DE69602970T2 - 5-(phenyl)-3-(4-piperidinyl)-1,3,4-oxadiazol-2(3h)-on-derivate verwendbar als 5-ht4- oder h3-rezeptorliganden - Google Patents
5-(phenyl)-3-(4-piperidinyl)-1,3,4-oxadiazol-2(3h)-on-derivate verwendbar als 5-ht4- oder h3-rezeptorligandenInfo
- Publication number
- DE69602970T2 DE69602970T2 DE69602970T DE69602970T DE69602970T2 DE 69602970 T2 DE69602970 T2 DE 69602970T2 DE 69602970 T DE69602970 T DE 69602970T DE 69602970 T DE69602970 T DE 69602970T DE 69602970 T2 DE69602970 T2 DE 69602970T2
- Authority
- DE
- Germany
- Prior art keywords
- group
- piperidin
- dihydro
- compound
- chloro
- 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.)
- Expired - Lifetime
Links
- -1 4-PIPERIDINYL Chemical class 0.000 title claims description 57
- 239000003446 ligand Substances 0.000 title description 4
- 102000005962 receptors Human genes 0.000 title description 4
- 108020003175 receptors Proteins 0.000 title description 4
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 90
- 239000000203 mixture Substances 0.000 claims description 68
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 10
- FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Chemical compound CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 claims description 9
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 7
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 claims description 7
- 239000012458 free base Substances 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- HDOWRFHMPULYOA-UHFFFAOYSA-N piperidin-4-ol Chemical compound OC1CCNCC1 HDOWRFHMPULYOA-UHFFFAOYSA-N 0.000 claims description 4
- 125000006239 protecting group Chemical group 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims description 3
- 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 claims description 3
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 239000012876 carrier material Substances 0.000 claims description 2
- 125000004981 cycloalkylmethyl group Chemical group 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- QNXSIUBBGPHDDE-UHFFFAOYSA-N indan-1-one Chemical compound C1=CC=C2C(=O)CCC2=C1 QNXSIUBBGPHDDE-UHFFFAOYSA-N 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000003386 piperidinyl group Chemical group 0.000 claims description 2
- 238000006268 reductive amination reaction Methods 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 1
- 230000003287 optical effect Effects 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 46
- 230000008018 melting Effects 0.000 description 44
- 238000002844 melting Methods 0.000 description 44
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 40
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 39
- 230000002829 reductive effect Effects 0.000 description 38
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 33
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 33
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 32
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
- 238000003756 stirring Methods 0.000 description 25
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 238000001914 filtration Methods 0.000 description 24
- 239000002904 solvent Substances 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 239000002244 precipitate Substances 0.000 description 17
- 239000007787 solid Substances 0.000 description 17
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
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- 239000012074 organic phase Substances 0.000 description 14
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- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
