JP2012505165A5 - - Google Patents
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- Publication number
- JP2012505165A5 JP2012505165A5 JP2011530350A JP2011530350A JP2012505165A5 JP 2012505165 A5 JP2012505165 A5 JP 2012505165A5 JP 2011530350 A JP2011530350 A JP 2011530350A JP 2011530350 A JP2011530350 A JP 2011530350A JP 2012505165 A5 JP2012505165 A5 JP 2012505165A5
- Authority
- JP
- Japan
- Prior art keywords
- compound
- piperazinyl
- formula
- carboxamide
- pharmaceutically acceptable
- 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
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- 150000001875 compounds Chemical class 0.000 claims description 85
- -1 aryl amide Chemical class 0.000 claims description 39
- 239000003814 drug Substances 0.000 claims description 37
- 150000003839 salts Chemical class 0.000 claims description 37
- 229940079593 drug Drugs 0.000 claims description 32
- 239000012453 solvate Substances 0.000 claims description 25
- 230000003287 optical effect Effects 0.000 claims description 23
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 23
- 208000011117 substance-related disease Diseases 0.000 claims description 21
- 206010013663 drug dependence Diseases 0.000 claims description 18
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 201000010099 disease Diseases 0.000 claims description 13
- 229910052736 halogen Inorganic materials 0.000 claims description 13
- 125000001072 heteroaryl group Chemical group 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 150000002367 halogens Chemical class 0.000 claims description 12
- 208000018737 Parkinson disease Diseases 0.000 claims description 11
- 229910052801 chlorine Inorganic materials 0.000 claims description 11
- 229910052731 fluorine Inorganic materials 0.000 claims description 11
- 239000008194 pharmaceutical composition Substances 0.000 claims description 11
- 230000002265 prevention Effects 0.000 claims description 11
- 201000000980 schizophrenia Diseases 0.000 claims description 11
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 10
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims description 9
- 101150065749 Churc1 gene Proteins 0.000 claims description 9
- 102100038239 Protein Churchill Human genes 0.000 claims description 9
- 150000001408 amides Chemical class 0.000 claims description 9
- 125000005199 aryl carbonyloxy group Chemical group 0.000 claims description 9
- 229910052794 bromium Inorganic materials 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 claims description 9
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 229910052717 sulfur Inorganic materials 0.000 claims description 9
- 208000019901 Anxiety disease Diseases 0.000 claims description 8
- 108090000525 Dopamine D3 Receptors Proteins 0.000 claims description 8
- 230000036506 anxiety Effects 0.000 claims description 8
- 125000001769 aryl amino group Chemical group 0.000 claims description 8
- 125000004104 aryloxy group Chemical group 0.000 claims description 8
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 208000019116 sleep disease Diseases 0.000 claims description 8
- 102000004073 Dopamine D3 Receptors Human genes 0.000 claims description 7
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 230000035882 stress Effects 0.000 claims description 7
- 125000006727 (C1-C6) alkenyl group Chemical group 0.000 claims description 6
