JP2004513124A5 - - Google Patents
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- Publication number
- JP2004513124A5 JP2004513124A5 JP2002539343A JP2002539343A JP2004513124A5 JP 2004513124 A5 JP2004513124 A5 JP 2004513124A5 JP 2002539343 A JP2002539343 A JP 2002539343A JP 2002539343 A JP2002539343 A JP 2002539343A JP 2004513124 A5 JP2004513124 A5 JP 2004513124A5
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- benzo
- ethyl
- compound according
- methyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 claims 42
- 125000000217 alkyl group Chemical group 0.000 claims 29
- 229910052739 hydrogen Inorganic materials 0.000 claims 18
- 239000001257 hydrogen Substances 0.000 claims 18
- 125000003545 alkoxy group Chemical group 0.000 claims 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 9
- 125000003342 alkenyl group Chemical group 0.000 claims 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims 8
- 150000002431 hydrogen Chemical class 0.000 claims 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 7
- 150000002148 esters Chemical class 0.000 claims 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 7
- 150000003839 salts Chemical class 0.000 claims 7
- 229910052717 sulfur Inorganic materials 0.000 claims 7
- -1 1,1-dimethyl-2-propynyl Chemical group 0.000 claims 5
- 229910052794 bromium Inorganic materials 0.000 claims 5
- 229910052801 chlorine Inorganic materials 0.000 claims 5
- 239000000460 chlorine Substances 0.000 claims 5
- 229910052736 halogen Inorganic materials 0.000 claims 5
- 150000002367 halogens Chemical group 0.000 claims 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 5
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical group CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 4
- 125000000304 alkynyl group Chemical group 0.000 claims 4
- 229910052740 iodine Inorganic materials 0.000 claims 4
- 230000002265 prevention Effects 0.000 claims 4
- 125000001424 substituent group Chemical group 0.000 claims 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical group CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 4
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims 3
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 3
- 125000002947 alkylene group Chemical group 0.000 claims 3
- 230000006806 disease prevention Effects 0.000 claims 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical group [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 2
- 206010003210 Arteriosclerosis Diseases 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- 206010017533 Fungal infection Diseases 0.000 claims 2
- 208000002705 Glucose Intolerance Diseases 0.000 claims 2
- 206010018429 Glucose tolerance impaired Diseases 0.000 claims 2
- 208000035150 Hypercholesterolemia Diseases 0.000 claims 2
