RU2002118101A - Способ получения {2-[4-(α-фенил-п-хлорбензил)пиперазин-1-ил]-этокси}-уксусной кислоты и новые промежуточные соединения - Google Patents
Способ получения {2-[4-(α-фенил-п-хлорбензил)пиперазин-1-ил]-этокси}-уксусной кислоты и новые промежуточные соединенияInfo
- Publication number
- RU2002118101A RU2002118101A RU2002118101/04A RU2002118101A RU2002118101A RU 2002118101 A RU2002118101 A RU 2002118101A RU 2002118101/04 A RU2002118101/04 A RU 2002118101/04A RU 2002118101 A RU2002118101 A RU 2002118101A RU 2002118101 A RU2002118101 A RU 2002118101A
- Authority
- RU
- Russia
- Prior art keywords
- phenyl
- chlorobenzyl
- piperazin
- ethoxy
- acetamide
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract 5
- ZKLPARSLTMPFCP-UHFFFAOYSA-N Cetirizine Chemical compound C1CN(CCOCC(=O)O)CCN1C(C=1C=CC(Cl)=CC=1)C1=CC=CC=C1 ZKLPARSLTMPFCP-UHFFFAOYSA-N 0.000 title claims 2
- 239000000543 intermediate Substances 0.000 title 1
- -1 N,N-disubstituted {2-[-(alpha-phenyl-p-chlorobenzyl)piperazin-1-yl]ethoxy}acetamide Chemical class 0.000 claims abstract 3
- 125000003342 alkenyl group Chemical group 0.000 claims abstract 2
- 125000000217 alkyl group Chemical group 0.000 claims abstract 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 2
- 150000003839 salts Chemical class 0.000 claims 12
- 239000002253 acid Substances 0.000 claims 9
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 4
- DLYBHNLWSHLFON-UHFFFAOYSA-N n-[2-[4-[(4-chlorophenyl)-phenylmethyl]piperazin-1-yl]ethoxy]acetamide Chemical compound C1CN(CCONC(=O)C)CCN1C(C=1C=CC(Cl)=CC=1)C1=CC=CC=C1 DLYBHNLWSHLFON-UHFFFAOYSA-N 0.000 claims 4
- 239000002585 base Substances 0.000 claims 3
- 229910052751 metal Chemical class 0.000 claims 3
- 239000002184 metal Chemical class 0.000 claims 3
- LCUYPSMMXOBVHQ-UHFFFAOYSA-N 2-[2-[4-[(4-chlorophenyl)-phenylmethyl]piperazin-1-yl]ethoxy]-n,n-dimethylacetamide Chemical compound C1CN(CCOCC(=O)N(C)C)CCN1C(C=1C=CC(Cl)=CC=1)C1=CC=CC=C1 LCUYPSMMXOBVHQ-UHFFFAOYSA-N 0.000 claims 2
- 230000007062 hydrolysis Effects 0.000 claims 2
- 238000006460 hydrolysis reaction Methods 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 1
- 230000002378 acidificating effect Effects 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 150000007522 mineralic acids Chemical class 0.000 claims 1
- 150000007524 organic acids Chemical class 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 125000001424 substituent group Chemical group 0.000 abstract 2
- FCTNBBLCKLLKIN-UHFFFAOYSA-N 2-[2-[2-[(4-chlorophenyl)-phenylmethyl]piperazin-1-yl]ethoxy]acetic acid Chemical compound OC(=O)COCCN1CCNCC1C(C=1C=CC(Cl)=CC=1)C1=CC=CC=C1 FCTNBBLCKLLKIN-UHFFFAOYSA-N 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Immunology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pulmonology (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Claims (5)
1. Способ получения {2-[4-(α-фенил-п-хлорбензил)пиперазин-1-ил]этокси}уксусной кислоты формулы
или ее фармацевтически приемлемой кислотной аддитивной соли или соли металла путем гидролиза соответствующего ацетамида в щелочной или кислой среде и, при необходимости, превращения полученного продукта в кислотную аддитивную соль или соль металла и/или высвобождения основания из кислотной аддитивной соли или соли металла, отличающийся тем, что {2-[4-(α-фенил-п-хлорбензил)пиперазин-1-ил]этокси}ацетамид формулы
где R1 и R2 независимо представляют собой C1-4алкил, который может быть замещен фенилом, C2-4алкенил или циклогексил, или R1 и R2 образуют вместе с соседним атомом азота морфолиновую группу, или его кислотную аддитивную соль используют в качестве ацетамида, и, при необходимости, проводят гидролиз в присутствии межфазного катализатора.
