JP2012505238A5 - - Google Patents
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- JP2012505238A5 JP2012505238A5 JP2011531180A JP2011531180A JP2012505238A5 JP 2012505238 A5 JP2012505238 A5 JP 2012505238A5 JP 2011531180 A JP2011531180 A JP 2011531180A JP 2011531180 A JP2011531180 A JP 2011531180A JP 2012505238 A5 JP2012505238 A5 JP 2012505238A5
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- Prior art keywords
- item
- disorders
- compound
- bond
- gaba
- 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.)
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- 238000000034 method Methods 0.000 claims description 78
- 150000001875 compounds Chemical class 0.000 claims description 63
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 claims description 48
- 229960003692 gamma aminobutyric acid Drugs 0.000 claims description 23
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 21
- 208000035475 disorder Diseases 0.000 claims description 19
- SJZRECIVHVDYJC-UHFFFAOYSA-N 4-hydroxybutyric acid Chemical compound OCCCC(O)=O SJZRECIVHVDYJC-UHFFFAOYSA-N 0.000 claims description 16
- 125000006239 protecting group Chemical group 0.000 claims description 16
- UGJMXCAKCUNAIE-UHFFFAOYSA-N Gabapentin Chemical compound OC(=O)CC1(CN)CCCCC1 UGJMXCAKCUNAIE-UHFFFAOYSA-N 0.000 claims description 12
- 208000012902 Nervous system disease Diseases 0.000 claims description 12
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 12
- 239000003814 drug Substances 0.000 claims description 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 12
- 230000000202 analgesic effect Effects 0.000 claims description 11
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 claims description 11
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 claims description 11
- 208000019022 Mood disease Diseases 0.000 claims description 10
- 230000002378 acidificating effect Effects 0.000 claims description 10
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 10
- OGNSCSPNOLGXSM-UHFFFAOYSA-N (+/-)-DABA Natural products NCCC(N)C(O)=O OGNSCSPNOLGXSM-UHFFFAOYSA-N 0.000 claims description 9
- 230000001430 anti-depressive effect Effects 0.000 claims description 9
- 239000000935 antidepressant agent Substances 0.000 claims description 9
- 229940005513 antidepressants Drugs 0.000 claims description 9
- 229960001233 pregabalin Drugs 0.000 claims description 8
- AYXYPKUFHZROOJ-ZETCQYMHSA-N pregabalin Chemical compound CC(C)C[C@H](CN)CC(O)=O AYXYPKUFHZROOJ-ZETCQYMHSA-N 0.000 claims description 8
- KPYSYYIEGFHWSV-UHFFFAOYSA-N Baclofen Chemical compound OC(=O)CC(CN)C1=CC=C(Cl)C=C1 KPYSYYIEGFHWSV-UHFFFAOYSA-N 0.000 claims description 6
- 208000027520 Somatoform disease Diseases 0.000 claims description 6
- 229960000794 baclofen Drugs 0.000 claims description 6
- 229960002870 gabapentin Drugs 0.000 claims description 6
- 208000027753 pain disease Diseases 0.000 claims description 6
- 229960005318 vigabatrin Drugs 0.000 claims description 6
- PJDFLNIOAUIZSL-UHFFFAOYSA-N vigabatrin Chemical compound C=CC(N)CCC(O)=O PJDFLNIOAUIZSL-UHFFFAOYSA-N 0.000 claims description 6
- 208000024827 Alzheimer disease Diseases 0.000 claims description 5
- 208000019901 Anxiety disease Diseases 0.000 claims description 5
- 208000014644 Brain disease Diseases 0.000 claims description 5
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 5
- 206010010904 Convulsion Diseases 0.000 claims description 5
- 201000004311 Gilles de la Tourette syndrome Diseases 0.000 claims description 5
