JP2009526831A5 - - Google Patents
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- Publication number
- JP2009526831A5 JP2009526831A5 JP2008554868A JP2008554868A JP2009526831A5 JP 2009526831 A5 JP2009526831 A5 JP 2009526831A5 JP 2008554868 A JP2008554868 A JP 2008554868A JP 2008554868 A JP2008554868 A JP 2008554868A JP 2009526831 A5 JP2009526831 A5 JP 2009526831A5
- Authority
- JP
- Japan
- Prior art keywords
- ring
- hydrogen
- pyrone
- stereoisomer
- unit dosage
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 claims 22
- 125000001041 indolyl group Chemical group 0.000 claims 18
- 150000003839 salts Chemical class 0.000 claims 18
- 239000002552 dosage form Substances 0.000 claims 15
- 229910052739 hydrogen Inorganic materials 0.000 claims 15
- 239000001257 hydrogen Substances 0.000 claims 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 13
- ZPSJGADGUYYRKE-UHFFFAOYSA-N 2H-pyran-2-one Chemical group O=C1C=CC=CO1 ZPSJGADGUYYRKE-UHFFFAOYSA-N 0.000 claims 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 8
- 239000008194 pharmaceutical composition Substances 0.000 claims 8
- CVQUWLDCFXOXEN-UHFFFAOYSA-N Pyran-4-one Chemical compound O=C1C=COC=C1 CVQUWLDCFXOXEN-UHFFFAOYSA-N 0.000 claims 7
- 125000003118 aryl group Chemical group 0.000 claims 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 6
- 125000000217 alkyl group Chemical group 0.000 claims 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 5
- -1 nitro, amino Chemical group 0.000 claims 5
- 229910052760 oxygen Inorganic materials 0.000 claims 5
- 239000001301 oxygen Substances 0.000 claims 5
- 239000000825 pharmaceutical preparation Substances 0.000 claims 5
- 229910052717 sulfur Inorganic materials 0.000 claims 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 4
- 125000003342 alkenyl group Chemical group 0.000 claims 4
- 125000000304 alkynyl group Chemical group 0.000 claims 4
- 201000010099 disease Diseases 0.000 claims 4
- 125000005842 heteroatom Chemical group 0.000 claims 4
- 229910052757 nitrogen Inorganic materials 0.000 claims 4
- 239000011593 sulfur Substances 0.000 claims 4
- 238000011282 treatment Methods 0.000 claims 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 3
- 125000004122 cyclic group Chemical group 0.000 claims 3
- 206010012601 diabetes mellitus Diseases 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- 238000002360 preparation method Methods 0.000 claims 3
- 230000002265 prevention Effects 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- 238000011200 topical administration Methods 0.000 claims 3
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 claims 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims 2
- YJPIGAIKUZMOQA-UHFFFAOYSA-N Melatonin Natural products COC1=CC=C2N(C(C)=O)C=C(CCN)C2=C1 YJPIGAIKUZMOQA-UHFFFAOYSA-N 0.000 claims 2
- 206010033799 Paralysis Diseases 0.000 claims 2
- 125000004423 acyloxy group Chemical group 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 239000002249 anxiolytic agent Substances 0.000 claims 2
- 230000000949 anxiolytic effect Effects 0.000 claims 2
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 238000009472 formulation Methods 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 2
- DRLFMBDRBRZALE-UHFFFAOYSA-N melatonin Chemical compound COC1=CC=C2NC=C(CCNC(C)=O)C2=C1 DRLFMBDRBRZALE-UHFFFAOYSA-N 0.000 claims 2
- 229960003987 melatonin Drugs 0.000 claims 2
- 238000007911 parenteral administration Methods 0.000 claims 2
- 208000019116 sleep disease Diseases 0.000 claims 2
- 125000005504 styryl group Chemical group 0.000 claims 2
- 150000003573 thiols Chemical class 0.000 claims 2
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 2
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims 1
- UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 claims 1
- SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 claims 1