- 208000031226 Hyperlipidaemia Diseases 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 208000030852 Parasitic disease Diseases 0.000 claims 2
- 239000013543 active substance Substances 0.000 claims 2
- 125000004450 alkenylene group Chemical group 0.000 claims 2
- 208000011775 arteriosclerosis disease Diseases 0.000 claims 2
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 2
- 201000001883 cholelithiasis Diseases 0.000 claims 2
- 206010012601 diabetes mellitus Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 208000024386 fungal infectious disease Diseases 0.000 claims 2
- 208000001130 gallstones Diseases 0.000 claims 2
- 230000003463 hyperproliferative effect Effects 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- JXMYVJNDTTUIGS-UHFFFAOYSA-N n,2-dimethyl-n-[2-[[2-methyl-3-[4-(trifluoromethyl)phenyl]-1-benzothiophen-6-yl]oxy]ethyl]pyrimidin-4-amine Chemical compound C=1C=NC(C)=NC=1N(C)CCOC(C=C1SC=2C)=CC=C1C=2C1=CC=C(C(F)(F)F)C=C1 JXMYVJNDTTUIGS-UHFFFAOYSA-N 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 2
- 208000019553 vascular disease Diseases 0.000 claims 2
- PKDPUENCROCRCH-UHFFFAOYSA-N 1-piperazin-1-ylethanone Chemical compound CC(=O)N1CCNCC1 PKDPUENCROCRCH-UHFFFAOYSA-N 0.000 claims 1
- PDQRQJVPEFGVRK-UHFFFAOYSA-N 2,1,3-benzothiadiazole Chemical compound C1=CC=CC2=NSN=C21 PDQRQJVPEFGVRK-UHFFFAOYSA-N 0.000 claims 1
- BPRMUSLFSONHPV-UHFFFAOYSA-N 2-[3-[[3-(4-bromophenyl)-1,2-benzothiazol-6-yl]oxy]propyl-ethylamino]ethanol Chemical compound N=1SC2=CC(OCCCN(CCO)CC)=CC=C2C=1C1=CC=C(Br)C=C1 BPRMUSLFSONHPV-UHFFFAOYSA-N 0.000 claims 1
- LJYMMGAXOLXEQQ-UHFFFAOYSA-N 2-[4-[[3-(4-bromophenyl)-1,2-benzothiazol-6-yl]oxy]butyl-(2-hydroxyethyl)amino]ethanol Chemical compound N=1SC2=CC(OCCCCN(CCO)CCO)=CC=C2C=1C1=CC=C(Br)C=C1 LJYMMGAXOLXEQQ-UHFFFAOYSA-N 0.000 claims 1
- XHOKJNHLSGAYJL-UHFFFAOYSA-N 2-[4-[[3-(4-bromophenyl)-1,2-benzothiazol-6-yl]oxy]butyl-ethylamino]ethanol Chemical compound N=1SC2=CC(OCCCCN(CCO)CC)=CC=C2C=1C1=CC=C(Br)C=C1 XHOKJNHLSGAYJL-UHFFFAOYSA-N 0.000 claims 1
- RNUFGYJANLYFPZ-UHFFFAOYSA-N 2-[4-[[3-(4-bromophenyl)-2-methyl-1-benzothiophen-6-yl]oxy]butyl-(2-hydroxyethyl)amino]ethanol Chemical compound CC=1SC2=CC(OCCCCN(CCO)CCO)=CC=C2C=1C1=CC=C(Br)C=C1 RNUFGYJANLYFPZ-UHFFFAOYSA-N 0.000 claims 1
- WGFNYNVHQAKQPA-UHFFFAOYSA-N 2-[5-[3-(4-bromophenyl)-1,2-benzothiazol-6-yl]pent-4-ynyl-ethylamino]ethanol Chemical compound N=1SC2=CC(C#CCCCN(CCO)CC)=CC=C2C=1C1=CC=C(Br)C=C1 WGFNYNVHQAKQPA-UHFFFAOYSA-N 0.000 claims 1
- KWFNLXLYVMYTRB-UHFFFAOYSA-N 2-[5-[3-(4-chlorophenyl)-1,2-benzothiazol-6-yl]pent-4-ynyl-ethylamino]ethanol Chemical compound N=1SC2=CC(C#CCCCN(CCO)CC)=CC=C2C=1C1=CC=C(Cl)C=C1 KWFNLXLYVMYTRB-UHFFFAOYSA-N 0.000 claims 1
