AU766398B2 - Novel substituted pyridino arylpiperazines useful in the treatment of benign prostatic hyperplasia - Google Patents
Novel substituted pyridino arylpiperazines useful in the treatment of benign prostatic hyperplasia Download PDFInfo
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- AU766398B2 AU766398B2 AU33025/99A AU3302599A AU766398B2 AU 766398 B2 AU766398 B2 AU 766398B2 AU 33025/99 A AU33025/99 A AU 33025/99A AU 3302599 A AU3302599 A AU 3302599A AU 766398 B2 AU766398 B2 AU 766398B2
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- Australia
- Prior art keywords
- compound
- hydrogen
- phenyl
- alkyl
- substituted
- Prior art date
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- 206010004446 Benign prostatic hyperplasia Diseases 0.000 title claims description 25
- 208000004403 Prostatic Hyperplasia Diseases 0.000 title claims description 25
- 238000011282 treatment Methods 0.000 title description 16
- 150000001875 compounds Chemical class 0.000 claims description 89
- 239000000203 mixture Substances 0.000 claims description 48
- 229910052739 hydrogen Inorganic materials 0.000 claims description 39
- 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
- 150000002431 hydrogen Chemical class 0.000 claims description 30
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 25
- 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
- 238000000034 method Methods 0.000 claims description 21
- 229910052799 carbon Inorganic materials 0.000 claims description 14
- 108060003345 Adrenergic Receptor Proteins 0.000 claims description 11
- 102000017910 Adrenergic receptor Human genes 0.000 claims description 11
- 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
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 10
- 201000010099 disease Diseases 0.000 claims description 9
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- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 241000124008 Mammalia Species 0.000 claims description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
- 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
- 239000003814 drug Substances 0.000 claims description 6
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- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 239000011593 sulfur Chemical group 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 2
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 2
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- 230000000052 comparative effect Effects 0.000 claims 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
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- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 21
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- 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
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 7
- YEDUAINPPJYDJZ-UHFFFAOYSA-N 2-hydroxybenzothiazole Chemical compound C1=CC=C2SC(O)=NC2=C1 YEDUAINPPJYDJZ-UHFFFAOYSA-N 0.000 description 7
- -1 C 1 -salkyisulfonyl Chemical group 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
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- 229940125782 compound 2 Drugs 0.000 description 6
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- 239000000543 intermediate Substances 0.000 description 5
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- 150000004885 piperazines Chemical class 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
- 108020004635 Complementary DNA Proteins 0.000 description 4
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- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
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- 150000001540 azides Chemical class 0.000 description 4
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 4
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- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
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- 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
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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
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- A—HUMAN NECESSITIES
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Landscapes
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- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Urology & Nephrology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US7532198P | 1998-02-20 | 1998-02-20 | |
