ZA200507182B - 4-(2-phenylsulfanyl-phenyl)-1,2,3,6-tetrahydropyridine derivatives as serotonin reuptake inhibitors - Google Patents
4-(2-phenylsulfanyl-phenyl)-1,2,3,6-tetrahydropyridine derivatives as serotonin reuptake inhibitors Download PDFInfo
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- ZA200507182B ZA200507182B ZA200507182A ZA200507182A ZA200507182B ZA 200507182 B ZA200507182 B ZA 200507182B ZA 200507182 A ZA200507182 A ZA 200507182A ZA 200507182 A ZA200507182 A ZA 200507182A ZA 200507182 B ZA200507182 B ZA 200507182B
- Authority
- ZA
- South Africa
- Prior art keywords
- phenyl
- pyridine
- tetrahydro
- alk
- phenylsulfanyl
- Prior art date
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- 239000003772 serotonin uptake inhibitor Substances 0.000 title description 9
- TWNHYHUUTGSBCB-UHFFFAOYSA-N 4-(2-phenylsulfanylphenyl)-1,2,3,6-tetrahydropyridine Chemical class C1NCCC(C=2C(=CC=CC=2)SC=2C=CC=CC=2)=C1 TWNHYHUUTGSBCB-UHFFFAOYSA-N 0.000 title description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 121
- 239000001257 hydrogen Substances 0.000 claims description 121
- 150000002431 hydrogen Chemical group 0.000 claims description 93
- 150000001875 compounds Chemical class 0.000 claims description 69
- -1 2-Chloro-4-fluoro-phenylsulfanyl Chemical group 0.000 claims description 53
- 229910052736 halogen Inorganic materials 0.000 claims description 52
- 150000002367 halogens Chemical group 0.000 claims description 50
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 24
- 125000001424 substituent group Chemical group 0.000 claims description 24
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 20
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 20
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
- 125000005842 heteroatom Chemical group 0.000 claims description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims description 13
- 208000019901 Anxiety disease Diseases 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 9
- 206010041250 Social phobia Diseases 0.000 claims description 8
- 208000019906 panic disease Diseases 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 5
- 208000008811 Agoraphobia Diseases 0.000 claims description 4
- 208000019022 Mood disease Diseases 0.000 claims description 4
- 206010033664 Panic attack Diseases 0.000 claims description 4
- 206010034912 Phobia Diseases 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 201000001716 specific phobia Diseases 0.000 claims description 4
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims description 3
- GCQFBLRJZDCZEK-UHFFFAOYSA-N 4-[2-(2,4,6-trimethylphenyl)sulfanylphenyl]-1,2,3,6-tetrahydropyridine Chemical compound CC1=CC(C)=CC(C)=C1SC1=CC=CC=C1C1=CCNCC1 GCQFBLRJZDCZEK-UHFFFAOYSA-N 0.000 claims description 2
- IWAIKGCEKLIXEL-UHFFFAOYSA-N 4-[2-(2-bromo-4-fluorophenyl)sulfanylphenyl]-1,2,3,6-tetrahydropyridine Chemical compound BrC1=CC(F)=CC=C1SC1=CC=CC=C1C1=CCNCC1 IWAIKGCEKLIXEL-UHFFFAOYSA-N 0.000 claims description 2
- SZXJWASYHYTNSH-UHFFFAOYSA-N 4-[2-(2-ethylphenyl)sulfanylphenyl]-1,2,3,6-tetrahydropyridine Chemical compound CCC1=CC=CC=C1SC1=CC=CC=C1C1=CCNCC1 SZXJWASYHYTNSH-UHFFFAOYSA-N 0.000 claims description 2
- QNJYLSDKYNIIRZ-UHFFFAOYSA-N 4-[2-(2-methoxyphenyl)sulfanyl-5-methylphenyl]-1,2,3,6-tetrahydropyridine Chemical compound COC1=CC=CC=C1SC1=CC=C(C)C=C1C1=CCNCC1 QNJYLSDKYNIIRZ-UHFFFAOYSA-N 0.000 claims description 2