- 206010057672 Male sexual dysfunction Diseases 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- KFYZFGITXAGRAU-SNAWJCMRSA-N n-[(e)-4-[4-(2-methoxyphenyl)piperazin-1-yl]but-2-enyl]-2-oxo-3h-1,3-benzoxazole-5-carboxamide Chemical compound COC1=CC=CC=C1N1CCN(C\C=C\CNC(=O)C=2C=C3NC(=O)OC3=CC=2)CC1 KFYZFGITXAGRAU-SNAWJCMRSA-N 0.000 claims description 6
- YVJJXJMWTLSCLC-UHFFFAOYSA-N n-[4-[4-(2-methoxyphenyl)piperazin-1-yl]butyl]-2-oxo-3h-1,3-benzothiazole-6-carboxamide Chemical compound COC1=CC=CC=C1N1CCN(CCCCNC(=O)C=2C=C3SC(=O)NC3=CC=2)CC1 YVJJXJMWTLSCLC-UHFFFAOYSA-N 0.000 claims description 6
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 5
- 150000001263 acyl chlorides Chemical class 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000005842 heteroatom Chemical group 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- OUWBHSIWKJHFTM-SNAWJCMRSA-N n-[(e)-4-[4-(2-methoxyphenyl)piperazin-1-yl]but-2-enyl]-2-oxo-3h-1,3-benzoxazole-6-carboxamide Chemical compound COC1=CC=CC=C1N1CCN(C\C=C\CNC(=O)C=2C=C3OC(=O)NC3=CC=2)CC1 OUWBHSIWKJHFTM-SNAWJCMRSA-N 0.000 claims description 5
- BITJJALJCISCRB-IHWYPQMZSA-N n-[(z)-4-[4-(5-chloro-2-methylphenyl)piperazin-1-yl]but-2-enyl]-2-oxo-3h-1,3-benzoxazole-5-carboxamide Chemical compound CC1=CC=C(Cl)C=C1N1CCN(C\C=C/CNC(=O)C=2C=C3NC(=O)OC3=CC=2)CC1 BITJJALJCISCRB-IHWYPQMZSA-N 0.000 claims description 5
- BJCRWDBJVLWHSB-UHFFFAOYSA-N n-[4-[4-(2-methoxyphenyl)piperazin-1-yl]butyl]-2-oxo-3h-1,3-benzoxazole-6-carboxamide Chemical compound COC1=CC=CC=C1N1CCN(CCCCNC(=O)C=2C=C3OC(=O)NC3=CC=2)CC1 BJCRWDBJVLWHSB-UHFFFAOYSA-N 0.000 claims description 5
- VIZDBZXBKIEXRK-UHFFFAOYSA-N n-[4-[4-(5-chloro-2-methylphenyl)piperazin-1-yl]butyl]-2-oxo-3h-1,3-benzoxazole-5-carboxamide Chemical compound CC1=CC=C(Cl)C=C1N1CCN(CCCCNC(=O)C=2C=C3NC(=O)OC3=CC=2)CC1 VIZDBZXBKIEXRK-UHFFFAOYSA-N 0.000 claims description 5
- JXLORNVFUOOEDW-UHFFFAOYSA-N n-[4-[4-(5-chloro-2-methylphenyl)piperazin-1-yl]butyl]-2-oxo-3h-1,3-benzoxazole-6-carboxamide Chemical compound CC1=CC=C(Cl)C=C1N1CCN(CCCCNC(=O)C=2C=C3OC(=O)NC3=CC=2)CC1 JXLORNVFUOOEDW-UHFFFAOYSA-N 0.000 claims description 5
- 239000000654 additive Substances 0.000 claims description 4
- 125000005116 aryl carbamoyl group Chemical group 0.000 claims description 4
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 230000003832 immune regulation Effects 0.000 claims description 4
- 229910052740 iodine Inorganic materials 0.000 claims description 4
- 125000002950 monocyclic group Chemical group 0.000 claims description 4
- GFWSWYNCMRTUMO-UHFFFAOYSA-N n-[4-[4-(2-methoxyphenyl)piperazin-1-yl]butyl]-2-oxo-3h-1,3-benzothiazole-5-carboxamide Chemical compound COC1=CC=CC=C1N1CCN(CCCCNC(=O)C=2C=C3NC(=O)SC3=CC=2)CC1 GFWSWYNCMRTUMO-UHFFFAOYSA-N 0.000 claims description 4
- GJVFBWCTGUSGDD-UHFFFAOYSA-L pentamethonium bromide Chemical compound [Br-].[Br-].C[N+](C)(C)CCCCC[N+](C)(C)C GJVFBWCTGUSGDD-UHFFFAOYSA-L 0.000 claims description 4
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 3
- ASSKVPFEZFQQNQ-UHFFFAOYSA-N 2-benzoxazolinone Chemical group C1=CC=C2OC(O)=NC2=C1 ASSKVPFEZFQQNQ-UHFFFAOYSA-N 0.000 claims description 3
- YEDUAINPPJYDJZ-UHFFFAOYSA-N 2-hydroxybenzothiazole Chemical group C1=CC=C2SC(O)=NC2=C1 YEDUAINPPJYDJZ-UHFFFAOYSA-N 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- ASYHTIAJGDESLW-SNAWJCMRSA-N n-[(e)-4-[4-(2-methoxyphenyl)piperazin-1-yl]but-2-enyl]-2-oxo-3h-1,3-benzothiazole-6-carboxamide Chemical compound COC1=CC=CC=C1N1CCN(C\C=C\CNC(=O)C=2C=C3SC(=O)NC3=CC=2)CC1 ASYHTIAJGDESLW-SNAWJCMRSA-N 0.000 claims description 3
