HRP20050833A2 - Pyrroloimidazole derivatives, their preparation, pharmaceutical composition containing them, and their use as nootropic agents - Google Patents
Pyrroloimidazole derivatives, their preparation, pharmaceutical composition containing them, and their use as nootropic agents Download PDFInfo
- Publication number
- HRP20050833A2 HRP20050833A2 HR20050833A HRP20050833A HRP20050833A2 HR P20050833 A2 HRP20050833 A2 HR P20050833A2 HR 20050833 A HR20050833 A HR 20050833A HR P20050833 A HRP20050833 A HR P20050833A HR P20050833 A2 HRP20050833 A2 HR P20050833A2
- Authority
- HR
- Croatia
- Prior art keywords
- pyrrolo
- imidazole
- dione
- tetrahydro
- phenyl
- Prior art date
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- 238000002360 preparation method Methods 0.000 title claims abstract description 19
- 239000008194 pharmaceutical composition Substances 0.000 title abstract description 3
- 239000002664 nootropic agent Substances 0.000 title description 4
- MHOZZUICEDXVGD-UHFFFAOYSA-N pyrrolo[2,3-d]imidazole Chemical class C1=NC2=CC=NC2=N1 MHOZZUICEDXVGD-UHFFFAOYSA-N 0.000 title 1
- 238000000034 method Methods 0.000 claims abstract description 29
- 208000002193 Pain Diseases 0.000 claims abstract description 10
- 230000003070 anti-hyperalgesia Effects 0.000 claims abstract description 9
- 230000001777 nootropic effect Effects 0.000 claims abstract description 8
- 230000036407 pain Effects 0.000 claims abstract description 6
- 230000000202 analgesic effect Effects 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 122
- 125000000217 alkyl group Chemical group 0.000 claims description 25
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 17
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 16
- 150000001413 amino acids Chemical class 0.000 claims description 16
- 230000008569 process Effects 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 14
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical group [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 14
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 13
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- 150000003839 salts Chemical class 0.000 claims description 10
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- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 8
- 239000012453 solvate Substances 0.000 claims description 8
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- -1 hydroxy, thio, amino, carboxyl Chemical group 0.000 claims description 7
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
- 208000004296 neuralgia Diseases 0.000 claims description 7
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- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 206010065390 Inflammatory pain Diseases 0.000 claims description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 6
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
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- 125000001424 substituent group Chemical group 0.000 claims description 6
