UHFFFAOYSA-N tert-butyl 4-[4-chloro-n-[[3-(3,4,5-trimethoxyphenyl)phenyl]methyl]anilino]piperidine-1-carboxylate Chemical compound COC1=C(OC)C(OC)=CC(C=2C=C(CN(C3CCN(CC3)C(=O)OC(C)(C)C)C=3C=CC(Cl)=CC=3)C=CC=2)=C1 OXXDZXJPPCJQEW-UHFFFAOYSA-N 0.000 description 1
- SLWAAYQWHUYBTN-UHFFFAOYSA-N tert-butyl 4-[4-ethoxy-n-[[3-(3,4,5-trimethoxyphenyl)phenyl]methyl]anilino]piperidine-1-carboxylate Chemical compound C1=CC(OCC)=CC=C1N(C1CCN(CC1)C(=O)OC(C)(C)C)CC1=CC=CC(C=2C=C(OC)C(OC)=C(OC)C=2)=C1 SLWAAYQWHUYBTN-UHFFFAOYSA-N 0.000 description 1
- UYNWBAFBEGGNIE-UHFFFAOYSA-N tert-butyl 4-[4-fluoro-n-[[3-(3,4,5-trimethoxyphenyl)phenyl]methyl]anilino]piperidine-1-carboxylate Chemical compound COC1=C(OC)C(OC)=CC(C=2C=C(CN(C3CCN(CC3)C(=O)OC(C)(C)C)C=3C=CC(F)=CC=3)C=CC=2)=C1 UYNWBAFBEGGNIE-UHFFFAOYSA-N 0.000 description 1
- JWWBXXZAYYPWPY-UHFFFAOYSA-N tert-butyl 4-[4-methoxy-n-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]anilino]piperidine-1-carboxylate Chemical compound C1=CC(OC)=CC=C1N(C1CCN(CC1)C(=O)OC(C)(C)C)CC1=CC=NC(C=2C=C(OC)C(OC)=C(OC)C=2)=C1 JWWBXXZAYYPWPY-UHFFFAOYSA-N 0.000 description 1
- ZGQOXAXQQWSLJF-UHFFFAOYSA-N tert-butyl 4-[4-methoxy-n-[[5-(3,4,5-trimethoxyphenyl)pyridin-3-yl]methyl]anilino]piperidine-1-carboxylate Chemical compound C1=CC(OC)=CC=C1N(C1CCN(CC1)C(=O)OC(C)(C)C)CC1=CN=CC(C=2C=C(OC)C(OC)=C(OC)C=2)=C1 ZGQOXAXQQWSLJF-UHFFFAOYSA-N 0.000 description 1
- JNSLVWXPAYPJRW-UHFFFAOYSA-N tert-butyl 4-[4-methyl-n-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]anilino]piperidine-1-carboxylate Chemical compound COC1=C(OC)C(OC)=CC(C=2N=CC=C(CN(C3CCN(CC3)C(=O)OC(C)(C)C)C=3C=CC(C)=CC=3)C=2)=C1 JNSLVWXPAYPJRW-UHFFFAOYSA-N 0.000 description 1
- JPBKFPQAXVEHOB-UHFFFAOYSA-N tert-butyl 4-[4-methyl-n-[[3-(3,4,5-trimethoxyphenyl)phenyl]methyl]anilino]piperidine-1-carboxylate Chemical compound COC1=C(OC)C(OC)=CC(C=2C=C(CN(C3CCN(CC3)C(=O)OC(C)(C)C)C=3C=CC(C)=CC=3)C=CC=2)=C1 JPBKFPQAXVEHOB-UHFFFAOYSA-N 0.000 description 1
- VESDQPWJIFGCBT-UHFFFAOYSA-N tert-butyl 4-[4-methylsulfanyl-n-[[3-(3,4,5-trimethoxyphenyl)phenyl]methyl]anilino]piperidine-1-carboxylate Chemical compound COC1=C(OC)C(OC)=CC(C=2C=C(CN(C3CCN(CC3)C(=O)OC(C)(C)C)C=3C=CC(SC)=CC=3)C=CC=2)=C1 VESDQPWJIFGCBT-UHFFFAOYSA-N 0.000 description 1
- SHQZVRJTEDSZLV-UHFFFAOYSA-N tert-butyl 4-[4-methylsulfanyl-n-[[5-(3,4,5-trimethoxyphenyl)pyridin-3-yl]methyl]anilino]piperidine-1-carboxylate Chemical compound COC1=C(OC)C(OC)=CC(C=2C=C(CN(C3CCN(CC3)C(=O)OC(C)(C)C)C=3C=CC(SC)=CC=3)C=NC=2)=C1 SHQZVRJTEDSZLV-UHFFFAOYSA-N 0.000 description 1
- URZOWJSOWKKDGB-UHFFFAOYSA-N tert-butyl 4-[n-[[2-(3,4-dimethoxyphenyl)pyridin-4-yl]methyl]-4-methoxyanilino]piperidine-1-carboxylate Chemical compound C1=CC(OC)=CC=C1N(C1CCN(CC1)C(=O)OC(C)(C)C)CC1=CC=NC(C=2C=C(OC)C(OC)=CC=2)=C1 URZOWJSOWKKDGB-UHFFFAOYSA-N 0.000 description 1
- VCKXRGXJSOLLGH-UHFFFAOYSA-N tert-butyl 4-[n-[[2-(4-ethoxyphenyl)pyridin-4-yl]methyl]-4-methoxyanilino]piperidine-1-carboxylate Chemical compound C1=CC(OCC)=CC=C1C1=CC(CN(C2CCN(CC2)C(=O)OC(C)(C)C)C=2C=CC(OC)=CC=2)=CC=N1 VCKXRGXJSOLLGH-UHFFFAOYSA-N 0.000 description 1