2. Способ по п.1, отличающийся тем, что {2-[4-(α-фенил-п-хлорбензил)пиперазин-1-ил]этокси}ацетамид формулы II представляет собой (RS)-N,N-диметил-{2-[4-(α-фенил-п-хлорбензил)пиперазин-1-ил]этокси}ацетамид.
3. {2-[4-(α-Фенил-п-хлорбензил)пиперазин-1-ил]этокси}ацетамид формулы II, где R1 и R2 определены в п.1, или его кислая аддитивная соль.
4. (RS)-N,N-Диметил-{2-[4-(α-фенил-п-хлорбензил)пиперазин-1-ил]этокси}ацетамид или его кислотная аддитивная соль.
5. Способ получения {2-[4-(α-фенил-п-хлорбензил)пиперазин-1-ил]этокси}ацетамида формулы II, где R1 и R2 определены в п.1, или его кислотной аддитивной соли, отличающийся тем, что соль щелочного металла {2-[4-(α-фенил-п-хлорбензил-пиперазин-1-ил]}этанола формулы
подвергают реакции с 2-галогенацетамидом формулы
где R1 и R2 определены выше;
Х обозначает атом галогена, предпочтительней атом хлора,
и, при необходимости, полученное основание формулы II превращают в кислотную аддитивную соль с неорганической или органической кислотой, или основание высвобождают из его кислотной аддитивной соли.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU9904438A HU226641B1 (en) | 1999-11-30 | 1999-11-30 | Process for producing {2-[4-(alpha-phenyl-p-chloro-benzyl)-piperazine-1-yl]-ethoxy}-acetic acid |
| HUP9904438 | 1999-11-30 | ||
| HUP9904439 | 1999-11-30 | ||
| HU9904439A HU226639B1 (en) | 1999-11-30 | 1999-11-30 | {2-[4-(alpha-phenyl-p-chloro-benzyl)-piperazine-1-yl]-ethoxy}-acetic acid-amides and process for producing them |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2002118101A true RU2002118101A (ru) | 2004-01-20 |
| RU2248974C2 RU2248974C2 (ru) | 2005-03-27 |
Family
ID=90000077
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2002118101/04A RU2248974C2 (ru) | 1999-11-30 | 2000-11-29 | Способ получения {2-[4-(альфа-фенил-п-хлорбензил)пиперазин-1-ил]-этокси}-уксусной кислоты и новые промежуточные соединения |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US6908999B2 (ru) |
| EP (1) | EP1233954B1 (ru) |
| JP (1) | JP4763954B2 (ru) |
| AT (1) | ATE280165T1 (ru) |
| AU (1) | AU1874201A (ru) |
| BG (1) | BG65455B1 (ru) |
| CZ (1) | CZ304892B6 (ru) |
| DE (1) | DE60015177T2 (ru) |
| HR (1) | HRP20020470B1 (ru) |
| PL (1) | PL200046B1 (ru) |
| RU (1) | RU2248974C2 (ru) |
| SI (1) | SI1233954T1 (ru) |
| SK (1) | SK285641B6 (ru) |
| UA (1) | UA72949C2 (ru) |
| WO (1) | WO2001040211A1 (ru) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003009849A1 (en) * | 2001-07-26 | 2003-02-06 | Ucb, S.A. | Process for the preparation of 2-(2-(4-(bis(4-fluorophenyl)methyl)-piperazin-1-yl)ethoxy)acetic acid derivatives or corresponding salt forms thereof and intermediates therefor |
| AU2003237394A1 (en) * | 2002-06-05 | 2003-12-22 | Dr. Reddy's Laboratories Limited | Crystalline (2-(4-((4-chlorophenyl)-phenyl methyl)-1-piperazinyl) ethoxy) acetic acid dihydrochloride |
| HU227319B1 (en) * | 2005-12-08 | 2011-03-28 | Egis Gyogyszergyar Nyrt | Process for the production of (2-chloro-ethoxy)-acetic acid-n,n-dimethylamide and its intermediate and the novel intermediate |
| HU227325B1 (en) * | 2005-12-08 | 2011-03-28 | Egis Gyogyszergyar Nyrt | Process for the production of an intermediate of (dextro- and levo)- cetirizine |
