TW200825074A - Compounds - Google Patents
Compounds Download PDFInfo
- Publication number
- TW200825074A TW200825074A TW096130644A TW96130644A TW200825074A TW 200825074 A TW200825074 A TW 200825074A TW 096130644 A TW096130644 A TW 096130644A TW 96130644 A TW96130644 A TW 96130644A TW 200825074 A TW200825074 A TW 200825074A
- Authority
- TW
- Taiwan
- Prior art keywords
- methyl
- phenyl
- compound according
- trifluoromethyl
- thio
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims description 58
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 106
- 239000003814 drug Substances 0.000 claims abstract description 30
- 239000012453 solvate Substances 0.000 claims abstract description 25
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 7
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 102
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 86
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 54
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 50
- 201000010099 disease Diseases 0.000 claims description 45
- 239000000203 mixture Substances 0.000 claims description 42
- 229940095064 tartrate Drugs 0.000 claims description 40
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 33
- 239000007787 solid Substances 0.000 claims description 30
- -1 Hexyl tartrate Chemical compound 0.000 claims description 23
- FEWJPZIEWOKRBE-JCYAYHJZSA-L L-tartrate(2-) Chemical compound [O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O FEWJPZIEWOKRBE-JCYAYHJZSA-L 0.000 claims description 23
- 229940079593 drug Drugs 0.000 claims description 22
- 239000000126 substance Substances 0.000 claims description 20
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims description 14
- 235000002906 tartaric acid Nutrition 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- 239000011975 tartaric acid Substances 0.000 claims description 13
- 238000004458 analytical method Methods 0.000 claims description 11
- 239000013078 crystal Substances 0.000 claims description 8
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 8
- 238000001228 spectrum Methods 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 7
- OKTJSMMVPCPJKN-OUBTZVSYSA-N Carbon-13 Chemical compound [13C] OKTJSMMVPCPJKN-OUBTZVSYSA-N 0.000 claims description 6
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical group [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 5
- 102000004073 Dopamine D3 Receptors Human genes 0.000 claims description 5
- 108090000525 Dopamine D3 Receptors Proteins 0.000 claims description 5
- 241000124008 Mammalia Species 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 239000011593 sulfur Substances 0.000 claims description 5
- 229910052802 copper Inorganic materials 0.000 claims description 4
- 239000010949 copper Substances 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 238000002441 X-ray diffraction Methods 0.000 claims description 2
- 238000010586 diagram Methods 0.000 claims description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 1
- 239000005977 Ethylene Substances 0.000 claims 1
- 229910052790 beryllium Inorganic materials 0.000 claims 1
- ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 claims 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims 1
- 230000005855 radiation Effects 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 34
- 238000000034 method Methods 0.000 abstract description 18
- 150000003892 tartrate salts Chemical class 0.000 abstract description 7
- 230000008569 process Effects 0.000 abstract description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 45
- 238000012360 testing method Methods 0.000 description 33
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 30
- 239000000243 solution Substances 0.000 description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 27
- 239000000725 suspension Substances 0.000 description 23
- 150000003839 salts Chemical class 0.000 description 19
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 description 17
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 16