- JGWZKSKCPDXUPE-UHFFFAOYSA-N 4-[2-(2-tert-butylphenyl)sulfanylphenyl]-1,2,3,6-tetrahydropyridine Chemical compound CC(C)(C)C1=CC=CC=C1SC1=CC=CC=C1C1=CCNCC1 JGWZKSKCPDXUPE-UHFFFAOYSA-N 0.000 claims description 2
- WNOAWMWRNSWARI-UHFFFAOYSA-N 4-[2-(4-ethylphenyl)sulfanylphenyl]-1,2,3,6-tetrahydropyridine Chemical compound C1=CC(CC)=CC=C1SC1=CC=CC=C1C1=CCNCC1 WNOAWMWRNSWARI-UHFFFAOYSA-N 0.000 claims description 2
- QSPBRZOKFZWSCU-UHFFFAOYSA-N 4-[5-fluoro-2-(2-methoxyphenyl)sulfanylphenyl]-1,2,3,6-tetrahydropyridine Chemical compound COC1=CC=CC=C1SC1=CC=C(F)C=C1C1=CCNCC1 QSPBRZOKFZWSCU-UHFFFAOYSA-N 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 208000028173 post-traumatic stress disease Diseases 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 208000017194 Affective disease Diseases 0.000 claims 2
- QGRKONUHHGBHRB-UHFFFAOYSA-N 2,3-dichlorobenzenethiol Chemical compound SC1=CC=CC(Cl)=C1Cl QGRKONUHHGBHRB-UHFFFAOYSA-N 0.000 claims 1
- PUEZOCGQEOXEFL-UHFFFAOYSA-N 4-(5-fluoro-2-phenylsulfanylphenyl)-1,2,3,6-tetrahydropyridine Chemical compound C=1CNCCC=1C1=CC(F)=CC=C1SC1=CC=CC=C1 PUEZOCGQEOXEFL-UHFFFAOYSA-N 0.000 claims 1
- SZTIAPMIZKFVJG-UHFFFAOYSA-N 4-[2-(1,3-benzodioxol-5-ylsulfanyl)-5-methylphenyl]-1,2,3,6-tetrahydropyridine Chemical compound C=1C(C)=CC=C(SC=2C=C3OCOC3=CC=2)C=1C1=CCNCC1 SZTIAPMIZKFVJG-UHFFFAOYSA-N 0.000 claims 1
- AUUIZAOWVJHWEH-UHFFFAOYSA-N 4-[2-(1,3-benzodioxol-5-ylsulfanyl)phenyl]-1,2,3,6-tetrahydropyridine Chemical compound C1=C2OCOC2=CC=C1SC1=CC=CC=C1C1=CCNCC1 AUUIZAOWVJHWEH-UHFFFAOYSA-N 0.000 claims 1
- RIURRPLUMLANCF-UHFFFAOYSA-N 4-[2-(2,3-difluorophenyl)sulfanyl-5-methylphenyl]-1,2,3,6-tetrahydropyridine Chemical compound C=1CNCCC=1C1=CC(C)=CC=C1SC1=CC=CC(F)=C1F RIURRPLUMLANCF-UHFFFAOYSA-N 0.000 claims 1
- MHQSJTPUHOWIIZ-UHFFFAOYSA-N 4-[2-(2,4-dimethylphenyl)sulfanyl-5-(trifluoromethyl)phenyl]-1,2,3,6-tetrahydropyridine Chemical compound CC1=CC(C)=CC=C1SC1=CC=C(C(F)(F)F)C=C1C1=CCNCC1 MHQSJTPUHOWIIZ-UHFFFAOYSA-N 0.000 claims 1
- OFSKCUUWQWPTBI-UHFFFAOYSA-N 4-[2-(2,4-dimethylphenyl)sulfanyl-5-fluorophenyl]-1,2,3,6-tetrahydropyridine Chemical compound CC1=CC(C)=CC=C1SC1=CC=C(F)C=C1C1=CCNCC1 OFSKCUUWQWPTBI-UHFFFAOYSA-N 0.000 claims 1
- MVZIEXURSWGYQY-UHFFFAOYSA-N 4-[2-(2,4-dimethylphenyl)sulfanylphenyl]-1,2,3,6-tetrahydropyridine Chemical compound CC1=CC(C)=CC=C1SC1=CC=CC=C1C1=CCNCC1 MVZIEXURSWGYQY-UHFFFAOYSA-N 0.000 claims 1
- QZIRUKPAQOPECW-UHFFFAOYSA-N 4-[2-(2,5-dimethylphenyl)sulfanylphenyl]-1,2,3,6-tetrahydropyridine Chemical compound CC1=CC=C(C)C(SC=2C(=CC=CC=2)C=2CCNCC=2)=C1 QZIRUKPAQOPECW-UHFFFAOYSA-N 0.000 claims 1
- MYHHWKVODDESOL-UHFFFAOYSA-N 4-[2-(2-bromo-4-methylphenyl)sulfanylphenyl]-1,2,3,6-tetrahydropyridine Chemical compound BrC1=CC(C)=CC=C1SC1=CC=CC=C1C1=CCNCC1 MYHHWKVODDESOL-UHFFFAOYSA-N 0.000 claims 1
- IVKGPDWMOBTVDL-UHFFFAOYSA-N 4-[2-(2-chloro-4-fluorophenyl)sulfanyl-5-fluorophenyl]-1,2,3,6-tetrahydropyridine Chemical compound ClC1=CC(F)=CC=C1SC1=CC=C(F)C=C1C1=CCNCC1 IVKGPDWMOBTVDL-UHFFFAOYSA-N 0.000 claims 1
- JZFBROSOSVZQMZ-UHFFFAOYSA-N 4-[2-(2-chloro-4-methylphenyl)sulfanylphenyl]-1,2,3,6-tetrahydropyridine Chemical compound ClC1=CC(C)=CC=C1SC1=CC=CC=C1C1=CCNCC1 JZFBROSOSVZQMZ-UHFFFAOYSA-N 0.000 claims 1
- QDPYFXMXJMLMBT-UHFFFAOYSA-N 4-[2-(2-chlorophenyl)sulfanyl-5-fluorophenyl]-1,2,3,6-tetrahydropyridine Chemical compound C=1CNCCC=1C1=CC(F)=CC=C1SC1=CC=CC=C1Cl QDPYFXMXJMLMBT-UHFFFAOYSA-N 0.000 claims 1
