FI107151B - Menetelmä uusien terapeuttisesti käyttökelpoisten 2-[4-(4,4-bis(4-fluorifenyyli)butyyli)piperatsin-1-yyli]pyridin-3-yyli-karboksyyliestrereiden valmistamiseksi - Google Patents
Menetelmä uusien terapeuttisesti käyttökelpoisten 2-[4-(4,4-bis(4-fluorifenyyli)butyyli)piperatsin-1-yyli]pyridin-3-yyli-karboksyyliestrereiden valmistamiseksi Download PDFInfo
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- FI107151B FI107151B FI946085A FI946085A FI107151B FI 107151 B FI107151 B FI 107151B FI 946085 A FI946085 A FI 946085A FI 946085 A FI946085 A FI 946085A FI 107151 B FI107151 B FI 107151B
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- Finland
- Prior art keywords
- formula
- compound
- butyl
- fluorophenyl
- bis
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- 238000000034 method Methods 0.000 title claims description 18
- 238000002360 preparation method Methods 0.000 title claims description 5
- WOBPETXURNZKDO-UHFFFAOYSA-N 2-[4-[4,4-bis(4-fluorophenyl)butyl]piperazin-1-yl]pyridine-3-carboxylic acid Chemical class OC(=O)C1=CC=CN=C1N1CCN(CCCC(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)CC1 WOBPETXURNZKDO-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 54
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 12
- 150000003839 salts Chemical class 0.000 claims abstract description 10
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 9
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 7
- 150000002367 halogens Chemical class 0.000 claims abstract description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 6
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- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 3
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- -1 hydroxy, carbamoyl Chemical group 0.000 claims description 23
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- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- 239000003377 acid catalyst Substances 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
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- AHOUBRCZNHFOSL-YOEHRIQHSA-N (+)-Casbol Chemical compound C1=CC(F)=CC=C1[C@H]1[C@H](COC=2C=C3OCOC3=CC=2)CNCC1 AHOUBRCZNHFOSL-YOEHRIQHSA-N 0.000 description 1
- ZNDBZNGZPIYESD-UHFFFAOYSA-N (2-nitrophenyl) 2-[4-[4,4-bis(4-fluorophenyl)butyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound [O-][N+](=O)C1=CC=CC=C1OC(=O)C1=CC=CN=C1N1CCN(CCCC(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)CC1 ZNDBZNGZPIYESD-UHFFFAOYSA-N 0.000 description 1
- SYIYPHLCTOPIJE-UHFFFAOYSA-N (3-fluorophenyl) 2-[4-[4,4-bis(4-fluorophenyl)butyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound C1=CC(F)=CC=C1C(C=1C=CC(F)=CC=1)CCCN1CCN(C=2C(=CC=CN=2)C(=O)OC=2C=C(F)C=CC=2)CC1 SYIYPHLCTOPIJE-UHFFFAOYSA-N 0.000 description 1
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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
- C07D213/79—Acids; Esters
- C07D213/80—Acids; Esters in position 3
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Psychiatry (AREA)