- VSCBATMPTLKTOV-UHFFFAOYSA-N 2-tert-butylimino-n,n-diethyl-1,3-dimethyl-1,3,2$l^{5}-diazaphosphinan-2-amine Chemical compound CCN(CC)P1(=NC(C)(C)C)N(C)CCCN1C VSCBATMPTLKTOV-UHFFFAOYSA-N 0.000 claims description 5
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims description 5
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- VFNQLOPSYQVHTO-UHFFFAOYSA-N 1-[(4-methylphenyl)methyl]-3,6,7,7a-tetrahydropyrrolo[1,2-a]imidazole-2,5-dione Chemical compound C1=CC(C)=CC=C1CN1C(=O)CN2C(=O)CCC21 VFNQLOPSYQVHTO-UHFFFAOYSA-N 0.000 claims description 3
- DGYLCNVWDTVZNK-UHFFFAOYSA-N 1-benzyl-3,6,7,7a-tetrahydropyrrolo[1,2-a]imidazole-2,5-dione Chemical compound O=C1CN(C(CC2)=O)C2N1CC1=CC=CC=C1 DGYLCNVWDTVZNK-UHFFFAOYSA-N 0.000 claims description 3
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- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 3
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- 125000005843 halogen group Chemical group 0.000 claims description 3
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- QRWIBQDPXGDRCZ-NSHDSACASA-N (7as)-1-(2-methylphenyl)-3,6,7,7a-tetrahydropyrrolo[1,2-a]imidazole-2,5-dione Chemical compound CC1=CC=CC=C1N1C(=O)CN2C(=O)CC[C@@H]21 QRWIBQDPXGDRCZ-NSHDSACASA-N 0.000 claims description 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 2
- ZEABXXATIREXQL-UHFFFAOYSA-N 1-(2,6-dimethylphenyl)-3,6,7,7a-tetrahydropyrrolo[1,2-a]imidazole-2,5-dione Chemical compound CC1=CC=CC(C)=C1N1C(=O)CN2C(=O)CCC21 ZEABXXATIREXQL-UHFFFAOYSA-N 0.000 claims description 2
- WQEBXNDEOFIRLU-UHFFFAOYSA-N 1-(3,4-dimethylphenyl)-3,6,7,7a-tetrahydropyrrolo[1,2-a]imidazole-2,5-dione Chemical compound C1=C(C)C(C)=CC=C1N1C(=O)CN2C(=O)CCC21 WQEBXNDEOFIRLU-UHFFFAOYSA-N 0.000 claims description 2
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- MNTLLIAHJWUSOX-UHFFFAOYSA-N 1-(3-propan-2-ylphenyl)-3,6,7,7a-tetrahydropyrrolo[1,2-a]imidazole-2,5-dione Chemical compound CC(C)C1=CC=CC(N2C(CN3C(=O)CCC32)=O)=C1 MNTLLIAHJWUSOX-UHFFFAOYSA-N 0.000 claims description 2
- DUEICGOKWYPYJF-UHFFFAOYSA-N 1-(4-chloro-2-methylphenyl)-3,6,7,7a-tetrahydropyrrolo[1,2-a]imidazole-2,5-dione Chemical compound CC1=CC(Cl)=CC=C1N1C(=O)CN2C(=O)CCC21 DUEICGOKWYPYJF-UHFFFAOYSA-N 0.000 claims description 2
- MAAJXDAKIMDIRX-UHFFFAOYSA-N 1-(4-chloro-3-methylphenyl)-3,6,7,7a-tetrahydropyrrolo[1,2-a]imidazole-2,5-dione Chemical compound C1=C(Cl)C(C)=CC(N2C(CN3C(=O)CCC32)=O)=C1 MAAJXDAKIMDIRX-UHFFFAOYSA-N 0.000 claims description 2
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- XSMLJFJCISDAFX-UHFFFAOYSA-N 1-(4-ethylphenyl)-3,6,7,7a-tetrahydropyrrolo[1,2-a]imidazole-2,5-dione Chemical compound C1=CC(CC)=CC=C1N1C(=O)CN2C(=O)CCC21 XSMLJFJCISDAFX-UHFFFAOYSA-N 0.000 claims description 2
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- IEEXZTRJOZFMNF-UHFFFAOYSA-N 1-(4-methoxyphenyl)-3,6,7,7a-tetrahydropyrrolo[1,2-a]imidazole-2,5-dione Chemical compound C1=CC(OC)=CC=C1N1C(=O)CN2C(=O)CCC21 IEEXZTRJOZFMNF-UHFFFAOYSA-N 0.000 claims description 2
- IABKCVSRMMSOMZ-UHFFFAOYSA-N 1-(4-methylphenyl)-3,6,7,7a-tetrahydropyrrolo[1,2-a]imidazole-2,5-dione Chemical compound C1=CC(C)=CC=C1N1C(=O)CN2C(=O)CCC21 IABKCVSRMMSOMZ-UHFFFAOYSA-N 0.000 claims description 2