- KHISTYKSRSFTNE-UHFFFAOYSA-N 2-[[4-[3-(4-bromophenyl)-1,2-benzothiazol-6-yl]-2-methylbut-3-yn-2-yl]-ethylamino]ethanol Chemical compound N=1SC2=CC(C#CC(C)(C)N(CCO)CC)=CC=C2C=1C1=CC=C(Br)C=C1 KHISTYKSRSFTNE-UHFFFAOYSA-N 0.000 claims 1
- UAOFQHFGSPZGHT-UHFFFAOYSA-N 2-[ethyl-[2-methyl-4-[3-[4-(trifluoromethyl)phenyl]-1,2-benzothiazol-6-yl]but-3-yn-2-yl]amino]ethanol Chemical compound N=1SC2=CC(C#CC(C)(C)N(CCO)CC)=CC=C2C=1C1=CC=C(C(F)(F)F)C=C1 UAOFQHFGSPZGHT-UHFFFAOYSA-N 0.000 claims 1
- UKVUXZIUUJUSDZ-UHFFFAOYSA-N 2-[ethyl-[3-[2-methyl-3-[4-(trifluoromethyl)phenyl]-1-benzothiophen-6-yl]propyl]amino]ethanol Chemical compound CC=1SC2=CC(CCCN(CCO)CC)=CC=C2C=1C1=CC=C(C(F)(F)F)C=C1 UKVUXZIUUJUSDZ-UHFFFAOYSA-N 0.000 claims 1
- JHFTYDAOJCHPHL-UHFFFAOYSA-N 2-[ethyl-[4-[2-methyl-3-[4-(trifluoromethyl)phenyl]-1-benzothiophen-6-yl]butyl]amino]ethanol Chemical compound CC=1SC2=CC(CCCCN(CCO)CC)=CC=C2C=1C1=CC=C(C(F)(F)F)C=C1 JHFTYDAOJCHPHL-UHFFFAOYSA-N 0.000 claims 1
- ACNNKOBPYPBXMD-UHFFFAOYSA-N 2-[ethyl-[4-[3-[4-(trifluoromethyl)phenyl]-1,2-benzothiazol-6-yl]but-3-yn-2-yl]amino]ethanol Chemical compound N=1SC2=CC(C#CC(C)N(CCO)CC)=CC=C2C=1C1=CC=C(C(F)(F)F)C=C1 ACNNKOBPYPBXMD-UHFFFAOYSA-N 0.000 claims 1
- UZVJQRKJSYUQPR-UHFFFAOYSA-N 2-[ethyl-[4-[[3-[4-(trifluoromethyl)phenyl]-1,2-benzothiazol-6-yl]oxy]butyl]amino]ethanol Chemical compound N=1SC2=CC(OCCCCN(CCO)CC)=CC=C2C=1C1=CC=C(C(F)(F)F)C=C1 UZVJQRKJSYUQPR-UHFFFAOYSA-N 0.000 claims 1
- IDPMLDMRHZRSJI-UHFFFAOYSA-N 2-[ethyl-[5-[3-[4-(trifluoromethyl)phenyl]-1,2-benzothiazol-6-yl]pent-4-ynyl]amino]ethanol Chemical compound N=1SC2=CC(C#CCCCN(CCO)CC)=CC=C2C=1C1=CC=C(C(F)(F)F)C=C1 IDPMLDMRHZRSJI-UHFFFAOYSA-N 0.000 claims 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims 1
- KCXINOJHQKHNHB-UHFFFAOYSA-N 3-(4-bromophenyl)-6-(3-piperidin-1-ylpropoxy)-1,2-benzothiazole Chemical compound C1=CC(Br)=CC=C1C1=NSC2=CC(OCCCN3CCCCC3)=CC=C12 KCXINOJHQKHNHB-UHFFFAOYSA-N 0.000 claims 1
- GFBZAIYAMSYPFU-UHFFFAOYSA-N 3-(4-bromophenyl)-6-[4-(4-methylpiperazin-1-yl)butoxy]-1,2-benzothiazole Chemical compound C1CN(C)CCN1CCCCOC1=CC=C(C(=NS2)C=3C=CC(Br)=CC=3)C2=C1 GFBZAIYAMSYPFU-UHFFFAOYSA-N 0.000 claims 1
- MHQMIESFKJXZKW-UHFFFAOYSA-N 4-[3-(4-bromophenyl)-1,2-benzothiazol-6-yl]-n-ethyl-n-(2-methoxyethyl)butan-1-amine Chemical compound N=1SC2=CC(CCCCN(CC)CCOC)=CC=C2C=1C1=CC=C(Br)C=C1 MHQMIESFKJXZKW-UHFFFAOYSA-N 0.000 claims 1
- HUCJOSJUHORBLH-UHFFFAOYSA-N 4-[[3-(4-bromophenyl)-2-methyl-1,1-dioxo-1-benzothiophen-6-yl]oxy]-N,N-diethylbutan-1-amine Chemical compound CC=1S(=O)(=O)C2=CC(OCCCCN(CC)CC)=CC=C2C=1C1=CC=C(Br)C=C1 HUCJOSJUHORBLH-UHFFFAOYSA-N 0.000 claims 1
- GYBRWLTVLLBOPE-UHFFFAOYSA-N 4-[[3-(4-chlorophenyl)-1,1-dioxo-1,2-benzothiazol-6-yl]oxy]-N-ethyl-N-(2-methoxyethyl)butan-1-amine Chemical class N=1S(=O)(=O)C2=CC(OCCCCN(CC)CCOC)=CC=C2C=1C1=CC=C(Cl)C=C1 GYBRWLTVLLBOPE-UHFFFAOYSA-N 0.000 claims 1