- 206010021143 Hypoxia Diseases 0.000 claims description 5
- 229910019142 PO4 Inorganic materials 0.000 claims description 5
- 206010033864 Paranoia Diseases 0.000 claims description 5
- 208000027099 Paranoid disease Diseases 0.000 claims description 5
- 208000018737 Parkinson disease Diseases 0.000 claims description 5
- 208000028017 Psychotic disease Diseases 0.000 claims description 5
- 208000005793 Restless legs syndrome Diseases 0.000 claims description 5
- 208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 claims description 5
- 208000000323 Tourette Syndrome Diseases 0.000 claims description 5
- 208000016620 Tourette disease Diseases 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 5
- 150000001413 amino acids Chemical class 0.000 claims description 5
- 125000003277 amino group Chemical group 0.000 claims description 5
- 208000010877 cognitive disease Diseases 0.000 claims description 5
- 208000018459 dissociative disease Diseases 0.000 claims description 5
- 206010015037 epilepsy Diseases 0.000 claims description 5
- 230000007954 hypoxia Effects 0.000 claims description 5
- 150000002466 imines Chemical class 0.000 claims description 5
- 206010022437 insomnia Diseases 0.000 claims description 5
- 208000022821 personality disease Diseases 0.000 claims description 5
- 239000010452 phosphate Substances 0.000 claims description 5
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 claims description 5
- 201000000980 schizophrenia Diseases 0.000 claims description 5
- 125000000626 sulfinic acid group Chemical group 0.000 claims description 5
- 206010042772 syncope Diseases 0.000 claims description 5
- -1 opioid Substances 0.000 claims description 4
- 201000010099 disease Diseases 0.000 claims 2
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 claims 2
- 231100000331 toxic Toxicity 0.000 claims 2
- 230000002588 toxic effect Effects 0.000 claims 2
- CMWTZPSULFXXJA-UHFFFAOYSA-N Naproxen Natural products C1=C(C(C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 229960005181 morphine Drugs 0.000 claims 1
- CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical compound C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 claims 1
- 229960002009 naproxen Drugs 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 description 11
- 229940124597 therapeutic agent Drugs 0.000 description 10
- 239000012896 selective serotonin reuptake inhibitor Substances 0.000 description 8
- 229940124834 selective serotonin reuptake inhibitor Drugs 0.000 description 8
- 230000000694 effects Effects 0.000 description 5
- 230000002265 prevention Effects 0.000 description 5
- 230000001225 therapeutic effect Effects 0.000 description 5
- SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 4
- 229940100578 Acetylcholinesterase inhibitor Drugs 0.000 description 4
- CKLJMWTZIZZHCS-UWTATZPHSA-N D-aspartic acid Chemical compound OC(=O)[C@H](N)CC(O)=O CKLJMWTZIZZHCS-UWTATZPHSA-N 0.000 description 4
- HOKKHZGPKSLGJE-GSVOUGTGSA-N N-Methyl-D-aspartic acid Chemical compound CN[C@@H](C(O)=O)CC(O)=O HOKKHZGPKSLGJE-GSVOUGTGSA-N 0.000 description 4
- 239000005557 antagonist Substances 0.000 description 4
- 230000001773 anti-convulsant effect Effects 0.000 description 4
- 230000000648 anti-parkinson Effects 0.000 description 4
- 230000000561 anti-psychotic effect Effects 0.000 description 4
- 239000001961 anticonvulsive agent Substances 0.000 description 4
