KR20160098426A - 가바펜티노이드들 및 시그마 리셉터 리간드들 조합 - Google Patents
가바펜티노이드들 및 시그마 리셉터 리간드들 조합 Download PDFInfo
- Publication number
- KR20160098426A KR20160098426A KR1020167018971A KR20167018971A KR20160098426A KR 20160098426 A KR20160098426 A KR 20160098426A KR 1020167018971 A KR1020167018971 A KR 1020167018971A KR 20167018971 A KR20167018971 A KR 20167018971A KR 20160098426 A KR20160098426 A KR 20160098426A
- Authority
- KR
- South Korea
- Prior art keywords
- dichlorophenyl
- pyrazol
- yloxy
- substituted
- methyl
- 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.)
- Withdrawn
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- 239000003982 sigma receptor ligand Substances 0.000 title description 6
- 239000003446 ligand Substances 0.000 claims abstract description 33
- 239000011885 synergistic combination Substances 0.000 claims abstract description 18
- 230000002265 prevention Effects 0.000 claims abstract description 16
- 208000002193 Pain Diseases 0.000 claims description 69
- 150000001875 compounds Chemical class 0.000 claims description 58
- 230000036407 pain Effects 0.000 claims description 55
- UGJMXCAKCUNAIE-UHFFFAOYSA-N Gabapentin Chemical group OC(=O)CC1(CN)CCCCC1 UGJMXCAKCUNAIE-UHFFFAOYSA-N 0.000 claims description 46
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 43
- -1 -N = CR 8 R 9 Inorganic materials 0.000 claims description 42
- 150000003839 salts Chemical class 0.000 claims description 40
- 125000003118 aryl group Chemical group 0.000 claims description 33
- 229940002612 prodrug Drugs 0.000 claims description 27
- 239000000651 prodrug Substances 0.000 claims description 27
- 239000012453 solvate Substances 0.000 claims description 27
- 230000000694 effects Effects 0.000 claims description 24
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 23
- AYXYPKUFHZROOJ-ZETCQYMHSA-N pregabalin Chemical compound CC(C)C[C@H](CN)CC(O)=O AYXYPKUFHZROOJ-ZETCQYMHSA-N 0.000 claims description 23
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 22
- 229960002870 gabapentin Drugs 0.000 claims description 22
- 229960001233 pregabalin Drugs 0.000 claims description 22
- 238000011282 treatment Methods 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 208000004296 neuralgia Diseases 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 14
- 125000003342 alkenyl group Chemical group 0.000 claims description 13
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 13
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
- 229910052736 halogen Inorganic materials 0.000 claims description 13
- 150000002367 halogens Chemical class 0.000 claims description 13
- 125000000623 heterocyclic group Chemical group 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
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- 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
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- 125000003710 aryl alkyl group Chemical group 0.000 claims description 10
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 10
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 6