- JKZIVROKOGUVQP-UHFFFAOYSA-N 4-[2-(2-methoxy-5-methylphenyl)sulfanylphenyl]-1,2,3,6-tetrahydropyridine Chemical compound COC1=CC=C(C)C=C1SC1=CC=CC=C1C1=CCNCC1 JKZIVROKOGUVQP-UHFFFAOYSA-N 0.000 claims 1
- IPWXQZGYRWYUQE-UHFFFAOYSA-N 4-[2-(3,5-dimethylphenyl)sulfanylphenyl]-1,2,3,6-tetrahydropyridine Chemical compound CC1=CC(C)=CC(SC=2C(=CC=CC=2)C=2CCNCC=2)=C1 IPWXQZGYRWYUQE-UHFFFAOYSA-N 0.000 claims 1
- JYBXSOZYYOBNSR-UHFFFAOYSA-N 4-[2-(3-bromophenyl)sulfanyl-5-methylphenyl]-1,2,3,6-tetrahydropyridine Chemical compound C=1CNCCC=1C1=CC(C)=CC=C1SC1=CC=CC(Br)=C1 JYBXSOZYYOBNSR-UHFFFAOYSA-N 0.000 claims 1
- RXGKYSYDBNIRFX-UHFFFAOYSA-N 4-[2-(3-chloro-4-fluorophenyl)sulfanylphenyl]-1,2,3,6-tetrahydropyridine Chemical compound C1=C(Cl)C(F)=CC=C1SC1=CC=CC=C1C1=CCNCC1 RXGKYSYDBNIRFX-UHFFFAOYSA-N 0.000 claims 1
- GIEGWJVBVKIFKN-UHFFFAOYSA-N 4-[2-(3-chlorophenyl)sulfanyl-5-fluorophenyl]-1,2,3,6-tetrahydropyridine Chemical compound C=1CNCCC=1C1=CC(F)=CC=C1SC1=CC=CC(Cl)=C1 GIEGWJVBVKIFKN-UHFFFAOYSA-N 0.000 claims 1
- NQLRPJLAQBSPIC-UHFFFAOYSA-N 4-[2-(3-fluoro-4-methylphenyl)sulfanyl-5-methylphenyl]-1,2,3,6-tetrahydropyridine Chemical compound C=1CNCCC=1C1=CC(C)=CC=C1SC1=CC=C(C)C(F)=C1 NQLRPJLAQBSPIC-UHFFFAOYSA-N 0.000 claims 1
- BVFBNCRYXIKJMP-UHFFFAOYSA-N 4-[2-(3-methylphenyl)sulfanylphenyl]-1,2,3,6-tetrahydropyridine Chemical compound CC1=CC=CC(SC=2C(=CC=CC=2)C=2CCNCC=2)=C1 BVFBNCRYXIKJMP-UHFFFAOYSA-N 0.000 claims 1
- LJIDQQITESAHJB-UHFFFAOYSA-N 4-[2-(4-chloro-2-fluorophenyl)sulfanyl-5-fluorophenyl]-1,2,3,6-tetrahydropyridine Chemical compound C=1CNCCC=1C1=CC(F)=CC=C1SC1=CC=C(Cl)C=C1F LJIDQQITESAHJB-UHFFFAOYSA-N 0.000 claims 1
- ANRLWSIDTQDUNT-UHFFFAOYSA-N 4-[2-(4-chloro-2-methoxyphenyl)sulfanylphenyl]-1,2,3,6-tetrahydropyridine Chemical compound COC1=CC(Cl)=CC=C1SC1=CC=CC=C1C1=CCNCC1 ANRLWSIDTQDUNT-UHFFFAOYSA-N 0.000 claims 1
- JJIWRENZKQEFQZ-UHFFFAOYSA-N 4-[2-(4-chlorophenyl)sulfanyl-4-fluorophenyl]-1,2,3,6-tetrahydropyridine Chemical compound C=1C=C(Cl)C=CC=1SC1=CC(F)=CC=C1C1=CCNCC1 JJIWRENZKQEFQZ-UHFFFAOYSA-N 0.000 claims 1
- DXJAJOGZMSVQNA-UHFFFAOYSA-N 4-[2-(4-fluoro-2-methylphenyl)sulfanyl-5-methylphenyl]-1,2,3,6-tetrahydropyridine Chemical compound C=1CNCCC=1C1=CC(C)=CC=C1SC1=CC=C(F)C=C1C DXJAJOGZMSVQNA-UHFFFAOYSA-N 0.000 claims 1
- AEFCDVXGWWUALM-UHFFFAOYSA-N 4-[2-(4-fluoro-3-methoxyphenyl)sulfanyl-5-methylphenyl]-1,2,3,6-tetrahydropyridine Chemical compound C1=C(F)C(OC)=CC(SC=2C(=CC(C)=CC=2)C=2CCNCC=2)=C1 AEFCDVXGWWUALM-UHFFFAOYSA-N 0.000 claims 1
- NBKKRFYFKIWHFQ-UHFFFAOYSA-N 4-[2-(4-fluorophenyl)sulfanyl-5-methylphenyl]-1,2,3,6-tetrahydropyridine Chemical compound C=1CNCCC=1C1=CC(C)=CC=C1SC1=CC=C(F)C=C1 NBKKRFYFKIWHFQ-UHFFFAOYSA-N 0.000 claims 1
- MDYPWKBPZBMGRI-UHFFFAOYSA-N 4-[2-(4-methoxyphenyl)sulfanyl-5-methylphenyl]-1,2,3,6-tetrahydropyridine Chemical compound C1=CC(OC)=CC=C1SC1=CC=C(C)C=C1C1=CCNCC1 MDYPWKBPZBMGRI-UHFFFAOYSA-N 0.000 claims 1
- XOWCKPZUHHALSB-UHFFFAOYSA-N 4-[2-(4-methylphenyl)sulfanyl-5-(trifluoromethyl)phenyl]-1,2,3,6-tetrahydropyridine Chemical compound C1=CC(C)=CC=C1SC1=CC=C(C(F)(F)F)C=C1C1=CCNCC1 XOWCKPZUHHALSB-UHFFFAOYSA-N 0.000 claims 1
- PWZIAMWTPFSLOT-UHFFFAOYSA-N 4-[2-(4-tert-butylphenyl)sulfanylphenyl]-1,2,3,6-tetrahydropyridine Chemical compound C1=CC(C(C)(C)C)=CC=C1SC1=CC=CC=C1C1=CCNCC1 PWZIAMWTPFSLOT-UHFFFAOYSA-N 0.000 claims 1