- 206010002091 Anaesthesia Diseases 0.000 claims 1
- 208000019901 Anxiety disease Diseases 0.000 claims 1
- 208000024172 Cardiovascular disease Diseases 0.000 claims 1
- 208000000094 Chronic Pain Diseases 0.000 claims 1
- 208000019888 Circadian rhythm sleep disease Diseases 0.000 claims 1
- 208000006561 Cluster Headache Diseases 0.000 claims 1
- 206010048843 Cytomegalovirus chorioretinitis Diseases 0.000 claims 1
- 208000017701 Endocrine disease Diseases 0.000 claims 1
- 208000010412 Glaucoma Diseases 0.000 claims 1
- 206010022489 Insulin Resistance Diseases 0.000 claims 1
- 208000019695 Migraine disease Diseases 0.000 claims 1
- 208000001738 Nervous System Trauma Diseases 0.000 claims 1
- 208000012902 Nervous system disease Diseases 0.000 claims 1
- 208000002193 Pain Diseases 0.000 claims 1
- 208000006011 Stroke Diseases 0.000 claims 1
- 208000007271 Substance Withdrawal Syndrome Diseases 0.000 claims 1
- 206010046543 Urinary incontinence Diseases 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 230000002411 adverse Effects 0.000 claims 1
- 230000032683 aging Effects 0.000 claims 1
- 239000000556 agonist Substances 0.000 claims 1
- 150000001356 alkyl thiols Chemical class 0.000 claims 1
- 230000037005 anaesthesia Effects 0.000 claims 1
- 238000003975 animal breeding Methods 0.000 claims 1
- 239000005557 antagonist Substances 0.000 claims 1
- 230000000561 anti-psychotic effect Effects 0.000 claims 1
- 229940125708 antidiabetic agent Drugs 0.000 claims 1
- 239000003472 antidiabetic agent Substances 0.000 claims 1
- 230000036506 anxiety Effects 0.000 claims 1
- 125000005018 aryl alkenyl group Chemical group 0.000 claims 1
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- 229940125717 barbiturate Drugs 0.000 claims 1
- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 claims 1
- 229940049706 benzodiazepine Drugs 0.000 claims 1
- 230000033228 biological regulation Effects 0.000 claims 1
- 208000015294 blood coagulation disease Diseases 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 210000003169 central nervous system Anatomy 0.000 claims 1
- 208000015114 central nervous system disease Diseases 0.000 claims 1
- 230000027288 circadian rhythm Effects 0.000 claims 1
- 208000018912 cluster headache syndrome Diseases 0.000 claims 1
- 230000037410 cognitive enhancement Effects 0.000 claims 1
- 230000002920 convulsive effect Effects 0.000 claims 1
- 208000001763 cytomegalovirus retinitis Diseases 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 239000003995 emulsifying agent Substances 0.000 claims 1
- 208000030172 endocrine system disease Diseases 0.000 claims 1
- 206010015037 epilepsy Diseases 0.000 claims 1
- 230000002461 excitatory amino acid Effects 0.000 claims 1
- 239000003257 excitatory amino acid Substances 0.000 claims 1
- 208000026278 immune system disease Diseases 0.000 claims 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims 1
- 230000006698 induction Effects 0.000 claims 1
- 208000027866 inflammatory disease Diseases 0.000 claims 1
- 208000028867 ischemia Diseases 0.000 claims 1
- 206010027599 migraine Diseases 0.000 claims 1
- 230000001613 neoplastic effect Effects 0.000 claims 1
- 208000028412 nervous system injury Diseases 0.000 claims 1
- 210000002569 neuron Anatomy 0.000 claims 1
- 201000001119 neuropathy Diseases 0.000 claims 1
- 230000007823 neuropathy Effects 0.000 claims 1
- 229940127240 opiate Drugs 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 208000033808 peripheral neuropathy Diseases 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 239000006187 pill Substances 0.000 claims 1
- 239000003755 preservative agent Substances 0.000 claims 1
- 238000011321 prophylaxis Methods 0.000 claims 1
- 208000020016 psychiatric disease Diseases 0.000 claims 1
- 239000000932 sedative agent Substances 0.000 claims 1
- 230000001624 sedative effect Effects 0.000 claims 1