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000004104 aryloxy group Chemical group 0.000 claims description 5
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- 108090000312 Calcium Channels Proteins 0.000 claims description 4
- 102000003922 Calcium Channels Human genes 0.000 claims description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- HZJLMGJUIYTSMU-UHFFFAOYSA-N 1-[2-[1-(3,4-dichlorophenyl)-5-methylpyrazol-3-yl]oxyethyl]-4-methylpiperazine Chemical compound C1CN(C)CCN1CCOC1=NN(C=2C=C(Cl)C(Cl)=CC=2)C(C)=C1 HZJLMGJUIYTSMU-UHFFFAOYSA-N 0.000 claims description 3
- JLIOGNLMAGIFJN-UHFFFAOYSA-N 1-[2-[1-(3,4-dichlorophenyl)-5-methylpyrazol-3-yl]oxyethyl]piperazine Chemical compound N=1N(C=2C=C(Cl)C(Cl)=CC=2)C(C)=CC=1OCCN1CCNCC1 JLIOGNLMAGIFJN-UHFFFAOYSA-N 0.000 claims description 3
- XKGSRQAKFXSURB-UHFFFAOYSA-N 1-[2-[1-(3,4-dichlorophenyl)-5-methylpyrazol-3-yl]oxyethyl]piperidine Chemical compound N=1N(C=2C=C(Cl)C(Cl)=CC=2)C(C)=CC=1OCCN1CCCCC1 XKGSRQAKFXSURB-UHFFFAOYSA-N 0.000 claims description 3
- IZCFYFTZCBGMLV-UHFFFAOYSA-N 2-[1-(3,4-dichlorophenyl)-5-methylpyrazol-3-yl]oxy-n,n-diethylethanamine Chemical compound N1=C(OCCN(CC)CC)C=C(C)N1C1=CC=C(Cl)C(Cl)=C1 IZCFYFTZCBGMLV-UHFFFAOYSA-N 0.000 claims description 3
- HLAPBHGJHLAYSD-UHFFFAOYSA-N 4-[2-[1-(3,4-dichlorophenyl)-5-methylpyrazol-3-yl]oxyethyl]morpholine Chemical compound N=1N(C=2C=C(Cl)C(Cl)=CC=2)C(C)=CC=1OCCN1CCOCC1 HLAPBHGJHLAYSD-UHFFFAOYSA-N 0.000 claims description 3
- 230000005764 inhibitory process Effects 0.000 claims description 3
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- NWFCYGKUUJSQBC-GASCZTMLSA-N (2r,6s)-4-[4-[1-(3,4-dichlorophenyl)pyrazol-3-yl]oxybutyl]-2,6-dimethylmorpholine Chemical compound C1[C@@H](C)O[C@@H](C)CN1CCCCOC1=NN(C=2C=C(Cl)C(Cl)=CC=2)C=C1 NWFCYGKUUJSQBC-GASCZTMLSA-N 0.000 claims description 2
- WZWRZEMDVNTYDE-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)-3-(2-pyrrolidin-1-ylethoxy)pyrazole Chemical compound C1=C(Cl)C(Cl)=CC=C1N1N=C(OCCN2CCCC2)C=C1 WZWRZEMDVNTYDE-UHFFFAOYSA-N 0.000 claims description 2
- WBERJAVNUCODIT-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)-3-(3-pyrrolidin-1-ylpropoxy)pyrazole Chemical compound C1=C(Cl)C(Cl)=CC=C1N1N=C(OCCCN2CCCC2)C=C1 WBERJAVNUCODIT-UHFFFAOYSA-N 0.000 claims description 2
- SMFVSSIDEBMGKS-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)-3-(4-pyrrolidin-1-ylbutoxy)pyrazole Chemical compound C1=C(Cl)C(Cl)=CC=C1N1N=C(OCCCCN2CCCC2)C=C1 SMFVSSIDEBMGKS-UHFFFAOYSA-N 0.000 claims description 2
- TYQPLZVNSCAIFI-UHFFFAOYSA-N 1-[2-(5-methyl-1-naphthalen-2-ylpyrazol-3-yl)oxyethyl]piperidine Chemical compound N=1N(C=2C=C3C=CC=CC3=CC=2)C(C)=CC=1OCCN1CCCCC1 TYQPLZVNSCAIFI-UHFFFAOYSA-N 0.000 claims description 2
- BDZJQOPZDLUPID-UHFFFAOYSA-N 1-[2-[1-(3,4-dichlorophenyl)-4,5-dimethylpyrazol-3-yl]oxyethyl]piperidine Chemical compound CC1=C(C)N(C=2C=C(Cl)C(Cl)=CC=2)N=C1OCCN1CCCCC1 BDZJQOPZDLUPID-UHFFFAOYSA-N 0.000 claims description 2
- NHRAAWXMMGSTHI-UHFFFAOYSA-N 1-[2-[1-(3,4-dichlorophenyl)-5-phenylpyrazol-3-yl]oxyethyl]piperidine Chemical compound C1=C(Cl)C(Cl)=CC=C1N1C(C=2C=CC=CC=2)=CC(OCCN2CCCCC2)=N1 NHRAAWXMMGSTHI-UHFFFAOYSA-N 0.000 claims description 2
