HRP20170507T1 - Trpv1 antagonisti uključujući dihidroksi supstituente i njihove uporabe - Google Patents
Trpv1 antagonisti uključujući dihidroksi supstituente i njihove uporabe Download PDFInfo
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- HRP20170507T1 HRP20170507T1 HRP20170507TT HRP20170507T HRP20170507T1 HR P20170507 T1 HRP20170507 T1 HR P20170507T1 HR P20170507T T HRP20170507T T HR P20170507TT HR P20170507 T HRP20170507 T HR P20170507T HR P20170507 T1 HRP20170507 T1 HR P20170507T1
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- pharmaceutically acceptable
- crystal
- fumaric acid
- substance
- acceptable derivative
- Prior art date
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- 101150016206 Trpv1 gene Proteins 0.000 title 1
- 239000005557 antagonist Substances 0.000 title 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims 33
- 239000013078 crystal Substances 0.000 claims 18
- 239000000126 substance Substances 0.000 claims 16
- 239000001530 fumaric acid Substances 0.000 claims 15
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 15
- 150000003839 salts Chemical class 0.000 claims 9
- 239000012453 solvate Substances 0.000 claims 6
- 125000001475 halogen functional group Chemical group 0.000 claims 5
- 201000008482 osteoarthritis Diseases 0.000 claims 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 239000000843 powder Substances 0.000 claims 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 3
- 208000025865 Ulcer Diseases 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 125000004193 piperazinyl group Chemical group 0.000 claims 2
- 231100000397 ulcer Toxicity 0.000 claims 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 claims 1
- 229940092714 benzenesulfonic acid Drugs 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- BDAGIHXWWSANSR-UHFFFAOYSA-N formic acid Substances OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims 1
- 235000019253 formic acid Nutrition 0.000 claims 1
- 239000012458 free base Substances 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims 1
- 159000000000 sodium salts Chemical class 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 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
- A61K31/425—Thiazoles
- A61K31/428—Thiazoles condensed with carbocyclic rings
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- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
-
- 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
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- 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
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- 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
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/28—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C309/29—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton of non-condensed six-membered aromatic rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/28—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C309/29—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton of non-condensed six-membered aromatic rings
- C07C309/30—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton of non-condensed six-membered aromatic rings of six-membered aromatic rings substituted by alkyl groups
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/02—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
- C07C57/13—Dicarboxylic acids
- C07C57/15—Fumaric acid
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/235—Saturated compounds containing more than one carboxyl group
- C07C59/245—Saturated compounds containing more than one carboxyl group containing hydroxy or O-metal groups
- C07C59/255—Tartaric acid
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- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
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- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Physical Education & Sports Medicine (AREA)
- Urology & Nephrology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Immunology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Hydrogenated Pyridines (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Claims (17)
1. Tvar formule (I):
[image]
ili njen farmaceutski prihvatljivi derivat, pri čemu:
R1 je -halo;
R4 je -H;
svaki od R8 i R9 je nezavisno -H, -halo, -CH3 ili -CF3;
svaki halo je nezavisno -F, -Cl, -Br ili -I; i
m je cijeli broj 1;
gdje je metilna grupa vezana za piperazinski prsten (S)-2-metilna grupa; atom ugljika na a-b poziciji veze je u (S) konfiguraciji;
pri čemu je farmaceutski prihvatljivi derivat odabran iz grupe koja se sastoji od farmaceutski prihvatljive soli, polimorfa, pseudopolimorfa, solvata, ko-kristala, radioaktivno označenog oblika i/ili tautomera.
2. Tvar iz patentnog zahtjeva 1 pri čemu je farmaceutski prihvatljivi derivat farmaceutski prihvatljiva sol, radioaktivno označeni oblik, ili klorovodična kiselina, octena kiselina, benzensulfonska kiselina, p-toluensulfonska kiselina, ili ko-kristal fumarinske kiseline.
3. Tvar iz patentnog zahtjeva 2, pri čemu je farmaceutski prihvatljivi derivat sol fumarinske kiseline, ko-kristal fumarinske kiseline, ili njihova kombinacija.
