HRP20131086T1 - 4r,5s-enantiomer 2-(5-metil-2-okso-4-fenil-pirolidin-1-il)-acetamida s nootropskim djelovanjem - Google Patents
4r,5s-enantiomer 2-(5-metil-2-okso-4-fenil-pirolidin-1-il)-acetamida s nootropskim djelovanjem Download PDFInfo
- Publication number
- HRP20131086T1 HRP20131086T1 HRP20131086AT HRP20131086T HRP20131086T1 HR P20131086 T1 HRP20131086 T1 HR P20131086T1 HR P20131086A T HRP20131086A T HR P20131086AT HR P20131086 T HRP20131086 T HR P20131086T HR P20131086 T1 HRP20131086 T1 HR P20131086T1
- Authority
- HR
- Croatia
- Prior art keywords
- methyl
- oxo
- pyrrolidin
- phenyl
- acetamide
- Prior art date
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- ZTGRWYMPQCQTHD-UHFFFAOYSA-N 2-(2-methyl-5-oxo-3-phenylpyrrolidin-1-yl)acetamide Chemical compound C1C(=O)N(CC(N)=O)C(C)C1C1=CC=CC=C1 ZTGRWYMPQCQTHD-UHFFFAOYSA-N 0.000 title 1
- 230000001777 nootropic effect Effects 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 6
- 238000000034 method Methods 0.000 claims 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 4
- 239000003960 organic solvent Substances 0.000 claims 4
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 claims 3
- 230000009435 amidation Effects 0.000 claims 3
- 238000007112 amidation reaction Methods 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- PPGRVWNKZPOCIU-UHFFFAOYSA-N 2-[1-(4,5-dihydro-1,3-oxazol-2-yl)cyclopropyl]-4,5-dihydro-1,3-oxazole Chemical compound C1CC1(C=1OCCN=1)C1=NCCO1 PPGRVWNKZPOCIU-UHFFFAOYSA-N 0.000 claims 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 2
- FKNQFGJONOIPTF-UHFFFAOYSA-N Sodium cation Chemical compound [Na+] FKNQFGJONOIPTF-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 125000003368 amide group Chemical group 0.000 claims 2
- 229910021529 ammonia Inorganic materials 0.000 claims 2
- RKMJYPGOUBXWLP-YUZLPWPTSA-N diethyl 2-[(1r)-2-nitro-1-phenylpropyl]propanedioate Chemical compound CCOC(=O)C(C(=O)OCC)[C@@H](C(C)[N+]([O-])=O)C1=CC=CC=C1 RKMJYPGOUBXWLP-YUZLPWPTSA-N 0.000 claims 2
- 150000002148 esters Chemical class 0.000 claims 2
- 150000007530 organic bases Chemical class 0.000 claims 2
- 229910001415 sodium ion Inorganic materials 0.000 claims 2
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 claims 1
- WGSVFWFSJDAYBM-UHFFFAOYSA-N 2-nitroprop-1-enylbenzene Chemical compound [O-][N+](=O)C(C)=CC1=CC=CC=C1 WGSVFWFSJDAYBM-UHFFFAOYSA-N 0.000 claims 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims 1
- 238000007126 N-alkylation reaction Methods 0.000 claims 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims 1
- 235000011114 ammonium hydroxide Nutrition 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 230000007278 cognition impairment Effects 0.000 claims 1
- 230000037410 cognitive enhancement Effects 0.000 claims 1
- 238000006114 decarboxylation reaction Methods 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- WVWCPWNZJHBXJB-WEBCLNCGSA-N ethyl (3s,4r)-5-methyl-2-oxo-4-phenylpyrrolidine-3-carboxylate Chemical compound CC1NC(=O)[C@@H](C(=O)OCC)[C@@H]1C1=CC=CC=C1 WVWCPWNZJHBXJB-WEBCLNCGSA-N 0.000 claims 1
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 238000005984 hydrogenation reaction Methods 0.000 claims 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 claims 1
- 229940011051 isopropyl acetate Drugs 0.000 claims 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 claims 1
- BZQRBEVTLZHKEA-UHFFFAOYSA-L magnesium;trifluoromethanesulfonate Chemical compound [Mg+2].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F BZQRBEVTLZHKEA-UHFFFAOYSA-L 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000002664 nootropic agent Substances 0.000 claims 1
- 238000009738 saturating Methods 0.000 claims 1
- 239000012312 sodium hydride Substances 0.000 claims 1
- 229910000104 sodium hydride Inorganic materials 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member 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
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
- C07D207/27—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/4015—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil having oxo groups directly attached to the heterocyclic ring, e.g. piracetam, ethosuximide
-
- 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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member 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
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Biomedical Technology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Epidemiology (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Pyrrole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Claims (12)
1. Spoj, naznačen time, da jest 2-(5S-metil-2-okso-4R-fenil-pirolidin-1-il)-acetamid (I) formule
[image]
2. Spoj 2-(5S-metil-2-okso-4R-fenil-pirolidin-1-il)-acetamid, naznačen time, da jest za uporabu kao lijek.
3. Spoj 2-(5S-metil-2-okso-4R-fenil-pirolidin-1-il)-acetamid, naznačen time, da jest za uporabu kao nootropski lijek.
4. Spoj 2-(5S-metil-2-okso-4R-fenil-pirolidin-1-il)-acetamid, naznačen time, da jest za uporabu za kognitivno snaženje.
5. Spoj 2-(5S-metil-2-okso-4R-fenil-pirolidin-1-il)-acetamid, naznačen time, da jest za uporabu u liječenju kognitivnog deficita.