- ANIMBBRFUYNDDI-UHFFFAOYSA-N 4-[4-fluoro-2-(4-methylphenyl)sulfanylphenyl]-1,2,3,6-tetrahydropyridine Chemical compound C1=CC(C)=CC=C1SC1=CC(F)=CC=C1C1=CCNCC1 ANIMBBRFUYNDDI-UHFFFAOYSA-N 0.000 claims 1
- TUVCDLWJOSIGRL-UHFFFAOYSA-N 4-[5-bromo-2-(2,4-dimethylphenyl)sulfanylphenyl]-1,2,3,6-tetrahydropyridine Chemical compound CC1=CC(C)=CC=C1SC1=CC=C(Br)C=C1C1=CCNCC1 TUVCDLWJOSIGRL-UHFFFAOYSA-N 0.000 claims 1
- JDVDAXWYMVPZJC-UHFFFAOYSA-N 4-[5-fluoro-2-(2-fluoro-4-methoxyphenyl)sulfanylphenyl]-1,2,3,6-tetrahydropyridine Chemical compound FC1=CC(OC)=CC=C1SC1=CC=C(F)C=C1C1=CCNCC1 JDVDAXWYMVPZJC-UHFFFAOYSA-N 0.000 claims 1
- YRLHHXMJCNCMLO-UHFFFAOYSA-N 4-[5-fluoro-2-(3-methylphenyl)sulfanylphenyl]-1,2,3,6-tetrahydropyridine Chemical compound CC1=CC=CC(SC=2C(=CC(F)=CC=2)C=2CCNCC=2)=C1 YRLHHXMJCNCMLO-UHFFFAOYSA-N 0.000 claims 1
- NHJXUHYVMIDBFY-UHFFFAOYSA-N 4-[5-fluoro-2-(4-methoxyphenyl)sulfanylphenyl]-1,2,3,6-tetrahydropyridine Chemical compound C1=CC(OC)=CC=C1SC1=CC=C(F)C=C1C1=CCNCC1 NHJXUHYVMIDBFY-UHFFFAOYSA-N 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 101150006659 amdR gene Proteins 0.000 claims 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 24
- 125000001153 fluoro group Chemical group F* 0.000 description 8
- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 description 7
- 125000001246 bromo group Chemical group Br* 0.000 description 7
- 125000005322 morpholin-1-yl group Chemical group 0.000 description 7
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 7
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 125000001309 chloro group Chemical group Cl* 0.000 description 6
- 230000005764 inhibitory process Effects 0.000 description 6
- 125000003226 pyrazolyl group Chemical group 0.000 description 6
- 229940124834 selective serotonin reuptake inhibitor Drugs 0.000 description 6
- 230000000697 serotonin reuptake Effects 0.000 description 5
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- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 230000002301 combined effect Effects 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 230000012154 norepinephrine uptake Effects 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 3
- 229940005513 antidepressants Drugs 0.000 description 3
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- 230000001225 therapeutic effect Effects 0.000 description 3
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- YUUZWPWDOCQTJZ-UHFFFAOYSA-N 4-[2-(2-fluorophenyl)sulfanyl-5-methylphenyl]-1,2,3,6-tetrahydropyridine Chemical compound C=1CNCCC=1C1=CC(C)=CC=C1SC1=CC=CC=C1F YUUZWPWDOCQTJZ-UHFFFAOYSA-N 0.000 description 1
- XBODOAHDRZCFPN-UHFFFAOYSA-N 4-[2-(2-methoxyphenyl)sulfanylphenyl]-1,2,3,6-tetrahydropyridine Chemical compound COC1=CC=CC=C1SC1=CC=CC=C1C1=CCNCC1 XBODOAHDRZCFPN-UHFFFAOYSA-N 0.000 description 1
- GWOIXIXFXJRSEE-UHFFFAOYSA-N 4-[2-(2-methylphenyl)sulfanylphenyl]-1,2,3,6-tetrahydropyridine Chemical compound CC1=CC=CC=C1SC1=CC=CC=C1C1=CCNCC1 GWOIXIXFXJRSEE-UHFFFAOYSA-N 0.000 description 1
- GZJGOLWNJKWIFG-UHFFFAOYSA-N 4-[2-(3,4-dichlorophenyl)sulfanyl-5-methylphenyl]-1,2,3,6-tetrahydropyridine Chemical compound C=1CNCCC=1C1=CC(C)=CC=C1SC1=CC=C(Cl)C(Cl)=C1 GZJGOLWNJKWIFG-UHFFFAOYSA-N 0.000 description 1
- SVHGYUOTSWQDCM-UHFFFAOYSA-N 4-[2-(3,4-dimethylphenyl)sulfanylphenyl]-1,2,3,6-tetrahydropyridine Chemical compound C1=C(C)C(C)=CC=C1SC1=CC=CC=C1C1=CCNCC1 SVHGYUOTSWQDCM-UHFFFAOYSA-N 0.000 description 1
