SK6112003A3 - Amidoalkyl-piperidine and amidoalkyl-piperazine derivatives for the treatment of nervous system disorders - Google Patents
Amidoalkyl-piperidine and amidoalkyl-piperazine derivatives for the treatment of nervous system disorders Download PDFInfo
- Publication number
- SK6112003A3 SK6112003A3 SK611-2003A SK6112003A SK6112003A3 SK 6112003 A3 SK6112003 A3 SK 6112003A3 SK 6112003 A SK6112003 A SK 6112003A SK 6112003 A3 SK6112003 A3 SK 6112003A3
- Authority
- SK
- Slovakia
- Prior art keywords
- group
- alkyl
- phenyl
- heteroaryl
- aryl
- Prior art date
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- 238000011282 treatment Methods 0.000 title claims abstract description 53
- 208000012902 Nervous system disease Diseases 0.000 title claims description 9
- 229940066771 systemic antihistamines piperazine derivative Drugs 0.000 title abstract description 4
- 208000019901 Anxiety disease Diseases 0.000 claims abstract description 42
- 230000036506 anxiety Effects 0.000 claims abstract description 39
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 27
- 206010047700 Vomiting Diseases 0.000 claims abstract description 22
- 208000002193 Pain Diseases 0.000 claims abstract description 19
- 208000004296 neuralgia Diseases 0.000 claims abstract description 13
- 208000021722 neuropathic pain Diseases 0.000 claims abstract description 11
- 208000020925 Bipolar disease Diseases 0.000 claims abstract description 10
- 208000019695 Migraine disease Diseases 0.000 claims abstract description 10
- 208000003251 Pruritus Diseases 0.000 claims abstract description 10
- 208000005298 acute pain Diseases 0.000 claims abstract description 10
- 201000000980 schizophrenia Diseases 0.000 claims abstract description 10
- 208000016285 Movement disease Diseases 0.000 claims abstract description 7
- 206010012289 Dementia Diseases 0.000 claims abstract description 6
- 230000007803 itching Effects 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 375
- -1 nitro, cyano, amino Chemical group 0.000 claims description 199
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 137
- 125000003118 aryl group Chemical group 0.000 claims description 84
- 125000001072 heteroaryl group Chemical group 0.000 claims description 83
- 239000000203 mixture Substances 0.000 claims description 72
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 70
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 69
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 63
- 125000001424 substituent group Chemical group 0.000 claims description 63
- 125000000217 alkyl group Chemical group 0.000 claims description 43
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 43
- 229910052736 halogen Inorganic materials 0.000 claims description 40
- 238000000034 method Methods 0.000 claims description 40
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 38
- 229910052739 hydrogen Inorganic materials 0.000 claims description 35
- 150000002367 halogens Chemical class 0.000 claims description 31
- 239000001257 hydrogen Substances 0.000 claims description 31
- 229910052757 nitrogen Inorganic materials 0.000 claims description 31
- 229910052799 carbon Inorganic materials 0.000 claims description 27
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 27
- 150000003839 salts Chemical class 0.000 claims description 24
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 23
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 22
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 21
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 21
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 21
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 20
- 201000010099 disease Diseases 0.000 claims description 20
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 17
- 125000002757 morpholinyl group Chemical group 0.000 claims description 16
- 150000002431 hydrogen Chemical class 0.000 claims description 15