- DMWSTYPDOPLLHH-UHFFFAOYSA-N 4-[[3-(4-chlorophenyl)-1,1-dioxo-1,2-benzothiazol-6-yl]oxy]-N-methyl-N-propylbutan-1-amine Chemical compound N=1S(=O)(=O)C2=CC(OCCCCN(C)CCC)=CC=C2C=1C1=CC=C(Cl)C=C1 DMWSTYPDOPLLHH-UHFFFAOYSA-N 0.000 claims 1
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims 1
- BCVITIXNZHVWAU-UHFFFAOYSA-N 5-[3-(4-bromophenyl)-1,2-benzothiazol-6-yl]-n,n-dimethylpent-4-yn-1-amine Chemical compound N=1SC2=CC(C#CCCCN(C)C)=CC=C2C=1C1=CC=C(Br)C=C1 BCVITIXNZHVWAU-UHFFFAOYSA-N 0.000 claims 1
- JDILDCZOOLFYES-UHFFFAOYSA-N 5-[3-(4-chlorophenyl)-1,2-benzothiazol-6-yl]-n,n-diethylpent-4-yn-1-amine Chemical compound N=1SC2=CC(C#CCCCN(CC)CC)=CC=C2C=1C1=CC=C(Cl)C=C1 JDILDCZOOLFYES-UHFFFAOYSA-N 0.000 claims 1
- QJAHXASEUNAJOU-UHFFFAOYSA-N 6-[3-(azetidin-1-yl)prop-1-ynyl]-3-[4-(trifluoromethyl)phenyl]-1,2-benzothiazole Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=NSC2=CC(C#CCN3CCC3)=CC=C12 QJAHXASEUNAJOU-UHFFFAOYSA-N 0.000 claims 1
- KZZULBVTLOIGHX-UHFFFAOYSA-N 6-[5-(azetidin-1-yl)pent-1-ynyl]-3-[4-(trifluoromethyl)phenyl]-1,2-benzothiazole Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=NSC2=CC(C#CCCCN3CCC3)=CC=C12 KZZULBVTLOIGHX-UHFFFAOYSA-N 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- CWMWIBGIJRXEAV-UHFFFAOYSA-N C12=CC=C(OCCCCN(CCO)CCO)C=C2S(=O)(=O)C(C)=C1C1=CC=C(Br)C=C1 Chemical compound C12=CC=C(OCCCCN(CCO)CCO)C=C2S(=O)(=O)C(C)=C1C1=CC=C(Br)C=C1 CWMWIBGIJRXEAV-UHFFFAOYSA-N 0.000 claims 1
- ZNYOKIMEBCKOKM-UHFFFAOYSA-N C1CC1CN(C)CCCCOC(C=C1S(=O)(=O)N=2)=CC=C1C=2C1=CC=C(Cl)C=C1 Chemical compound C1CC1CN(C)CCCCOC(C=C1S(=O)(=O)N=2)=CC=C1C=2C1=CC=C(Cl)C=C1 ZNYOKIMEBCKOKM-UHFFFAOYSA-N 0.000 claims 1
- DWQADYVYNZIFSX-UHFFFAOYSA-N CC=1S(=O)(=O)C2=CC(OCCCCN(CC)CCOC)=CC=C2C=1C1=CC=C(Br)C=C1 Chemical compound CC=1S(=O)(=O)C2=CC(OCCCCN(CC)CCOC)=CC=C2C=1C1=CC=C(Br)C=C1 DWQADYVYNZIFSX-UHFFFAOYSA-N 0.000 claims 1
- LSAKTSBJHIYLGI-UHFFFAOYSA-N CC=1S(=O)(=O)C2=CC(OCCCCN(CC)CCOC)=CC=C2C=1C1=CC=C(C(F)(F)F)C=C1 Chemical compound CC=1S(=O)(=O)C2=CC(OCCCCN(CC)CCOC)=CC=C2C=1C1=CC=C(C(F)(F)F)C=C1 LSAKTSBJHIYLGI-UHFFFAOYSA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- VYCNMWPMIDJMHB-UHFFFAOYSA-N N-methyl-5-[3-[4-(trifluoromethyl)phenyl]-1,2-benzothiazol-6-yl]pent-4-yn-1-amine Chemical compound CNCCCC#CC1=CC2=C(C(=NS2)C2=CC=C(C=C2)C(F)(F)F)C=C1 VYCNMWPMIDJMHB-UHFFFAOYSA-N 0.000 claims 1
- JALRPZGOYKXXIW-UHFFFAOYSA-N N=1S(=O)(=O)C2=CC(OCCCCN(C)C)=CC=C2C=1C1=CC=C(Br)C=C1 Chemical compound N=1S(=O)(=O)C2=CC(OCCCCN(C)C)=CC=C2C=1C1=CC=C(Br)C=C1 JALRPZGOYKXXIW-UHFFFAOYSA-N 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000002757 morpholinyl group Chemical group 0.000 claims 1
- HTVDZSAAYOIGBC-UHFFFAOYSA-N n,n-dimethyl-4-[[3-[4-(trifluoromethyl)phenyl]-1,2-benzothiazol-6-yl]oxy]butan-1-amine Chemical compound N=1SC2=CC(OCCCCN(C)C)=CC=C2C=1C1=CC=C(C(F)(F)F)C=C1 HTVDZSAAYOIGBC-UHFFFAOYSA-N 0.000 claims 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000004193 piperazinyl group Chemical group 0.000 claims 1
