NZ506462A - Substituted pyridino arylpiperazines, pharmaceuticals thereof, and their use in the treatment of benign prostatic hyperplasia or any diseases associated with alpha-1a adrenergic receptors - Google Patents
Substituted pyridino arylpiperazines, pharmaceuticals thereof, and their use in the treatment of benign prostatic hyperplasia or any diseases associated with alpha-1a adrenergic receptorsInfo
- Publication number
- NZ506462A NZ506462A NZ506462A NZ50646299A NZ506462A NZ 506462 A NZ506462 A NZ 506462A NZ 506462 A NZ506462 A NZ 506462A NZ 50646299 A NZ50646299 A NZ 50646299A NZ 506462 A NZ506462 A NZ 506462A
- Authority
- NZ
- New Zealand
- Prior art keywords
- hydrogen
- compound
- phenyl
- substituted
- alkyl
- Prior art date
Links
- 206010004446 Benign prostatic hyperplasia Diseases 0.000 title claims abstract description 30
- 208000004403 Prostatic Hyperplasia Diseases 0.000 title claims abstract description 30
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims abstract description 9
- 201000010099 disease Diseases 0.000 title claims abstract description 8
- 108020004102 alpha-1 Adrenergic Receptor Proteins 0.000 title claims abstract description 7
- 102000030619 alpha-1 Adrenergic Receptor Human genes 0.000 title claims description 6
- 239000003814 drug Substances 0.000 title claims description 4
- 238000011282 treatment Methods 0.000 title abstract description 20
- 150000001875 compounds Chemical class 0.000 claims abstract description 80
- 102000005962 receptors Human genes 0.000 claims abstract description 15
- 108020003175 receptors Proteins 0.000 claims abstract description 15
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 9
- 230000027455 binding Effects 0.000 claims abstract description 6
- 238000004519 manufacturing process Methods 0.000 claims abstract 3
- 239000000203 mixture Substances 0.000 claims description 48
- 229910052739 hydrogen Inorganic materials 0.000 claims description 38
- 239000001257 hydrogen Substances 0.000 claims description 38
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 37
- 235000011468 Albizia julibrissin Nutrition 0.000 claims description 36
- 241001070944 Mimosa Species 0.000 claims description 36
- 150000002431 hydrogen Chemical class 0.000 claims description 29
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 25
- 210000002307 prostate Anatomy 0.000 claims description 23
- 229910052736 halogen Inorganic materials 0.000 claims description 22
- 150000002367 halogens Chemical class 0.000 claims description 22
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 21
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 11
- 229910052760 oxygen Inorganic materials 0.000 claims description 11
- 239000001301 oxygen Substances 0.000 claims description 11
- 239000005557 antagonist Substances 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 108060003345 Adrenergic Receptor Proteins 0.000 claims description 8
- 102000017910 Adrenergic receptor Human genes 0.000 claims description 8
- -1 Ci.5alkylsulfonyl Chemical group 0.000 claims description 8
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 239000011593 sulfur Chemical group 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 241000124008 Mammalia Species 0.000 claims description 5
- 238000012512 characterization method Methods 0.000 claims description 4
- 238000010367 cloning Methods 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 230000000144 pharmacologic effect Effects 0.000 claims description 4
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 238000011471 prostatectomy Methods 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 2
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 150000002825 nitriles Chemical class 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 238000012937 correction Methods 0.000 claims 1
- 230000008520 organization Effects 0.000 claims 1
- 241000894007 species Species 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 14
- 239000000543 intermediate Substances 0.000 abstract description 6