- WPJOIAJAKXXQBD-NSCUHMNNSA-N n-[(e)-4-[4-(5-chloro-2-methylphenyl)piperazin-1-yl]but-2-enyl]-2-oxo-3h-1,3-benzoxazole-6-carboxamide Chemical compound CC1=CC=C(Cl)C=C1N1CCN(C\C=C\CNC(=O)C=2C=C3OC(=O)NC3=CC=2)CC1 WPJOIAJAKXXQBD-NSCUHMNNSA-N 0.000 claims description 3
- YSJAMWLYJCEAQA-UHFFFAOYSA-N n-[4-[4-(2-methoxyphenyl)piperazin-1-yl]butyl]-2-oxo-3h-1,3-benzoxazole-5-carboxamide Chemical compound COC1=CC=CC=C1N1CCN(CCCCNC(=O)C=2C=C3NC(=O)OC3=CC=2)CC1 YSJAMWLYJCEAQA-UHFFFAOYSA-N 0.000 claims description 3
- FZLXHYUSNDHAFI-UHFFFAOYSA-N n-[4-[4-(5-chloro-2-methylphenyl)piperazin-1-yl]butyl]-2-oxo-3h-1,3-benzothiazole-5-carboxamide Chemical compound CC1=CC=C(Cl)C=C1N1CCN(CCCCNC(=O)C=2C=C3NC(=O)SC3=CC=2)CC1 FZLXHYUSNDHAFI-UHFFFAOYSA-N 0.000 claims description 3
- KAJSEQCXUPCWNB-UHFFFAOYSA-N n-[4-[4-(5-chloro-2-methylphenyl)piperazin-1-yl]butyl]-2-oxo-3h-1,3-benzothiazole-6-carboxamide Chemical compound CC1=CC=C(Cl)C=C1N1CCN(CCCCNC(=O)C=2C=C3SC(=O)NC3=CC=2)CC1 KAJSEQCXUPCWNB-UHFFFAOYSA-N 0.000 claims description 3
- 230000000996 additive effect Effects 0.000 claims description 2
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 2
- 208000035475 disorder Diseases 0.000 claims 2
- 235000002639 sodium chloride Nutrition 0.000 description 38
- 238000000034 method Methods 0.000 description 29
- 241001465754 Metazoa Species 0.000 description 28
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 27
- 238000006243 chemical reaction Methods 0.000 description 26
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 26
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- 238000012360 testing method Methods 0.000 description 21
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
- 239000000203 mixture Substances 0.000 description 19
- 230000000694 effects Effects 0.000 description 18
- 238000002360 preparation method Methods 0.000 description 18
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 17
- 239000000047 product Substances 0.000 description 16
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 15
- 238000002474 experimental method Methods 0.000 description 15
- 238000003756 stirring Methods 0.000 description 15
- 229940125904 compound 1 Drugs 0.000 description 13
- 239000002552 dosage form Substances 0.000 description 13
- 239000003446 ligand Substances 0.000 description 13
- 229960005181 morphine Drugs 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 239000007787 solid Substances 0.000 description 12
- 229910000029 sodium carbonate Inorganic materials 0.000 description 11
- 239000011780 sodium chloride Substances 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 230000027455 binding Effects 0.000 description 10
- 229960003878 haloperidol Drugs 0.000 description 10
- 239000000460 chlorine Substances 0.000 description 9
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 9
- KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 description 8
- 101150049660 DRD2 gene Proteins 0.000 description 8
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- VMWNQDUVQKEIOC-CYBMUJFWSA-N apomorphine Chemical compound C([C@H]1N(C)CC2)C3=CC=C(O)C(O)=C3C3=C1C2=CC=C3 VMWNQDUVQKEIOC-CYBMUJFWSA-N 0.000 description 8
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- 239000000969 carrier Substances 0.000 description 7
- 235000019441 ethanol Nutrition 0.000 description 7
- 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 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