- 125000002950 monocyclic group Chemical group 0.000 claims description 14
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 14
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 13
- 239000008194 pharmaceutical composition Substances 0.000 claims description 13
- 125000005936 piperidyl group Chemical group 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 11
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 11
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 10
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 210000000653 nervous system Anatomy 0.000 claims description 9
- 239000003937 drug carrier Substances 0.000 claims description 8
- 125000004193 piperazinyl group Chemical group 0.000 claims description 8
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 7
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 7
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 7
- 125000004076 pyridyl group Chemical group 0.000 claims description 7
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 7
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 6
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 6
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
- 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 claims description 5
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 5
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 5
- LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical group NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 claims description 4
- DGYIJVNZSDYBOE-UHFFFAOYSA-N [CH2]C1=CC=NC=C1 Chemical group [CH2]C1=CC=NC=C1 DGYIJVNZSDYBOE-UHFFFAOYSA-N 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 4
- 125000003944 tolyl group Chemical group 0.000 claims description 4
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 3
- 125000004174 2-benzimidazolyl group Chemical group [H]N1C(*)=NC2=C([H])C([H])=C([H])C([H])=C12 0.000 claims description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 125000005322 morpholin-1-yl group Chemical group 0.000 claims description 2
- AMPSKISTSYREGO-UHFFFAOYSA-N n-phenyl-2-[1-[3-(2-pyridin-2-ylethynyl)benzoyl]piperidin-4-yl]acetamide Chemical compound C=1C=CC=CC=1NC(=O)CC(CC1)CCN1C(=O)C(C=1)=CC=CC=1C#CC1=CC=CC=N1 AMPSKISTSYREGO-UHFFFAOYSA-N 0.000 claims description 2
- 210000005036 nerve Anatomy 0.000 claims description 2
- 125000001984 thiazolidinyl group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 9
- 125000003282 alkyl amino group Chemical group 0.000 claims 2
- 125000005215 cycloalkylheteroaryl group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- NFXMTXDIZMQSEC-UHFFFAOYSA-N n-(2,4-difluorophenyl)-2-[1-[3-(2-pyridin-2-ylethynyl)benzoyl]piperidin-4-yl]acetamide Chemical compound FC1=CC(F)=CC=C1NC(=O)CC1CCN(C(=O)C=2C=C(C=CC=2)C#CC=2N=CC=CC=2)CC1 NFXMTXDIZMQSEC-UHFFFAOYSA-N 0.000 claims 1
- ZZYPNFRQRIAOSY-UHFFFAOYSA-N n-(4-hydroxyphenyl)-2-[1-[3-(2-pyridin-2-ylethynyl)benzoyl]piperidin-4-yl]acetamide Chemical compound C1=CC(O)=CC=C1NC(=O)CC1CCN(C(=O)C=2C=C(C=CC=2)C#CC=2N=CC=CC=2)CC1 ZZYPNFRQRIAOSY-UHFFFAOYSA-N 0.000 claims 1
- ADIVVGOGYWTDNH-BUHFOSPRSA-N n-phenyl-2-[4-[2-[(e)-2-pyridin-2-ylethenyl]benzoyl]piperazin-1-yl]acetamide Chemical compound C=1C=CC=CC=1NC(=O)CN(CC1)CCN1C(=O)C1=CC=CC=C1\C=C\C1=CC=CC=N1 ADIVVGOGYWTDNH-BUHFOSPRSA-N 0.000 claims 1
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims 1
- 208000035475 disorder Diseases 0.000 abstract description 7
- 230000001154 acute effect Effects 0.000 abstract description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 231
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 115
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 102
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 90
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 89
- 239000000243 solution Substances 0.000 description 80
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 79