- RPHAQZOJDAXZSR-UHFFFAOYSA-N 4-[2-(3,5-dichlorophenyl)sulfanylphenyl]-1,2,3,6-tetrahydropyridine Chemical compound ClC1=CC(Cl)=CC(SC=2C(=CC=CC=2)C=2CCNCC=2)=C1 RPHAQZOJDAXZSR-UHFFFAOYSA-N 0.000 description 1
- YFPWBRPRMAYQAQ-UHFFFAOYSA-N 4-[2-(3-chloro-2-fluorophenyl)sulfanyl-5-methylphenyl]-1,2,3,6-tetrahydropyridine Chemical compound C=1CNCCC=1C1=CC(C)=CC=C1SC1=CC=CC(Cl)=C1F YFPWBRPRMAYQAQ-UHFFFAOYSA-N 0.000 description 1
- BPEKNTQEJVLZHM-UHFFFAOYSA-N 4-[2-(3-chloro-2-methylphenyl)sulfanylphenyl]-1,2,3,6-tetrahydropyridine Chemical compound CC1=C(Cl)C=CC=C1SC1=CC=CC=C1C1=CCNCC1 BPEKNTQEJVLZHM-UHFFFAOYSA-N 0.000 description 1
- HVEBYYLFYABXGV-UHFFFAOYSA-N 4-[2-(3-fluoro-2-methylphenyl)sulfanyl-5-methylphenyl]-1,2,3,6-tetrahydropyridine Chemical compound C=1CNCCC=1C1=CC(C)=CC=C1SC1=CC=CC(F)=C1C HVEBYYLFYABXGV-UHFFFAOYSA-N 0.000 description 1
- PHDZOIVGCWIKAA-UHFFFAOYSA-N 4-[2-(3-fluoro-2-methylphenyl)sulfanylphenyl]-1,2,3,6-tetrahydropyridine Chemical compound CC1=C(F)C=CC=C1SC1=CC=CC=C1C1=CCNCC1 PHDZOIVGCWIKAA-UHFFFAOYSA-N 0.000 description 1
- WUMRRIKTMDPWPS-UHFFFAOYSA-N 4-[2-(3-fluorophenyl)sulfanyl-5-methylphenyl]-1,2,3,6-tetrahydropyridine Chemical compound C=1CNCCC=1C1=CC(C)=CC=C1SC1=CC=CC(F)=C1 WUMRRIKTMDPWPS-UHFFFAOYSA-N 0.000 description 1
- UJCZUXVQHRYIFH-UHFFFAOYSA-N 4-[2-(4-chloro-2-methoxyphenyl)sulfanyl-5-methylphenyl]-1,2,3,6-tetrahydropyridine Chemical compound COC1=CC(Cl)=CC=C1SC1=CC=C(C)C=C1C1=CCNCC1 UJCZUXVQHRYIFH-UHFFFAOYSA-N 0.000 description 1
- OGFBYSACUMWPKJ-UHFFFAOYSA-N 4-[2-(4-chlorophenyl)sulfanyl-5-(trifluoromethyl)phenyl]-1,2,3,6-tetrahydropyridine Chemical compound C=1CNCCC=1C1=CC(C(F)(F)F)=CC=C1SC1=CC=C(Cl)C=C1 OGFBYSACUMWPKJ-UHFFFAOYSA-N 0.000 description 1
- CTSBYCFRHIWIAV-UHFFFAOYSA-N 4-[2-(4-fluoro-3-methoxyphenyl)sulfanylphenyl]-1,2,3,6-tetrahydropyridine Chemical compound C1=C(F)C(OC)=CC(SC=2C(=CC=CC=2)C=2CCNCC=2)=C1 CTSBYCFRHIWIAV-UHFFFAOYSA-N 0.000 description 1
- OAWTVXGLRKJOMY-UHFFFAOYSA-N 4-[2-[3-(trifluoromethyl)phenyl]sulfanylphenyl]-1,2,3,6-tetrahydropyridine Chemical compound FC(F)(F)C1=CC=CC(SC=2C(=CC=CC=2)C=2CCNCC=2)=C1 OAWTVXGLRKJOMY-UHFFFAOYSA-N 0.000 description 1
- QTEHEQGCXGNKEP-UHFFFAOYSA-N 4-[3-fluoro-2-(4-methoxyphenyl)sulfanylphenyl]-1,2,3,6-tetrahydropyridine Chemical compound C1=CC(OC)=CC=C1SC1=C(F)C=CC=C1C1=CCNCC1 QTEHEQGCXGNKEP-UHFFFAOYSA-N 0.000 description 1
- OGHCEUDSMGFZIS-UHFFFAOYSA-N 4-[4-fluoro-2-(4-methoxyphenyl)sulfanylphenyl]-1,2,3,6-tetrahydropyridine Chemical compound C1=CC(OC)=CC=C1SC1=CC(F)=CC=C1C1=CCNCC1 OGHCEUDSMGFZIS-UHFFFAOYSA-N 0.000 description 1
- BSFODEXXVBBYOC-UHFFFAOYSA-N 8-[4-(dimethylamino)butan-2-ylamino]quinolin-6-ol Chemical compound C1=CN=C2C(NC(CCN(C)C)C)=CC(O)=CC2=C1 BSFODEXXVBBYOC-UHFFFAOYSA-N 0.000 description 1
- 102000007527 Autoreceptors Human genes 0.000 description 1
- 108010071131 Autoreceptors Proteins 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- MUQNGPZZQDCDFT-JNQJZLCISA-N Halcinonide Chemical group C1CC2=CC(=O)CC[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H]3OC(C)(C)O[C@@]3(C(=O)CCl)[C@@]1(C)C[C@@H]2O MUQNGPZZQDCDFT-JNQJZLCISA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 201000001880 Sexual dysfunction Diseases 0.000 description 1
- 208000012981 Traumatic Stress disease Diseases 0.000 description 1
- 229940123445 Tricyclic antidepressant Drugs 0.000 description 1
- 208000026345 acute stress disease Diseases 0.000 description 1