- Vascular Medicine (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Urology & Nephrology (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE9201956A SE9201956D0 (sv) | 1992-06-25 | 1992-06-25 | Novel nicotinicacid esters |
| SE9201956 | 1992-06-25 | ||
| SE9300565 | 1993-02-22 | ||
| PCT/SE1993/000565 WO1994000434A1 (en) | 1992-06-25 | 1993-06-23 | Novel nicotinic acid esters |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI946085L FI946085L (fi) | 1994-12-23 |
| FI946085A0 FI946085A0 (fi) | 1994-12-23 |
| FI107151B true FI107151B (fi) | 2001-06-15 |
Family
ID=20386602
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI946085A FI107151B (fi) | 1992-06-25 | 1994-12-23 | Menetelmä uusien terapeuttisesti käyttökelpoisten 2-[4-(4,4-bis(4-fluorifenyyli)butyyli)piperatsin-1-yyli]pyridin-3-yyli-karboksyyliestrereiden valmistamiseksi |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US5658910A (cs) |
| EP (2) | EP1120410B1 (cs) |
| JP (1) | JP3306827B2 (cs) |
| KR (1) | KR100302216B1 (cs) |
| CN (1) | CN1085981C (cs) |
| AT (2) | ATE278671T1 (cs) |
| AU (1) | AU681346B2 (cs) |
| BG (1) | BG62000B1 (cs) |
| CA (1) | CA2139112C (cs) |
| CZ (1) | CZ281975B6 (cs) |
| DE (2) | DE69333655D1 (cs) |
| DK (1) | DK0673368T3 (cs) |
| EE (1) | EE03122B1 (cs) |
| ES (1) | ES2169044T3 (cs) |
| FI (1) | FI107151B (cs) |
| HU (2) | HU220613B1 (cs) |
| IL (1) | IL106135A (cs) |
| NO (1) | NO302945B1 (cs) |
| NZ (1) | NZ253823A (cs) |
| PH (1) | PH31417A (cs) |
| PT (1) | PT673368E (cs) |
| RO (1) | RO115725B1 (cs) |
| RU (1) | RU2127732C1 (cs) |
| SE (1) | SE9201956D0 (cs) |
| SK (1) | SK279393B6 (cs) |
| WO (1) | WO1994000434A1 (cs) |
| ZA (1) | ZA934596B (cs) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6632823B1 (en) * | 1997-12-22 | 2003-10-14 | Merck & Co., Inc. | Substituted pyridine compounds useful as modulators of acetylcholine receptors |
| US7045519B2 (en) * | 1998-06-19 | 2006-05-16 | Chiron Corporation | Inhibitors of glycogen synthase kinase 3 |
| EP1087963B1 (en) | 1998-06-19 | 2004-08-25 | Chiron Corporation | Inhibitors of glycogen synthase kinase 3 |
| ES2244437T3 (es) * | 1999-05-04 | 2005-12-16 | Schering Corporation | Derivados de piperazina utiles como antagonistas de ccr5. |
| SE9904673D0 (sv) * | 1999-12-20 | 1999-12-20 | Astra Pharma Inc | Novel compounds |
| US7229994B2 (en) * | 2001-05-18 | 2007-06-12 | Astrazeneca Ab | 4(phenyl-piperazinyl-methyl) benzamide derivatives and their use for the treatment of pain anxiety or gastrointestinal disorders |
| GB0224917D0 (en) * | 2002-10-25 | 2002-12-04 | Novartis Ag | Organic compounds |
| FR2902426B1 (fr) * | 2006-06-19 | 2008-09-05 | Pierre Fabre Medicament Sa | Derives de cinnamoyl-piperazine |
| KR102325422B1 (ko) * | 2018-05-09 | 2021-11-11 | 주식회사 엘지화학 | 엔테로펩티다아제 억제 활성을 나타내는 신규 화합물 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4457931A (en) * | 1982-09-27 | 1984-07-03 | Selvi & C. S.P.A. | Piperazine derivatives with anticholinergic and/or antihistaminic activity |
| EP0264883A3 (en) * | 1986-10-21 | 1990-04-04 | Banyu Pharmaceutical Co., Ltd. | Substituted pyridine derivatives |
| SE8701375D0 (sv) * | 1987-04-02 | 1987-04-02 | Leo Ab | Novel pyridyl- and pyrimidyl derivatives |