- XWKUMYOXZKWURS-UHFFFAOYSA-N tert-butyl 4-[n-[[3-(3,4,5-trimethoxyphenyl)phenyl]methyl]anilino]piperidine-1-carboxylate Chemical compound COC1=C(OC)C(OC)=CC(C=2C=C(CN(C3CCN(CC3)C(=O)OC(C)(C)C)C=3C=CC=CC=3)C=CC=2)=C1 XWKUMYOXZKWURS-UHFFFAOYSA-N 0.000 description 1
- XUNKQAKFXFVKLV-UHFFFAOYSA-N tert-butyl 4-[n-[[5-(3,4,5-trimethoxyphenyl)pyridin-3-yl]methyl]anilino]piperidine-1-carboxylate Chemical compound COC1=C(OC)C(OC)=CC(C=2C=C(CN(C3CCN(CC3)C(=O)OC(C)(C)C)C=3C=CC=CC=3)C=NC=2)=C1 XUNKQAKFXFVKLV-UHFFFAOYSA-N 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 210000003606 umbilical vein Anatomy 0.000 description 1
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
- 235000012141 vanillin Nutrition 0.000 description 1
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
- 239000003871 white petrolatum Substances 0.000 description 1
Classifications
-
- 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
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
- A61K31/4545—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring hetero atom, e.g. pipamperone, anabasine
-
- 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
- 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
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- 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
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- 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
- 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
- C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D211/62—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals 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
- 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
-
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Pulmonology (AREA)
- Epidemiology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Urology & Nephrology (AREA)
- Immunology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Vascular Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US09/941,684 US6395753B1 (en) | 2001-08-30 | 2001-08-30 | Cyclic amine compounds and pharmaceutical composition containing the same |
US09/983,928 US6498169B1 (en) | 2001-08-30 | 2001-10-26 | Cyclic amine compounds and pharmaceutical composition containing the same |
US10/107,180 US6605620B1 (en) | 2001-08-30 | 2002-03-28 | Cyclic amine compounds and pharmaceutical composition containing the same |
US10/191,534 US6867221B2 (en) | 2001-08-30 | 2002-07-10 | Cyclic amine compounds and pharmaceutical composition containing the same |
PCT/JP2002/008650 WO2003020703A1 (fr) | 2001-08-30 | 2002-08-28 | Compose d'amine cyclique |
Publications (2)
Publication Number | Publication Date |
---|---|
NO20040877L NO20040877L (no) | 2004-02-25 |
NO327074B1 true NO327074B1 (no) | 2009-04-14 |
Family
ID=27493564
