MX2014005611A - Derivados de carboxamida y urea basados en pirazolilo, sustituidos, que contienen una porcion fenilo sustituida con un grupo que contiene n como ligandos del receptor de vanilloide. - Google Patents
Derivados de carboxamida y urea basados en pirazolilo, sustituidos, que contienen una porcion fenilo sustituida con un grupo que contiene n como ligandos del receptor de vanilloide.Info
- Publication number
- MX2014005611A MX2014005611A MX2014005611A MX2014005611A MX2014005611A MX 2014005611 A MX2014005611 A MX 2014005611A MX 2014005611 A MX2014005611 A MX 2014005611A MX 2014005611 A MX2014005611 A MX 2014005611A MX 2014005611 A MX2014005611 A MX 2014005611A
- Authority
- MX
- Mexico
- Prior art keywords
- methyl
- phenyl
- pyrazol
- fluoro
- trifluoromethyl
- Prior art date
Links
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 title claims abstract description 9
- 108010062740 TRPV Cation Channels Proteins 0.000 title abstract description 18
- 102000011040 TRPV Cation Channels Human genes 0.000 title abstract description 17
- 125000003226 pyrazolyl group Chemical group 0.000 title abstract description 5
- 239000003446 ligand Substances 0.000 title abstract description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 title abstract 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 title description 10
- 150000001875 compounds Chemical class 0.000 claims abstract description 202
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- 229910052731 fluorine Inorganic materials 0.000 claims description 150
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 150
- 229910052801 chlorine Inorganic materials 0.000 claims description 130
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 129
- 229910052739 hydrogen Inorganic materials 0.000 claims description 123
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 114
- 239000000203 mixture Substances 0.000 claims description 109
- -1 CH3 Chemical group 0.000 claims description 87
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 77
- 229910052794 bromium Inorganic materials 0.000 claims description 65
- 101100495923 Schizosaccharomyces pombe (strain 972 / ATCC 24843) chr2 gene Proteins 0.000 claims description 64
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 62
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 55
- 125000000217 alkyl group Chemical group 0.000 claims description 44
- 102100029613 Transient receptor potential cation channel subfamily V member 1 Human genes 0.000 claims description 37
- 108050004388 Transient receptor potential cation channel subfamily V member 1 Proteins 0.000 claims description 37
- YKPUWZUDDOIDPM-SOFGYWHQSA-N capsaicin Chemical compound COC1=CC(CNC(=O)CCCC\C=C\C(C)C)=CC=C1O YKPUWZUDDOIDPM-SOFGYWHQSA-N 0.000 claims description 36
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 35
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 24
- 229910052757 nitrogen Inorganic materials 0.000 claims description 23
- 150000003839 salts Chemical class 0.000 claims description 23
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- 125000001424 substituent group Chemical group 0.000 claims description 22
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 20
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- 101150016206 Trpv1 gene Proteins 0.000 claims description 18
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- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 17
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- OUEKLNJUMVZULZ-UHFFFAOYSA-N 2-[4-(2-aminoethoxy)-3-methoxyphenyl]-n-[3-(3,4-dimethylphenyl)propyl]acetamide;hydron;chloride Chemical compound Cl.C1=C(OCCN)C(OC)=CC(CC(=O)NCCCC=2C=C(C)C(C)=CC=2)=C1 OUEKLNJUMVZULZ-UHFFFAOYSA-N 0.000 claims description 5