- 239000000932 sedative agent Substances 0.000 description 16
- 229940125723 sedative agent Drugs 0.000 description 16
- 235000019439 ethyl acetate Nutrition 0.000 description 15
- 239000000523 sample Substances 0.000 description 15
- 239000002249 anxiolytic agent Substances 0.000 description 14
- 239000002585 base Substances 0.000 description 14
- 239000012044 organic layer Substances 0.000 description 14
- 239000002904 solvent Substances 0.000 description 14
- 238000004128 high performance liquid chromatography Methods 0.000 description 13
- 239000006187 pill Substances 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 238000005481 NMR spectroscopy Methods 0.000 description 12
- RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 description 12
- 239000012071 phase Substances 0.000 description 12
- 229960001367 tartaric acid Drugs 0.000 description 12
- 239000002775 capsule Substances 0.000 description 11
- 208000019901 Anxiety disease Diseases 0.000 description 10
- 206010012335 Dependence Diseases 0.000 description 10
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 10
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 10
- 208000028017 Psychotic disease Diseases 0.000 description 10
- 210000003802 sputum Anatomy 0.000 description 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- 206010036790 Productive cough Diseases 0.000 description 9
- 206010013663 drug dependence Diseases 0.000 description 9
- 239000012535 impurity Substances 0.000 description 9
- 208000024794 sputum Diseases 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 239000007789 gas Substances 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 125000001305 1,2,4-triazol-3-yl group Chemical group [H]N1N=C([*])N=C1[H] 0.000 description 7
- 240000006890 Erythroxylum coca Species 0.000 description 7
- 238000007792 addition Methods 0.000 description 7
- 230000000949 anxiolytic effect Effects 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- 235000008957 cocaer Nutrition 0.000 description 7
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 7
- 239000012458 free base Substances 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 201000009032 substance abuse Diseases 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- LPHGQDQBBGAPDZ-UHFFFAOYSA-N Isocaffeine Natural products CN1C(=O)N(C)C(=O)C2=C1N(C)C=N2 LPHGQDQBBGAPDZ-UHFFFAOYSA-N 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- 239000008896 Opium Substances 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 229940125713 antianxiety drug Drugs 0.000 description 6
- 229940005530 anxiolytics Drugs 0.000 description 6
- 229960001948 caffeine Drugs 0.000 description 6
- VJEONQKOZGKCAK-UHFFFAOYSA-N caffeine Natural products CN1C(=O)N(C)C(=O)C2=C1C=CN2C VJEONQKOZGKCAK-UHFFFAOYSA-N 0.000 description 6
- 210000004027 cell Anatomy 0.000 description 6
- 229960001027 opium Drugs 0.000 description 6
- 239000002245 particle Substances 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 201000000980 schizophrenia Diseases 0.000 description 6
- 208000011117 substance-related disease Diseases 0.000 description 6
- 208000024891 symptom Diseases 0.000 description 6
- 239000003826 tablet Substances 0.000 description 6
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 description 5
- KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 description 5
- 241000218236 Cannabis Species 0.000 description 5
- 206010012289 Dementia Diseases 0.000 description 5
- 208000006558 Dental Calculus Diseases 0.000 description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
- 208000019022 Mood disease Diseases 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
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- 229960003920 cocaine Drugs 0.000 description 5
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- 235000019788 craving Nutrition 0.000 description 5
- 208000035475 disorder Diseases 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 239000007924 injection Substances 0.000 description 5
- 238000002347 injection Methods 0.000 description 5
