JP5080260B2 - バニロイドｔｒｐｖ１受容体に拮抗するスルホンアミド化合物 - Google Patents
バニロイドｔｒｐｖ１受容体に拮抗するスルホンアミド化合物 Download PDFInfo
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- JP5080260B2 JP5080260B2 JP2007537190A JP2007537190A JP5080260B2 JP 5080260 B2 JP5080260 B2 JP 5080260B2 JP 2007537190 A JP2007537190 A JP 2007537190A JP 2007537190 A JP2007537190 A JP 2007537190A JP 5080260 B2 JP5080260 B2 JP 5080260B2
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- benzyl
- methoxy
- hydroxy
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- -1 Sulfonamide compounds Chemical class 0.000 title claims description 15
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- 102000015336 Nerve Growth Factor Human genes 0.000 description 1
- 208000007920 Neurogenic Inflammation Diseases 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229940126422 TRPV1 antagonist Drugs 0.000 description 1
- 108010037150 Transient Receptor Potential Channels Proteins 0.000 description 1
- 102000011753 Transient Receptor Potential Channels Human genes 0.000 description 1
- LJOOWESTVASNOG-UFJKPHDISA-N [(1s,3r,4ar,7s,8s,8as)-3-hydroxy-8-[2-[(4r)-4-hydroxy-6-oxooxan-2-yl]ethyl]-7-methyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl] (2s)-2-methylbutanoate Chemical compound C([C@H]1[C@@H](C)C=C[C@H]2C[C@@H](O)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)CC1C[C@@H](O)CC(=O)O1 LJOOWESTVASNOG-UFJKPHDISA-N 0.000 description 1
- LGDAGYXJBDILKZ-UHFFFAOYSA-N [2-methyl-1,1-dioxo-3-(pyridin-2-ylcarbamoyl)-1$l^{6},2-benzothiazin-4-yl] 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)OC=1C2=CC=CC=C2S(=O)(=O)N(C)C=1C(=O)NC1=CC=CC=N1 LGDAGYXJBDILKZ-UHFFFAOYSA-N 0.000 description 1
- QLIVJHPAXXVACX-UHFFFAOYSA-N [4-(acetamidomethyl)-2-methoxyphenyl] acetate;acetyl acetate Chemical compound CC(=O)OC(C)=O.COC1=CC(CNC(C)=O)=CC=C1OC(C)=O QLIVJHPAXXVACX-UHFFFAOYSA-N 0.000 description 1
- JWUHYRWHQWUEOC-UHFFFAOYSA-N [4-(acetamidomethyl)-5-chloro-2-methoxyphenyl] acetate 1-chloropyrrolidine-2,5-dione Chemical compound ClN1C(CCC1=O)=O.ClC1=C(CNC(C)=O)C=C(C(=C1)OC(C)=O)OC JWUHYRWHQWUEOC-UHFFFAOYSA-N 0.000 description 1
- WLCCGBFJINRVGU-UHFFFAOYSA-N [4-(acetamidomethyl)-5-iodo-2-methoxyphenyl] acetate Chemical compound COC1=CC(CNC(C)=O)=C(I)C=C1OC(C)=O WLCCGBFJINRVGU-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 230000003042 antagnostic effect Effects 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 239000012131 assay buffer Substances 0.000 description 1
- KGNDCEVUMONOKF-UGPLYTSKSA-N benzyl n-[(2r)-1-[(2s,4r)-2-[[(2s)-6-amino-1-(1,3-benzoxazol-2-yl)-1,1-dihydroxyhexan-2-yl]carbamoyl]-4-[(4-methylphenyl)methoxy]pyrrolidin-1-yl]-1-oxo-4-phenylbutan-2-yl]carbamate Chemical compound C1=CC(C)=CC=C1CO[C@H]1CN(C(=O)[C@@H](CCC=2C=CC=CC=2)NC(=O)OCC=2C=CC=CC=2)[C@H](C(=O)N[C@@H](CCCCN)C(O)(O)C=2OC3=CC=CC=C3N=2)C1 KGNDCEVUMONOKF-UGPLYTSKSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 238000011088 calibration curve Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 238000012875 competitive assay Methods 0.000 description 1
- 230000009137 competitive binding Effects 0.000 description 1
- 229940126543 compound 14 Drugs 0.000 description 1
- 229940125833 compound 23 Drugs 0.000 description 1
- 229940127204 compound 29 Drugs 0.000 description 1
- 210000000795 conjunctiva Anatomy 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229960000684 cytarabine Drugs 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 229940088598 enzyme Drugs 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 238000003818 flash chromatography Methods 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000010191 image analysis Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 230000003834 intracellular effect Effects 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 150000002540 isothiocyanates Chemical class 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000010413 mother solution Substances 0.000 description 1
- IXTPVFWNVNHEGT-UHFFFAOYSA-N n-[4-(2-phenylethylsulfamoyl)phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1S(=O)(=O)NCCC1=CC=CC=C1 IXTPVFWNVNHEGT-UHFFFAOYSA-N 0.000 description 1
- 229940053128 nerve growth factor Drugs 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000009871 nonspecific binding Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 230000036407 pain Effects 0.000 description 1
- 210000003200 peritoneal cavity Anatomy 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 238000003653 radioligand binding assay Methods 0.000 description 1
- 229940044551 receptor antagonist Drugs 0.000 description 1
- 239000002464 receptor antagonist Substances 0.000 description 1
- 102000005962 receptors Human genes 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 230000027425 release of sequestered calcium ion into cytosol Effects 0.000 description 1