- ZRKJSQZRBMJLSH-UHFFFAOYSA-N 1-[2-[1-(3,4-dichlorophenyl)-5-propan-2-ylpyrazol-3-yl]oxyethyl]piperidine Chemical compound N=1N(C=2C=C(Cl)C(Cl)=CC=2)C(C(C)C)=CC=1OCCN1CCCCC1 ZRKJSQZRBMJLSH-UHFFFAOYSA-N 0.000 claims description 2
- PUZILSCHNRFUBL-UHFFFAOYSA-N 1-[2-[1-(3,4-dichlorophenyl)pyrazol-3-yl]oxyethyl]piperidine Chemical compound C1=C(Cl)C(Cl)=CC=C1N1N=C(OCCN2CCCCC2)C=C1 PUZILSCHNRFUBL-UHFFFAOYSA-N 0.000 claims description 2
- UJVRCYKFYBUMPY-UHFFFAOYSA-N 1-[2-[1-(4-methoxyphenyl)-5-methylpyrazol-3-yl]oxyethyl]piperidine Chemical compound C1=CC(OC)=CC=C1N1C(C)=CC(OCCN2CCCCC2)=N1 UJVRCYKFYBUMPY-UHFFFAOYSA-N 0.000 claims description 2
- RGFIAPCESXOYMJ-UHFFFAOYSA-N 1-[4-[1-(3,4-dichlorophenyl)-5-methylpyrazol-3-yl]oxybutyl]-4-methylpiperazine Chemical compound C1CN(C)CCN1CCCCOC1=NN(C=2C=C(Cl)C(Cl)=CC=2)C(C)=C1 RGFIAPCESXOYMJ-UHFFFAOYSA-N 0.000 claims description 2
- PKBREWIOYKTNBB-UHFFFAOYSA-N 1-[4-[1-(3,4-dichlorophenyl)-5-methylpyrazol-3-yl]oxybutyl]-4-phenylpiperidine Chemical compound N=1N(C=2C=C(Cl)C(Cl)=CC=2)C(C)=CC=1OCCCCN(CC1)CCC1C1=CC=CC=C1 PKBREWIOYKTNBB-UHFFFAOYSA-N 0.000 claims description 2
- XKEZHFHUXSUJGC-UHFFFAOYSA-N 1-[4-[1-(3,4-dichlorophenyl)-5-methylpyrazol-3-yl]oxybutyl]piperidine Chemical compound N=1N(C=2C=C(Cl)C(Cl)=CC=2)C(C)=CC=1OCCCCN1CCCCC1 XKEZHFHUXSUJGC-UHFFFAOYSA-N 0.000 claims description 2
- GPJDXYIXLDTRMO-UHFFFAOYSA-N 1-[4-[1-(3,4-dichlorophenyl)pyrazol-3-yl]oxybutyl]piperidine Chemical compound C1=C(Cl)C(Cl)=CC=C1N1N=C(OCCCCN2CCCCC2)C=C1 GPJDXYIXLDTRMO-UHFFFAOYSA-N 0.000 claims description 2
- 125000000586 2-(4-morpholinyl)ethoxy group Chemical group [H]C([H])(O*)C([H])([H])N1C([H])([H])C([H])([H])OC([H])([H])C1([H])[H] 0.000 claims description 2
- CESIREDMWGMYGW-UHFFFAOYSA-N 2-[1-(3,4-dichlorophenyl)-4,5-dimethylpyrazol-3-yl]oxy-n,n-diethylethanamine Chemical compound CC1=C(C)C(OCCN(CC)CC)=NN1C1=CC=C(Cl)C(Cl)=C1 CESIREDMWGMYGW-UHFFFAOYSA-N 0.000 claims description 2
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- PPRYPHBDCCNNFF-UHFFFAOYSA-N 2-[2-[1-(3,4-dichlorophenyl)-5-propan-2-ylpyrazol-3-yl]oxyethyl]-3,4-dihydro-1h-isoquinoline Chemical compound CC(C)C1=CC(OCCN2CC3=CC=CC=C3CC2)=NN1C1=CC=C(Cl)C(Cl)=C1 PPRYPHBDCCNNFF-UHFFFAOYSA-N 0.000 claims description 2
- BXKUTCWIZMNQHG-UHFFFAOYSA-N 2-[4-[1-(3,4-dichlorophenyl)-5-methylpyrazol-3-yl]oxybutyl]-3,4-dihydro-1h-isoquinoline Chemical compound CC1=CC(OCCCCN2CC3=CC=CC=C3CC2)=NN1C1=CC=C(Cl)C(Cl)=C1 BXKUTCWIZMNQHG-UHFFFAOYSA-N 0.000 claims description 2
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 2
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- A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
- A61K31/197—Carboxylic acids, e.g. valproic acid having an amino group the amino and the carboxyl groups being attached to the same acyclic carbon chain, e.g. gamma-aminobutyric acid [GABA], beta-alanine, epsilon-aminocaproic acid or pantothenic acid
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- A61K31/4164—1,3-Diazoles