4. Tvar iz patentnog zahtjeva 1 koja ima formulu (II):
[image]
ili njen farmaceutski prihvatljivi derivat, pri čemu:
R4 je -H;
R8 je -H, -F ili -CH3;
R9 je -H, -halo, -CH3 ili -CF3; i
svaki halo je nezavisno -F, -Cl, -Br ili -I; i
gdje je metilna grupa vezana za piperazinski prsten (S)-2-metilna grupa; atom ugljika na a-b poziciji veze je u (S) konfiguraciji;
pri čemu je farmaceutski prihvatljivi derivat odabran iz grupe koja se sastoji od farmaceutski prihvatljive soli, polimorfa, pseudopolimorfa, solvata, ko-kristala, radioaktivno označenog oblika i/ili tautomera.
5. Tvar iz patentnog zahtjeva 4, pri čemu je farmaceutski prihvatljivi derivat
(i) farmaceutski prihvatljiva sol, ili ko-kristal fumarinske kiseline; ili
(ii) sol fumarinske kiseline, ko-kristal fumarinske kiseline ili njihova kombinacija.
6. Tvar iz patentnog zahtjeva 5, opcije (i), pri čemu je farmaceutski prihvatljivi derivat sol klorovodične kiseline, natrijeva sol, kalijeva sol, sol p-toluensulfonske kiseline, sol fumarinske kiseline ili ko-kristal fumarinske kiseline.
7. Tvar iz patentnog zahtjeva 4 ili njen farmaceutski prihvatljivi derivat, koji je
[image]
ili
pri čemu je farmaceutski prihvatljivi derivat odabran iz grupe koja se sastoji od farmaceutski prihvatljive soli, polimorfa, pseudopolimorfa, solvata, ko-kristala, radioaktivno označenog oblika i/ili tautomera.
8. Tvar iz bilo kojeg od patentnih zahtjeva 1 ili 7, koja je
(i) sol fumarinske kiseline, ko-kristal fumarinske kiseline ili njihova kombinacija, ili
(ii) slobodna baza.
9. Tvar iz bilo kojeg od patentnih zahtjeva 1-8 ili njen farmaceutski prihvatljivi derivat za uporabu u liječenju boli, boli povezane s osteoartritisom, osteoartritisa, UI, čira, IBD, ili IBS, pri čemu je farmaceutski prihvatljivi derivat odabran iz grupe koja se sastoji od farmaceutski prihvatljive soli, polimorfa, pseudopolimorfa, solvata, ko-kristala, radioaktivno označenog oblika i/ili tautomera.
10. Produkt kombiniranja tvari iz bilo kojeg od patentnih zahtjeva 1-8 s fumarinskom kiselinom, pri čemu je molarni omjer u produktu oko 1:0.5 (tvar formule (I) ili (II): fumarinska kiselina).
11. Sastav obuhvaća
(i) tvar iz bilo kojeg od patentnih zahtjeva 1-8 ili njen farmaceutski prihvatljivi derivat; ili
(ii) produkt iz patentnog zahtjeva 10;
i farmaceutski prihvatljivi nosač ili ekscipijens, pri čemu je farmaceutski prihvatljivi derivat odabran iz grupe koja se sastoji od farmaceutski prihvatljive soli, polimorfa, pseudopolimorfa, solvata, ko-kristala, radioaktivno označenog oblika i/ili tautomera.
12. Produkt iz patentnog zahtjeva 10 ili njegov farmaceutski prihvatljivi derivat za uporabu u liječenju boli, boli povezane s osteoartritisom, osteoartritisa, UI, čira, IBD, ili IBS, pri čemu je farmaceutski prihvatljivi derivat odabran iz grupe koja se sastoji od farmaceutski prihvatljive soli, polimorfa, pseudopolimorfa, solvata, ko-kristala, radioaktivno označenog oblika i/ili tautomera.
13. Tvar iz patentnog zahtjeva 4 koja ima strukturu:
[image]
ili njen ko-kristal fumarinske kiseline.
14. Tvar iz patentnog zahtjeva 13 u obliku ko-kristala kombinacije tvari
[image]
s fumarinskom kiselinom, pri čemu je molarni omjer u ko-kristalu približno 1:0.5 (tvar):(fumarinska kiselina).
15. Ko-kristal fumarinske kiseline iz patentnog zahtjeva 13 ili patentnog zahtjeva 14 ima uzorak praškastog raspršenja x-zraka koji sadrži pik na svakom od 6.5°±0.2°, 12.5°±0.2°, 16.8°±0.2° i 25.3°±0.2°.