- 150000004885 piperazines Chemical class 0.000 abstract description 6
- 102100024349 Alpha-1A adrenergic receptor Human genes 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 99
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 32
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 26
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 23
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 22
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 21
- 239000000047 product Substances 0.000 description 20
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- 238000004440 column chromatography Methods 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 14
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 13
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- 230000000694 effects Effects 0.000 description 12
- 210000001519 tissue Anatomy 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 11
- 150000001412 amines Chemical class 0.000 description 11
- 239000007787 solid Substances 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 238000005160 1H NMR spectroscopy Methods 0.000 description 10
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
- 239000006260 foam Substances 0.000 description 8
- SONNWYBIRXJNDC-VIFPVBQESA-N phenylephrine Chemical compound CNC[C@H](O)C1=CC=CC(O)=C1 SONNWYBIRXJNDC-VIFPVBQESA-N 0.000 description 8
- 229960001802 phenylephrine Drugs 0.000 description 8
- YEDUAINPPJYDJZ-UHFFFAOYSA-N 2-hydroxybenzothiazole Chemical compound C1=CC=C2SC(O)=NC2=C1 YEDUAINPPJYDJZ-UHFFFAOYSA-N 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 235000019439 ethyl acetate Nutrition 0.000 description 7
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 241000282472 Canis lupus familiaris Species 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 210000004027 cell Anatomy 0.000 description 6
- 229940125782 compound 2 Drugs 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- DBEPLOCGEIEOCV-WSBQPABSSA-N finasteride Chemical compound N([C@@H]1CC2)C(=O)C=C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H](C(=O)NC(C)(C)C)[C@@]2(C)CC1 DBEPLOCGEIEOCV-WSBQPABSSA-N 0.000 description 5
- 239000012528 membrane Substances 0.000 description 5
- 210000002460 smooth muscle Anatomy 0.000 description 5
- QJULELIONYLITF-UHFFFAOYSA-N 1-(2-propan-2-yloxyphenyl)piperazine Chemical compound CC(C)OC1=CC=CC=C1N1CCNCC1 QJULELIONYLITF-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- 108020004635 Complementary DNA Proteins 0.000 description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical class OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- 150000001540 azides Chemical class 0.000 description 4
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- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 4
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
- 230000003068 static effect Effects 0.000 description 4
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- NVKAWKQGWWIWPM-ABEVXSGRSA-N 17-β-hydroxy-5-α-Androstan-3-one Chemical compound C1C(=O)CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CC[C@H]21 NVKAWKQGWWIWPM-ABEVXSGRSA-N 0.000 description 3
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- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 229940125904 compound 1 Drugs 0.000 description 3
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
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- BRLQWZUYTZBJKN-GSVOUGTGSA-N (+)-Epichlorohydrin Chemical compound ClC[C@@H]1CO1 BRLQWZUYTZBJKN-GSVOUGTGSA-N 0.000 description 2
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- GSOZMIFQWCNBHZ-UHFFFAOYSA-N (3-azido-2-hydroxypropyl) 4-methylbenzenesulfonate Chemical compound CC1=CC=C(S(=O)(=O)OCC(O)CN=[N+]=[N-])C=C1 GSOZMIFQWCNBHZ-UHFFFAOYSA-N 0.000 description 2
- MIQRUWUVLIWVAW-STTHPYEQSA-N 2-[[2-(4-hydroxy-2-iodanylphenyl)ethylamino]methyl]-3,4-dihydro-2h-naphthalen-1-one Chemical compound [125I]C1=CC(O)=CC=C1CCNCC1C(=O)C2=CC=CC=C2CC1 MIQRUWUVLIWVAW-STTHPYEQSA-N 0.000 description 2