- UEQLEBAXFRLMHS-UHFFFAOYSA-N 1-(4-methylsulfonylphenyl)-3,6,7,7a-tetrahydropyrrolo[1,2-a]imidazole-2,5-dione Chemical compound C1=CC(S(=O)(=O)C)=CC=C1N1C(=O)CN2C(=O)CCC21 UEQLEBAXFRLMHS-UHFFFAOYSA-N 0.000 claims description 2
- MELSJYIFDQJVGE-UHFFFAOYSA-N 1-(4-propan-2-ylphenyl)-3,6,7,7a-tetrahydropyrrolo[1,2-a]imidazole-2,5-dione Chemical compound C1=CC(C(C)C)=CC=C1N1C(=O)CN2C(=O)CCC21 MELSJYIFDQJVGE-UHFFFAOYSA-N 0.000 claims description 2
- VZCMMNMNGIPJGF-UHFFFAOYSA-N 1-(5-fluoro-2-methylphenyl)-3,6,7,7a-tetrahydropyrrolo[1,2-a]imidazole-2,5-dione Chemical compound CC1=CC=C(F)C=C1N1C(=O)CN2C(=O)CCC21 VZCMMNMNGIPJGF-UHFFFAOYSA-N 0.000 claims description 2
- CSQHNICETCRZIA-UHFFFAOYSA-N 1-(5-methylpyridin-2-yl)-3,6,7,7a-tetrahydropyrrolo[1,2-a]imidazole-2,5-dione Chemical compound N1=CC(C)=CC=C1N1C(=O)CN2C(=O)CCC21 CSQHNICETCRZIA-UHFFFAOYSA-N 0.000 claims description 2
- OOOYLKZJENWPCZ-UHFFFAOYSA-N 1-[2-(trifluoromethyl)phenyl]-3,6,7,7a-tetrahydropyrrolo[1,2-a]imidazole-2,5-dione Chemical compound FC(F)(F)C1=CC=CC=C1N1C(=O)CN2C(=O)CCC21 OOOYLKZJENWPCZ-UHFFFAOYSA-N 0.000 claims description 2
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- 150000004760 silicates Chemical class 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000000101 thioether group Chemical group 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 230000008733 trauma Effects 0.000 description 1
- 229940124549 vasodilator Drugs 0.000 description 1
- 239000003071 vasodilator agent Substances 0.000 description 1
- 235000019871 vegetable fat Nutrition 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/12—Antidiarrhoeals
-
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- 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
- A61P25/08—Antiepileptics; Anticonvulsants
-
- 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
- A61P25/28—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
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Cardiology (AREA)
- Hospice & Palliative Care (AREA)
- Heart & Thoracic Surgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicinal Preparation (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT000573A ITMI20030573A1 (it) | 2003-03-24 | 2003-03-24 | Composti ad azione nootropica, loro preparazione, |
| PCT/EP2004/050339 WO2004085438A2 (en) | 2003-03-24 | 2004-03-22 | Pyrroloimidazole derivatives, their preparation, pharmaceutical composition containing them, and their use as nootropic agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20050833A2 true HRP20050833A2 (en) | 2006-02-28 |
Family
ID=33042696
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR20050833A HRP20050833A2 (en) | 2003-03-24 | 2005-09-22 | Pyrroloimidazole derivatives, their preparation, pharmaceutical composition containing them, and their use as nootropic agents |
Country Status (24)
| Country | Link |
|---|---|
| US (3) | US7544705B2 (ja) |
| EP (1) | EP1608655B8 (ja) |
| JP (1) | JP4920408B2 (ja) |
| CN (1) | CN100522963C (ja) |
| AT (1) | ATE401327T1 (ja) |
| AU (1) | AU2004224087B2 (ja) |