16. Ko-kristal fumarinske kiseline iz patentnog zahtjeva 13 ili patentnog zahtjeva 14 ima uzorak praškastog raspršenja x-zraka koji sadrži pik na svakom od 6.5°±0.2°, 8.6°±0.2°, 12.5°±0.2°, 14.0°±0.2°, 16.8°±0.2°, 18.7°±0.2° i 25.3°±0.2°.
17. Ko-kristal fumarinske kiseline iz patentnog zahtjeva 13 ili patentnog zahtjeva 14 ima uzorak praškastog raspršenja x-zraka koji sadrži pik na svakom od 6.5°±0.2°, 8.6°±0.2°, 12.5°±0.2°, 14.0°±0.2°, 16.8°±0.2°, 18.7°±0.2°, 20.4°±0.2°, 21.3°±0.2°, 22.0°±0.2°, 23.2°±0.2°, 25.3°±0.2° i 38.5°±0.2°.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201161499989P | 2011-06-22 | 2011-06-22 | |
PCT/IB2012/001252 WO2012176061A1 (en) | 2011-06-22 | 2012-06-21 | Trpv1 antagonists including dihydroxy substituent and uses thereof |
EP12735333.2A EP2723732B1 (en) | 2011-06-22 | 2012-06-21 | Trpv1 antagonists including dihydroxy substituent and uses thereof |
Publications (1)
Publication Number | Publication Date |
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HRP20170507T1 true HRP20170507T1 (hr) | 2017-06-02 |
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HRP20170507TT HRP20170507T1 (hr) | 2011-06-22 | 2017-03-29 | Trpv1 antagonisti uključujući dihidroksi supstituente i njihove uporabe |
Country Status (32)
Country | Link |
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US (4) | US9273043B2 (hr) |
EP (2) | EP2723732B1 (hr) |
JP (1) | JP5699251B2 (hr) |
KR (2) | KR20150055094A (hr) |
CN (2) | CN105693712A (hr) |
AR (1) | AR086709A1 (hr) |
AU (1) | AU2012273652B2 (hr) |
BR (1) | BR112013032658A2 (hr) |
CA (1) | CA2837178C (hr) |
CL (1) | CL2013003550A1 (hr) |
CO (1) | CO6852081A2 (hr) |
CY (1) | CY1119111T1 (hr) |
DK (1) | DK2723732T3 (hr) |
ES (1) | ES2620528T3 (hr) |
HR (1) | HRP20170507T1 (hr) |
HU (1) | HUE031372T2 (hr) |
IL (1) | IL229817A (hr) |
LT (1) | LT2723732T (hr) |
ME (1) | ME02609B (hr) |
MX (1) | MX354015B (hr) |
MY (1) | MY185061A (hr) |
PE (1) | PE20141531A1 (hr) |
PL (1) | PL2723732T3 (hr) |
PT (1) | PT2723732T (hr) |
RS (1) | RS55701B1 (hr) |
RU (1) | RU2621708C2 (hr) |
SG (2) | SG10201605163PA (hr) |
SI (1) | SI2723732T1 (hr) |
TW (1) | TWI453205B (hr) |
UA (1) | UA113288C2 (hr) |
WO (1) | WO2012176061A1 (hr) |
ZA (1) | ZA201400419B (hr) |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
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EP2723732B1 (en) * | 2011-06-22 | 2017-01-18 | Purdue Pharma LP | Trpv1 antagonists including dihydroxy substituent and uses thereof |
KR101933622B1 (ko) * | 2012-10-09 | 2018-12-28 | 삼성전자주식회사 | 소포를 모니터링하기 위한 조성물, 키트 및 이를 이용하여 소포를 모니터링하는 방법 |
WO2017022370A1 (ja) * | 2015-07-31 | 2017-02-09 | 株式会社村田製作所 | アンテナ整合回路、アンテナ回路、フロントエンド回路および通信装置 |
RU2755206C1 (ru) | 2020-05-20 | 2021-09-14 | Федеральное государственное бюджетное учреждение науки Тихоокеанский институт биоорганической химии им. Г.Б. Елякова Дальневосточного отделения Российской академии наук (ТИБОХ ДВО РАН) | Средство пролонгированного анальгетического действия и лекарственный препарат на его основе |
CN113077942B (zh) * | 2021-04-12 | 2021-12-17 | 西北工业大学 | 一种基于功率超声制备智能柔性导电薄膜及其应用 |
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