- IBRSSZOHCGUTHI-UHFFFAOYSA-N 2-chloropyridine-3-carboxylic acid Chemical compound OC(=O)C1=CC=CN=C1Cl IBRSSZOHCGUTHI-UHFFFAOYSA-N 0.000 description 2
- ILBAQNFTHRLAEH-UHFFFAOYSA-N 2-phenoxypyridine-3-carbonyl chloride Chemical compound ClC(=O)C1=CC=CN=C1OC1=CC=CC=C1 ILBAQNFTHRLAEH-UHFFFAOYSA-N 0.000 description 2
- CQGAXJGXGLVFGJ-UHFFFAOYSA-N 2-phenoxypyridine-3-carboxylic acid Chemical compound OC(=O)C1=CC=CN=C1OC1=CC=CC=C1 CQGAXJGXGLVFGJ-UHFFFAOYSA-N 0.000 description 2
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- MUMGGOZAMZWBJJ-DYKIIFRCSA-N Testostosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 MUMGGOZAMZWBJJ-DYKIIFRCSA-N 0.000 description 2
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- VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 description 2
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- 125000003118 aryl group Chemical group 0.000 description 2
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- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 2
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
- C07D213/82—Amides; Imides in position 3
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- A61P13/00—Drugs for disorders of the urinary system
- A61P13/08—Drugs for disorders of the urinary system of the prostate
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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Landscapes
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- Urology & Nephrology (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US7532198P | 1998-02-20 | 1998-02-20 | |
| PCT/US1999/003608 WO1999042448A1 (en) | 1998-02-20 | 1999-02-19 | Novel substituted pyridino arylpiperazines useful in the treatment of benign prostatic hyperplasia |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NZ506462A true NZ506462A (en) | 2003-07-25 |
Family
ID=22124955
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ506462A NZ506462A (en) | 1998-02-20 | 1999-02-19 | Substituted pyridino arylpiperazines, pharmaceuticals thereof, and their use in the treatment of benign prostatic hyperplasia or any diseases associated with alpha-1a adrenergic receptors |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US6218396B1 (enExample) |
| EP (1) | EP1054868B1 (enExample) |
| JP (1) | JP2002503724A (enExample) |
| KR (1) | KR100591028B1 (enExample) |
| CN (1) | CN1121390C (enExample) |
| AR (1) | AR014626A1 (enExample) |
| AT (1) | ATE250580T1 (enExample) |
| AU (1) | AU766398B2 (enExample) |
| BR (1) | BR9909647A (enExample) |
| CZ (1) | CZ294136B6 (enExample) |
| DE (1) | DE69911582T2 (enExample) |
| DK (1) | DK1054868T3 (enExample) |
| ES (1) | ES2209468T3 (enExample) |
| HU (1) | HUP0100781A3 (enExample) |
| IL (2) | IL137954A0 (enExample) |
| NO (1) | NO317103B1 (enExample) |
| NZ (1) | NZ506462A (enExample) |
| PL (1) | PL342339A1 (enExample) |
| PT (1) | PT1054868E (enExample) |
| TR (1) | TR200003220T2 (enExample) |
| TW (1) | TW565555B (enExample) |
| WO (1) | WO1999042448A1 (enExample) |
| ZA (1) | ZA991315B (enExample) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1269807C (zh) * | 1997-05-12 | 2006-08-16 | 奥索-麦克尼尔药品公司 | 可用于治疗良性前列腺肥大的芳基取代哌嗪 |
| ES2282279T3 (es) | 2000-08-08 | 2007-10-16 | Ortho-Mcneil Pharmaceutical, Inc. | No-imidazol ariloxipiperidina como ligandos del receptor h3. |
| JP3878178B2 (ja) * | 2001-12-28 | 2007-02-07 | 武田薬品工業株式会社 | 排尿障害予防治療剤 |
| USD545208S1 (en) | 2006-09-27 | 2007-06-26 | 001 Corporation | Perfume bottle and cap |
| EP2077262A4 (en) * | 2006-10-23 | 2011-12-28 | Takeda Pharmaceutical | IMINOPYRIDINE DERIVATIVE AND USE THEREOF |
| MX2010011652A (es) * | 2008-04-23 | 2010-12-06 | Takeda Pharmaceutical | Derivados de iminopiridina y uso de los mismos. |
| US8481569B2 (en) | 2008-04-23 | 2013-07-09 | Takeda Pharmaceutical Company Limited | Iminopyridine derivatives and use thereof |
| US20110039892A1 (en) * | 2008-04-23 | 2011-02-17 | Takeda Pharmaceutical Company Limited | Iminopyridine derivative and use thereof |
| CN103980195A (zh) * | 2014-04-28 | 2014-08-13 | 广州医科大学 | 酰胺类苯基哌嗪衍生物及其盐与在制备治疗良性前列腺增生症药物中的应用 |
