ME02483B - 4-[2-[[5-metil-1-(2-naftalenil)-1h-pirazol-3-il]oksi]etil]morfolin hidrohlorid i solvati - Google Patents
4-[2-[[5-metil-1-(2-naftalenil)-1h-pirazol-3-il]oksi]etil]morfolin hidrohlorid i solvatiInfo
- Publication number
- ME02483B ME02483B MEP-2016-154A MEP15416A ME02483B ME 02483 B ME02483 B ME 02483B ME P15416 A MEP15416 A ME P15416A ME 02483 B ME02483 B ME 02483B
- Authority
- ME
- Montenegro
- Prior art keywords
- methyl
- naphthalenyl
- oxy
- ethyl
- morpholine
- Prior art date
Links
- -1 2-NAPHTHALENYL Chemical class 0.000 title claims 21
- 239000012453 solvate Substances 0.000 title claims 7
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 title 1
- 238000000034 method Methods 0.000 claims 16
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 13
- DGPGXHRHNRYVDH-UHFFFAOYSA-N 4-[2-(5-methyl-1-naphthalen-2-ylpyrazol-3-yl)oxyethyl]morpholine Chemical compound N=1N(C=2C=C3C=CC=CC3=CC=2)C(C)=CC=1OCCN1CCOCC1 DGPGXHRHNRYVDH-UHFFFAOYSA-N 0.000 claims 9
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims 9
- 238000002360 preparation method Methods 0.000 claims 9
- 230000003197 catalytic effect Effects 0.000 claims 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 5
- 238000000634 powder X-ray diffraction Methods 0.000 claims 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 4
- 230000008020 evaporation Effects 0.000 claims 4
- 238000001704 evaporation Methods 0.000 claims 4
- 239000002904 solvent Substances 0.000 claims 4
- SHRYQZBTQDMGLZ-UHFFFAOYSA-N 4-[2-(5-methyl-1-naphthalen-2-ylpyrazol-3-yl)oxyethyl]morpholine;hydrochloride Chemical compound Cl.N=1N(C=2C=C3C=CC=CC3=CC=2)C(C)=CC=1OCCN1CCOCC1 SHRYQZBTQDMGLZ-UHFFFAOYSA-N 0.000 claims 3
- 239000012296 anti-solvent Substances 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- 229920001223 polyethylene glycol Polymers 0.000 claims 3
- 229920002451 polyvinyl alcohol Polymers 0.000 claims 3
- 239000000243 solution Substances 0.000 claims 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 2
- 239000004743 Polypropylene Substances 0.000 claims 2
- 229920002125 Sokalan® Polymers 0.000 claims 2
- 229910052802 copper Inorganic materials 0.000 claims 2
- 239000010949 copper Substances 0.000 claims 2
- 238000002425 crystallisation Methods 0.000 claims 2
- 230000008025 crystallization Effects 0.000 claims 2
- 238000009792 diffusion process Methods 0.000 claims 2
- 239000007788 liquid Substances 0.000 claims 2
- 229920002401 polyacrylamide Polymers 0.000 claims 2
- 229920000642 polymer Polymers 0.000 claims 2
- 229920001155 polypropylene Polymers 0.000 claims 2
- 229920001343 polytetrafluoroethylene Polymers 0.000 claims 2
- 229920000036 polyvinylpyrrolidone Polymers 0.000 claims 2
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 claims 2
- 239000001267 polyvinylpyrrolidone Substances 0.000 claims 2
- 230000005855 radiation Effects 0.000 claims 2
- 239000007787 solid Substances 0.000 claims 2
- 229920002292 Nylon 6 Polymers 0.000 claims 1
- 238000002441 X-ray diffraction Methods 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- JXYZHMPRERWTPM-UHFFFAOYSA-N hydron;morpholine;chloride Chemical compound Cl.C1COCCN1 JXYZHMPRERWTPM-UHFFFAOYSA-N 0.000 claims 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 claims 1
- 229920000352 poly(styrene-co-divinylbenzene) Polymers 0.000 claims 1
- 229920002492 poly(sulfone) Polymers 0.000 claims 1
- 239000004926 polymethyl methacrylate Substances 0.000 claims 1
- 229920002689 polyvinyl acetate Polymers 0.000 claims 1
- 239000011118 polyvinyl acetate Substances 0.000 claims 1