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- 239000000725 suspension Substances 0.000 description 12
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 10
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 10
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- 238000004440 column chromatography Methods 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 7
- 239000002585 base Substances 0.000 description 7
- 239000000741 silica gel Substances 0.000 description 7
- 229910002027 silica gel Inorganic materials 0.000 description 7
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 5
- LDECUSDQMXVUMP-UHFFFAOYSA-N benzyl 3-[6-[[2-(butylamino)-1-[3-methoxycarbonyl-4-(2-methoxy-2-oxoethoxy)phenyl]-2-oxoethyl]-hexylamino]-6-oxohexyl]-4-methyl-2-oxo-6-(4-phenylphenyl)-1,6-dihydropyrimidine-5-carboxylate Chemical compound O=C1NC(C=2C=CC(=CC=2)C=2C=CC=CC=2)C(C(=O)OCC=2C=CC=CC=2)=C(C)N1CCCCCC(=O)N(CCCCCC)C(C(=O)NCCCC)C1=CC=C(OCC(=O)OC)C(C(=O)OC)=C1 LDECUSDQMXVUMP-UHFFFAOYSA-N 0.000 description 5
- 210000001519 tissue Anatomy 0.000 description 5
- 208000019901 Anxiety disease Diseases 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 4
- 230000036506 anxiety Effects 0.000 description 4
- 239000000010 aprotic solvent Substances 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 229940076279 serotonin Drugs 0.000 description 4
- 230000009870 specific binding Effects 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- RLKMOPWWGZKHOP-UHFFFAOYSA-N 1-butylpiperidin-4-ol Chemical compound CCCCN1CCC(O)CC1 RLKMOPWWGZKHOP-UHFFFAOYSA-N 0.000 description 3
- QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 3
- WMPPDTMATNBGJN-UHFFFAOYSA-N 2-phenylethylbromide Chemical compound BrCCC1=CC=CC=C1 WMPPDTMATNBGJN-UHFFFAOYSA-N 0.000 description 3
- KLPBRQIQIHTCRI-UHFFFAOYSA-N 4-amino-5-chloro-2-(cyclopropylmethoxy)benzoic acid Chemical compound C1=C(Cl)C(N)=CC(OCC2CC2)=C1C(O)=O KLPBRQIQIHTCRI-UHFFFAOYSA-N 0.000 description 3
- ABQHXSZKQQZAML-UHFFFAOYSA-N 5-(4-amino-5-chloro-2-methoxyphenyl)-3-piperidin-4-yl-1,3,4-oxadiazol-2-one Chemical compound COC1=CC(N)=C(Cl)C=C1C(OC1=O)=NN1C1CCNCC1 ABQHXSZKQQZAML-UHFFFAOYSA-N 0.000 description 3
- NUSGHOZCGBGOGB-UHFFFAOYSA-N 5-(5-chloro-2,3-dihydro-1-benzofuran-7-yl)-3-piperidin-4-yl-1,3,4-oxadiazol-2-one Chemical compound C=1C(Cl)=CC=2CCOC=2C=1C(OC1=O)=NN1C1CCNCC1 NUSGHOZCGBGOGB-UHFFFAOYSA-N 0.000 description 3
- AYWZMFWXMUZADG-UHFFFAOYSA-N 5-(5-chloro-2,3-dihydro-1-benzofuran-7-yl)-3h-1,3,4-oxadiazol-2-one Chemical compound C=1C(Cl)=CC=2CCOC=2C=1C1=NNC(=O)O1 AYWZMFWXMUZADG-UHFFFAOYSA-N 0.000 description 3
- 108091005482 5-HT4 receptors Proteins 0.000 description 3
- 208000024827 Alzheimer disease Diseases 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
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- ZNJHFNUEQDVFCJ-UHFFFAOYSA-M sodium;2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid;hydroxide Chemical compound [OH-].[Na+].OCCN1CCN(CCS(O)(=O)=O)CC1 ZNJHFNUEQDVFCJ-UHFFFAOYSA-M 0.000 description 3
- PWQLFIKTGRINFF-UHFFFAOYSA-N tert-butyl 4-hydroxypiperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(O)CC1 PWQLFIKTGRINFF-UHFFFAOYSA-N 0.000 description 3
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- BAUWRHPMUVYFOD-UHFFFAOYSA-N 1-methylpiperidin-4-ol Chemical compound CN1CCC(O)CC1 BAUWRHPMUVYFOD-UHFFFAOYSA-N 0.000 description 2
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- RVEATKYEARPWRE-UHFFFAOYSA-N 4-amino-5-chloro-2-methoxybenzoic acid Chemical compound COC1=CC(N)=C(Cl)C=C1C(O)=O RVEATKYEARPWRE-UHFFFAOYSA-N 0.000 description 2