| CN108530391B (zh) * | 2018-05-17 | 2022-05-17 | 袁牧 | 一种酰胺类芳基哌嗪衍生物及其制备方法与应用 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2027898A6 (es) * | 1991-01-24 | 1992-06-16 | Espanola Prod Quimicos | Procedimiento de preparacion de nuevos derivados de la 2-metoxifenilpiperacina. |
| US5403847A (en) | 1992-11-13 | 1995-04-04 | Synaptic Pharmaceutical Corporation | Use of α1C specific compounds to treat benign prostatic hyperlasia |
| IT1266582B1 (it) * | 1993-07-30 | 1997-01-09 | Recordati Chem Pharm | Derivati (di)azacicloesanici e diazacicloeptanici |
| DE4425146A1 (de) * | 1994-07-15 | 1996-01-18 | Basf Ag | Verwendung heterocyclischer Verbindungen |
| US5688795A (en) * | 1994-11-08 | 1997-11-18 | Syntex (U.S.A.) Inc. | 3-(4-phenylpiperazin-1-yl)propyl-amino, thio and oxy!-pyridine, pyrimidine and benzene derivatives as α1 -adrenoceptor antagonists |
| AU8130298A (en) * | 1997-07-15 | 1999-02-10 | Sankyo Company Limited | Piperazine derivatives |
-
1999
- 1999-02-18 US US09/252,313 patent/US6218396B1/en not_active Expired - Lifetime
- 1999-02-18 ZA ZA9901315A patent/ZA991315B/xx unknown
- 1999-02-19 CN CN99803027A patent/CN1121390C/zh not_active Expired - Fee Related
- 1999-02-19 KR KR1020007009156A patent/KR100591028B1/ko not_active Expired - Fee Related
- 1999-02-19 HU HU0100781A patent/HUP0100781A3/hu unknown
- 1999-02-19 AU AU33025/99A patent/AU766398B2/en not_active Ceased
- 1999-02-19 PL PL99342339A patent/PL342339A1/xx unknown
- 1999-02-19 JP JP2000532400A patent/JP2002503724A/ja active Pending
- 1999-02-19 IL IL13795499A patent/IL137954A0/xx active IP Right Grant
- 1999-02-19 WO PCT/US1999/003608 patent/WO1999042448A1/en not_active Ceased
- 1999-02-19 DK DK99934281T patent/DK1054868T3/da active
- 1999-02-19 NZ NZ506462A patent/NZ506462A/en unknown
- 1999-02-19 CZ CZ20003044A patent/CZ294136B6/cs not_active IP Right Cessation
- 1999-02-19 EP EP99934281A patent/EP1054868B1/en not_active Expired - Lifetime
- 1999-02-19 TR TR2000/03220T patent/TR200003220T2/xx unknown
- 1999-02-19 ES ES99934281T patent/ES2209468T3/es not_active Expired - Lifetime
- 1999-02-19 BR BR9909647-1A patent/BR9909647A/pt not_active Application Discontinuation
- 1999-02-19 AT AT99934281T patent/ATE250580T1/de not_active IP Right Cessation
- 1999-02-19 PT PT99934281T patent/PT1054868E/pt unknown
- 1999-02-19 DE DE69911582T patent/DE69911582T2/de not_active Expired - Fee Related
- 1999-02-23 AR ARP990100675A patent/AR014626A1/es active IP Right Grant
- 1999-04-02 TW TW088102511A patent/TW565555B/zh not_active IP Right Cessation
-
2000
- 2000-08-18 IL IL137954A patent/IL137954A/en not_active IP Right Cessation
- 2000-08-18 NO NO20004141A patent/NO317103B1/no not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| JP2002503724A (ja) | 2002-02-05 |
| CN1121390C (zh) | 2003-09-17 |
| EP1054868A1 (en) | 2000-11-29 |
| AU766398B2 (en) | 2003-10-16 |
| IL137954A0 (en) | 2001-10-31 |
| DE69911582D1 (de) | 2003-10-30 |
| US6218396B1 (en) | 2001-04-17 |
| CZ20003044A3 (cs) | 2001-04-11 |
| NO20004141L (no) | 2000-10-19 |
| HUP0100781A2 (hu) | 2001-08-28 |
| ZA991315B (en) | 2000-11-20 |
| AR014626A1 (es) | 2001-03-28 |
| TW565555B (en) | 2003-12-11 |
| WO1999042448A1 (en) | 1999-08-26 |
| TR200003220T2 (tr) | 2001-04-20 |
| HK1030776A1 (en) | 2001-05-18 |
| CN1291188A (zh) | 2001-04-11 |
| IL137954A (en) | 2007-06-03 |
| DK1054868T3 (da) | 2003-12-22 |
| KR20010041115A (ko) | 2001-05-15 |
| CZ294136B6 (cs) | 2004-10-13 |
| ES2209468T3 (es) | 2004-06-16 |
| BR9909647A (pt) | 2000-11-21 |
| ATE250580T1 (de) | 2003-10-15 |
| NO20004141D0 (no) | 2000-08-18 |
| AU3302599A (en) | 1999-09-06 |
| KR100591028B1 (ko) | 2006-06-22 |
| PL342339A1 (en) | 2001-06-04 |
| EP1054868B1 (en) | 2003-09-24 |
| HUP0100781A3 (en) | 2002-12-28 |
| DE69911582T2 (de) | 2005-09-15 |
| PT1054868E (pt) | 2004-01-30 |
| NO317103B1 (no) | 2004-08-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PSEA | Patent sealed | ||
| RENW | Renewal (renewal fees accepted) | ||
| RENW | Renewal (renewal fees accepted) |