- 229960003965 antiepileptics Drugs 0.000 description 4
- 239000000939 antiparkinson agent Substances 0.000 description 4
- 239000002249 anxiolytic agent Substances 0.000 description 4
- 230000000949 anxiolytic effect Effects 0.000 description 4
- 239000000544 cholinesterase inhibitor Substances 0.000 description 4
- 239000003937 drug carrier Substances 0.000 description 4
- 239000003112 inhibitor Substances 0.000 description 4
- 239000002899 monoamine oxidase inhibitor Substances 0.000 description 4
- 229960002748 norepinephrine Drugs 0.000 description 4
- SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 4
- 208000017194 Affective disease Diseases 0.000 description 3
- 208000023105 Huntington disease Diseases 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- 230000001154 acute effect Effects 0.000 description 3
- 230000002411 adverse Effects 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 230000001684 chronic effect Effects 0.000 description 3
- 230000004968 inflammatory condition Effects 0.000 description 3
- 208000009132 Catalepsy Diseases 0.000 description 1
- 208000012661 Dyskinesia Diseases 0.000 description 1
- 206010044565 Tremor Diseases 0.000 description 1
- 206010047853 Waxy flexibility Diseases 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 229940124277 aminobutyric acid Drugs 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 208000010118 dystonia Diseases 0.000 description 1
- 230000003340 mental effect Effects 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10380008P | 2008-10-08 | 2008-10-08 | |
| US61/103,800 | 2008-10-08 | ||
| PCT/US2009/060058 WO2010042759A2 (en) | 2008-10-08 | 2009-10-08 | Gaba conjugates and methods of use thereof |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015032554A Division JP6167123B2 (ja) | 2008-10-08 | 2015-02-23 | Ｇａｂａコンジュゲートおよびそれらの使用方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2012505238A JP2012505238A (ja) | 2012-03-01 |
| JP2012505238A5 true JP2012505238A5 (https=) | 2012-05-24 |
Family
ID=42101220
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011531180A Withdrawn JP2012505238A (ja) | 2008-10-08 | 2009-10-08 | Ｇａｂａコンジュゲートおよびそれらの使用方法 |
| JP2015032554A Active JP6167123B2 (ja) | 2008-10-08 | 2015-02-23 | Ｇａｂａコンジュゲートおよびそれらの使用方法 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015032554A Active JP6167123B2 (ja) | 2008-10-08 | 2015-02-23 | Ｇａｂａコンジュゲートおよびそれらの使用方法 |
Country Status (11)
| Country | Link |
|---|---|
| US (3) | US8268887B2 (https=) |
| EP (2) | EP2344447B1 (https=) |
| JP (2) | JP2012505238A (https=) |
| KR (1) | KR101810246B1 (https=) |
| CN (2) | CN105330603A (https=) |
| AU (1) | AU2009302241B2 (https=) |
| BR (1) | BRPI0919811B1 (https=) |
| CA (1) | CA2740087C (https=) |
| ES (1) | ES2589915T3 (https=) |
| HK (1) | HK1220970A1 (https=) |
| WO (1) | WO2010042759A2 (https=) |
Families Citing this family (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2589915T3 (es) | 2008-10-08 | 2016-11-17 | Xgene Pharmaceutical Inc | Conjugados de GABA y métodos de utilización de los mismos |
| AU2010223045A1 (en) * | 2009-03-12 | 2011-11-03 | Luitpold Pharmaceuticals, Inc. | GABA-linked anthracycline-lipid conjugates |
| EP2421808B1 (en) | 2009-04-23 | 2013-07-31 | Concert Pharmaceuticals Inc. | 4-hydroxybutyric acid analogs |
| AR082499A1 (es) * | 2010-08-23 | 2012-12-12 | Gruenenthal Gmbh | Compuestos utiles para trastornos del sistema nervioso, inflamatorios, estomacales y como analgesicos |