- 230000001270 agonistic effect Effects 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 230000003042 antagnostic effect Effects 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 1
- 229960001653 citalopram Drugs 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000392 cycloalkenyl group Chemical group 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 230000000994 depressogenic effect Effects 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 229940000406 drug candidate Drugs 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 229940028332 halog Drugs 0.000 description 1
- 230000000971 hippocampal effect Effects 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 239000004050 mood stabilizer Substances 0.000 description 1
- 229940127237 mood stabilizer Drugs 0.000 description 1
- 230000008450 motivation Effects 0.000 description 1
- QXLNAYIFEMXTDZ-UHFFFAOYSA-N n-[4-methoxy-3-(4-methylpiperazin-1-yl)phenyl]-4-[2-methyl-4-(5-methyl-1,3,4-oxadiazol-2-yl)phenyl]benzamide Chemical compound C1=C(N2CCN(C)CC2)C(OC)=CC=C1NC(=O)C(C=C1)=CC=C1C(C(=C1)C)=CC=C1C1=NN=C(C)O1 QXLNAYIFEMXTDZ-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000002547 new drug Substances 0.000 description 1
- 239000004031 partial agonist Substances 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229940076279 serotonin Drugs 0.000 description 1
- 230000013275 serotonin uptake Effects 0.000 description 1
- 231100000872 sexual dysfunction Toxicity 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 230000005062 synaptic transmission Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000000472 traumatic effect Effects 0.000 description 1
- 239000003029 tricyclic antidepressant agent Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Classifications
-
- 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
- C07D211/68—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 one double bond between ring members or between a ring member and a non-ring member
- C07D211/70—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 one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
- C07D405/02—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
- C07D405/12—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 linked by a chain containing hetero atoms as chain links
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (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)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Psychiatry (AREA)
- Anesthesiology (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DKPA200300518 | 2003-04-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200507182B true ZA200507182B (en) | 2006-12-27 |
Family
ID=35432910
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200507182A ZA200507182B (en) | 2003-04-04 | 2004-04-02 | 4-(2-phenylsulfanyl-phenyl)-1,2,3,6-tetrahydropyridine derivatives as serotonin reuptake inhibitors |
Country Status (28)
| Country | Link |
|---|---|
| US (1) | US20070173522A1 (de) |
| EP (1) | EP1613594B1 (de) |
| JP (1) | JP2006522029A (de) |
| KR (1) | KR20060021825A (de) |
| CN (1) | CN100384822C (de) |
| AR (1) | AR043964A1 (de) |
| AT (1) | ATE390413T1 (de) |
| AU (1) | AU2004226319A1 (de) |
| BR (1) | BRPI0408453A (de) |
| CA (1) | CA2521172A1 (de) |
| CL (1) | CL2004000730A1 (de) |
| CO (1) | CO5700777A2 (de) |
| DE (1) | DE602004012724T2 (de) |