- 239000000843 powder Substances 0.000 claims 1
- 239000012047 saturated solution Substances 0.000 claims 1
- 239000000725 suspension Substances 0.000 claims 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
- A61K31/4152—1,2-Diazoles having oxo groups directly attached to the heterocyclic ring, e.g. antipyrine, phenylbutazone, sulfinpyrazone
-
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
- A61K31/4155—1,2-Diazoles non condensed and containing further heterocyclic rings
-
- 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
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
- C07D231/18—One oxygen or sulfur atom
- C07D231/20—One oxygen atom attached in position 3 or 5
- C07D231/22—One oxygen atom attached in position 3 or 5 with aryl radicals attached to ring nitrogen atoms
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pain & Pain Management (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Claims (17)
1. čvrsti oblik hidrohloridne soli 4-[2-[[5-metil-1-(2-naftalenil)-1 H-pirazol-3-il]oksi]etil]morfolina, koji je polimorfna faza, oblik l ima model rendgenske difrakcije praha koji pokazuje karakteristične najviše vrednosti pri uglu refleksije [28 u stepenima] od oko 5.9, 8.1, 11.3, 11.7, 14.2, 15.1, 15.8, 16.3, 16.8,17.8, 18.1' 18.6, 19.8, 20,9, 21,9, 22,8, 23,0, 23,2, 23,6, 23,9, 24,3, 25,0, 25,1' 28,0, 28,3, 28,6, 29,0,29,2, 30,7, i 30,9; sa 28 vrednostima koje se dobijaju korišćenjem zračenja bakra (CuKa1 1,54060 A).
2. Polimorfni ili solvatirani čvrsti oblik hidrohlorid soli 4-[2-[[5-metil-1-(2-naftalenil)-1 H-pirazol-3- il]oksi]etil]morfolina, koji se bira iz grupe koja se sastoji od: a) polimorfne faze, oblik ll sa modelom rendgenske difrakcije praha koji pokazuje karakteristične najviše vrednosti pod uglom refleksije [28 u stepenima] od oko 5,776, 11,629, 14,558, 15,737, 15,891, 16,420,16,740, 17,441, 17,635, 18,056, 18,219, 19,232, 19,712, 20,140, 20,685, 21,135, 21,889, 22,108, 22,478, 22,763, 23,219, 23,454, 23,782, 24,689, 25,065, i 25,671; b) polimorfne faze, oblik ill sa modelom rendgenske difrakcije praha koji pokazuje karakteristične najviše vrednosti pod uglom refleksije [28 u stepenima] od oko 5,437, 5,714, 10,918, 11,546, 12,704, 13,344, 13,984, 14,505, 15,606, 15,824, 16,164, 16,646, 17,333, 17,837, 18,719, 18,878, 19,236, 19,533, 20,142, 20,689, 21,337, 22,008, 22,929, 23,596, 24,748, 25,064, 25,207, 25,737, i 26,148; e) polimorfne faze, oblik IV sa modelom rendgenske difrakcije praha koji pokazuje karakteristične najviše vrednosti pod uglom refleksije [28 u stepenima] od oko 5,805, 11,685, 15,559, 15,804, 16,397, 16,879, 17,357, 17,465, 17,621, 19,112, 19,435, 19,923, 21,224, 21,987, 22,167, 22,412, 2,852, 23,059, 23,359, 23,855, 24,092, 25,722, 26,054, 26,649, i 27,780; d) solvat dioksana koji ima model rendgenske difrakcije praha koji pokazuje karakteristične najviše vrednosti pod uglom refrakcije [28 u stepenima] od oko 4,734, 9,317, 11,390, 13,614, 14,290, 14,815, 16,211, 16,432, 16,782, 17,741, 18,056, 18,329, 18,724, 19,070, 19,494, 20,436, 20,762, 21,587, 22,000, 22,935, 23,084, 23,551' 23,891' 24,721' i 25,078; i e) hloroform solvat koji ima model rendgenske difrakcije praha koji pokazuje karakteristične najviše vrednosti pod uglom refleksije [28 u stepenima] od oko 11,370, 13,396, 14,048, 15,01O, 15,303, 16,117, 16,804, 17,040, 17,830, 18,029, 18,661, 18,859, 19,190, 20,150, 20,434, 21,424, 22,279, 22,871' 23,449, 23,918, 24,343, 24,709, 24,820, 25,459, i 26,199; sa 28 vrednostima koje se dobijaju korišćenjem zračenja bakra (CuKa1 1,54060 A).