- 230000001953 sensory effect Effects 0.000 claims 1
- 239000003215 serotonin 5-HT2 receptor antagonist Substances 0.000 claims 1
- 208000022925 sleep disturbance Diseases 0.000 claims 1
- 230000003860 sleep quality Effects 0.000 claims 1
- 208000020685 sleep-wake disease Diseases 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 230000006641 stabilisation Effects 0.000 claims 1
- 238000011105 stabilization Methods 0.000 claims 1
- 230000000638 stimulation Effects 0.000 claims 1
- 125000004434 sulfur atom Chemical group 0.000 claims 1
- 238000013268 sustained release Methods 0.000 claims 1
- 239000012730 sustained-release form Substances 0.000 claims 1
- 230000002123 temporal effect Effects 0.000 claims 1
- 229940125725 tranquilizer Drugs 0.000 claims 1
- 239000003204 tranquilizing agent Substances 0.000 claims 1
- 230000002936 tranquilizing effect Effects 0.000 claims 1
- 230000004584 weight gain Effects 0.000 claims 1
- 235000019786 weight gain Nutrition 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US77332206P | 2006-02-15 | 2006-02-15 | |
| US60/773,322 | 2006-02-15 | ||
| PCT/IB2007/000330 WO2007093880A2 (en) | 2006-02-15 | 2007-02-13 | Novel pyrone-indole derivatives and process for their preparation |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2009526831A JP2009526831A (ja) | 2009-07-23 |
| JP2009526831A5 true JP2009526831A5 (https=) | 2010-04-02 |
| JP5248332B2 JP5248332B2 (ja) | 2013-07-31 |
Family
ID=38283075
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008554868A Active JP5248332B2 (ja) | 2006-02-15 | 2007-02-13 | 新規ピロン誘導体及びそれらの合成方法 |
Country Status (21)
| Country | Link |
|---|---|
| US (3) | US7635710B2 (https=) |
| EP (1) | EP1991541B1 (https=) |
| JP (1) | JP5248332B2 (https=) |
| KR (1) | KR101207736B1 (https=) |
| CN (1) | CN101374833B (https=) |
| AU (1) | AU2007216226B2 (https=) |
| BR (1) | BRPI0706992C8 (https=) |
| CA (1) | CA2642465C (https=) |
| DK (1) | DK1991541T3 (https=) |
| EA (1) | EA015605B1 (https=) |
| ES (1) | ES2428873T3 (https=) |
| IL (1) | IL193236A (https=) |
| NO (1) | NO339826B1 (https=) |
| NZ (1) | NZ569797A (https=) |
| PL (1) | PL1991541T3 (https=) |
| PT (1) | PT1991541E (https=) |
| SI (1) | SI1991541T1 (https=) |
| TW (1) | TWI501960B (https=) |
| UA (1) | UA104988C2 (https=) |
| WO (1) | WO2007093880A2 (https=) |
| ZA (1) | ZA200806799B (https=) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6262118B1 (en) * | 1999-06-04 | 2001-07-17 | Metabolex, Inc. | Use of (-) (3-trihalomethylphenoxy) (4-halophenyl) acetic acid derivatives for treatment of insulin resistance, type 2 diabetes and hyperlipidemia |
| US7576131B2 (en) * | 1999-06-04 | 2009-08-18 | Metabolex, Inc. | Use of (-) (3-trihalomethylphenoxy) (4-halophenyl) acetic acid derivatives for treatment of insulin resistance, type 2 diabetes, hyperlipidemia and hyperuricemia |
| CN103319467B (zh) * | 2013-06-15 | 2015-10-14 | 湖南科技大学 | 一种4-[5-羟基-4-吡喃酮-2-基亚甲氨基]-3-巯基-1,2,4-三唑化合物及用途 |
| ES2694049T3 (es) | 2014-01-14 | 2018-12-17 | Astellas Pharma Inc. | Compuesto de indol |
| RU2561045C1 (ru) * | 2014-07-15 | 2015-08-20 | Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования "Кубанский государственный университет" (ФГБОУ ВПО "КубГУ") | Нейропротекторное фармакологическое средство |
| WO2016039750A1 (en) | 2014-09-11 | 2016-03-17 | Halliburton Energy Services, Inc. | Cyanamide-based carbon dioxide and/or hydrogen sulfide scavengers and methods of use in subterranean operations |
| HUE059559T2 (hu) | 2015-02-25 | 2022-12-28 | Univ California | 5HT agonisták az epilepsziás rendellenességek kezelésére |
| CN109843286A (zh) * | 2016-08-23 | 2019-06-04 | 纽里姆药物有限公司 | 治疗瘙痒和/或搔痒的方法 |
| JP2020529440A (ja) | 2017-08-04 | 2020-10-08 | オービッド・セラピューティクス・インコーポレイテッドＯｖｉｄ Ｔｈｅｒａｐｅｕｔｉｃｓ Ｉｎｃ． | 糖尿病および関連する状態の処置におけるガボキサドールの使用 |
| EP3749697A4 (en) | 2018-02-05 | 2021-11-03 | Bio-Rad Laboratories, Inc. | CHROMATOGRAPHY RESIN WITH LIGAND MIXED MODE ANIONIC / HYDROPHOBIC EXCHANGE |