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- 241000699666 Mus <mouse, genus> Species 0.000 description 6
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- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 6
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- 239000008103 glucose Substances 0.000 description 5
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- OBKXILSZNIKPPO-SNAWJCMRSA-N (e)-4-[4-(2-methoxyphenyl)piperazin-1-yl]but-2-en-1-amine Chemical compound COC1=CC=CC=C1N1CCN(C\C=C\CN)CC1 OBKXILSZNIKPPO-SNAWJCMRSA-N 0.000 description 4
- UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 description 4
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- UFJPFLDFMPVGRW-UHFFFAOYSA-N 4-[4-(2-methoxyphenyl)piperazin-1-yl]butan-1-amine Chemical compound COC1=CC=CC=C1N1CCN(CCCCN)CC1 UFJPFLDFMPVGRW-UHFFFAOYSA-N 0.000 description 4
- OFEXISMCKCHYRA-UHFFFAOYSA-N 4-[4-(5-chloro-2-methylphenyl)piperazin-1-yl]butan-1-amine Chemical compound CC1=CC=C(Cl)C=C1N1CCN(CCCCN)CC1 OFEXISMCKCHYRA-UHFFFAOYSA-N 0.000 description 4
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- BXVHZIIFSRZVTC-UHFFFAOYSA-N 2-chloro-5-(2-methylphenyl)piperazine Chemical compound ClC1NCC(NC1)C1=C(C=CC=C1)C BXVHZIIFSRZVTC-UHFFFAOYSA-N 0.000 description 3
- QCYNXOWNRBRMFN-UHFFFAOYSA-N 2-oxo-3h-1,3-benzothiazole-6-carbonyl chloride Chemical compound ClC(=O)C1=CC=C2NC(=O)SC2=C1 QCYNXOWNRBRMFN-UHFFFAOYSA-N 0.000 description 3
- USZSGINUZRHINQ-UHFFFAOYSA-N 2-oxo-3h-1,3-benzothiazole-6-carboxylic acid Chemical compound OC(=O)C1=CC=C2NC(=O)SC2=C1 USZSGINUZRHINQ-UHFFFAOYSA-N 0.000 description 3
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000009471 action Effects 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 239000000556 agonist Substances 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
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| US9227944B2 (en) * | 2008-10-10 | 2016-01-05 | Institute Of Pharmacology And Toxicology Academy Of Military Science P.L.A. China | Dopamine D3 receptor ligands and preparation and medical uses of the same |
| CN103073524B (zh) * | 2013-01-25 | 2015-06-10 | 宁波市微循环与莨菪类药研究所 | 4-[4-(取代苯基)哌嗪基-1]-丁胺甲酸取代芳香酯衍生物及其制备方法 |
| AR094929A1 (es) | 2013-02-28 | 2015-09-09 | Bristol Myers Squibb Co | Derivados de fenilpirazol como inhibidores potentes de rock1 y rock2 |
| CN105102448B (zh) | 2013-02-28 | 2018-03-06 | 百时美施贵宝公司 | 作为rock1和rock2抑制剂的苯基吡唑衍生物 |
| CN105461608B (zh) * | 2015-11-23 | 2017-11-28 | 东南大学 | 二氢吲哚‑2‑酮类d3受体配体及其制备方法和用途 |
| EP3495363B1 (en) | 2016-07-28 | 2023-08-23 | Shionogi & Co., Ltd | Nitrogen-containing condensed ring compounds having dopamine d3 receptor antagonistic effect |
| CN109419802B (zh) * | 2017-08-28 | 2023-01-13 | 中国人民解放军军事医学科学院毒物药物研究所 | 具有多巴胺d3受体调节活性的化合物及其用途 |
| CN108329282B (zh) * | 2018-01-16 | 2022-01-07 | 新乡医学院 | 一种苯基哌嗪类衍生物及其制备方法和应用 |
| WO2019146740A1 (ja) | 2018-01-26 | 2019-08-01 | 塩野義製薬株式会社 | ドーパミンｄ３受容体拮抗作用を有する環式化合物 |
| KR20200112910A (ko) | 2018-01-26 | 2020-10-05 | 시오노기 앤드 컴파니, 리미티드 | 도파민 d3 수용체 길항 작용을 갖는 축환 화합물 |
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| FR2613365B1 (fr) | 1987-04-01 | 1989-07-28 | Adir | Nouveaux derives de l'amino tetrahydro-5, 6, 7, 8 naphto (2, 3b) furanne, leurs procedes de preparation et les compositions pharmaceutiques qui les contiennent |
| US5656762A (en) | 1990-12-28 | 1997-08-12 | Neurogen Corporation | 4-piperidino-and piperazinomethyl-2-phenylimidazole derivatives, dopamine receptor subtype specific ligands |