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- IKYCZSUNGFRBJS-UHFFFAOYSA-N Euphorbia factor RL9 = U(1) = Resiniferatoxin Natural products COC1=CC(O)=CC(CC(=O)OCC=2CC3(O)C(=O)C(C)=CC3C34C(C)CC5(OC(O4)(CC=4C=CC=CC=4)OC5C3C=2)C(C)=C)=C1 IKYCZSUNGFRBJS-UHFFFAOYSA-N 0.000 claims description 5
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- OPZKBPQVWDSATI-KHPPLWFESA-N N-Vanillyloleamide Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)NCC1=CC=C(O)C(OC)=C1 OPZKBPQVWDSATI-KHPPLWFESA-N 0.000 claims description 5
- QVLMCRFQGHWOPM-ZKWNWVNESA-N N-arachidonoyl vanillylamine Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)NCC1=CC=C(O)C(OC)=C1 QVLMCRFQGHWOPM-ZKWNWVNESA-N 0.000 claims description 5
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- OPZKBPQVWDSATI-UHFFFAOYSA-N oleoyl vanillylamide Natural products CCCCCCCCC=CCCCCCCCC(=O)NCC1=CC=C(O)C(OC)=C1 OPZKBPQVWDSATI-UHFFFAOYSA-N 0.000 claims description 5
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- UYUBCEMLBCXZSF-UHFFFAOYSA-N 1-[4-(aminomethyl)-3-fluorophenyl]-3-[[5-tert-butyl-2-(3-chlorophenyl)pyrazol-3-yl]methyl]urea Chemical compound C=1C=CC(Cl)=CC=1N1N=C(C(C)(C)C)C=C1CNC(=O)NC1=CC=C(CN)C(F)=C1 UYUBCEMLBCXZSF-UHFFFAOYSA-N 0.000 claims description 3
- UYBSMAPSMSFRMS-UHFFFAOYSA-N 1-[4-(methanesulfonamidomethyl)-3-methoxyphenyl]-3-[[2-(3-methylphenyl)-5-(trifluoromethyl)pyrazol-3-yl]methyl]urea Chemical compound C1=C(CNS(C)(=O)=O)C(OC)=CC(NC(=O)NCC=2N(N=C(C=2)C(F)(F)F)C=2C=C(C)C=CC=2)=C1 UYBSMAPSMSFRMS-UHFFFAOYSA-N 0.000 claims description 3
- DFJBELNJVAHAPB-UHFFFAOYSA-N 1-[[2-(3-chlorophenyl)-5-(trifluoromethyl)pyrazol-3-yl]methyl]-3-[4-[(sulfamoylamino)methyl]phenyl]urea Chemical compound C1=CC(CNS(=O)(=O)N)=CC=C1NC(=O)NCC1=CC(C(F)(F)F)=NN1C1=CC=CC(Cl)=C1 DFJBELNJVAHAPB-UHFFFAOYSA-N 0.000 claims description 3
- UEKWDKARUNPETP-UHFFFAOYSA-N 1-[[5-tert-butyl-2-(3-chlorophenyl)pyrazol-3-yl]methyl]-3-[3-fluoro-4-[(sulfamoylamino)methyl]phenyl]urea Chemical compound C=1C=CC(Cl)=CC=1N1N=C(C(C)(C)C)C=C1CNC(=O)NC1=CC=C(CNS(N)(=O)=O)C(F)=C1 UEKWDKARUNPETP-UHFFFAOYSA-N 0.000 claims description 3
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- XXPHJAQKJCBFIU-UHFFFAOYSA-N 2-[3-chloro-4-(methanesulfonamidomethyl)phenyl]-n-[[2-(3-chlorophenyl)-5-(trifluoromethyl)pyrazol-3-yl]methyl]propanamide Chemical compound C=1C=C(CNS(C)(=O)=O)C(Cl)=CC=1C(C)C(=O)NCC1=CC(C(F)(F)F)=NN1C1=CC=CC(Cl)=C1 XXPHJAQKJCBFIU-UHFFFAOYSA-N 0.000 claims description 3
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- AJALSFSHXGWQCS-UHFFFAOYSA-N n-[[5-tert-butyl-2-(3-chlorophenyl)pyrazol-3-yl]methyl]-2-[4-[(dimethylamino)methyl]-3-fluorophenyl]propanamide Chemical compound C=1C=C(CN(C)C)C(F)=CC=1C(C)C(=O)NCC1=CC(C(C)(C)C)=NN1C1=CC=CC(Cl)=C1 AJALSFSHXGWQCS-UHFFFAOYSA-N 0.000 claims description 3
- PBAPGSNOGCGWRI-UHFFFAOYSA-N 1-[3-fluoro-4-(methanesulfonamidomethyl)phenyl]-3-[[2-(3-fluorophenyl)-5-(trifluoromethyl)pyrazol-3-yl]methyl]urea Chemical compound C1=C(F)C(CNS(=O)(=O)C)=CC=C1NC(=O)NCC1=CC(C(F)(F)F)=NN1C1=CC=CC(F)=C1 PBAPGSNOGCGWRI-UHFFFAOYSA-N 0.000 claims description 2
- FGCPWHKEQJIHHO-UHFFFAOYSA-N 1-[3-fluoro-4-(methanesulfonamidomethyl)phenyl]-3-[[2-(3-methoxyphenyl)-5-(trifluoromethyl)pyrazol-3-yl]methyl]urea Chemical compound COC1=CC=CC(N2C(=CC(=N2)C(F)(F)F)CNC(=O)NC=2C=C(F)C(CNS(C)(=O)=O)=CC=2)=C1 FGCPWHKEQJIHHO-UHFFFAOYSA-N 0.000 claims description 2
- QXOHXXSFLSEBQD-UHFFFAOYSA-N 1-[3-fluoro-4-(methanesulfonamidomethyl)phenyl]-3-[[2-(3-methylphenyl)-5-(trifluoromethyl)pyrazol-3-yl]methyl]urea Chemical compound CC1=CC=CC(N2C(=CC(=N2)C(F)(F)F)CNC(=O)NC=2C=C(F)C(CNS(C)(=O)=O)=CC=2)=C1 QXOHXXSFLSEBQD-UHFFFAOYSA-N 0.000 claims description 2
