CZ294136B6 - Substituované pyridinoarylpiperaziny použitelné při léčení benigního zbytnění prostaty - Google Patents
Substituované pyridinoarylpiperaziny použitelné při léčení benigního zbytnění prostaty Download PDFInfo
- Publication number
- CZ294136B6 CZ294136B6 CZ20003044A CZ20003044A CZ294136B6 CZ 294136 B6 CZ294136 B6 CZ 294136B6 CZ 20003044 A CZ20003044 A CZ 20003044A CZ 20003044 A CZ20003044 A CZ 20003044A CZ 294136 B6 CZ294136 B6 CZ 294136B6
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- CZ
- Czechia
- Prior art keywords
- alkyl
- substituted
- hydrogen
- phenyl
- formula
- Prior art date
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- 238000011282 treatment Methods 0.000 title claims abstract description 23
- 206010004446 Benign prostatic hyperplasia Diseases 0.000 title claims abstract description 22
- 208000004403 Prostatic Hyperplasia Diseases 0.000 title claims abstract description 22
- 150000001875 compounds Chemical class 0.000 claims abstract description 73
- 108060003345 Adrenergic Receptor Proteins 0.000 claims abstract description 8
- 102000017910 Adrenergic receptor Human genes 0.000 claims abstract description 8
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- 125000000217 alkyl group Chemical group 0.000 claims description 58
- 239000000203 mixture Substances 0.000 claims description 51
- 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 36
- 150000002431 hydrogen Chemical class 0.000 claims description 24
- 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
- 125000003545 alkoxy group Chemical group 0.000 claims description 19
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- 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
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- -1 alkyl hydrogen Chemical class 0.000 claims description 8
- 125000003282 alkyl amino group Chemical group 0.000 claims description 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 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
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- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 239000011593 sulfur Chemical group 0.000 claims description 6
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
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- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
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- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000005185 naphthylcarbonyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 claims description 2
- 150000002825 nitriles Chemical class 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims 1
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
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- 229940125782 compound 2 Drugs 0.000 description 6
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- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 6
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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 6
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- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 208000019206 urinary tract infection Diseases 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—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
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/08—Drugs for disorders of the urinary system of the prostate
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- 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 (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US7532198P | 1998-02-20 | 1998-02-20 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CZ20003044A3 CZ20003044A3 (cs) | 2001-04-11 |
| CZ294136B6 true CZ294136B6 (cs) | 2004-10-13 |
Family
ID=22124955
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CZ20003044A CZ294136B6 (cs) | 1998-02-20 | 1999-02-19 | Substituované pyridinoarylpiperaziny použitelné při léčení benigního zbytnění prostaty |
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 |
| 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 |
| AU766398B2 (en) | 2003-10-16 |
| 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 |
|---|---|---|---|
| MM4A | Patent lapsed due to non-payment of fee |
Effective date: 20100219 |