| KR101976218B1 (ko) * | 2011-02-14 | 2019-05-07 | 콘서트 파마슈티컬즈, 인크. | 4-히드록시부티르산 중수소화 유사체 |
| WO2012161798A1 (en) * | 2011-02-25 | 2012-11-29 | Catabasis Pharmaceuticals, Inc. | Fatty acid gamma aminobutyric acid (gaba) conjugates and their uses |
| CN103193669B (zh) * | 2013-02-27 | 2014-10-01 | 南京医科大学 | nNOS-Capon解偶联化合物及其制备方法和应用 |
| EP3148969B1 (en) | 2014-06-02 | 2020-11-11 | Ketogen Inc. | Compounds for the treatment of seizures and other central nervous system disorders and conditions |
| CA3045004A1 (en) * | 2015-12-16 | 2017-06-22 | Achelios Therapeutics, Inc. | Methods and compositions for treating peripheral neuropathy |
| CN105777586A (zh) * | 2016-04-14 | 2016-07-20 | 安徽省逸欣铭医药科技有限公司 | S（+）氨己烯酸酯衍生物及其制备方法和用途 |
| US11602513B1 (en) | 2016-07-22 | 2023-03-14 | Flamel Ireland Limited | Modified release gamma-hydroxybutyrate formulations having improved pharmacokinetics |
| US11986451B1 (en) | 2016-07-22 | 2024-05-21 | Flamel Ireland Limited | Modified release gamma-hydroxybutyrate formulations having improved pharmacokinetics |
| UY37341A (es) | 2016-07-22 | 2017-11-30 | Flamel Ireland Ltd | Formulaciones de gamma-hidroxibutirato de liberación modificada con farmacocinética mejorada |
| US12186296B1 (en) | 2016-07-22 | 2025-01-07 | Flamel Ireland Limited | Modified release gamma-hydroxybutyrate formulations having improved pharmacokinetics |
| US12478604B1 (en) | 2016-07-22 | 2025-11-25 | Flamel Ireland Limited | Modified release gamma-hydroxybutyrate formulations having improved pharmacokinetics |
| US11504347B1 (en) | 2016-07-22 | 2022-11-22 | Flamel Ireland Limited | Modified release gamma-hydroxybutyrate formulations having improved pharmacokinetics |
| US11602512B1 (en) | 2016-07-22 | 2023-03-14 | Flamel Ireland Limited | Modified release gamma-hydroxybutyrate formulations having improved pharmacokinetics |
| WO2018075730A1 (en) * | 2016-10-21 | 2018-04-26 | Axim Biotechnologies, Inc. | Suppositories comprising cannabinoids |
| ES2969301T3 (es) * | 2017-02-02 | 2024-05-17 | Otolanum Ag | Composición intranasal que comprende betahistina |
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| CN108863873A (zh) * | 2018-06-26 | 2018-11-23 | 台州学院 | 一种硫烯丙基碳酸酯类化合物及其制备方法 |
| KR102107304B1 (ko) * | 2018-08-24 | 2020-05-06 | (주)엠앤씨생명과학 | 천연 리포좀, 그 제조방법 및 이를 포함하는 식품 조성물 |
| EP3930702A1 (en) | 2019-03-01 | 2022-01-05 | Flamel Ireland Limited | Gamma-hydroxybutyrate compositions having improved pharmacokinetics in the fed state |
| WO2023019154A1 (en) * | 2021-08-11 | 2023-02-16 | Tris Pharma, Inc. | Oxybate polyethylene glycol prodrugs |
| CN114452256A (zh) * | 2021-12-31 | 2022-05-10 | 浙江大学 | 脊髓损伤靶向药物、聚合物-疏水化合物胶束及其制备方法 |
| US11779557B1 (en) | 2022-02-07 | 2023-10-10 | Flamel Ireland Limited | Modified release gamma-hydroxybutyrate formulations having improved pharmacokinetics |
| US11583510B1 (en) | 2022-02-07 | 2023-02-21 | Flamel Ireland Limited | Methods of administering gamma hydroxybutyrate formulations after a high-fat meal |
| JP2025516040A (ja) * | 2022-05-02 | 2025-05-26 | ザ リージェンツ オブ ザ ユニヴァーシティー オブ カリフォルニア | 鼻腔内バクロフェン |
| CN117843589A (zh) * | 2022-10-09 | 2024-04-09 | 天津谷堆生物医药科技有限公司 | 取代3-氟苯丙酸酯类化合物及其制备方法、药物组合及用途 |
| CN120530092A (zh) * | 2022-11-24 | 2025-08-22 | 昌郁医药公司 | 萘普生和普瑞巴林1-(酰氧基)-烷基氨基甲酸酯药物缀合物纯化方法 |
| WO2024196851A1 (en) * | 2023-03-17 | 2024-09-26 | Northwestern University | Bicyclic compounds as inactivators of oat and gaba-at |
| CN116585298A (zh) * | 2023-06-30 | 2023-08-15 | 江苏海洋大学 | 一种偶联药物及其组合物和应用 |