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 54
- 239000002904 solvent Substances 0.000 description 54
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 52
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 51
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 49
- 239000000047 product Substances 0.000 description 48
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- 238000009833 condensation Methods 0.000 description 42
- 230000005494 condensation Effects 0.000 description 42
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 40
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- 229920005989 resin Polymers 0.000 description 38
- 239000007821 HATU Substances 0.000 description 36
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 34
- 150000007530 organic bases Chemical class 0.000 description 34
- 235000019439 ethyl acetate Nutrition 0.000 description 33
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 33
- 241001465754 Metazoa Species 0.000 description 31
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 30
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- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 27
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- YEDUAINPPJYDJZ-UHFFFAOYSA-N 2-hydroxybenzothiazole Chemical compound C1=CC=C2SC(O)=NC2=C1 YEDUAINPPJYDJZ-UHFFFAOYSA-N 0.000 description 19
- 229940079593 drug Drugs 0.000 description 19
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 19
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 19
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- 235000002639 sodium chloride Nutrition 0.000 description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 17
- 239000000654 additive Substances 0.000 description 17
- 239000003054 catalyst Substances 0.000 description 17
- 235000019441 ethanol Nutrition 0.000 description 17
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 16
- 239000002253 acid Substances 0.000 description 16
- 125000000304 alkynyl group Chemical group 0.000 description 16
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
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- 241000699670 Mus sp. Species 0.000 description 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
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- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 13
- 125000003342 alkenyl group Chemical group 0.000 description 13
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 13
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- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 13
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 12
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- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 12
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- 229910052740 iodine Inorganic materials 0.000 description 12
- 239000012071 phase Substances 0.000 description 12
- 239000000725 suspension Substances 0.000 description 12
- 239000010410 layer Substances 0.000 description 11
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 10
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- 125000005842 heteroatom Chemical group 0.000 description 10
- 229910052763 palladium Inorganic materials 0.000 description 10
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 10
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- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical class CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 9
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 9
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- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 6
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- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 6
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- 230000002269 spontaneous effect Effects 0.000 description 6
- PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 6