- WNMCTSHHWRPDNQ-UHFFFAOYSA-N 5-(4-amino-5-chloro-2-methoxyphenyl)-3-(1-methylpiperidin-4-yl)-1,3,4-oxadiazol-2-one Chemical compound COC1=CC(N)=C(Cl)C=C1C(OC1=O)=NN1C1CCN(C)CC1 WNMCTSHHWRPDNQ-UHFFFAOYSA-N 0.000 description 2
- IVAVPGIRMLIZIK-UHFFFAOYSA-N 5-(4-amino-5-chloro-2-methoxyphenyl)-3-[1-(2-phenylethyl)piperidin-4-yl]-1,3,4-oxadiazol-2-one Chemical compound COC1=CC(N)=C(Cl)C=C1C(OC1=O)=NN1C1CCN(CCC=2C=CC=CC=2)CC1 IVAVPGIRMLIZIK-UHFFFAOYSA-N 0.000 description 2
- BQNIHLDTULCIEK-UHFFFAOYSA-N 5-(5-amino-6-chloro-2,3-dihydro-1,4-benzodioxin-8-yl)-3-[1-(4,4,4-trifluorobutyl)piperidin-4-yl]-1,3,4-oxadiazol-2-one Chemical compound C1=2OCCOC=2C(N)=C(Cl)C=C1C(OC1=O)=NN1C1CCN(CCCC(F)(F)F)CC1 BQNIHLDTULCIEK-UHFFFAOYSA-N 0.000 description 2
- WLWMWCGUHCKKOH-UHFFFAOYSA-N 5-(5-amino-6-chloro-2,3-dihydro-1,4-benzodioxin-8-yl)-3-piperidin-4-yl-1,3,4-oxadiazol-2-one Chemical compound C1=2OCCOC=2C(N)=C(Cl)C=C1C(OC1=O)=NN1C1CCNCC1 WLWMWCGUHCKKOH-UHFFFAOYSA-N 0.000 description 2
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- JVKROPCXEGJZRU-UHFFFAOYSA-N 5-chloro-1-[4-(dimethylamino)piperidin-1-yl]pentan-1-one Chemical compound CN(C)C1CCN(C(=O)CCCCCl)CC1 JVKROPCXEGJZRU-UHFFFAOYSA-N 0.000 description 2
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- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 2
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- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- 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
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- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9513253A FR2741070B1 (fr) | 1995-11-09 | 1995-11-09 | Derives de 5-phenyl-3-(piperidin-4-yl)-1,3,4-oxadiazol-2(3h) -one, leur preparation et leur application en therapeutique |
| FR9513252A FR2741069B1 (fr) | 1995-11-09 | 1995-11-09 | Derives de 5-phenyl-3-(piperidin-4-yl)-1,3,4-oxadiazol-2(3h) -one, leur preparation et leur application en therapeutique |
| FR9602663A FR2745574B1 (fr) | 1996-03-04 | 1996-03-04 | Derives de 5-phenyl-3-(piperidin-4-yl)-1, 3, 4-oxadiazol-2 (3h)-one, leur preparation et leur application en therapeutique |
| PCT/FR1996/001730 WO1997017345A1 (fr) | 1995-11-09 | 1996-11-05 | Derives de 5-phenyl-3-(piperidin-4-yl)-1,3,4-oxadiazol-2(3h)-one, utiles comme ligands des recepteurs 5-ht4 ou h¿3? |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69602970D1 DE69602970D1 (de) | 1999-07-22 |
| DE69602970T2 true DE69602970T2 (de) | 2000-01-20 |
Family
ID=27253120
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69602970T Expired - Lifetime DE69602970T2 (de) | 1995-11-09 | 1996-11-05 | 5-(phenyl)-3-(4-piperidinyl)-1,3,4-oxadiazol-2(3h)-on-derivate verwendbar als 5-ht4- oder h3-rezeptorliganden |
Country Status (29)
| Country | Link |
|---|---|
| US (1) | US5929089A (enExample) |
| EP (1) | EP0863897B1 (enExample) |
| JP (1) | JP4263240B2 (enExample) |
| CN (1) | CN1077891C (enExample) |
| AR (1) | AR004708A1 (enExample) |
| AT (1) | ATE181328T1 (enExample) |
| AU (1) | AU707325B2 (enExample) |
| BG (1) | BG63463B1 (enExample) |
| BR (1) | BR9611311A (enExample) |
| CA (1) | CA2236357C (enExample) |
| CO (1) | CO4770968A1 (enExample) |
| CZ (1) | CZ287268B6 (enExample) |
| DE (1) | DE69602970T2 (enExample) |
| EE (1) | EE03487B1 (enExample) |
| ES (1) | ES2135934T3 (enExample) |
| GR (1) | GR3030823T3 (enExample) |
| HU (1) | HUP0001168A3 (enExample) |
| IL (1) | IL124364A (enExample) |
| MX (1) | MX9803696A (enExample) |
| NO (1) | NO309606B1 (enExample) |
| NZ (1) | NZ321626A (enExample) |
| PL (1) | PL186204B1 (enExample) |
| RU (1) | RU2167160C2 (enExample) |