- NRSZMRWOQBNOSY-UHFFFAOYSA-N 1-[3-fluoro-4-(methanesulfonamidomethyl)phenyl]-3-[[2-(3-propan-2-ylphenyl)-5-(trifluoromethyl)pyrazol-3-yl]methyl]urea Chemical compound CC(C)C1=CC=CC(N2C(=CC(=N2)C(F)(F)F)CNC(=O)NC=2C=C(F)C(CNS(C)(=O)=O)=CC=2)=C1 NRSZMRWOQBNOSY-UHFFFAOYSA-N 0.000 claims description 2
- OMMCVRGFXJFDAD-UHFFFAOYSA-N 1-[3-fluoro-4-(methanesulfonamidomethyl)phenyl]-3-[[5-(trifluoromethyl)-2-[3-(trifluoromethyl)phenyl]pyrazol-3-yl]methyl]urea Chemical compound C1=C(F)C(CNS(=O)(=O)C)=CC=C1NC(=O)NCC1=CC(C(F)(F)F)=NN1C1=CC=CC(C(F)(F)F)=C1 OMMCVRGFXJFDAD-UHFFFAOYSA-N 0.000 claims description 2
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- VWBWQOUWDOULQN-UHFFFAOYSA-N nmp n-methylpyrrolidone Chemical compound CN1CCCC1=O.CN1CCCC1=O VWBWQOUWDOULQN-UHFFFAOYSA-N 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 230000008058 pain sensation Effects 0.000 description 1
- 230000037040 pain threshold Effects 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- UQPUONNXJVWHRM-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 UQPUONNXJVWHRM-UHFFFAOYSA-N 0.000 description 1
- 230000035778 pathophysiological process Effects 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 208000033808 peripheral neuropathy Diseases 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 230000035790 physiological processes and functions Effects 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 229950010765 pivalate Drugs 0.000 description 1
- 239000011505 plaster Substances 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- FYRHIOVKTDQVFC-UHFFFAOYSA-M potassium phthalimide Chemical compound [K+].C1=CC=C2C(=O)[N-]C(=O)C2=C1 FYRHIOVKTDQVFC-UHFFFAOYSA-M 0.000 description 1
- 238000004237 preparative chromatography Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 229960002429 proline Drugs 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 230000002685 pulmonary effect Effects 0.000 description 1
- 125000003072 pyrazolidinyl group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 230000020341 sensory perception of pain Effects 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
- 125000004853 tetrahydropyridinyl group Chemical group N1(CCCC=C1)* 0.000 description 1
- 125000003554 tetrahydropyrrolyl group Chemical group 0.000 description 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
- 125000001984 thiazolidinyl group Chemical group 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 239000012588 trypsin Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- GTLDTDOJJJZVBW-UHFFFAOYSA-N zinc cyanide Chemical compound [Zn+2].N#[C-].N#[C-] GTLDTDOJJJZVBW-UHFFFAOYSA-N 0.000 description 1
Classifications
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- 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
- C07D231/12—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
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- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Diabetes (AREA)
- Pain & Pain Management (AREA)
- Physical Education & Sports Medicine (AREA)
- Rheumatology (AREA)
- Pulmonology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Virology (AREA)
- Hematology (AREA)
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- Dermatology (AREA)
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- Hospice & Palliative Care (AREA)
- Oncology (AREA)
- Child & Adolescent Psychology (AREA)
- Otolaryngology (AREA)
- Communicable Diseases (AREA)
- Biotechnology (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP11008913 | 2011-11-09 | ||