- BSVHTRRLCAVQCZ-JDEXMCKMSA-N (2s)-1-[(2s)-1-[(2s)-1-[(2s)-1-[(2s)-1-[(2s)-1-[(2s)-2-[[(2s)-1-[(2s)-2-[[(2s)-2-amino-3-(4-hydroxyphenyl)propanoyl]amino]-3-carboxypropanoyl]pyrrolidine-2-carbonyl]amino]propanoyl]pyrrolidine-2-carbonyl]pyrrolidine-2-carbonyl]pyrrolidine-2-carbonyl]pyrro Chemical compound C([C@H](N)C(=O)N[C@@H](CC(O)=O)C(=O)N1CCC[C@H]1C(=O)N[C@@H](C)C(=O)N1[C@@H](CCC1)C(=O)N1[C@@H](CCC1)C(=O)N1[C@@H](CCC1)C(=O)N1[C@@H](CCC1)C(=O)N1[C@@H](CCC1)C(=O)N1[C@@H](CCC1)C(O)=O)C1=CC=C(O)C=C1 BSVHTRRLCAVQCZ-JDEXMCKMSA-N 0.000 description 5
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Classifications
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- 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
- C07D401/08—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 alicyclic rings
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- 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
- C07D213/72—Nitrogen atoms
- C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
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- 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
- C07D211/10—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 radicals containing only carbon and hydrogen atoms attached to ring carbon atoms
- C07D211/16—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 radicals containing only carbon and hydrogen atoms attached to ring carbon atoms with acylated ring nitrogen atom
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- 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
- C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
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- 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
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/40—Radicals substituted by oxygen atoms
- C07D307/46—Doubly bound oxygen atoms, or two oxygen atoms singly bound to the same carbon atom
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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
- C07D401/10—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 aromatic rings
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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
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- 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
- C07D405/02—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 two hetero rings
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
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- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Hospice & Palliative Care (AREA)
- Rheumatology (AREA)
- Otolaryngology (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Furan Compounds (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US24411700P | 2000-10-27 | 2000-10-27 | |
| PCT/US2001/051096 WO2002040466A2 (en) | 2000-10-27 | 2001-10-23 | Amidoalkyl-piperidine and amidoalkyl-piperazine derivatives for treating of nervous systems disorders |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SK6112003A3 true SK6112003A3 (en) | 2004-04-06 |
Family
ID=22921433
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK611-2003A SK6112003A3 (en) | 2000-10-27 | 2001-10-23 | Amidoalkyl-piperidine and amidoalkyl-piperazine derivatives for the treatment of nervous system disorders |
Country Status (24)
| Country | Link |
|---|---|
| US (2) | US20020183316A1 (cs) |
| EP (1) | EP1334098A2 (cs) |
| JP (1) | JP2004513944A (cs) |
| KR (1) | KR20030068547A (cs) |
| CN (1) | CN1483030A (cs) |
| AU (1) | AU2002239761A1 (cs) |
| BG (1) | BG107789A (cs) |
| BR (1) | BR0114983A (cs) |
| CA (1) | CA2427296A1 (cs) |
| CZ (1) | CZ20031386A3 (cs) |
| EE (1) | EE200300167A (cs) |
| HR (1) | HRP20030340A2 (cs) |
| HU (1) | HUP0400832A3 (cs) |
| IL (1) | IL155589A0 (cs) |
| MX (1) | MXPA03003817A (cs) |
| NO (1) | NO20031903L (cs) |
| NZ (1) | NZ525547A (cs) |
| PL (1) | PL361947A1 (cs) |
| RU (1) | RU2003115612A (cs) |