6. Postupak za pripravljanje spoja (I) prema patentnom zahtjevu 1, naznačen time, da uključuje sljedeće korake:
a) dodavanje 2-nitroprop-1-enilbenzena dietil malonatu u prisutnosti kompleksa katalizatora koji se sastoji od kiralnog 2,2'-ciklopropiliden-bis-oksazolina, magnezijevog triflata i organske baze;
b) konverziju dietil 2-(2-nitro-1R-fenilpropil)malonata u enantiomerni 5S-metil-4R-fenilpirolidin-2-on hidrogeniranjem dietil 2-(2-nitro-1R-fenilpropil)malonata u prisutnosti Ni Reney, rezoluciju dijastereoizomerne smjese etil 5-metil-2-okso-4(R)-fenilpirolidin-3(S)-karboksilata u odvojene 5S,4R- i 5R,4-enantiomere, dekarboksiliranje etil 5(S)-metil-2-okso-4(R)-fenilpirolidin-3(S)-karboksilata u otopinu izo-propil acetata u prisutnosti para-toluensulfonske kiseline;
c) supstituciju vodika u amidnoj skupini 5S-metil-4R-fenilpirolidin-2-ona natrijevim ionom u prikladnom organskom otapalu;
d) N-alkiliranje N-metaliranog 5S-metil-4R-fenilpirolidin-2-ona esterima halooctene kiseline u prikladnom organskom otapalu;
e) amidiranje etil 2-(5S-metil-2-okso-4R-fenil-pirolidin-1-il)-acetata amonijakom u prikladnom otapalu.
7. Postupak prema patentnom zahtjevu 6, naznačen time, da u koraku a) kiralni 2,2'-ciklopropiliden-bis(oksazolin) jest (3aR,3'aR,8aS,8'aS)-2,2'-ciklopropiliden bis-[3a,8a]-dihidro-8H-indeno-[1,2-d]-oksazol.
8. Postupak prema patentnom zahtjevu 6, naznačen time, da se u koraku a) organska baza odabire iz skupine koja sadrži morfolin, N-metilmorfolin i njihove smjese.
9. Postupak prema patentnom zahtjevu 6, naznačen time, da se u koraku c) natrijev ion uvodi u amidnu skupinu 5S-metil-4R-fenilpirolidin-2-ona natrijevim hidridom.
10. Postupak prema patentnom zahtjevu 6, naznačen time, da u koraku d) ester halooctene kiseline jest etil bromoacetat.
11. Postupak prema patentnom zahtjevu 6, naznačen time, da se u koraku e) amidiranje etil 2-(5S-metil-2-okso-4R-fenil-pirolidin-1-il)-acetata ostvaruje u vodenoj otopini amonijaka ili njegovoj smjesi s prikladnim organskim otapalom.
12. Postupak prema patentnom zahtjevu 6, naznačen time, da se u koraku e) amidiranje etil 2-(5S-metil-2-okso-4R-fenil-pirolidin-1-il)-acetata ostvaruje u prikladnom organskom otapalu njegovom saturacijom plinovitim amonijakom.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| LVP-09-193A LV14346B (lv) | 2009-11-05 | 2009-11-05 | 2-(4-Fenil-5-metil-2-oksopirolidin-1-il)-acetamīda 4R,5S-enantiomērs ar nootropo aktivitāti |
| PCT/EP2010/066767 WO2011054888A1 (en) | 2009-11-05 | 2010-11-04 | 4r,5s-enantiomer of 2-(5-methyl-2-oxo-4-phenyl-pyrrolidin-1-yl)-acetamide with nootropic activity |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20131086T1 true HRP20131086T1 (hr) | 2013-12-20 |
Family
ID=43466928
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20131086AT HRP20131086T1 (hr) | 2009-11-05 | 2013-11-13 | 4r,5s-enantiomer 2-(5-metil-2-okso-4-fenil-pirolidin-1-il)-acetamida s nootropskim djelovanjem |
Country Status (18)
| Country | Link |
|---|---|
| US (2) | US8791273B2 (hr) |
| EP (1) | EP2496555B1 (hr) |
| JP (1) | JP2013510081A (hr) |
| CN (1) | CN102596905B (hr) |
| AR (1) | AR078904A1 (hr) |
| CA (1) | CA2780040C (hr) |
| CY (1) | CY1114881T1 (hr) |
| DK (1) | DK2496555T3 (hr) |
| EA (1) | EA019890B1 (hr) |
| ES (1) | ES2434024T3 (hr) |
| HR (1) | HRP20131086T1 (hr) |
| LV (1) | LV14346B (hr) |
| PL (1) | PL2496555T3 (hr) |
| PT (1) | PT2496555E (hr) |
| RS (1) | RS53014B (hr) |
| SI (1) | SI2496555T1 (hr) |
| UA (1) | UA107367C2 (hr) |