| DK (1) | DK1613594T3 (de) |
| EA (1) | EA009282B1 (de) |
| ES (1) | ES2301979T3 (de) |
| HK (1) | HK1090051A1 (de) |
| HR (1) | HRP20080243T3 (de) |
| IS (1) | IS8007A (de) |
| MX (1) | MXPA05010678A (de) |
| NO (1) | NO20055205L (de) |
| NZ (1) | NZ541944A (de) |
| PL (1) | PL1613594T3 (de) |
| PT (1) | PT1613594E (de) |
| SI (1) | SI1613594T1 (de) |
| UA (1) | UA81300C2 (de) |
| WO (1) | WO2004087662A1 (de) |
| ZA (1) | ZA200507182B (de) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4667366B2 (ja) | 2003-04-04 | 2011-04-13 | ハー・ルンドベック・アクチエゼルスカベット | セロトニン再取り込み阻害剤としての４−（２−フェニルスルファニル−フェニル）−ピペリジン誘導体 |
| EP1792629A4 (de) | 2004-08-25 | 2010-08-25 | Takeda Pharmaceutical | Mittel zur prävention/behandlung von stressbedingter harninkontinenz und vorsorgeuntersuchungsverfahren dafür |
| EP2018863B9 (de) | 2006-05-16 | 2015-02-18 | Takeda Pharmaceutical Company Limited | Kondensierte, heterocyclische Verbindung und ihre Verwendung |
| US20100266504A1 (en) | 2007-11-15 | 2010-10-21 | Takahiro Matsumoto | Condensed pyridine derivative and use thereof |
| UA98698C2 (en) * | 2008-03-03 | 2012-06-11 | Х. Луннбек А/С | Phenylsulfanylphenyl-piperidines and process for the preparation thereof |
| JPWO2011071136A1 (ja) | 2009-12-11 | 2013-04-22 | アステラス製薬株式会社 | 線維筋痛症治療剤 |
| EP2930171A1 (de) * | 2014-04-07 | 2015-10-14 | LEK Pharmaceuticals d.d. | Synthese von Vortioxetin über (2,4-Dimethylphenyl) (2-Iodophenyl)sulfan-Zwischenprodukt |
| CN105294554B (zh) * | 2015-11-18 | 2017-11-07 | 乳源瑶族自治县大众药品贸易有限公司 | 苯基哌嗪衍生物及其使用方法和用途 |
| JPWO2019131902A1 (ja) | 2017-12-27 | 2020-12-10 | 武田薬品工業株式会社 | 腹圧性尿失禁および便失禁の治療薬 |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3803143A (en) * | 1969-09-08 | 1974-04-09 | Eisai Co Ltd | 6-amino alkylene 6,7-dihydro-5h-dibenzo (b,g),(1,5)thiazocines |
| US4018830A (en) * | 1969-09-22 | 1977-04-19 | Merck & Co., Inc. | Phenylthioaralkylamines |
| US4055665A (en) * | 1974-11-25 | 1977-10-25 | Merck & Co., Inc. | Treating arrythmia with phenylthioaralkylamines |
| US4066654A (en) * | 1975-04-16 | 1978-01-03 | G. D. Searle & Co. | 1-triarylalkyl-4-phenyl-4-piperidine carboxylic acids and derivatives |
| US4056632A (en) * | 1975-07-21 | 1977-11-01 | Burroughs Wellcome Co. | 2-Hydroxymethyl-2'-aminomethyl-diphenylsulfides and method of use |
| US4241071A (en) * | 1977-01-27 | 1980-12-23 | American Hoechst Corporation | Antidepressant (α-phenyl-2-tolyl)azacycloalkanes |
| DE2802306A1 (de) * | 1977-01-27 | 1978-08-10 | Hoechst Ag | Azacycloalkane, azacycloalkene und ihre derivate |
| US4198417A (en) * | 1979-01-10 | 1980-04-15 | American Hoechst Corporation | Phenoxyphenylpiperidines |
| US4198419A (en) * | 1979-01-10 | 1980-04-15 | American Hoechst Corporation | Phenylthiophenylpiperidines |
| GB8912971D0 (en) * | 1989-06-06 | 1989-07-26 | Wellcome Found | Halogen substituted diphenylsulfides |
| KR100524159B1 (ko) * | 1999-10-13 | 2005-10-25 | 화이자 프로덕츠 인코포레이티드 | 모노아민 재흡수 억제제로서 유용한 비아릴 에테르 유도체 |
| US6410736B1 (en) * | 1999-11-29 | 2002-06-25 | Pfizer Inc. | Biaryl ether derivatives useful as monoamine reuptake inhibitors |
| CZ20022319A3 (cs) * | 1999-12-30 | 2002-10-16 | H. Lundbeck A/S | Substituovaná fenylpiperazinová sloučenina a farmaceutický prostředek, který ji obsahuje |
| US6436938B1 (en) * | 2001-01-22 | 2002-08-20 | Pfizer Inc. | Combination treatment for depression |