- 125000005936 piperidyl group Chemical group 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP00123826 | 2000-11-02 | ||
| PCT/EP2001/012451 WO2002036584A1 (en) | 2000-11-02 | 2001-10-26 | Cholesterol lowering benzo`b! thiophenes and benzo`d! isothiazoles |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2004513124A JP2004513124A (ja) | 2004-04-30 |
| JP2004513124A5 true JP2004513124A5 (https=) | 2005-04-07 |
| JP4012064B2 JP4012064B2 (ja) | 2007-11-21 |
Family
ID=8170270
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2002539343A Expired - Fee Related JP4012064B2 (ja) | 2000-11-02 | 2001-10-26 | コレステロールを低下させるベンゾ〔ｂ〕チオフェンおよびベンゾ〔ｄ〕イソチアゾール |
Country Status (21)
| Country | Link |
|---|---|
| US (3) | US6951879B2 (https=) |
| EP (1) | EP1334094B1 (https=) |
| JP (1) | JP4012064B2 (https=) |
| KR (1) | KR100545430B1 (https=) |
| CN (1) | CN1261429C (https=) |
| AR (1) | AR034271A1 (https=) |
| AT (1) | ATE286042T1 (https=) |
| AU (2) | AU2002214029B2 (https=) |
| BR (1) | BR0115075A (https=) |
| CA (1) | CA2426009C (https=) |
| DE (1) | DE60108164T2 (https=) |
| DK (1) | DK1334094T3 (https=) |
| ES (1) | ES2233703T3 (https=) |
| GT (1) | GT200100220A (https=) |
| MX (1) | MXPA03003845A (https=) |
| PA (1) | PA8531601A1 (https=) |
| PE (1) | PE20020600A1 (https=) |
| PT (1) | PT1334094E (https=) |
| UY (1) | UY27009A1 (https=) |
| WO (1) | WO2002036584A1 (https=) |
| ZA (1) | ZA200302742B (https=) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100566175B1 (ko) | 2000-08-16 | 2006-03-29 | 에프. 호프만-라 로슈 아게 | 신규한 아미노사이클로헥산 유도체 |
| US7012077B2 (en) * | 2001-12-20 | 2006-03-14 | Hoffmann-La Roche Inc. | Substituted cyclohexane derivatives |
| EP1647549A1 (en) * | 2004-10-14 | 2006-04-19 | Laboratoire Theramex | Indazoles, benzisoxazoles and benzisothiazoles as estrogenic agents |
| US7446210B2 (en) * | 2004-10-26 | 2008-11-04 | Janssen Pharmaceutica N.V. | Factor Xa compounds |
| JP2008544987A (ja) * | 2005-06-30 | 2008-12-11 | バイエル・クロツプサイエンス・アクチエンゲゼルシヤフト | 殺虫性の（二置換プロペニル）フェニルアルキル置換複素環式環を調製するための改善された方法 |
| FR2913019A1 (fr) * | 2007-02-23 | 2008-08-29 | Cerep Sa | Composes heterocycliques comme agents anti-neoplasiques ou inhibiteurs de proliferation cellulaire |
| CN101918416A (zh) * | 2007-11-29 | 2010-12-15 | 兰贝克赛实验室有限公司 | 制备取代的1,3-氧硫杂环戊烷,尤其是拉米夫定的方法和中间体 |
| WO2009069011A1 (en) * | 2007-11-29 | 2009-06-04 | Ranbaxy Laboratories Limited | Process for the preparation of substituted 1,3-oxathiolanes |
| CN103596570B (zh) * | 2010-12-27 | 2018-02-16 | 密苏里大学管委会 | 作为抗癌治疗的蛋白质靶的氧化鲨烯环化酶 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3598839A (en) * | 1969-06-30 | 1971-08-10 | Parke Davis & Co | Phenylbenzothiophene compounds |