3. Postupak za pripremu polimorfne faze, oblik l kako je definisano u patentnom zahtevu 1, koji obuhvata: a) rastvaranje 4-[2-[[5-metil-1-{2-naftalenil)-1 H-pirazol-3-il]oksi]etil]morfolin hidrohlorida u pogodnom rastvaraču, i b) isparavanje rastvarača.
4. Postupak prema patentnom zahtevu 3, pri čemu se 4-[2-[[5-metil-1-(2-naftalenil)-1 H-pirazol-3- il}oksi]etil]morfolin hidrohlorid rastvara na temperaturi koja se kreće u opsegu do 120 oc i/ili rastvarač isparava na temperaturi koja se kreće u opsegu od -21 oc do 60 °C.
5. Postupak za pripremu polimorfne faze, oblik l kako je definisano u patentnom zahtevu 1, pri čemu se u rastvor koji obuhvata 4-[2-[[5-metil-1-(2-naftalenil)-1 H-pirazol-3-il]oksi}etil]morfolin hidrohlorid umeša i odgovarajući antirastvarač.
6. Postupak prema patentnom zahtevu 5, pri čemu se mešavina izvodi na temperaturi koja se kreće u opsegu od sobne temperature do 90 °C.
7. Postupak prema patentnom zahtevu 5, pri čemu se mešavina izvodi difuzijom tečnost-tečnost ili difuzijom gas-tečnost.
8. Postupak prema patentnom zahtevu 3, pri čemu se voda dodaje u rastvor.
9. Postupak za pripremu polimorfne faze, oblik l kako je definisano u patentnom zahtevu 1, pri čemu se priprema suspenzija koja obuhvata 4-[2-[[5-metil-1-(2-naftalenil)-1 H-pirazol-3-il]oksi]etil]morfolin hidrohlorida.
10. Postupak prema patentnom zahtevu 9, pri čemu se mešavina održava na temperaturi koja se kreće u opsegu od sobne temperature do 80 °C.
11. Postupak za pripremu polimorfne faze, oblik ll kako je definisano u patentnom zahtevu 2, koja obuhvata: a) rastvaranje hidrohlorid soli 4-[2-[[5-metil-1-(2-naftalenil)-1 H-pirazol-3-il]oksi]etil]morfolin u vodi u prisustvu katalitičkih količina poli(vinil alkohola), i b) isparavanje vode.
12. Postupak za pripremu polimorfne faze, oblik 111 kako je definisano u patentnom zahtevu 2, koji obuhvata: a) rastvaranje hidrohlorid soli 4-[2-[[5-metil-1-(2-naftalenil)-1 H-pirazol-3-il}oksi]etil]morfolina u vodi ili acetonu u prisustvu katalitičkih količina poli(etilen glikola), i b) isparavanje vode ili acetona; ili obuhvata: a) rastvaranje hidrohlorid soli 4-[2-[[5-metil-1-(2-naftalenil)-1 H-pirazol-3-il]oksi]etil]morfolina u vodi u prisustvu katalitičkih količina poli(etilen glikola), i b) dodavanje diizopropil etra kao antirastvarača.
13. Postupak za pripremu polimorfne faze, oblik IV kako je definisano u patentnom zahtevu 2, koji obuhvata: a) rastvaranje hidrohlorid soli 4-[2-[[5-metil-1-(2-naftalenil)-1 H-pirazol-3-il]oksi]etil]morfolina u hloroformu u prisustvu katalitičkih količina polimera izabranog iz grupe koja se sastoji od: polivinil pirolidona, poli(akrilne kiseline), polipropilena, poli(stiren-ko-divinilbenzena), poli(tetrafluoroetilena), poli(vinil alkohola), poliakrilamida i pli(metil metakrilata), i b) dodavanje diizopropil etra kao antirastvarača.