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO20040877A NO327074B1 (no) | 2001-08-30 | 2004-02-25 | Cyklisk aminforbindelse, slike forbindelser for bruk som medikament, farmasoytiske blandinger inneholdende slike samt anvendelse av disse for fremstilling av medisin for behandling av sykdommer. |
Country Status (10)
Country | Link |
---|---|
US (1) | US6867221B2 (zh) |
EP (1) | EP1422219A4 (zh) |
CN (1) | CN100406441C (zh) |
AU (1) | AU2002328576B8 (zh) |
CA (1) | CA2461963C (zh) |
HU (1) | HUP0401733A3 (zh) |
NO (1) | NO327074B1 (zh) |
NZ (1) | NZ531498A (zh) |
TW (1) | TWI254706B (zh) |
WO (1) | WO2003020703A1 (zh) |
Families Citing this family (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
MY134200A (en) * | 2002-04-12 | 2007-11-30 | Kowa Co | Method for treating cancer |
EP1568691A4 (en) * | 2002-12-06 | 2010-08-25 | Kowa Co | ACCELERATOR FOR ERYTHROPOETIN PRODUCTION |
MXPA05009771A (es) | 2003-03-14 | 2005-10-26 | Ono Pharmaceutical Co | Derivados heterociclicos que contienen nitrogeno y medicamentos que los contienen como el ingrediente activo. |
EP1674100A4 (en) * | 2003-10-10 | 2010-04-14 | Kowa Co | INHIBITOR OF ANGIOGENESIS |
ES2331579T3 (es) * | 2004-08-27 | 2010-01-08 | Astellas Pharma Inc. | Derivado de 2-fenilpiridina. |
AU2005283326B2 (en) | 2004-09-13 | 2011-07-21 | Ono Pharmaceutical Co., Ltd. | Nitrogenous heterocyclic derivative and medicine containing the same as an active ingredient |
WO2006082834A1 (ja) * | 2005-02-02 | 2006-08-10 | Kowa Co., Ltd. | ケラチノサイト増殖に起因する疾患の予防・治療剤 |
BRPI0708731A2 (pt) | 2006-03-10 | 2011-06-07 | Ono Pharmaceutical Co | derivado heterocìclico nitrogenado, e agente farmacêutico compreendendo o derivado como ingrediente ativo |
EP2080759A4 (en) | 2006-10-13 | 2011-01-12 | Kowa Co | INDUCER OF -GLOBINE GAMA |
US8071779B2 (en) | 2006-12-18 | 2011-12-06 | Inspire Pharmaceuticals, Inc. | Cytoskeletal active rho kinase inhibitor compounds, composition and use |
US20100022517A1 (en) * | 2006-12-18 | 2010-01-28 | Richards Lori A | Ophthalmic formulation of rho kinase inhibitor compound |
US7858666B2 (en) | 2007-06-08 | 2010-12-28 | Mannkind Corporation | IRE-1α inhibitors |
US8809538B2 (en) | 2009-01-12 | 2014-08-19 | Array Biopharma Inc. | Piperidine-containing compounds and use thereof |
BR112014010401A8 (pt) | 2011-11-03 | 2017-12-19 | Theravance Inc | Inibidores do vírus da hepatite c rod-like que contêm o fragmento {2-[4-(bifenil-4-il)-1h-imidazo-2-il] pirrolidina-1-carbonilmetil}amina |
GB201708652D0 (en) | 2017-05-31 | 2017-07-12 | Mission Therapeutics Ltd | Novel compounds and uses |
Family Cites Families (18)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CH514581A (de) * | 1967-02-21 | 1971-10-31 | Sandoz Ag | Verfahren zur Herstellung neuer Essigsäure-Derivate |
US3546229A (en) * | 1967-07-14 | 1970-12-08 | Sandoz Ag | Derivatives of acetic acid |
JPH0971564A (ja) * | 1995-07-06 | 1997-03-18 | Japan Tobacco Inc | ベンズアミドオキシム誘導体及びその医薬用途 |