| GR75101B (https=) * | 1980-10-23 | 1984-07-13 | Pfizer | |
| GB8417559D0 (en) * | 1984-07-10 | 1984-08-15 | Pfizer Ltd | Anti-diarrhoeal agents |
| DE3905364A1 (de) | 1989-02-22 | 1990-08-23 | Hoechst Ag | Substituierte pyrimidin-derivate, verfahren zu ihrer herstellung und ihre verwendung als tool |
| EP0530149A1 (de) * | 1991-08-30 | 1993-03-03 | Ciba-Geigy Ag | Schädlingsbekämpfungsmittel |
| US5482949A (en) * | 1993-03-19 | 1996-01-09 | Eli Lilly And Company | Sulfonate derivatives of 3-aroylbenzo[b]thiophenes |
| CA2190699A1 (en) * | 1995-12-08 | 1997-06-09 | Johannes Aebi | Tertiary amines |
| CA2190708A1 (en) * | 1995-12-08 | 1997-06-09 | Johannes Aebi | Aminoalkyl substituted benzo-heterocyclic compounds |
| UA56197C2 (uk) | 1996-11-08 | 2003-05-15 | Зенека Лімітед | Гетероциклічні похідні |
-
2001
- 2001-10-26 ES ES01982445T patent/ES2233703T3/es not_active Expired - Lifetime
- 2001-10-26 AU AU2002214029A patent/AU2002214029B2/en not_active Ceased
- 2001-10-26 CN CNB018182046A patent/CN1261429C/zh not_active Expired - Fee Related
- 2001-10-26 WO PCT/EP2001/012451 patent/WO2002036584A1/en not_active Ceased
- 2001-10-26 CA CA002426009A patent/CA2426009C/en not_active Expired - Fee Related
- 2001-10-26 AT AT01982445T patent/ATE286042T1/de active
- 2001-10-26 JP JP2002539343A patent/JP4012064B2/ja not_active Expired - Fee Related
- 2001-10-26 DK DK01982445T patent/DK1334094T3/da active
- 2001-10-26 MX MXPA03003845A patent/MXPA03003845A/es active IP Right Grant
- 2001-10-26 EP EP01982445A patent/EP1334094B1/en not_active Expired - Lifetime
- 2001-10-26 KR KR1020037006161A patent/KR100545430B1/ko not_active Expired - Fee Related
- 2001-10-26 AU AU1402902A patent/AU1402902A/xx active Pending
- 2001-10-26 DE DE60108164T patent/DE60108164T2/de not_active Expired - Lifetime
- 2001-10-26 PT PT01982445T patent/PT1334094E/pt unknown
- 2001-10-26 BR BR0115075-8A patent/BR0115075A/pt not_active Application Discontinuation
- 2001-10-30 PE PE2001001078A patent/PE20020600A1/es not_active Application Discontinuation
- 2001-10-31 GT GT200100220A patent/GT200100220A/es unknown
- 2001-10-31 US US09/999,424 patent/US6951879B2/en not_active Expired - Fee Related
- 2001-11-01 PA PA20018531601A patent/PA8531601A1/es unknown
- 2001-11-01 AR ARP010105115A patent/AR034271A1/es unknown
- 2001-11-01 UY UY27009A patent/UY27009A1/es not_active Application Discontinuation
-
2003
- 2003-04-08 ZA ZA200302742A patent/ZA200302742B/en unknown
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2005
- 2005-07-08 US US11/178,164 patent/US7173043B2/en not_active Expired - Fee Related
-
2006
- 2006-12-06 US US11/634,573 patent/US7449483B2/en not_active Expired - Fee Related
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