| PCT/EP2012/072141 WO2013068462A1 (en) | 2011-11-09 | 2012-11-08 | Substituted pyrazolyl-based carboxamide and urea derivatives bearing a phenyl moiety substituted with an n-containing group as vanilloid receptor ligands |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MX2014005611A true MX2014005611A (es) | 2014-07-30 |
Family
ID=47143123
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MX2014005611A MX2014005611A (es) | 2011-11-09 | 2012-11-08 | Derivados de carboxamida y urea basados en pirazolilo, sustituidos, que contienen una porcion fenilo sustituida con un grupo que contiene n como ligandos del receptor de vanilloide. |
Country Status (13)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW201625568A (zh) * | 2014-11-24 | 2016-07-16 | 歌林達有限公司 | 作爲類香草素受體之配位體ｉｉ之經取代以噁唑及噻唑爲主之甲醯胺及脲衍生物 |
| CN114920697A (zh) * | 2022-05-16 | 2022-08-19 | 河南应用技术职业学院 | 杂环基取代的茚满丙酰胺类化合物及其应用 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999012910A1 (fr) * | 1997-09-11 | 1999-03-18 | Nissan Chemical Industries, Ltd. | Composes a base de pyrazole et agent de lutte contre les maladies vegetales |
| PE20110285A1 (es) * | 2005-10-19 | 2011-06-04 | Gruenenthal Chemie | Derivados de sulfonamidofenil propionamida como ligandos del receptor vaniloide del subtipo 1 |
| CN101679297B (zh) * | 2006-12-08 | 2012-01-11 | 埃克塞利希斯股份有限公司 | Lxr和fxr调节剂 |
| NZ580411A (en) * | 2007-04-16 | 2012-06-29 | Gruenenthal Chemie | Novel vanilloid receptor ligands and the use thereof for the production of pharmaceuticals |
| DE102007018151A1 (de) * | 2007-04-16 | 2008-10-23 | Günenthal GmbH | Neue Vanilloid-Rezeptor Liganden und ihre Verwendung zur Herstellung von Arzneimitteln |
| CN106243037A (zh) * | 2009-05-07 | 2016-12-21 | 格吕伦塔尔有限公司 | 作为香草类化合物受体之配体的取代的苯基脲及苯基酰胺 |
| DK2427436T3 (da) * | 2009-05-07 | 2013-04-02 | Gruenenthal Gmbh | Substituerede aromatiske carboxamid og urea derivater som vanilloidreceptorligander. |
| EP2776424A1 (en) * | 2011-11-09 | 2014-09-17 | Grünenthal GmbH | Substituted pyrazolyl-based carboxamide and urea derivatives bearing a phenyl moiety substituted with an n-cyclic group as vanilloid receptor ligands |
-
2012
- 2012-11-08 CA CA2854935A patent/CA2854935A1/en not_active Abandoned
- 2012-11-08 BR BR112014010957A patent/BR112014010957A2/pt not_active IP Right Cessation
- 2012-11-08 KR KR1020147015425A patent/KR20140096351A/ko not_active Withdrawn
- 2012-11-08 IN IN847KON2014 patent/IN2014KN00847A/en unknown
- 2012-11-08 JP JP2014540454A patent/JP2014532742A/ja active Pending
- 2012-11-08 EP EP12781341.8A patent/EP2776399A1/en not_active Withdrawn
- 2012-11-08 WO PCT/EP2012/072141 patent/WO2013068462A1/en active Application Filing
- 2012-11-08 AU AU2012334066A patent/AU2012334066A1/en not_active Abandoned
- 2012-11-08 HK HK15102577.0A patent/HK1202116A1/xx unknown
- 2012-11-08 AR ARP120104203A patent/AR088701A1/es unknown
- 2012-11-08 MX MX2014005611A patent/MX2014005611A/es not_active Application Discontinuation
- 2012-11-08 CN CN201280055195.9A patent/CN103906736A/zh active Pending
- 2012-11-08 TW TW101141482A patent/TW201326134A/zh unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IN2014KN00847A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 2015-10-02 |
| BR112014010957A2 (pt) | 2017-06-06 |
| CA2854935A1 (en) | 2013-05-16 |
| HK1202116A1 (en) | 2015-09-18 |
| AU2012334066A1 (en) | 2014-05-22 |
| TW201326134A (zh) | 2013-07-01 |
| AR088701A1 (es) | 2014-06-25 |
| KR20140096351A (ko) | 2014-08-05 |
| JP2014532742A (ja) | 2014-12-08 |
| WO2013068462A1 (en) | 2013-05-16 |
| EP2776399A1 (en) | 2014-09-17 |
| CN103906736A (zh) | 2014-07-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FA | Abandonment or withdrawal |