- 229960002715 nicotine Drugs 0.000 description 5
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 208000019116 sleep disease Diseases 0.000 description 5
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 4
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 4
- 208000000044 Amnesia Diseases 0.000 description 4
- 208000031091 Amnestic disease Diseases 0.000 description 4
- FEWJPZIEWOKRBE-LWMBPPNESA-L D-tartrate(2-) Chemical compound [O-]C(=O)[C@@H](O)[C@H](O)C([O-])=O FEWJPZIEWOKRBE-LWMBPPNESA-L 0.000 description 4
- 206010013654 Drug abuse Diseases 0.000 description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
- 206010033864 Paranoia Diseases 0.000 description 4
- 208000027099 Paranoid disease Diseases 0.000 description 4
- 201000001880 Sexual dysfunction Diseases 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 230000006986 amnesia Effects 0.000 description 4
- 229940025084 amphetamine Drugs 0.000 description 4
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- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 4
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
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- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 4
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- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical group C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
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- 125000002971 oxazolyl group Chemical group 0.000 description 3
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- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical compound [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 3
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- NNJPGOLRFBJNIW-HNNXBMFYSA-N (-)-demecolcine Chemical compound C1=C(OC)C(=O)C=C2[C@@H](NC)CCC3=CC(OC)=C(OC)C(OC)=C3C2=C1 NNJPGOLRFBJNIW-HNNXBMFYSA-N 0.000 description 2
- CXBDYQVECUFKRK-UHFFFAOYSA-N 1-methoxybutane Chemical compound CCCCOC CXBDYQVECUFKRK-UHFFFAOYSA-N 0.000 description 2
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- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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- Reproductive Health (AREA)
- Otolaryngology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
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| GBGB0616574.0A GB0616574D0 (en) | 2006-08-21 | 2006-08-21 | Compounds |
| PCT/EP2006/008314 WO2007022980A1 (en) | 2005-08-22 | 2006-08-21 | Use of azabicyclo hexane derivatives |
Publications (1)
| Publication Number | Publication Date |
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| TW200825074A true TW200825074A (en) | 2008-06-16 |
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| Application Number | Title | Priority Date | Filing Date |
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| TW096130644A TW200825074A (en) | 2006-08-21 | 2007-08-20 | Compounds |
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| Country | Link |
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| US (1) | US20080058398A1 (enExample) |
| EP (1) | EP2054054A1 (enExample) |
| JP (1) | JP5315244B2 (enExample) |
| KR (1) | KR101495362B1 (enExample) |
| CN (1) | CN101528221B (enExample) |
| AR (1) | AR062471A1 (enExample) |
| AU (1) | AU2007287527B2 (enExample) |
| BR (1) | BRPI0716454A2 (enExample) |
| CA (1) | CA2661437A1 (enExample) |
| CL (1) | CL2007002422A1 (enExample) |
| CO (1) | CO6150139A2 (enExample) |
| CR (1) | CR10638A (enExample) |
| EA (1) | EA017917B1 (enExample) |
| GB (1) | GB0616574D0 (enExample) |
| IL (1) | IL196976A0 (enExample) |
| MA (1) | MA30672B1 (enExample) |
| MX (1) | MX2009001941A (enExample) |
| NO (1) | NO20090834L (enExample) |
| PE (1) | PE20080609A1 (enExample) |
| TW (1) | TW200825074A (enExample) |
| WO (1) | WO2008022994A1 (enExample) |
| ZA (1) | ZA200900886B (enExample) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
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| ATE451364T1 (de) * | 2004-02-23 | 2009-12-15 | Glaxo Group Ltd | Als modulatoren des dopamin-d3-rezeptors geeignete azabicycloä3.1.0ühexanderivate |