14. Postupak za pripremu dioksan solvata kako je definisano u patentnom zahtevu 2, koji obuhvata postupak izabran iz postupaka: a) mlevenje kapljicama rastvarača koje obhvata: a) punjenje hidrohlorid soli 4-[2-[[5-metil-1-(2-naftalenil)-1 H-pirazol-3-il]oksi]etil]morfolina zajedno sa katalitičkim količinama dioksana u posudu sa mlinom loptašem; i b) mlevenje; i b) kristalizacije iz vrućeg zasićenog rastvora dioksana.
15. Postupak za pripremu hloroform solvata kako je definisano u patentnom zahtevu 2, koji obuhvata: a) rastvaranje hidrohlorid soli 4-[2-([5-metil-1-(2-naftalenil)-1 H-pirazol-3-il]oksi]etil]morfolina u hloroformu u prisustvu katalitičkih količina polimera izabranog iz grupe koja se sastoji od poli(etilen glikola), polivinil pirolidona, poli(akrilne kiseline), nailona 6/6, polipropilena, poli(tetrafluoroetilena), poli(vinil acetata), poli(vinil alkohola), poliakrilamida i polisulfona; i b) bilo isparavanje hloroforma ili kristalizacija u vrućem zasićenom rastvoru hloroforma.
16. Upotreba polimorfne faze, oblik l, polimorfne faze, oblik 111, polimorfne faze, oblik IV, dioksan solvata ili hloroform solvata kako je definisano u patentnom zahtevu 2 za dobijanje faze, oblik l hidrohlorid soli 4-[2-[[5-metil-1-(2-naftalenil)-1H-pirazol-3-il]oksi]etil]morfolina kako je definisnao u patentnom zahtevu 1.
17. Postupak za pripremu faze, oblik l hidrohlorid soli 4-[2-[[5-metil-1-(2-naftalenil)-1 Hpirazol-3- il]oksi]etil]morfolina kako je definisano u patentnom zahtevu 1 koji obuhvata korak zagrevanja kristalnih formi faze ll, faze lli i/ili faze IV ovog jedinjenja kako je definisano u patentnom zahtevu 2 na temperaturi između 140 oci 170 oc.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP10382025A EP2361904A1 (en) | 2010-02-04 | 2010-02-04 | 4-[-2-[[5-methyl-1-(2-naphtalenyl)-1h-pyrazol-3-yl]oxy]ethyl]morpholine hydrochloride and crystalline forms thereof |
| EP10382226A EP2426112A1 (en) | 2010-08-09 | 2010-08-09 | 4-[-2-[[5-methyl-1-(2-naphtalenyl)-1h-pyrazol-3-yl]oxy]ethyl]morpholine hydrochloride polymorphs and solvates |
| EP11702056.0A EP2531177B8 (en) | 2010-02-04 | 2011-02-04 | 4-[2-[[5-methyl-1-(2-naphthalenyl)-1h-pyrazol-3-yl]oxy]ethyl]morpholine hydrochloride polymorphs and solvates |
| PCT/EP2011/051630 WO2011095579A1 (en) | 2010-02-04 | 2011-02-04 | 4-[-2-[[5-methyl-1-(2-naphtalenyl)-1h-pyrazol-3-yl]oxy]ethyl]morpholine hydrochloride polymorphs and solvates |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ME02483B true ME02483B (me) | 2017-02-20 |
Family
ID=43897079
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MEP-2016-154A ME02483B (me) | 2010-02-04 | 2011-02-04 | 4-[2-[[5-metil-1-(2-naftalenil)-1h-pirazol-3-il]oksi]etil]morfolin hidrohlorid i solvati |
Country Status (32)
| Country | Link |
|---|---|
| US (2) | US9051275B2 (me) |
| EP (1) | EP2531177B8 (me) |
| JP (1) | JP5894086B2 (me) |
| KR (2) | KR20180063379A (me) |
| CN (1) | CN102753155B (me) |
| AR (1) | AR080133A1 (me) |
| AU (1) | AU2011212476B2 (me) |
| BR (1) | BR112012018958A8 (me) |
| CA (1) | CA2788024C (me) |
| CO (1) | CO6592093A2 (me) |