| US60/075321 | 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 (2)
| Publication Number | Publication Date |
|---|---|
| AU3302599A AU3302599A (en) | 1999-09-06 |
| AU766398B2 true AU766398B2 (en) | 2003-10-16 |
Family
ID=22124955
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU33025/99A Ceased AU766398B2 (en) | 1998-02-20 | 1999-02-19 | Novel substituted pyridino arylpiperazines useful in the treatment of benign prostatic hyperplasia |
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 |
|---|---|---|---|---|
| EP0984777B1 (en) * | 1997-05-12 | 2003-09-17 | Ortho-Mcneil Pharmaceutical, Inc. | Arylsubstituted piperazines useful in the treatement of benign prostatic hyperlasia |
| HUP0302893A3 (en) | 2000-08-08 | 2006-04-28 | Ortho Mcneil Pharm Inc | Non-imidazole aryloxypiperidines and pharmaceutical compositions containing them and their use |
| CN1589153A (zh) * | 2001-12-28 | 2005-03-02 | 武田药品工业株式会社 | 排尿紊乱的预防或治疗 |
| USD545208S1 (en) | 2006-09-27 | 2007-06-26 | 001 Corporation | Perfume bottle and cap |
| EP2535330A3 (en) * | 2006-10-23 | 2012-12-26 | Takeda Pharmaceutical Company Limited | Iminopyridine derivative and use thereof |
| US20110039892A1 (en) * | 2008-04-23 | 2011-02-17 | Takeda Pharmaceutical Company Limited | Iminopyridine derivative and use thereof |
| CN102066327B (zh) * | 2008-04-23 | 2013-05-29 | 武田药品工业株式会社 | 亚氨基吡啶衍生物及其用途 |
| US8481569B2 (en) | 2008-04-23 | 2013-07-09 | Takeda Pharmaceutical Company Limited | Iminopyridine derivatives 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 |
| WO1999003833A1 (fr) * | 1997-07-15 | 1999-01-28 | Sankyo Company, Limited | Derives de piperazine |
-
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 HU HU0100781A patent/HUP0100781A3/hu unknown
- 1999-02-19 ES ES99934281T patent/ES2209468T3/es not_active Expired - Lifetime
- 1999-02-19 TR TR2000/03220T patent/TR200003220T2/xx unknown
- 1999-02-19 PT PT99934281T patent/PT1054868E/pt unknown
- 1999-02-19 CZ CZ20003044A patent/CZ294136B6/cs not_active IP Right Cessation
- 1999-02-19 DE DE69911582T patent/DE69911582T2/de not_active Expired - Fee Related
- 1999-02-19 AU AU33025/99A patent/AU766398B2/en not_active Ceased
- 1999-02-19 PL PL99342339A patent/PL342339A1/xx unknown
- 1999-02-19 NZ NZ506462A patent/NZ506462A/en unknown
- 1999-02-19 EP EP99934281A patent/EP1054868B1/en not_active Expired - Lifetime
- 1999-02-19 WO PCT/US1999/003608 patent/WO1999042448A1/en not_active Ceased
- 1999-02-19 BR BR9909647-1A patent/BR9909647A/pt not_active Application Discontinuation
- 1999-02-19 IL IL13795499A patent/IL137954A0/xx active IP Right Grant
- 1999-02-19 DK DK99934281T patent/DK1054868T3/da active
- 1999-02-19 JP JP2000532400A patent/JP2002503724A/ja active Pending
- 1999-02-19 KR KR1020007009156A patent/KR100591028B1/ko not_active Expired - Fee Related
- 1999-02-19 AT AT99934281T patent/ATE250580T1/de not_active IP Right Cessation
- 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 NO NO20004141A patent/NO317103B1/no not_active IP Right Cessation
- 2000-08-18 IL IL137954A patent/IL137954A/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DK1054868T3 (da) | 2003-12-22 |
| AR014626A1 (es) | 2001-03-28 |
| TR200003220T2 (tr) | 2001-04-20 |
| PL342339A1 (en) | 2001-06-04 |
| ES2209468T3 (es) | 2004-06-16 |
| HK1030776A1 (en) | 2001-05-18 |
| KR100591028B1 (ko) | 2006-06-22 |
| NO20004141D0 (no) | 2000-08-18 |
| KR20010041115A (ko) | 2001-05-15 |
| CN1291188A (zh) | 2001-04-11 |
| JP2002503724A (ja) | 2002-02-05 |
| EP1054868B1 (en) | 2003-09-24 |
| WO1999042448A1 (en) | 1999-08-26 |
| TW565555B (en) | 2003-12-11 |
| CZ294136B6 (cs) | 2004-10-13 |
| IL137954A (en) | 2007-06-03 |
| BR9909647A (pt) | 2000-11-21 |
| PT1054868E (pt) | 2004-01-30 |
| NO317103B1 (no) | 2004-08-09 |
| NO20004141L (no) | 2000-10-19 |
| ZA991315B (en) | 2000-11-20 |
| ATE250580T1 (de) | 2003-10-15 |
| IL137954A0 (en) | 2001-10-31 |
| CN1121390C (zh) | 2003-09-17 |
| US6218396B1 (en) | 2001-04-17 |
| DE69911582T2 (de) | 2005-09-15 |
| DE69911582D1 (de) | 2003-10-30 |
| AU3302599A (en) | 1999-09-06 |
| CZ20003044A3 (cs) | 2001-04-11 |
| EP1054868A1 (en) | 2000-11-29 |
| HUP0100781A2 (hu) | 2001-08-28 |
| NZ506462A (en) | 2003-07-25 |
| HUP0100781A3 (en) | 2002-12-28 |
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Legal Events
| Date | Code | Title | Description |
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| FGA | Letters patent sealed or granted (standard patent) |