- 238000003345 scintillation counting Methods 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 238000013222 sprague-dawley male rat Methods 0.000 description 1
- 238000012453 sprague-dawley rat model Methods 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 239000000085 vanilloid receptor antagonist Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C335/04—Derivatives of thiourea
- C07C335/16—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C335/18—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by singly-bound oxygen atoms
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/30—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/45—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups at least one of the singly-bound nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom, e.g. N-acylaminosulfonamides
- C07C311/47—Y being a hetero atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C335/04—Derivatives of thiourea
- C07C335/06—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to acyclic carbon atoms
- C07C335/10—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to acyclic carbon atoms of an unsaturated carbon skeleton
- C07C335/12—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to acyclic carbon atoms of an unsaturated carbon skeleton the carbon skeleton containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C335/04—Derivatives of thiourea
- C07C335/16—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ITMI2004A002042 | 2004-10-26 | ||
| IT002042A ITMI20042042A1 (it) | 2004-10-26 | 2004-10-26 | Derivati solfonammidici antagonisti del recettore dei vanilloidi trpv1 |
| PCT/EP2005/011206 WO2006045498A1 (en) | 2004-10-26 | 2005-10-18 | Sulfonamido compounds that antagonise the vanilloid trpv1 receptor |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2008517884A JP2008517884A (ja) | 2008-05-29 |
| JP2008517884A5 JP2008517884A5 (enExample) | 2008-12-25 |
| JP5080260B2 true JP5080260B2 (ja) | 2012-11-21 |
Family
ID=35501228
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007537190A Expired - Fee Related JP5080260B2 (ja) | 2004-10-26 | 2005-10-18 | バニロイドｔｒｐｖ１受容体に拮抗するスルホンアミド化合物 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US7579378B2 (enExample) |
| EP (1) | EP1805138B1 (enExample) |
| JP (1) | JP5080260B2 (enExample) |
| AT (1) | ATE389634T1 (enExample) |
| DE (1) | DE602005005512T2 (enExample) |
| ES (1) | ES2303275T3 (enExample) |
| IT (1) | ITMI20042042A1 (enExample) |
| WO (1) | WO2006045498A1 (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2006225496A1 (en) * | 2005-03-19 | 2006-09-28 | Amorepacific Corporation | Novel compounds, isomer thereof, or pharmaceutically acceptable salts thereof as vanilloid receptor antagonist; and pharmaceutical compositions containing the same |
| WO2009081222A1 (en) | 2007-12-21 | 2009-07-02 | Glenmark Pharmaceuticals, S.A. | Substituted tricyclic pyridine or pyrimidine vanilloid receptor ligands |
| CN106146362B (zh) * | 2015-04-15 | 2018-04-03 | 南京理工大学 | 一种合成c‑7280948的方法 |
| CN107759477A (zh) * | 2017-11-20 | 2018-03-06 | 阿里化学(常州)有限公司 | 一种对硝基苯乙胺盐酸盐的生产制备方法 |
| EP4074317A1 (en) | 2021-04-14 | 2022-10-19 | Bayer AG | Phosphorus derivatives as novel sos1 inhibitors |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2154323C (en) * | 1994-07-21 | 2001-03-27 | Tomoaki Nagai | Aminobenzenesulfonamide derivative and recording medium using the same |
| AU2001280229B2 (en) | 2000-08-21 | 2006-12-07 | Pacific Corporation | Novel thiourea derivatives and the pharmaceutical compositions containing the same |
| JP2004506714A (ja) * | 2000-08-21 | 2004-03-04 | パシフィック コーポレーション | 新規チオ尿素化合物及びこれを含有する薬学的組成物 |
| WO2002070467A1 (en) * | 2001-02-26 | 2002-09-12 | 4Sc Ag | Derivatives of diphenylurea, diphenyloxalic acid diamide and diphenylsulfuric acid diamide and their use as medicaments |
-
2004
- 2004-10-26 IT IT002042A patent/ITMI20042042A1/it unknown
-
2005
- 2005-10-18 JP JP2007537190A patent/JP5080260B2/ja not_active Expired - Fee Related
- 2005-10-18 DE DE602005005512T patent/DE602005005512T2/de not_active Expired - Lifetime
- 2005-10-18 US US11/577,857 patent/US7579378B2/en not_active Expired - Fee Related
- 2005-10-18 EP EP05796943A patent/EP1805138B1/en not_active Expired - Lifetime
- 2005-10-18 WO PCT/EP2005/011206 patent/WO2006045498A1/en not_active Ceased
- 2005-10-18 ES ES05796943T patent/ES2303275T3/es not_active Expired - Lifetime
- 2005-10-18 AT AT05796943T patent/ATE389634T1/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| US20090118374A1 (en) | 2009-05-07 |
| ATE389634T1 (de) | 2008-04-15 |
| US7579378B2 (en) | 2009-08-25 |
| ES2303275T3 (es) | 2008-08-01 |
| WO2006045498A1 (en) | 2006-05-04 |
| DE602005005512D1 (de) | 2008-04-30 |
| EP1805138B1 (en) | 2008-03-19 |
| ITMI20042042A1 (it) | 2005-01-26 |
| EP1805138A1 (en) | 2007-07-11 |
| JP2008517884A (ja) | 2008-05-29 |
| DE602005005512T2 (de) | 2009-04-16 |
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