| SK (1) | SK6112003A3 (cs) |
| TW (1) | TWI258476B (cs) |
| UA (1) | UA75899C2 (cs) |
| WO (1) | WO2002040466A2 (cs) |
| ZA (1) | ZA200304064B (cs) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1425029A4 (en) | 2001-08-10 | 2006-06-07 | Palatin Technologies Inc | PEPTIDOMIMETICS OF BIOLOGICALLY ACTIVE METALLOPEPTIDES |
| US7354923B2 (en) | 2001-08-10 | 2008-04-08 | Palatin Technologies, Inc. | Piperazine melanocortin-specific compounds |
| US7732451B2 (en) | 2001-08-10 | 2010-06-08 | Palatin Technologies, Inc. | Naphthalene-containing melanocortin receptor-specific small molecule |
| US7655658B2 (en) | 2001-08-10 | 2010-02-02 | Palatin Technologies, Inc. | Thieno [2,3-D]pyrimidine-2,4-dione melanocortin-specific compounds |
| US7456184B2 (en) * | 2003-05-01 | 2008-11-25 | Palatin Technologies Inc. | Melanocortin receptor-specific compounds |
| US7718802B2 (en) | 2001-08-10 | 2010-05-18 | Palatin Technologies, Inc. | Substituted melanocortin receptor-specific piperazine compounds |
| GB0218326D0 (en) * | 2002-08-07 | 2002-09-11 | Glaxo Group Ltd | Compounds |
| US7727991B2 (en) | 2003-05-01 | 2010-06-01 | Palatin Technologies, Inc. | Substituted melanocortin receptor-specific single acyl piperazine compounds |
| US7968548B2 (en) | 2003-05-01 | 2011-06-28 | Palatin Technologies, Inc. | Melanocortin receptor-specific piperazine compounds with diamine groups |
| US7727990B2 (en) | 2003-05-01 | 2010-06-01 | Palatin Technologies, Inc. | Melanocortin receptor-specific piperazine and keto-piperazine compounds |
| US20050124625A1 (en) * | 2003-10-21 | 2005-06-09 | Salvati Mark E. | Piperazine derivatives and their use as modulators of nuclear hormone receptor function |
| US7709484B1 (en) | 2004-04-19 | 2010-05-04 | Palatin Technologies, Inc. | Substituted melanocortin receptor-specific piperazine compounds |
| DK2937341T3 (en) | 2004-12-30 | 2017-09-11 | Janssen Pharmaceutica Nv | 4- (BENZYL) -PIPERAZINE-1-CARBOXYLIC ACID PHENYLAMIDE DERIVATIVES AND RELATED COMPOUNDS AS MODULATORS OF FATTY ACID HYDROLASE (FAAH) FOR TREATING ANALYSIS, PAIN AND OTHER CONDITIONS |
| EP2520567A3 (en) | 2006-02-23 | 2012-12-12 | Shionogi & Co., Ltd. | Nitrogen-containing heterocycle derivatives substituted with cyclic group |
| US7834017B2 (en) | 2006-08-11 | 2010-11-16 | Palatin Technologies, Inc. | Diamine-containing, tetra-substituted piperazine compounds having identical 1- and 4-substituents |
| ME01308B (me) | 2006-10-18 | 2013-12-20 | Pfizer Prod Inc | Jedinjenja biaril etra uree |
| KR101451799B1 (ko) | 2007-05-14 | 2014-10-16 | 에스케이바이오팜 주식회사 | 신규 카바모일옥시 아릴알칸 아릴피페라진계 화합물, 이를함유하는 약제학적 조성물 및 상기 화합물 투여에 의한통증, 불안증 및 우울증 치료 방법 |
| US20090325964A1 (en) * | 2008-05-23 | 2009-12-31 | Wyeth | Piperazine Metabotropic Glutamate Receptor 5 (MGLUR5) Negative Allosteric Modulators For Anxiety/Depression |
| UA108233C2 (uk) | 2010-05-03 | 2015-04-10 | Модулятори активності гідролази амідів жирних кислот | |
| HU230744B1 (hu) * | 2012-11-30 | 2018-01-29 | CHINOIN Gyógyszer és Vegyészeti Termékek Gyára Zrt. | Új eljárás travoprost előállítására |
| KR101796390B1 (ko) | 2015-07-24 | 2017-11-09 | 동국대학교 산학협력단 | Blt 저해 활성을 갖는 신규 화합물 및 이를 유효성분으로 포함하는 염증성 질환 예방 또는 치료용 조성물 |
| WO2017018750A1 (ko) * | 2015-07-24 | 2017-02-02 | 동국대학교 산학협력단 | Blt 저해 활성을 갖는 신규 화합물 및 이를 유효성분으로 포함하는 염증성 질환 예방 또는 치료용 조성물 |
| MA45656A (fr) | 2016-07-14 | 2021-03-24 | Pfizer | Nouveaux pyrimidine carboxamides utilisées comme inhibiteurs de l'enzyme vanin-1 |
| WO2018135918A1 (ko) * | 2017-01-23 | 2018-07-26 | 동국대학교 산학협력단 | Blt 저해 활성을 갖는 화합물을 유효성분으로 포함하는 만성 폐쇄성 폐질환 예방 또는 치료용 약학적 조성물 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0071433A1 (en) * | 1981-07-28 | 1983-02-09 | Kowa Company, Ltd. | Medicine for the treatment of diabetes |
| US4746737A (en) * | 1985-07-26 | 1988-05-24 | Kowa Co., Ltd. | Phenyl guanidinobenzoate derivatives which have protease inhibitory activity |