| KR102034448B1 (ko) | 2017-12-20 | 2019-10-18 | 주식회사 포스코 | 강재 및 이의 제조 방법 |
| JP7654243B2 (ja) * | 2020-02-28 | 2025-04-01 | 国立大学法人東海国立大学機構 | 変異型ｇタンパク質共役型受容体 |
| CN117209454A (zh) * | 2023-09-11 | 2023-12-12 | 迪嘉药业集团股份有限公司 | 一种左西替利嗪钠新晶型及其制备方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FI75816C (fi) * | 1981-02-06 | 1988-08-08 | Ucb Sa | Foerfarande foer framstaellning av terapeutiskt aktiv 2-/4-(difenylmetyl)-1-piperazinyl/-aettiksyror eller dess amid. |
| ZA82752B (en) * | 1981-02-06 | 1982-12-29 | Ucb Sa | 2-(4-(diphenylmethyl)-1-piperazinyl)-acetic acids and their amides |
| US5347060A (en) * | 1991-07-24 | 1994-09-13 | Mobil Oil Corporation | Phase-transfer catalysis with onium-containing synthetic mesoporous crystalline material |
| GB9305282D0 (en) * | 1993-03-15 | 1993-05-05 | Ucb Sa | Enantiomers of 1-(4-chlorophenyl)phenylmethyl)-4-(4-methylphenyl)sulphonyl)piperazine |
| BE1010094A3 (fr) * | 1996-04-10 | 1997-12-02 | Ucb Sa | Nouveaux [2-(1-piperazinyl)ethoxy] methyle substitues. |
| CA2180993A1 (en) * | 1996-07-11 | 1998-01-12 | Yong Tao | Methods for the manufacture of cetirizine |
-
2000
- 2000-11-29 SK SK752-2002A patent/SK285641B6/sk not_active IP Right Cessation
- 2000-11-29 HR HR20020470A patent/HRP20020470B1/xx not_active IP Right Cessation
- 2000-11-29 SI SI200030569T patent/SI1233954T1/xx unknown
- 2000-11-29 DE DE60015177T patent/DE60015177T2/de not_active Expired - Lifetime
- 2000-11-29 AT AT00981508T patent/ATE280165T1/de not_active IP Right Cessation
- 2000-11-29 CZ CZ2002-1712A patent/CZ304892B6/cs not_active IP Right Cessation
- 2000-11-29 RU RU2002118101/04A patent/RU2248974C2/ru not_active IP Right Cessation
- 2000-11-29 JP JP2001541895A patent/JP4763954B2/ja not_active Expired - Fee Related
- 2000-11-29 PL PL354677A patent/PL200046B1/pl unknown
- 2000-11-29 WO PCT/HU2000/000123 patent/WO2001040211A1/en not_active Ceased
- 2000-11-29 AU AU18742/01A patent/AU1874201A/en not_active Abandoned
- 2000-11-29 UA UA2002065341A patent/UA72949C2/ru unknown
- 2000-11-29 US US10/148,704 patent/US6908999B2/en not_active Expired - Fee Related
- 2000-11-29 EP EP00981508A patent/EP1233954B1/en not_active Expired - Lifetime
-
2002
- 2002-05-30 BG BG106760A patent/BG65455B1/bg unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CZ304892B6 (cs) | 2015-01-07 |
| HRP20020470B1 (hr) | 2009-04-30 |
| DE60015177T2 (de) | 2005-10-27 |
| JP2003515600A (ja) | 2003-05-07 |
| SI1233954T1 (en) | 2005-02-28 |
| CZ20021712A3 (cs) | 2002-09-11 |
| WO2001040211A1 (en) | 2001-06-07 |
| DE60015177D1 (de) | 2004-11-25 |
| AU1874201A (en) | 2001-06-12 |
| EP1233954A1 (en) | 2002-08-28 |
| PL354677A1 (en) | 2004-02-09 |
| UA72949C2 (ru) | 2005-05-16 |
| RU2248974C2 (ru) | 2005-03-27 |
| HRP20020470A2 (en) | 2004-04-30 |
| US20030092911A1 (en) | 2003-05-15 |
| JP4763954B2 (ja) | 2011-08-31 |
| PL200046B1 (pl) | 2008-11-28 |
| SK7522002A3 (en) | 2002-11-06 |
| BG106760A (en) | 2003-04-30 |
| US6908999B2 (en) | 2005-06-21 |
| BG65455B1 (bg) | 2008-08-29 |
| EP1233954B1 (en) | 2004-10-20 |
| ATE280165T1 (de) | 2004-11-15 |
| SK285641B6 (sk) | 2007-05-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | The patent is invalid due to non-payment of fees |
Effective date: 20161130 |