| WO (1) | WO2011054888A1 (hr) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3127539A1 (en) | 2015-08-03 | 2017-02-08 | Latvian Institute Of Organic Synthesis | Use of 2-(5s-methyl-2-oxo-4r-phenyl-pyrrolidin-1-yl)-acetamide in the treatment of seizures |
| RU2711655C1 (ru) * | 2019-09-13 | 2020-01-20 | Федеральное государственное бюджетное образовательное учреждение высшего образования "Российский национальный исследовательский медицинский университет имени Н.И. Пирогова" Министерства здравоохранения Российской Федерации | Способ крупномасштабного синтеза калиевой соли 2-[2-(2-оксо-4-фенилпирролидин-1-ил)ацетамидо]этансульфокислоты |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2186236B1 (hr) * | 1972-05-03 | 1975-08-01 | Logeais Labor Jacques | |
| CN1040747C (zh) * | 1994-05-07 | 1998-11-18 | 中国科学院昆明植物研究所 | N－取代基－4－取代苯基－5－烷基－5－取代苄基吡咯烷酮－2,其中间体,其合成方其法及应用 |
| JPWO2002053153A1 (ja) * | 2000-12-28 | 2004-04-30 | 第一製薬株式会社 | 神経因性疼痛治療及び予防薬 |
| JPWO2005061454A1 (ja) * | 2003-12-24 | 2007-07-12 | 秀樹 大山 | 脳血管障害慢性期の重度失語症に対する治療剤又は治療方法 |
| GB0412019D0 (en) * | 2004-05-28 | 2004-06-30 | Novartis Ag | Organic compounds |
| LV13630B (en) * | 2006-03-16 | 2007-12-20 | Olainfarm As | Method of preparation and use of pharmaceutically active n-carbamoylmethyl-4(r)-phenyl-2-pyrrolidinone |
-
2009
- 2009-11-05 LV LVP-09-193A patent/LV14346B/lv unknown
-
2010
- 2010-04-11 UA UAA201206776A patent/UA107367C2/ru unknown
- 2010-11-04 PT PT107763393T patent/PT2496555E/pt unknown
- 2010-11-04 US US13/508,184 patent/US8791273B2/en not_active Expired - Fee Related
- 2010-11-04 DK DK10776339.3T patent/DK2496555T3/da active
- 2010-11-04 JP JP2012535876A patent/JP2013510081A/ja active Pending
- 2010-11-04 WO PCT/EP2010/066767 patent/WO2011054888A1/en active Application Filing
- 2010-11-04 SI SI201030416T patent/SI2496555T1/sl unknown
- 2010-11-04 CN CN201080050216.9A patent/CN102596905B/zh not_active Expired - Fee Related
- 2010-11-04 AR ARP100104073A patent/AR078904A1/es not_active Application Discontinuation
- 2010-11-04 PL PL10776339T patent/PL2496555T3/pl unknown
- 2010-11-04 RS RS20130474A patent/RS53014B/en unknown
- 2010-11-04 EP EP10776339.3A patent/EP2496555B1/en active Active
- 2010-11-04 EA EA201200536A patent/EA019890B1/ru unknown
- 2010-11-04 CA CA2780040A patent/CA2780040C/en not_active Expired - Fee Related
- 2010-11-04 ES ES10776339T patent/ES2434024T3/es active Active
-
2013
- 2013-11-13 HR HRP20131086AT patent/HRP20131086T1/hr unknown
- 2013-11-27 CY CY20131101066T patent/CY1114881T1/el unknown
-
2014
- 2014-06-16 US US14/305,382 patent/US20140296317A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| US8791273B2 (en) | 2014-07-29 |
| LV14346B (lv) | 2011-07-20 |
| CY1114881T1 (el) | 2016-12-14 |
| CN102596905B (zh) | 2014-07-16 |
| CA2780040C (en) | 2014-04-08 |
| US20140296317A1 (en) | 2014-10-02 |
| DK2496555T3 (da) | 2013-11-11 |
| SI2496555T1 (sl) | 2013-12-31 |
| PT2496555E (pt) | 2013-12-02 |
| CA2780040A1 (en) | 2011-05-12 |
| EP2496555A1 (en) | 2012-09-12 |
| US20120215010A1 (en) | 2012-08-23 |
| CN102596905A (zh) | 2012-07-18 |
| UA107367C2 (xx) | 2014-12-25 |
| LV14346A (lv) | 2011-05-20 |
| PL2496555T3 (pl) | 2014-01-31 |
| ES2434024T3 (es) | 2013-12-13 |
| EA019890B1 (ru) | 2014-07-30 |
| JP2013510081A (ja) | 2013-03-21 |
| WO2011054888A1 (en) | 2011-05-12 |
| RS53014B (en) | 2014-04-30 |
| AR078904A1 (es) | 2011-12-14 |
| EA201200536A1 (ru) | 2012-09-28 |
| EP2496555B1 (en) | 2013-08-28 |
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