| CY (1) | CY1117886T1 (me) |
| DK (1) | DK2531177T3 (me) |
| EC (1) | ECSP12012039A (me) |
| ES (1) | ES2586212T3 (me) |
| HR (1) | HRP20160937T1 (me) |
| HU (1) | HUE029738T2 (me) |
| IL (1) | IL221277A (me) |
| MA (1) | MA34047B1 (me) |
| ME (1) | ME02483B (me) |
| MX (1) | MX339193B (me) |
| NZ (1) | NZ601316A (me) |
| PH (1) | PH12012501510A1 (me) |
| PL (1) | PL2531177T3 (me) |
| PT (1) | PT2531177T (me) |
| RS (1) | RS55046B1 (me) |
| RU (1) | RU2560150C2 (me) |
| SG (2) | SG182628A1 (me) |
| SI (1) | SI2531177T1 (me) |
| SM (1) | SMT201600264B (me) |
| TN (1) | TN2012000347A1 (me) |
| TW (1) | TWI568729B (me) |
| WO (1) | WO2011095579A1 (me) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| TW201206893A (en) | 2010-07-09 | 2012-02-16 | Abbott Healthcare Products Bv | Bisaryl (thio) morpholine derivatives as S1P modulators |
| TW201643169A (zh) | 2010-07-09 | 2016-12-16 | 艾伯維股份有限公司 | 作為s1p調節劑的螺-哌啶衍生物 |
| TWI522361B (zh) | 2010-07-09 | 2016-02-21 | 艾伯維公司 | 作為s1p調節劑的稠合雜環衍生物 |
| 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 |
| EP2524694A1 (en) | 2011-05-19 | 2012-11-21 | Laboratorios Del. Dr. Esteve, S.A. | Use of sigma ligands in diabetes type-2 associated pain |
| EP2792352A1 (en) | 2013-04-16 | 2014-10-22 | Laboratorios Del. Dr. Esteve, S.A. | Alpha-2 adrenoreceptor and sigma receptor ligand combinations |
| TN2016000228A1 (en) | 2013-12-17 | 2017-10-06 | Esteve Labor Dr | SEROTONIN-NOREPINEPHRINE REUPTAKE INHIBITORS (SNRIs) AND SIGMA RECEPTOR LIGANDS COMBINATIONS. |
| AU2014364644A1 (en) | 2013-12-17 | 2016-06-23 | Laboratorios Del Dr. Esteve, S.A. | Gabapentinoids and Sigma receptor ligands combinations |
| AR108682A1 (es) | 2016-06-06 | 2018-09-12 | Esteve Labor Dr | Derivados de pirazol-3-iloxi ligandos del receptor sigma |
| AR109024A1 (es) | 2016-07-12 | 2018-10-17 | Esteve Labor Dr | Uso de ligandos del receptor sigma en el dolor post-herpético |
| WO2018059420A1 (zh) * | 2016-09-27 | 2018-04-05 | 苏州科睿思制药有限公司 | E52862盐酸盐晶型h及其制备方法 |
| WO2019068771A1 (en) | 2017-10-04 | 2019-04-11 | Esteve Pharmaceuticals, S.A. | USE OF SIGMA RECEPTOR LIGANDS AGAINST AGE-RELATED COGNITIVE DISORDERS |
| US11535632B2 (en) | 2019-10-31 | 2022-12-27 | ESCAPE Bio, Inc. | Solid forms of an S1P-receptor modulator |
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|---|---|---|---|---|
| NZ243065A (en) * | 1991-06-13 | 1995-07-26 | Lundbeck & Co As H | Piperidine derivatives and pharmaceutical compositions |
| CA2576144C (en) * | 2004-08-27 | 2012-12-11 | Laboratorios Del Dr. Esteve, S.A. | Sigma receptor inhibitors |
| JP2009528315A (ja) * | 2006-03-01 | 2009-08-06 | ラボラトリオス・デル・ドクトル・エステベ・ソシエダッド・アノニマ | シグマ受容体阻害剤としてのピラゾール誘導体 |
| US7695199B2 (en) | 2006-07-20 | 2010-04-13 | Finisar Corporation | Optical subassembly having insertable cylindrical sleeve |
| CN101328155B (zh) * | 2007-06-20 | 2010-11-03 | 上海医药工业研究院 | 噁唑烷衍生物及其制备方法和应用 |
| EP2113501A1 (en) * | 2008-04-25 | 2009-11-04 | Laboratorios Del. Dr. Esteve, S.A. | 5-Methyl-1-(naphthalen-2-YL)-1H-Pyrazoles useful as sigma receptor inhibitors |
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