| BR (1) | BRPI0408601A (ja) |
| CA (1) | CA2520008C (ja) |
| CY (1) | CY1108401T1 (ja) |
| DE (1) | DE602004015089D1 (ja) |
| DK (1) | DK1608655T3 (ja) |
| EA (1) | EA009558B1 (ja) |
| ES (1) | ES2309534T3 (ja) |
| HK (1) | HK1083837A1 (ja) |
| HR (1) | HRP20050833A2 (ja) |
| IT (1) | ITMI20030573A1 (ja) |
| NO (1) | NO20054898L (ja) |
| NZ (1) | NZ543154A (ja) |
| PL (2) | PL1608655T3 (ja) |
| PT (1) | PT1608655E (ja) |
| RS (1) | RS20050725A (ja) |
| SI (1) | SI1608655T1 (ja) |
| WO (1) | WO2004085438A2 (ja) |
| ZA (1) | ZA200508578B (ja) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ITMI20030573A1 (it) * | 2003-03-24 | 2004-09-25 | Nikem Research Srl | Composti ad azione nootropica, loro preparazione, |
| EP1925304A1 (en) * | 2006-11-15 | 2008-05-28 | Nikem Research S.R.L. | Pyrrolo[1,2-a]imidazoledione effective in the treatment of peripheral neurotoxicity induced by chemotherapeutic agents |
| AU2012201853B2 (en) * | 2007-04-16 | 2013-06-27 | Neurotune Ag | Use of dimiracetam in the treatment of chronic pain |
| ITMI20070770A1 (it) | 2007-04-16 | 2008-10-17 | Brane Discovery S R L | Impiego di dimiracetam nel trattamento del dolore cronico |
| ES2637497T3 (es) | 2008-10-16 | 2017-10-13 | The Johns Hopkins University | Procedimientos y composiciones para la mejora de la función cognitiva |
| US9125898B2 (en) | 2008-11-14 | 2015-09-08 | Neurotune Ag | Acetam derivatives for pain relief |
| CN109662964A (zh) * | 2010-02-09 | 2019-04-23 | 约翰斯.霍普金斯大学 | 用于改善认知功能的方法和组合物 |
| US8476453B2 (en) * | 2010-07-26 | 2013-07-02 | Neurotune Ag | Process for the preparation of dimiracetam |
| CA2891122C (en) | 2012-11-14 | 2021-07-20 | The Johns Hopkins University | Methods and compositions for treating schizophrenia |
| US10806717B2 (en) | 2013-03-15 | 2020-10-20 | The Johns Hopkins University | Methods and compositions for improving cognitive function |
| AU2014228512A1 (en) | 2013-03-15 | 2015-10-01 | Agenebio, Inc. | Methods and compositions for improving cognitive function |
| CA2986598C (en) | 2015-05-22 | 2023-09-26 | Agenebio, Inc. | Extended release pharmaceutical compositions of levetiracetam |
| JOP20190251A1 (ar) | 2017-05-31 | 2019-10-21 | Metys Pharmaceuticals AG | تركيبات تآزرية تشتمل على (r)-ديميراسيتام (1) و(s)-ديميراسيتام (2) بنسبة غير راسيمية |
| CA3117283A1 (en) | 2018-12-04 | 2020-06-11 | Metys Pharmaceuticals AG | Synergistic compositions comprising r-2-(substituted-sulfonyl)-hexahydro-pyrrolo[1,2-a]pyrazin-6(2h)-ones and s-2-(substituted-sulfonyl)-hexahydro-pyrrolo[1,2-a]pyrazin-6(2h)-ones in a non-racemic ratio |
| CA3117350A1 (en) | 2018-12-04 | 2020-06-11 | Metys Pharmaceuticals AG | Synergistic compositions comprising (r)-2-(2-oxopyrrolidin-1-yl)butanamide and (s)-2-(2-oxopyrrolidin-1-yl)butanamide in a non-racemic ratio |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4582838A (en) * | 1984-08-24 | 1986-04-15 | Warner-Lambert Company | Derivatives of dihydro-1H-pyrrolo[1,2-c]imidazol-3,5-dione as cognition activators |
| IT1233860B (it) * | 1988-02-08 | 1992-04-21 | Isf Spa | Derivati del peridroazacicloalca (1,2-a) imidazolo ad attivita' nootropa |