| GB0507601D0 (en) * | 2005-04-14 | 2005-05-18 | Glaxo Group Ltd | Compounds |
| GB0507602D0 (en) * | 2005-04-14 | 2005-05-18 | Glaxo Group Ltd | Compounds |
| JP5068747B2 (ja) * | 2005-06-14 | 2012-11-07 | グラクソ グループ リミテッド | ドーパミンｄ３受容体のモジュレーターとしてのアザビシクロ［３．１．０］ヘキサン誘導体 |
| GB0512099D0 (en) * | 2005-06-14 | 2005-07-20 | Glaxo Group Ltd | Compounds |
| ATE487715T1 (de) * | 2005-08-22 | 2010-11-15 | Glaxo Group Ltd | Triazolderivate als modulatoren von dopamin-d3- rezeptoren |
| GB0517187D0 (en) * | 2005-08-22 | 2005-09-28 | Glaxo Group Ltd | Compounds |
| GB0517191D0 (en) | 2005-08-22 | 2005-09-28 | Glaxo Group Ltd | Compounds |
| GB0517193D0 (en) * | 2005-08-22 | 2005-09-28 | Glaxo Group Ltd | Novel use |
| GB0517175D0 (en) | 2005-08-22 | 2005-09-28 | Glaxo Group Ltd | Compounds |
| ATE498619T1 (de) * | 2006-04-03 | 2011-03-15 | Glaxo Group Ltd | Azabicycloä3.1.0ühexanderivate als modulatoren von dopamin-d3-rezeptoren |
| US8222266B2 (en) * | 2006-04-03 | 2012-07-17 | Glaxo Group Limited | Azabicyclo [3.1.0] hexyl derivatives as modulators of dopamine D3 receptors |
| US9133159B2 (en) | 2007-06-06 | 2015-09-15 | Neurovance, Inc. | 1-heteroaryl-3-azabicyclo[3.1.0]hexanes, methods for their preparation and their use as medicaments |
| WO2008153937A2 (en) * | 2007-06-06 | 2008-12-18 | Dov Pharmaceutical, Inc. | Novel 1- heteroaryl-3-azabicyclo[3.1.0]hexanes, methods for their preparation and their use as medicaments |
| US11447484B2 (en) | 2018-01-26 | 2022-09-20 | Shionogi & Co., Ltd. | Cyclic compound having dopamine D3 receptor antagonistic effect |
| US12115154B2 (en) | 2020-12-16 | 2024-10-15 | Srx Cardio, Llc | Compounds for the modulation of proprotein convertase subtilisin/kexin type 9 (PCSK9) |
| TWI860849B (zh) | 2021-09-14 | 2024-11-01 | 美商美國禮來大藥廠 | Sstr4促效劑鹽 |
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| JP4260941B2 (ja) * | 1998-11-09 | 2009-04-30 | 株式会社片山製薬所 | アゼチジン−３−オール |
| DE60022742D1 (de) * | 1999-03-15 | 2006-02-02 | Novo Nordisk As | Salz des (2r,3r,4r)-3,4-dihydroxy-2-hydroxmethylpyrrolidins |
| GB0019228D0 (en) * | 2000-08-04 | 2000-09-27 | Smithkline Beecham Plc | Novel pharmaceutical |
| ATE451364T1 (de) * | 2004-02-23 | 2009-12-15 | Glaxo Group Ltd | Als modulatoren des dopamin-d3-rezeptors geeignete azabicycloä3.1.0ühexanderivate |
| SE526837C2 (sv) * | 2004-02-24 | 2005-11-08 | Kongsberg Automotive Asa | Växelspakstransmission |
| CN1984903A (zh) * | 2004-06-30 | 2007-06-20 | 伊莱利利公司 | 1－(吲哚－6－羰基－d－苯基甘氨酰基)－4－(1－甲基哌啶－4－基)哌嗪d－酒石酸盐 |
| GB0517193D0 (en) * | 2005-08-22 | 2005-09-28 | Glaxo Group Ltd | Novel use |
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- 2009-02-09 IL IL196976A patent/IL196976A0/en unknown
- 2009-02-20 CO CO09017330A patent/CO6150139A2/es unknown
- 2009-02-23 NO NO20090834A patent/NO20090834L/no not_active Application Discontinuation
- 2009-02-25 CR CR10638A patent/CR10638A/es not_active Application Discontinuation
- 2009-02-27 MA MA31673A patent/MA30672B1/fr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PE20080609A1 (es) | 2008-07-26 |
| MX2009001941A (es) | 2009-03-05 |
| WO2008022994A1 (en) | 2008-02-28 |
| CA2661437A1 (en) | 2008-02-28 |
| NO20090834L (no) | 2009-03-19 |
| MA30672B1 (fr) | 2009-08-03 |
| JP5315244B2 (ja) | 2013-10-16 |
| AU2007287527A1 (en) | 2008-02-28 |
| AR062471A1 (es) | 2008-11-12 |
| EA017917B1 (ru) | 2013-04-30 |
| GB0616574D0 (en) | 2006-09-27 |
| JP2010501519A (ja) | 2010-01-21 |
| CR10638A (es) | 2009-03-20 |
| CN101528221B (zh) | 2013-05-08 |
| KR101495362B1 (ko) | 2015-02-24 |
| EP2054054A1 (en) | 2009-05-06 |
| CO6150139A2 (es) | 2010-04-20 |
| ZA200900886B (en) | 2011-05-25 |
| CL2007002422A1 (es) | 2008-03-14 |
| US20080058398A1 (en) | 2008-03-06 |
| AU2007287527B2 (en) | 2013-01-31 |
| IL196976A0 (en) | 2009-11-18 |
| EA200970211A1 (ru) | 2009-08-28 |
| KR20090052327A (ko) | 2009-05-25 |
| BRPI0716454A2 (pt) | 2014-03-04 |
| CN101528221A (zh) | 2009-09-09 |
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