| SE8803429D0 (sv) * | 1988-09-28 | 1988-09-28 | Pharmacia Ab | Novel pyridyl- and pyrimidyl derivatives |
| JP2664238B2 (ja) * | 1989-03-01 | 1997-10-15 | 日清製粉株式会社 | ニコチン酸またはそのエステル誘導体 |
| US4956368A (en) * | 1989-07-24 | 1990-09-11 | Bristol-Myers Company | Metabolites and prodrug formulations of 8-[4-[4-(1,2-benzisothiazol-3-yl)-1-piperazinyl]butyl]-8-azaspiro[4.5]decane-7,9-dione |
| EP0441226A1 (en) * | 1990-01-29 | 1991-08-14 | J. URIACH & CIA. S.A. | (cyanomethyl)pyridines useful as PAF antagonists |
| IE911774A1 (en) * | 1990-06-11 | 1991-12-18 | Akzo Nv | Pyridinylpiperazine derivatives |
| SE9201239D0 (sv) * | 1992-04-21 | 1992-04-21 | Kabi Pharmacia Ab | Agents for treating substance abuse disorders |
| SE9202265D0 (sv) * | 1992-07-31 | 1992-07-31 | Kabi Pharmacia Ab | Novel- pyridyl and pyrimidylpiperazine derivatives |
-
1992
- 1992-06-25 SE SE9201956A patent/SE9201956D0/xx unknown
-
1993
- 1993-06-23 SK SK1585-94A patent/SK279393B6/sk not_active IP Right Cessation
- 1993-06-23 KR KR1019940704643A patent/KR100302216B1/ko not_active Expired - Fee Related
- 1993-06-23 HU HU9403786A patent/HU220613B1/hu not_active IP Right Cessation
- 1993-06-23 RO RO94-02087A patent/RO115725B1/ro unknown
- 1993-06-23 JP JP50226894A patent/JP3306827B2/ja not_active Expired - Fee Related
- 1993-06-23 AT AT01108668T patent/ATE278671T1/de not_active IP Right Cessation
- 1993-06-23 DE DE69333655T patent/DE69333655D1/de not_active Expired - Lifetime
- 1993-06-23 PT PT93915075T patent/PT673368E/pt unknown
- 1993-06-23 AT AT93915075T patent/ATE209634T1/de not_active IP Right Cessation
- 1993-06-23 US US08/362,475 patent/US5658910A/en not_active Expired - Lifetime
- 1993-06-23 DK DK93915075T patent/DK0673368T3/da active
- 1993-06-23 AU AU45193/93A patent/AU681346B2/en not_active Ceased
- 1993-06-23 EP EP01108668A patent/EP1120410B1/en not_active Expired - Lifetime
- 1993-06-23 EP EP93915075A patent/EP0673368B1/en not_active Expired - Lifetime
- 1993-06-23 CZ CZ943274A patent/CZ281975B6/cs not_active IP Right Cessation
- 1993-06-23 CA CA002139112A patent/CA2139112C/en not_active Expired - Fee Related
- 1993-06-23 DE DE69331234T patent/DE69331234T2/de not_active Expired - Fee Related
- 1993-06-23 ES ES93915075T patent/ES2169044T3/es not_active Expired - Lifetime
- 1993-06-23 RU RU94046310A patent/RU2127732C1/ru not_active IP Right Cessation
- 1993-06-23 NZ NZ253823A patent/NZ253823A/en not_active IP Right Cessation
- 1993-06-23 WO PCT/SE1993/000565 patent/WO1994000434A1/en active IP Right Grant
- 1993-06-24 IL IL10613593A patent/IL106135A/en not_active IP Right Cessation
- 1993-06-25 CN CN93116250A patent/CN1085981C/zh not_active Expired - Fee Related
- 1993-06-25 ZA ZA934596A patent/ZA934596B/xx unknown
-
1994
- 1994-11-17 EE EE9400400A patent/EE03122B1/xx not_active IP Right Cessation
- 1994-12-22 BG BG99289A patent/BG62000B1/bg unknown
- 1994-12-23 NO NO945022A patent/NO302945B1/no not_active IP Right Cessation
- 1994-12-23 FI FI946085A patent/FI107151B/fi active
-
1995
- 1995-05-23 HU HU95P/P00139P patent/HU210875A9/hu unknown
-
1998
- 1998-06-24 PH PH4640898A patent/PH31417A/en unknown
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