JP3808921B2 (ja) * | 1995-11-20 | 2006-08-16 | 興和株式会社 | 細胞接着阻害剤 |
WO1997040837A1 (en) | 1996-04-30 | 1997-11-06 | Hoechst Marion Roussel, Inc. | Method of inhibiting vascular cell adhesion molecule-1 and treating chronic inflammatory diseases with 2,6-di-alkyl-4-silyl-phenols |
JP3577183B2 (ja) | 1996-06-17 | 2004-10-13 | 花王株式会社 | 動脈硬化症予防・治療剤 |
WO1998016497A1 (fr) * | 1996-10-11 | 1998-04-23 | Kowa Co., Ltd. | Nouveaux composes de diamide et medicaments les contenant |
JPH10147568A (ja) | 1996-11-19 | 1998-06-02 | Mitsui Chem Inc | ナフタレン誘導体およびそれを有効成分として含有する医薬品 |
JPH10182550A (ja) | 1996-12-25 | 1998-07-07 | Mitsui Chem Inc | ヒドロキシ安息香酸誘導体およびそれを有効成分として含有する医薬品 |
JPH1193282A (ja) * | 1997-09-19 | 1999-04-06 | Ronbikku Japan:Kk | 建築部材間のシール装置 |
JP4139453B2 (ja) | 1997-09-24 | 2008-08-27 | 興和株式会社 | 細胞接着阻害剤 |
JP2000086641A (ja) | 1998-09-11 | 2000-03-28 | Kyorin Pharmaceut Co Ltd | 2−置換ベンゾチアゾール誘導体及びその製造法 |
JP2000319277A (ja) | 1999-05-11 | 2000-11-21 | Ono Pharmaceut Co Ltd | 縮合ピラジン化合物およびその化合物を有効成分とする薬剤 |
EP1179341B1 (en) * | 1999-05-18 | 2005-11-09 | Teijin Limited | Remedies or preventives for diseases in association with chemokines |
AU779610B2 (en) * | 1999-08-04 | 2005-02-03 | Teijin Limited | Cyclic amine CCR3 antagonists |
SE9902987D0 (sv) | 1999-08-24 | 1999-08-24 | Astra Pharma Prod | Novel compounds |
WO2002020477A1 (fr) | 2000-09-07 | 2002-03-14 | Kowa Co., Ltd. | Inhibiteurs de l'apoptose |
US6395753B1 (en) | 2001-08-30 | 2002-05-28 | Kowa Co., Ltd. | Cyclic amine compounds and pharmaceutical composition containing the same |
-
2002
- 2002-07-10 US US10/191,534 patent/US6867221B2/en not_active Expired - Fee Related
- 2002-08-28 CA CA2461963A patent/CA2461963C/en not_active Expired - Fee Related
- 2002-08-28 EP EP02762881A patent/EP1422219A4/en not_active Withdrawn
- 2002-08-28 CN CNB028171403A patent/CN100406441C/zh not_active Expired - Fee Related
- 2002-08-28 NZ NZ531498A patent/NZ531498A/en not_active IP Right Cessation
- 2002-08-28 WO PCT/JP2002/008650 patent/WO2003020703A1/ja active IP Right Grant
- 2002-08-28 AU AU2002328576A patent/AU2002328576B8/en not_active Ceased
- 2002-08-28 HU HU0401733A patent/HUP0401733A3/hu unknown
- 2002-08-29 TW TW091119680A patent/TWI254706B/zh not_active IP Right Cessation
-
2004
- 2004-02-25 NO NO20040877A patent/NO327074B1/no not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
TWI254706B (en) | 2006-05-11 |
EP1422219A1 (en) | 2004-05-26 |
CN1604893A (zh) | 2005-04-06 |
NO20040877L (no) | 2004-02-25 |
AU2002328576B8 (en) | 2008-05-15 |
NZ531498A (en) | 2005-07-29 |
HUP0401733A3 (en) | 2009-06-29 |
CN100406441C (zh) | 2008-07-30 |
WO2003020703A1 (fr) | 2003-03-13 |
AU2002328576B2 (en) | 2008-04-03 |
CA2461963A1 (en) | 2003-03-13 |
HUP0401733A2 (hu) | 2004-12-28 |
EP1422219A4 (en) | 2005-08-17 |
US6867221B2 (en) | 2005-03-15 |
US20040010147A1 (en) | 2004-01-15 |
CA2461963C (en) | 2010-08-17 |
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