| SI (1) | SI0863897T1 (enExample) |
| SK (1) | SK282335B6 (enExample) |
| TR (1) | TR199800827T2 (enExample) |
| TW (1) | TW371303B (enExample) |
| UA (1) | UA50748C2 (enExample) |
| WO (1) | WO1997017345A1 (enExample) |
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW467902B (en) * | 1996-07-31 | 2001-12-11 | Bristol Myers Squibb Co | Diphenyl heterocycles as potassium channel modulators |
| FR2762316B1 (fr) * | 1997-04-18 | 1999-12-17 | Sanofi Synthelabo | Derives de 5-aryl-3-(8-azabicyclo[3.2.1] octan-3-yl)-1,3,4- oxadiazol-2(3h)-one, leur preparation et leur application en therapeutique |
| EP0980370A1 (fr) * | 1997-05-06 | 2000-02-23 | Sanofi-Synthelabo | Derives de 5-phenyl-1,3,4-oxadiazol-2(3h)-one et leur utilisation comme ligands 5-ht4 |
| FR2763068B1 (fr) | 1997-05-06 | 1999-06-04 | Synthelabo | Derives de 3-(pyrrolidin-3-yl)-1,3,4-oxadiazol-2(3h)-one, leur preparation et leur application en therapeutique |
| GB9715816D0 (en) * | 1997-07-25 | 1997-10-01 | Black James Foundation | Histamine H receptor ligands |
| US6960579B1 (en) | 1998-05-19 | 2005-11-01 | Alcon Manufacturing, Ltd. | Serotonergic 5HT7 receptor compounds for treating ocular and CNS disorders |
| KR20010073153A (ko) | 1998-09-18 | 2001-07-31 | 제임스 에이. 아노 | 녹내장 치료용의 세로토닌성 5ｈｔ2 작용제 |
| EP1173168A2 (en) * | 1999-04-28 | 2002-01-23 | Respiratorius AB | Compound for use as a medicament for treatment of disorders involving bronchocontraction |
| WO2000076500A2 (en) * | 1999-06-15 | 2000-12-21 | Respiratorius Ab | Compound for use as a medicament for treatment of disorders involving bronchocontraction |
| AU2001281119A1 (en) * | 2000-08-08 | 2002-02-18 | Ortho-Mcneil Pharmaceutical, Inc. | Bicyclic compounds as h3 receptor ligands |
| JP5279161B2 (ja) | 2000-08-08 | 2013-09-04 | オーソ−マクニール・フアーマシユーチカル・インコーポレーテツド | 非イミダゾールアリールオキシアルキルアミン |
| BR0113161A (pt) | 2000-08-08 | 2004-04-06 | Ortho Mcneil Pharm Inc | Arilóxi piperidinas não imidazóis |
| DE60234453D1 (de) | 2001-07-02 | 2009-12-31 | High Point Pharmaceuticals Llc | Substituierte piperazin- und diazepanderivate zur verwendung als histamin h3 rezeptormodulatoren |
| US7208497B2 (en) | 2001-07-02 | 2007-04-24 | Novo Nordisk A/S | Substituted piperazines and diazepanes |
| EP1430027B1 (en) | 2001-09-14 | 2010-09-01 | High Point Pharmaceuticals, LLC | Novel aminoazetidine, -pyrrolidine and -piperidine derivatives |
| US20030186963A1 (en) | 2001-09-14 | 2003-10-02 | Dorwald Florencio Zaragoza | Substituted piperidines |
| US6673829B2 (en) | 2001-09-14 | 2004-01-06 | Novo Nordisk A/S | Aminoazetidine,-pyrrolidine and -piperidine derivatives |
| EP1434765B1 (en) * | 2001-09-14 | 2009-12-02 | High Point Pharmaceuticals, LLC | Substituted piperidines with selective binding to histamine h3-receptor |
| JP4563675B2 (ja) | 2001-10-12 | 2010-10-13 | ハイ・ポイント・ファーマスーティカルズ、エルエルシー | 置換ピペリジン類、およびヒスタミンｈ３受容体関連疾患の治療のためのその使用 |
| US7064135B2 (en) | 2001-10-12 | 2006-06-20 | Novo Nordisk Inc. | Substituted piperidines |
| WO2003051352A1 (en) | 2001-12-14 | 2003-06-26 | Alcon, Inc. | Aminoalkyl-benzofuran-5-ol compounds for the treatment of glaucoma |
| US20030236259A1 (en) * | 2002-02-05 | 2003-12-25 | Rolf Hohlweg | Novel aryl- and heteroarylpiperazines |
| GB0211230D0 (en) | 2002-05-16 | 2002-06-26 | Medinnova Sf | Treatment of heart failure |
| US7332508B2 (en) * | 2002-12-18 | 2008-02-19 | Novo Nordisk A/S | Substituted homopiperidine, piperidine or pyrrolidine derivatives |
| GB0325956D0 (en) * | 2003-11-06 | 2003-12-10 | Addex Pharmaceuticals Sa | Novel compounds |