| WO2025250613A1 (en) * | 2024-05-29 | 2025-12-04 | Xgene Pharmaceutical Inc. | Method of treating pain using topical naproxen and pregabalin conjugate formulations |
| CN118902084A (zh) * | 2024-08-08 | 2024-11-08 | 天津华德益宝生命科学研发有限公司 | 一种美容养颜含γ-氨基丁酸的海洋特膳食品 |
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| GB0405200D0 (en) | 2004-03-08 | 2004-04-21 | Pfizer Ltd | Combinations comprising alpha-2-delta ligands |
| WO2005102390A2 (en) | 2004-04-22 | 2005-11-03 | Pfizer Japan, Inc. | Combinations comprising alpha-2-delta ligands and nmda receptor antagonists |
| KR20080005429A (ko) | 2005-04-19 | 2008-01-11 | 알자 코포레이션 | 트라마돌 및 가바펜틴을 포함하는 물질의 배합물 |
| EP2272537A3 (en) * | 2005-06-07 | 2014-10-22 | Ramot at Tel-Aviv University Ltd. | Salts of conjugated psychotropic drugs and processes of preparing same |
| US7994220B2 (en) | 2005-09-28 | 2011-08-09 | Cypress Bioscience, Inc. | Milnacipran for the long-term treatment of fibromyalgia syndrome |
| MXPA05011735A (es) | 2005-11-01 | 2007-04-30 | Leopoldo Espinosa Abdala | Composiciones farmaceuticas que comprenden combinaciones de analgesicos y anticonvulsivantes para el tratamiento del dolor agudo y cronico. |
| EP1820502A1 (en) | 2006-02-10 | 2007-08-22 | Laboratorios Del Dr. Esteve, S.A. | Active substance combination comprising azolylcarbinol compounds |
| WO2008010223A2 (en) * | 2006-07-17 | 2008-01-24 | Ramot At Tel Aviv University Ltd. | Conjugates comprising a psychotropic drug or a gaba agonist and an organic acid and their use in treating pain and other cns disorders |
| WO2008011016A2 (en) | 2006-07-18 | 2008-01-24 | Dynogen Pharmaceuticals, Inc. | Treating gastroesophageal reflux disease with 5-ht3- and gaba receptor agonists |
| WO2008009663A1 (en) | 2006-07-19 | 2008-01-24 | Boehringer Ingelheim International Gmbh | Treatment of pain |
| US20080161393A1 (en) * | 2006-12-08 | 2008-07-03 | Barrett Ronald W | Use of prodrugs of GABA analogs for treating disease |
| ES2589915T3 (es) | 2008-10-08 | 2016-11-17 | Xgene Pharmaceutical Inc | Conjugados de GABA y métodos de utilización de los mismos |
-
2009
- 2009-10-08 ES ES09819911.0T patent/ES2589915T3/es active Active
- 2009-10-08 EP EP09819911.0A patent/EP2344447B1/en active Active
- 2009-10-08 KR KR1020117010420A patent/KR101810246B1/ko active Active
- 2009-10-08 WO PCT/US2009/060058 patent/WO2010042759A2/en not_active Ceased
- 2009-10-08 EP EP16159660.6A patent/EP3075722A1/en not_active Withdrawn
- 2009-10-08 AU AU2009302241A patent/AU2009302241B2/en active Active
- 2009-10-08 US US12/576,136 patent/US8268887B2/en active Active
- 2009-10-08 CA CA2740087A patent/CA2740087C/en active Active
- 2009-10-08 JP JP2011531180A patent/JP2012505238A/ja not_active Withdrawn
- 2009-10-08 BR BRPI0919811-3A patent/BRPI0919811B1/pt active IP Right Grant
- 2009-10-08 CN CN201510667046.3A patent/CN105330603A/zh active Pending
- 2009-10-08 CN CN200980145237.6A patent/CN102216257B/zh active Active
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2012
- 2012-08-09 US US13/571,268 patent/US9186341B2/en active Active
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2015
- 2015-02-23 JP JP2015032554A patent/JP6167123B2/ja active Active
- 2015-10-09 US US14/879,752 patent/US10478412B2/en active Active
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2016
- 2016-07-28 HK HK16109028.9A patent/HK1220970A1/zh unknown
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