| DE3601397A1 (de) * | 1986-01-18 | 1987-07-23 | Bayer Ag | Substituierte 1,4-dihydropyridin-3-carbonsaeurepiperazide, verfahren zu ihrer herstellung und ihre verwendung in arzneimitteln |
| JP3003148B2 (ja) * | 1989-01-05 | 2000-01-24 | 藤沢薬品工業株式会社 | チアゾール化合物、その製造法およびそれを含有する医薬組成物 |
| DE4102024A1 (de) * | 1991-01-24 | 1992-07-30 | Thomae Gmbh Dr K | Biphenylderivate, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung |
| US5525623A (en) * | 1993-03-12 | 1996-06-11 | Arris Pharmaceutical Corporation | Compositions and methods for the treatment of immunomediated inflammatory disorders |
| US5892039A (en) * | 1995-08-31 | 1999-04-06 | Schering Corporation | Piperazino derivatives as neurokinin antagonists |
| FR2744449B1 (fr) * | 1996-02-02 | 1998-04-24 | Pf Medicament | Nouvelles piperazines aromatiques derivees de cycloazanes substitues, ainsi que leur procede de preparation, les compositions pharmaceutiques et leur utilisation comme medicaments |
-
2001
- 2001-10-22 US US10/001,725 patent/US20020183316A1/en not_active Abandoned
- 2001-10-23 HR HR20030340A patent/HRP20030340A2/hr not_active Application Discontinuation
- 2001-10-23 CZ CZ20031386A patent/CZ20031386A3/cs unknown
- 2001-10-23 PL PL01361947A patent/PL361947A1/xx not_active Application Discontinuation
- 2001-10-23 HU HU0400832A patent/HUP0400832A3/hu unknown
- 2001-10-23 RU RU2003115612/04A patent/RU2003115612A/ru not_active Application Discontinuation
- 2001-10-23 WO PCT/US2001/051096 patent/WO2002040466A2/en not_active Application Discontinuation
- 2001-10-23 SK SK611-2003A patent/SK6112003A3/sk not_active Application Discontinuation
- 2001-10-23 MX MXPA03003817A patent/MXPA03003817A/es not_active Application Discontinuation
- 2001-10-23 BR BR0114983-0A patent/BR0114983A/pt not_active IP Right Cessation
- 2001-10-23 CA CA002427296A patent/CA2427296A1/en not_active Abandoned
- 2001-10-23 KR KR10-2003-7005908A patent/KR20030068547A/ko not_active Ceased
- 2001-10-23 UA UA2003054763A patent/UA75899C2/uk unknown
- 2001-10-23 JP JP2002543477A patent/JP2004513944A/ja active Pending
- 2001-10-23 AU AU2002239761A patent/AU2002239761A1/en not_active Abandoned
- 2001-10-23 EP EP01987558A patent/EP1334098A2/en not_active Withdrawn
- 2001-10-23 EE EEP200300167A patent/EE200300167A/xx unknown
- 2001-10-23 IL IL15558901A patent/IL155589A0/xx unknown
- 2001-10-23 NZ NZ525547A patent/NZ525547A/en unknown
- 2001-10-23 CN CNA018213936A patent/CN1483030A/zh active Pending
-
2002
- 2002-07-24 TW TW091116418A patent/TWI258476B/zh not_active IP Right Cessation
-
2003
- 2003-04-28 NO NO20031903A patent/NO20031903L/no not_active Application Discontinuation
- 2003-05-09 BG BG107789A patent/BG107789A/bg unknown
- 2003-05-26 ZA ZA200304064A patent/ZA200304064B/en unknown
-
2004
- 2004-07-23 US US10/898,130 patent/US20050004136A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| WO2002040466A2 (en) | 2002-05-23 |
| US20020183316A1 (en) | 2002-12-05 |
| HUP0400832A2 (hu) | 2004-07-28 |
| AU2002239761A1 (en) | 2002-05-27 |
| NO20031903D0 (no) | 2003-04-28 |
| JP2004513944A (ja) | 2004-05-13 |
| NZ525547A (en) | 2004-11-26 |
| EE200300167A (et) | 2003-08-15 |
| RU2003115612A (ru) | 2004-12-27 |
| BG107789A (bg) | 2004-02-27 |
| WO2002040466A3 (en) | 2002-08-29 |
| EP1334098A2 (en) | 2003-08-13 |
| NO20031903L (no) | 2003-06-25 |
| KR20030068547A (ko) | 2003-08-21 |
| TWI258476B (en) | 2006-07-21 |
| BR0114983A (pt) | 2003-09-23 |
| CZ20031386A3 (cs) | 2004-02-18 |
| CA2427296A1 (en) | 2002-05-23 |
| HRP20030340A2 (en) | 2005-04-30 |
| MXPA03003817A (es) | 2004-10-15 |
| HUP0400832A3 (en) | 2004-10-28 |
| UA75899C2 (en) | 2006-06-15 |
| PL361947A1 (en) | 2004-10-18 |
| IL155589A0 (en) | 2003-11-23 |
| CN1483030A (zh) | 2004-03-17 |
| ZA200304064B (en) | 2004-08-26 |
| US20050004136A1 (en) | 2005-01-06 |
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| Date | Code | Title | Description |
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| FC9A | Refused patent application |