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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Landscapes
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- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
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- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
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- Chemical Kinetics & Catalysis (AREA)
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
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| EP13382517 | 2013-12-17 | ||
| EP13382517.4 | 2013-12-17 | ||
| PCT/EP2014/077992 WO2015091505A1 (en) | 2013-12-17 | 2014-12-16 | Gabapentinoids and sigma receptor ligands combinations |
Publications (1)
| Publication Number | Publication Date |
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| KR20160098426A true KR20160098426A (ko) | 2016-08-18 |
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| US (1) | US20160310501A1 (OSRAM) |
| EP (1) | EP3082790A1 (OSRAM) |
| JP (1) | JP2017503765A (OSRAM) |
| KR (1) | KR20160098426A (OSRAM) |
| CN (1) | CN105873580B (OSRAM) |
| AR (1) | AR101637A1 (OSRAM) |
| AU (1) | AU2014364644A1 (OSRAM) |
| CA (1) | CA2933057A1 (OSRAM) |
| IL (1) | IL245977A0 (OSRAM) |
| MA (1) | MA39146A1 (OSRAM) |
| MX (1) | MX2016007286A (OSRAM) |
| PH (1) | PH12016501095A1 (OSRAM) |
| SG (1) | SG11201604478UA (OSRAM) |
| TN (1) | TN2016000229A1 (OSRAM) |
| TW (1) | TW201607539A (OSRAM) |
| WO (1) | WO2015091505A1 (OSRAM) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| EP2116539A1 (en) | 2008-04-25 | 2009-11-11 | Laboratorios Del. Dr. Esteve, S.A. | 1-aryl-3-aminoalkoxy-pyrazoles as sigma ligands enhancing analgesic effects of opioids and attenuating the dependency thereof |
| EP2353591A1 (en) | 2010-02-04 | 2011-08-10 | Laboratorios Del. Dr. Esteve, S.A. | Sigma ligands for potentiating the analgesic effect of opioids and opiates in post-operative pain and attenuating the dependency thereof |
| EP2353598A1 (en) | 2010-02-04 | 2011-08-10 | Laboratorios Del. Dr. Esteve, S.A. | Sigma ligands for use in the prevention and/or treatment of postoperative pain |
| EP2388005A1 (en) | 2010-05-21 | 2011-11-23 | Laboratorios Del. Dr. Esteve, S.A. | Sigma ligands for the prevention and/or treatment of emesis induced by chemotherapy or radiotherapy |
| EP2415471A1 (en) | 2010-08-03 | 2012-02-08 | Laboratorios Del. Dr. Esteve, S.A. | Use of sigma ligands in opioid-induced hyperalgesia |
| EP2524694A1 (en) | 2011-05-19 | 2012-11-21 | Laboratorios Del. Dr. Esteve, S.A. | Use of sigma ligands in diabetes type-2 associated pain |
| CA2933511A1 (en) | 2013-12-17 | 2015-06-25 | Laboratorios Del Dr. Esteve, S.A. | Serotonin-norepinephrine reuptake inhibitors (snris) and sigma receptor ligands combinations |
| CA3085939A1 (en) * | 2017-12-19 | 2019-06-27 | University Of Tennessee Research Foundation | W/o/w microemulsions for ocular administration |
| US11034669B2 (en) | 2018-11-30 | 2021-06-15 | Nuvation Bio Inc. | Pyrrole and pyrazole compounds and methods of use thereof |
| CN120437109B (zh) * | 2025-07-09 | 2025-09-26 | 湖南一格制药有限公司 | 一种稳定性优异的苯磺酸美洛加巴林制剂组合物 |