| US7737163B2 (en) | 2004-06-15 | 2010-06-15 | Pfizer Inc. | Benzimidazolone carboxylic acid derivatives |
| AU2005254800B2 (en) | 2004-06-15 | 2010-12-09 | Pfizer Inc. | Benzimidazolone carboxylic acid derivatives |
| EP1902028A2 (en) * | 2005-07-04 | 2008-03-26 | Novo Nordisk A/S | Histamine h3 receptor antagonists |
| EP1959951B1 (en) * | 2005-12-01 | 2009-12-23 | F. Hoffmann-la Roche AG | Heteroaryl substituted piperidine derivatives as l-cpt1 inhibitors |
| ATE538116T1 (de) | 2006-05-29 | 2012-01-15 | High Point Pharmaceuticals Llc | 3-(1,3-benyodioxol-5-yl)-6- (4- cyclopropylpiperazin-1-yl)-pyridazin, dessen salze und solvate und dessen verwendung als histamin-h3-rezeptorantagonist |
| EP2014656A3 (en) * | 2007-06-11 | 2011-08-24 | High Point Pharmaceuticals, LLC | New heteocyclic h3 antagonists |
| SI2758394T1 (sl) | 2011-09-19 | 2015-05-29 | Suven Life Sciences Limited | Heteroaril spojine kot 5-ht4 receptor ligandi |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5055476A (en) * | 1990-08-13 | 1991-10-08 | Hoechst-Roussel Pharmaceuticals Incorporated | 3-(1,2-benzisoxazol-3-yl)-4-pyridinamines and derivatives |
| CA2116024A1 (en) * | 1991-08-20 | 1993-03-04 | Francis David King | 5-ht4 receptor antagonists |
| SG49153A1 (en) * | 1991-09-12 | 1998-05-18 | Smithkline Beecham Plc | 5-HT4 receptor antagonists |
| CA2129112A1 (en) * | 1992-02-06 | 1993-08-19 | Francis David King | Benzopyran, benzothiopyran and benzofuran derivatives as 5-ht4 antagonists |
| GB9219163D0 (en) * | 1992-09-10 | 1992-10-28 | Smithkline Beecham Plc | Pharmaceuticals |
| JPH06157518A (ja) * | 1992-11-27 | 1994-06-03 | Yamanouchi Pharmaceut Co Ltd | 新規なオキサジアゾール誘導体又はその塩 |
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1996
- 1996-11-05 AU AU75001/96A patent/AU707325B2/en not_active Ceased
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- 1996-11-05 SK SK599-98A patent/SK282335B6/sk not_active IP Right Cessation
- 1996-11-05 CZ CZ19981421A patent/CZ287268B6/cs not_active IP Right Cessation
- 1996-11-05 ES ES96937390T patent/ES2135934T3/es not_active Expired - Lifetime
- 1996-11-05 AT AT96937390T patent/ATE181328T1/de active
- 1996-11-05 HU HU0001168A patent/HUP0001168A3/hu unknown
- 1996-11-05 BR BR9611311A patent/BR9611311A/pt not_active IP Right Cessation
- 1996-11-05 RU RU98110976/04A patent/RU2167160C2/ru not_active IP Right Cessation
- 1996-11-05 EE EE9800155A patent/EE03487B1/xx not_active IP Right Cessation
- 1996-11-05 EP EP96937390A patent/EP0863897B1/fr not_active Expired - Lifetime
- 1996-11-05 TR TR1998/00827T patent/TR199800827T2/xx unknown
- 1996-11-05 US US09/068,390 patent/US5929089A/en not_active Expired - Lifetime
- 1996-11-05 WO PCT/FR1996/001730 patent/WO1997017345A1/fr not_active Ceased
- 1996-11-05 DE DE69602970T patent/DE69602970T2/de not_active Expired - Lifetime
- 1996-11-05 SI SI9630092T patent/SI0863897T1/xx not_active IP Right Cessation
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- 1996-11-05 IL IL12436496A patent/IL124364A/xx not_active IP Right Cessation
- 1996-11-05 CA CA002236357A patent/CA2236357C/en not_active Expired - Fee Related
- 1996-11-07 TW TW085113594A patent/TW371303B/zh not_active IP Right Cessation
- 1996-11-08 CO CO96059097A patent/CO4770968A1/es unknown
- 1996-11-08 AR ARP960105098A patent/AR004708A1/es active IP Right Grant
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1998
- 1998-04-28 BG BG102412A patent/BG63463B1/bg unknown
- 1998-05-07 NO NO982092A patent/NO309606B1/no not_active IP Right Cessation
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1999
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