| US5200406A (en) * | 1988-02-08 | 1993-04-06 | I.S.F. Societa Per Azioni | Pharmaceutically useful 2,5-dioxo-1H-octahydroimidazo[1,2-A]azepines |
| JP3400466B2 (ja) * | 1991-10-28 | 2003-04-28 | 日本水産株式会社 | 高純度エイコサペンタエン酸またはそのエステルの製造方法 |
| GB9123641D0 (en) * | 1991-11-07 | 1992-01-02 | Isf Spa | Process |
| ITMI20030573A1 (it) * | 2003-03-24 | 2004-09-25 | Nikem Research Srl | Composti ad azione nootropica, loro preparazione, |
| EP1925304A1 (en) * | 2006-11-15 | 2008-05-28 | Nikem Research S.R.L. | Pyrrolo[1,2-a]imidazoledione effective in the treatment of peripheral neurotoxicity induced by chemotherapeutic agents |
-
2003
- 2003-03-24 IT IT000573A patent/ITMI20030573A1/it unknown
-
2004
- 2004-03-22 RS YUP-2005/0725A patent/RS20050725A/sr unknown
- 2004-03-22 WO PCT/EP2004/050339 patent/WO2004085438A2/en active IP Right Grant
- 2004-03-22 PL PL04741432T patent/PL1608655T3/pl unknown
- 2004-03-22 BR BRPI0408601-5A patent/BRPI0408601A/pt not_active Application Discontinuation
- 2004-03-22 ES ES04741432T patent/ES2309534T3/es not_active Expired - Lifetime
- 2004-03-22 AU AU2004224087A patent/AU2004224087B2/en not_active Ceased
- 2004-03-22 CA CA2520008A patent/CA2520008C/en not_active Expired - Fee Related
- 2004-03-22 EP EP04741432A patent/EP1608655B8/en not_active Expired - Lifetime
- 2004-03-22 AT AT04741432T patent/ATE401327T1/de not_active IP Right Cessation
- 2004-03-22 JP JP2006505479A patent/JP4920408B2/ja not_active Expired - Fee Related
- 2004-03-22 PT PT04741432T patent/PT1608655E/pt unknown
- 2004-03-22 DK DK04741432T patent/DK1608655T3/da active
- 2004-03-22 US US10/550,483 patent/US7544705B2/en not_active Expired - Fee Related
- 2004-03-22 PL PL378939A patent/PL378939A1/pl unknown
- 2004-03-22 DE DE602004015089T patent/DE602004015089D1/de not_active Expired - Lifetime
- 2004-03-22 SI SI200430868T patent/SI1608655T1/sl unknown
- 2004-03-22 CN CNB2004800055916A patent/CN100522963C/zh not_active Expired - Fee Related
- 2004-03-22 NZ NZ543154A patent/NZ543154A/en unknown
- 2004-03-22 EA EA200501501A patent/EA009558B1/ru not_active IP Right Cessation
-
2005
- 2005-09-22 HR HR20050833A patent/HRP20050833A2/hr not_active Application Discontinuation
- 2005-10-21 ZA ZA200508578A patent/ZA200508578B/en unknown
- 2005-10-24 NO NO20054898A patent/NO20054898L/no not_active Application Discontinuation
-
2006
- 2006-03-30 HK HK06103951A patent/HK1083837A1/xx not_active IP Right Cessation
-
2008
- 2008-10-08 CY CY20081101113T patent/CY1108401T1/el unknown
-
2009
- 2009-02-13 US US12/378,475 patent/US7732473B2/en not_active Expired - Fee Related
-
2010
- 2010-02-17 US US12/658,973 patent/US20100173945A1/en not_active Abandoned
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| A1OB | Publication of a patent application | ||
| ARAI | Request for the grant of a patent on the basis of the submitted results of a substantive examination of a patent application | ||
| PPPP | Transfer of rights |
Owner name: BRANE DISCOVERY S.R.L., IN IN LIQUIDAZIONE, IT |
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