| AU7513494A (en) | 1993-08-06 | 1995-02-28 | Upjohn Company, The | 2-aminoindans as selective dopamine d3 ligands |
| US6756388B1 (en) | 1993-10-12 | 2004-06-29 | Pfizer Inc. | Benzothiophenes and related compounds as estrogen agonists |
| DE4425146A1 (de) * | 1994-07-15 | 1996-01-18 | Basf Ag | Verwendung heterocyclischer Verbindungen |
| FR2742149B1 (fr) | 1995-12-11 | 1998-02-13 | Inst Nat Sante Rech Med | Nouveaux derives de 2-naphtamides et leurs applications therapeutiques |
| IL126747A0 (en) | 1996-05-11 | 1999-08-17 | Smithkline Beecham Plc | Tetrahydroisoquinoline derivatives as modulators of dopamine D3 receptors |
| US6143762A (en) | 1996-08-14 | 2000-11-07 | Smithkline Beecham, Plc | Tetrahydroisoquinoline derivatives and their pharmaceutical use |
| JP2002501506A (ja) | 1997-05-03 | 2002-01-15 | スミスクライン・ビーチャム・パブリック・リミテッド・カンパニー | ドーパミンｄ▲下３▼受容体のモジュレーターとしてのテトラヒドロイソキノリン誘導体 |
| GB9821978D0 (en) | 1998-10-08 | 1998-12-02 | Smithkline Beecham Plc | Compounds |
| AR022230A1 (es) | 1999-01-12 | 2002-09-04 | Abbott Gmbh & Co Kg | Compuestos de triazol, composicion farmaceutica que los comprende y uso de los mismos para preparar dicha composicion |
| KR20030068164A (ko) | 2000-11-30 | 2003-08-19 | 랜박시 래보러터리스 리미티드 | 우로-선택성 α1-아드레날린 수용체 차단제로 유용한1,4-이치환된 피페라진 유도체 |
| KR100394083B1 (ko) | 2000-12-04 | 2003-08-06 | 학교법인 성신학원 | 도파민 ｄ3 및 ｄ4 수용체의 선택적 활성을 지닌 신규4,5-디히드로이소옥사졸릴알킬피페라진 유도체와, 이의제조방법 |
| HUP0103987A3 (en) | 2001-09-28 | 2004-11-29 | Richter Gedeon Vegyeszet | Phenylpiperazinylalkyl carboxylic acid amid derivatives, process for their preparation, pharmaceutical compositions containing them and their intermediates |
| GB0130219D0 (en) | 2001-12-18 | 2002-02-06 | Pfizer Ltd | Compounds for the treatment of sexual dysfunction |
| DE10232020A1 (de) | 2002-07-04 | 2004-02-26 | Friedrich-Alexander-Universität Erlangen-Nürnberg | Neurorezeptoraktive Heteroarencarboxamide |
| ES2280799T3 (es) * | 2002-07-04 | 2007-09-16 | Schwarz Pharma Ag | Heteroarencarboxamidas para su utilizacion como ligandos de dopamina-d3 para el tratamiento enfermedades del snc (sistema nervioso central). |
| US20040204422A1 (en) | 2003-04-14 | 2004-10-14 | Abbott Gmbh & Co. Kg. | N-[(Piperazinyl)hetaryl]arylsulfonamide compounds |
| JP4904267B2 (ja) | 2004-08-09 | 2012-03-28 | アボット ゲーエムベーハー ウント カンパニー カーゲー | ドーパミンｄ３受容体の調節に応答する障害の治療に好適な４−ピペラジニル−ピリミジン化合物 |
| DE602005016836D1 (de) | 2004-11-26 | 2009-11-05 | Janssen Pharmaceutica Nv | Chotischer und anxiolytischer aktivität |
| FR2878524B1 (fr) | 2004-12-01 | 2007-01-19 | Bioprojet Soc Civ Ile | Nouveaux derives d'arylpiperazine |
| DE102004063797A1 (de) * | 2004-12-30 | 2006-07-13 | Schwarz Pharma Ag | Sauerstoffhaltige annelierte Phenylpiperazin- und Phenyldiazepancarboxamide |
| GB0517187D0 (en) | 2005-08-22 | 2005-09-28 | Glaxo Group Ltd | Compounds |
| TW200831498A (en) * | 2006-10-13 | 2008-08-01 | Otsuka Pharma Co Ltd | Heterocyclic compound |
| JP2008115175A (ja) * | 2006-10-13 | 2008-05-22 | Otsuka Pharmaceut Co Ltd | 複素環化合物 |
| EP2184272A4 (en) * | 2007-08-21 | 2011-11-09 | Shionogi & Co | PIPERAZINE DERIVATIVE |
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- 2009-09-28 US US13/123,368 patent/US8829001B2/en active Active
- 2009-09-28 JP JP2011530350A patent/JP5701213B2/ja active Active
- 2009-09-28 EP EP09818738.8A patent/EP2354136B1/en active Active
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