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| DE2460891C2 (de) | 1974-12-21 | 1982-09-23 | Gödecke AG, 1000 Berlin | 1-Aminomethyl-1-cycloalkanessigsäuren und deren Ester, Verfahren zu deren Herstellung und diese Verbindungen enthaltende Arzneimittel |
| AU9137091A (en) | 1990-11-27 | 1992-06-25 | Northwestern University | Gaba and l-glutamic acid analogs for antiseizure treatment |
| WO1993023383A1 (en) | 1992-05-20 | 1993-11-25 | Northwestern University | Gaba and l-glutamic acid analogs for antiseizure treatment |
| CN1303059C (zh) | 1997-10-27 | 2007-03-07 | 沃尼尔·朗伯公司 | 作为药物的环状氨基酸及其衍生物 |
| PL348305A1 (en) | 1997-12-16 | 2002-05-20 | Warner Lambert Co | Novel amines as pharmaceutical agents |
| CN1131855C (zh) | 1997-12-16 | 2003-12-24 | 沃尼尔·朗伯公司 | 1－取代－1－氨基甲基－环烷衍生物(=加巴喷丁类似物)、其制备及其在治疗神经病方面的用途 |
| BR9814287A (pt) | 1997-12-16 | 2000-10-03 | Warner Lambert Co | "4(3)-aminometil-(tio)piran 4(3) substituìdo ou derivados da piperidina (= análogos da gabapentina), sua preparação e seu uso no tratamento de desordens neurológicas" |
| JP2002516312A (ja) | 1998-05-26 | 2002-06-04 | ワーナー−ランバート・カンパニー | カルシウムチャンネルのα２δサブユニットに対する親和性を有する立体配座的に制約されたアミノ酸化合物 |
| US6166072A (en) | 1998-08-03 | 2000-12-26 | Allelix Neuroscience, Inc. | Amino acid derivatives |
| AU1602100A (en) | 1998-11-25 | 2000-06-13 | Warner-Lambert Company | Improved gamma amino butyric acid analogs |
| JP2002538221A (ja) * | 1999-03-10 | 2002-11-12 | ワーナー−ランバート・カンパニー | 抗てんかん作用を有する化合物を包含する鎮痛組成物およびその使用方法 |
| MXPA01011955A (es) | 1999-05-26 | 2003-09-04 | Warner Lambert Co | Aminoacidos policiclicos, fusionados, como agentes farmaceuticos. |
| BR0011039A (pt) | 1999-05-28 | 2002-02-26 | Warner Lambert Co | Análogos de gaba substituìdos com 3-heteroarilalquila |
| DK1187832T3 (da) | 1999-06-02 | 2003-03-10 | Warner Lambert Co | Aminoheterocycler, som er anvendelige som farmaceutiske midler |
| SK12822003A3 (sk) | 2001-04-19 | 2004-04-06 | Warner - Lambert Company Llc | Fúzne bicyklické alebo tricyklické aminokyseliny |
| US7696199B2 (en) | 2004-08-27 | 2010-04-13 | Laboratorios Del Dr. Esteve, S.A. | Sigma receptor inhibitors |
| EP1820502A1 (en) * | 2006-02-10 | 2007-08-22 | Laboratorios Del Dr. Esteve, S.A. | Active substance combination comprising azolylcarbinol compounds |
| EP2116539A1 (en) * | 2008-04-25 | 2009-11-11 | Laboratorios Del. Dr. Esteve, S.A. | 1-aryl-3-aminoalkoxy-pyrazoles as sigma ligands enhancing analgesic effects of opioids and attenuating the dependency thereof |
| EP2292236A1 (en) | 2009-08-14 | 2011-03-09 | Laboratorios Del. Dr. Esteve, S.A. | Sigma ligands for the prevention or treatment of pain induced by chemotherapy |
| EP2335688A1 (en) | 2009-11-25 | 2011-06-22 | Laboratorios Del. Dr. Esteve, S.A. | Pharmaceutical compositions comprising sigma receptor ligands |
| PH12012501027A1 (en) | 2009-11-25 | 2022-04-01 | Esteve Labor Dr | 4-[2-[[5-methyl-1-(2-naphtalenyl)-1h-pyrazol-3-yl]oxy]ethyl]morpholine salts |
| HUE029738T2 (en) | 2010-02-04 | 2017-04-28 | Esteve Labor Dr | 4- [2 - [[5-Methyl-1- (2-naphthalenyl) -1H-pyrazol-3-yl] oxy] ethyl] morpholine hydrochloride polymorphs and solvates |