| US20020107244A1 (en) * | 2001-02-02 | 2002-08-08 | Howard Harry R. | Combination treatment for depression |
| UA81749C2 (uk) * | 2001-10-04 | 2008-02-11 | Х. Луннбек А/С | Фенілпіперазинові похідні як інгібітори зворотного захоплення серотоніну |
-
2004
- 2004-02-04 UA UAA200508779A patent/UA81300C2/uk unknown
- 2004-04-02 EP EP04725299A patent/EP1613594B1/de not_active Expired - Lifetime
- 2004-04-02 ZA ZA200507182A patent/ZA200507182B/en unknown
- 2004-04-02 CA CA002521172A patent/CA2521172A1/en not_active Abandoned
- 2004-04-02 WO PCT/DK2004/000243 patent/WO2004087662A1/en active IP Right Grant
- 2004-04-02 PL PL04725299T patent/PL1613594T3/pl unknown
- 2004-04-02 US US10/551,869 patent/US20070173522A1/en not_active Abandoned
- 2004-04-02 PT PT04725299T patent/PT1613594E/pt unknown
- 2004-04-02 ES ES04725299T patent/ES2301979T3/es not_active Expired - Lifetime
- 2004-04-02 KR KR1020057018870A patent/KR20060021825A/ko not_active Application Discontinuation
- 2004-04-02 CL CL200400730A patent/CL2004000730A1/es unknown
- 2004-04-02 BR BRPI0408453-5A patent/BRPI0408453A/pt not_active IP Right Cessation
- 2004-04-02 AU AU2004226319A patent/AU2004226319A1/en not_active Abandoned
- 2004-04-02 DK DK04725299T patent/DK1613594T3/da active
- 2004-04-02 JP JP2006504348A patent/JP2006522029A/ja active Pending
- 2004-04-02 DE DE602004012724T patent/DE602004012724T2/de not_active Expired - Fee Related
- 2004-04-02 EA EA200501579A patent/EA009282B1/ru not_active IP Right Cessation
- 2004-04-02 CN CNB2004800094713A patent/CN100384822C/zh not_active Expired - Fee Related
- 2004-04-02 NZ NZ541944A patent/NZ541944A/en unknown
- 2004-04-02 AT AT04725299T patent/ATE390413T1/de not_active IP Right Cessation
- 2004-04-02 MX MXPA05010678A patent/MXPA05010678A/es active IP Right Grant
- 2004-04-02 SI SI200430727T patent/SI1613594T1/sl unknown
- 2004-04-02 AR ARP040101130A patent/AR043964A1/es not_active Application Discontinuation
-
2005
- 2005-08-29 IS IS8007A patent/IS8007A/is unknown
- 2005-11-02 CO CO05111852A patent/CO5700777A2/es unknown
- 2005-11-04 NO NO20055205A patent/NO20055205L/no unknown
-
2006
- 2006-09-26 HK HK06110721A patent/HK1090051A1/xx not_active IP Right Cessation
-
2008
- 2008-06-03 HR HR20080243T patent/HRP20080243T3/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PT1613594E (pt) | 2008-07-01 |
| MXPA05010678A (es) | 2005-12-12 |
| AR043964A1 (es) | 2005-08-17 |
| EP1613594A1 (de) | 2006-01-11 |
| CO5700777A2 (es) | 2006-11-30 |
| US20070173522A1 (en) | 2007-07-26 |
| UA81300C2 (en) | 2007-12-25 |
| NO20055205L (no) | 2005-11-04 |
| WO2004087662A1 (en) | 2004-10-14 |
| CL2004000730A1 (es) | 2005-02-18 |
| CN100384822C (zh) | 2008-04-30 |
| AU2004226319A1 (en) | 2004-10-14 |
| ES2301979T3 (es) | 2008-07-01 |
| HRP20080243T3 (en) | 2009-04-30 |
| HK1090051A1 (en) | 2006-12-15 |
| CN1777585A (zh) | 2006-05-24 |
| DE602004012724D1 (de) | 2008-05-08 |
| CA2521172A1 (en) | 2004-10-14 |
| ATE390413T1 (de) | 2008-04-15 |
| EA009282B1 (ru) | 2007-12-28 |
| DK1613594T3 (da) | 2008-07-14 |
| JP2006522029A (ja) | 2006-09-28 |
| KR20060021825A (ko) | 2006-03-08 |
| IS8007A (is) | 2005-08-29 |
| BRPI0408453A (pt) | 2006-04-04 |
| PL1613594T3 (pl) | 2008-09-30 |
| SI1613594T1 (sl) | 2008-08-31 |
| EA200501579A1 (ru) | 2006-04-28 |
| DE602004012724T2 (de) | 2009-04-09 |
| EP1613594B1 (de) | 2008-03-26 |
| NZ541944A (en) | 2008-05-30 |
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