| WO2020061410A1 (en) | 2018-09-20 | 2020-03-26 | Ovid Therapeutics Inc. | Use of gaboxadol for the treatment of tourette syndrome, tics and stuttering |
| WO2020131856A1 (en) | 2018-12-17 | 2020-06-25 | Ovid Therapeutics Inc. | Use of gaboxadol for the treatment of non-24 hour sleep-wake disorder |
| US12478610B2 (en) | 2020-05-11 | 2025-11-25 | Orit MALKA | Compositions of tryptophol derivatives and 4-ethyl-phenol derivatives, and methods of using same |
| WO2022238905A1 (en) | 2021-05-11 | 2022-11-17 | Neurim Pharmaceuticals (1991) Ltd. | Method for diagnosing and treating subjects having single nucleotide polymorphisms in chromosome 2, 2:107,510,000-107,540,000 locus |
| IL321429A (en) | 2023-01-13 | 2025-08-01 | Neurim Pharmaceuticals 1991 Ltd | Piromelatine for treating parasomnias associated with loss of rem sleep atonia |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA222247A (en) | 1922-08-15 | Hubert Rogers Reginald | Pocket container for confections | |
| IT1196849B (it) | 1986-02-16 | 1988-11-25 | Rotta Research Lab | Nuovi derivati degli acidi 5 pentilammino 5 oxo pentaoico e 4 pentilammino 4 oxo butanoico ad attivita antagonista della colecistochinina e procedimento per la loro preparazione |
| AU8876591A (en) | 1990-11-02 | 1992-05-26 | Upjohn Company, The | Indole-3-methanamines useful as anti-diabetic, anti-obesity and anti-atherosclerotic agents |
| US5840751A (en) * | 1993-11-19 | 1998-11-24 | Warner-Lambert Company | 5,6-dihydropyrone derivatives as protease inhibitors and antiviral agents |
| EP0841063A1 (en) * | 1996-03-27 | 1998-05-13 | Toray Industries, Inc. | Ketone derivatives and medicinal use thereof |
| IL130169A (en) | 1999-05-27 | 2006-08-20 | Neurim Pharma 1991 | Indole derivatives, and pharmaceutical preparations, skin protection preparations, and cosmetics containing them |
| EP1324993A2 (en) * | 2000-04-18 | 2003-07-09 | Cytovia, Inc. | Substituted 1,4-thiazepine and analogs as activators of caspases and inducers of apoptosis and the use thereof |
| PE20060303A1 (es) | 2004-06-23 | 2006-05-19 | Wyeth Corp | Metabolitos de indolilalquilamina como ligandos de 5-hidroxitriptamina-6 |
| US7834050B2 (en) * | 2006-03-29 | 2010-11-16 | Duke University | Small molecule insulin mimetics absent quinones |
-
2007
- 2007-02-12 US US11/705,030 patent/US7635710B2/en active Active
- 2007-02-13 ES ES07733884T patent/ES2428873T3/es active Active
- 2007-02-13 DK DK07733884.6T patent/DK1991541T3/da active
- 2007-02-13 PL PL07733884T patent/PL1991541T3/pl unknown
- 2007-02-13 UA UAA200808838A patent/UA104988C2/uk unknown
- 2007-02-13 SI SI200731333T patent/SI1991541T1/sl unknown
- 2007-02-13 NZ NZ569797A patent/NZ569797A/en unknown
- 2007-02-13 BR BRPI0706992A patent/BRPI0706992C8/pt active IP Right Grant
- 2007-02-13 JP JP2008554868A patent/JP5248332B2/ja active Active
- 2007-02-13 EP EP07733884.6A patent/EP1991541B1/en active Active
- 2007-02-13 EA EA200801580A patent/EA015605B1/ru unknown
- 2007-02-13 WO PCT/IB2007/000330 patent/WO2007093880A2/en not_active Ceased
- 2007-02-13 CA CA2642465A patent/CA2642465C/en active Active
- 2007-02-13 AU AU2007216226A patent/AU2007216226B2/en active Active
- 2007-02-13 KR KR1020087022304A patent/KR101207736B1/ko active Active
- 2007-02-13 PT PT77338846T patent/PT1991541E/pt unknown
- 2007-02-13 CN CN2007800039654A patent/CN101374833B/zh active Active
- 2007-02-26 TW TW096106545A patent/TWI501960B/zh active
-
2008
- 2008-08-04 IL IL193236A patent/IL193236A/en active IP Right Grant
- 2008-08-06 ZA ZA200806799A patent/ZA200806799B/xx unknown
- 2008-09-12 NO NO20083905A patent/NO339826B1/no unknown
-
2009
- 2009-11-04 US US12/612,001 patent/US8242163B2/en active Active
-
2012
- 2012-07-13 US US13/549,181 patent/US8569355B2/en active Active
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