| EP2353591A1 (en) * | 2010-02-04 | 2011-08-10 | Laboratorios Del. Dr. Esteve, S.A. | Sigma ligands for potentiating the analgesic effect of opioids and opiates in post-operative pain and attenuating the dependency thereof |
| EP2388005A1 (en) | 2010-05-21 | 2011-11-23 | Laboratorios Del. Dr. Esteve, S.A. | Sigma ligands for the prevention and/or treatment of emesis induced by chemotherapy or radiotherapy |
| EP2415471A1 (en) * | 2010-08-03 | 2012-02-08 | Laboratorios Del. Dr. Esteve, S.A. | Use of sigma ligands in opioid-induced hyperalgesia |
| EP2426111A1 (en) * | 2010-08-09 | 2012-03-07 | Laboratorios Del. Dr. Esteve, S.A. | 4-[-2-[[5-methyl-1-(2-naphtalenyl)-1h-pyrazol-3-yl]oxy]ethyl]morpholine hydrochloride amorphous solid forms |
| EP2460519A1 (en) | 2010-12-03 | 2012-06-06 | Laboratorios Del. Dr. Esteve, S.A. | Use of sigma ligands in bone cancer pain |
| EP2524694A1 (en) * | 2011-05-19 | 2012-11-21 | Laboratorios Del. Dr. Esteve, S.A. | Use of sigma ligands in diabetes type-2 associated pain |
| EP2818166A1 (en) * | 2013-06-26 | 2014-12-31 | Laboratorios del Dr. Esteve S.A. | Use of sigma receptor ligands for the prevention and treatment of pain associated to interstitial cystitis/bladder pain syndrome (IC/BPS) |
-
2014
- 2014-12-16 EP EP14823952.8A patent/EP3082790A1/en not_active Withdrawn
- 2014-12-16 SG SG11201604478UA patent/SG11201604478UA/en unknown
- 2014-12-16 MX MX2016007286A patent/MX2016007286A/es unknown
- 2014-12-16 TW TW103143904A patent/TW201607539A/zh unknown
- 2014-12-16 TN TN2016000229A patent/TN2016000229A1/en unknown
- 2014-12-16 JP JP2016536584A patent/JP2017503765A/ja not_active Ceased
- 2014-12-16 CA CA2933057A patent/CA2933057A1/en not_active Abandoned
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- 2014-12-16 US US15/104,752 patent/US20160310501A1/en not_active Abandoned
- 2014-12-16 WO PCT/EP2014/077992 patent/WO2015091505A1/en not_active Ceased
- 2014-12-16 CN CN201480072218.6A patent/CN105873580B/zh not_active Expired - Fee Related
- 2014-12-16 KR KR1020167018971A patent/KR20160098426A/ko not_active Withdrawn
- 2014-12-16 AU AU2014364644A patent/AU2014364644A1/en not_active Abandoned
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2016
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- 2016-06-08 PH PH12016501095A patent/PH12016501095A1/en unknown
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| MX2016007286A (es) | 2016-08-04 |
| AR101637A1 (es) | 2017-01-04 |
| MA39146A1 (fr) | 2017-11-30 |
| TW201607539A (zh) | 2016-03-01 |
| EP3082790A1 (en) | 2016-10-26 |
| PH12016501095A1 (en) | 2016-07-11 |
| JP2017503765A (ja) | 2017-02-02 |
| CA2933057A1 (en) | 2015-06-25 |
| TN2016000229A1 (en) | 2017-10-06 |
| CN105873580A (zh) | 2016-08-17 |
| SG11201604478UA (en) | 2016-07-28 |
| AU2014364644A1 (en) | 2016-06-23 |
| IL245977A0 (en) | 2016-07-31 |
| CN105873580B (zh) | 2020-08-25 |
| WO2015091505A1 (en) | 2015-06-25 |
| US20160310501A1 (en) | 2016-10-27 |
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