IL132107A - Substituted phenyl derivatives, their preparation and use - Google Patents
Substituted phenyl derivatives, their preparation and useInfo
- Publication number
- IL132107A IL132107A IL13210798A IL13210798A IL132107A IL 132107 A IL132107 A IL 132107A IL 13210798 A IL13210798 A IL 13210798A IL 13210798 A IL13210798 A IL 13210798A IL 132107 A IL132107 A IL 132107A
- Authority
- IL
- Israel
- Prior art keywords
- urea
- hydroxy
- tetrazolyl
- phenyl
- compound
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 title claims description 13
- 150000001875 compounds Chemical class 0.000 claims abstract description 76
- 208000007056 sickle cell anemia Diseases 0.000 claims abstract description 20
- 150000003839 salts Chemical class 0.000 claims abstract description 19
- LUBJCRLGQSPQNN-UHFFFAOYSA-N 1-Phenylurea Chemical compound NC(=O)NC1=CC=CC=C1 LUBJCRLGQSPQNN-UHFFFAOYSA-N 0.000 claims description 102
- -1 2-hydroxy-4-oxo-pyrimidyl Chemical group 0.000 claims description 92
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 31
- 108010062745 Chloride Channels Proteins 0.000 claims description 27
- 102000011045 Chloride Channels Human genes 0.000 claims description 27
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 25
- 239000004202 carbamide Substances 0.000 claims description 17
- 208000035475 disorder Diseases 0.000 claims description 17
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 16
- 201000010099 disease Diseases 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 13
- 125000001072 heteroaryl group Chemical group 0.000 claims description 12
- 206010048962 Brain oedema Diseases 0.000 claims description 11
- 208000010412 Glaucoma Diseases 0.000 claims description 11
- 206010012735 Diarrhoea Diseases 0.000 claims description 10
- 206010020772 Hypertension Diseases 0.000 claims description 10
- 206010028980 Neoplasm Diseases 0.000 claims description 10
- 208000001132 Osteoporosis Diseases 0.000 claims description 10
- 239000002934 diuretic Substances 0.000 claims description 10
- 230000001882 diuretic effect Effects 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 208000028867 ischemia Diseases 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- 239000008194 pharmaceutical composition Substances 0.000 claims description 9
- 239000004305 biphenyl Substances 0.000 claims description 8
- 235000010290 biphenyl Nutrition 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 241001465754 Metazoa Species 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 6
- 150000002431 hydrogen Chemical group 0.000 claims description 6
- 125000003282 alkyl amino group Chemical group 0.000 claims description 5
- 230000000172 allergic effect Effects 0.000 claims description 5
- 208000010668 atopic eczema Diseases 0.000 claims description 5
- 125000004122 cyclic group Chemical group 0.000 claims description 5
- 230000004968 inflammatory condition Effects 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 208000025865 Ulcer Diseases 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 4
- 231100000397 ulcer Toxicity 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- JFGXFYKXRPMSJT-UHFFFAOYSA-N 1-[4-bromo-2-(2h-tetrazol-5-yl)phenyl]-1-(3-pyridin-3-ylphenyl)urea Chemical compound C=1C=C(Br)C=C(C=2NN=NN=2)C=1N(C(=O)N)C(C=1)=CC=CC=1C1=CC=CN=C1 JFGXFYKXRPMSJT-UHFFFAOYSA-N 0.000 claims description 2
- GAHLXGAQEUNMBN-UHFFFAOYSA-N 4-[4-[n-carbamoyl-3-(trifluoromethyl)anilino]-3-(2h-tetrazol-5-yl)phenyl]-n,n-diethylbenzamide Chemical compound C1=CC(C(=O)N(CC)CC)=CC=C1C(C=C1C=2NN=NN=2)=CC=C1N(C(N)=O)C1=CC=CC(C(F)(F)F)=C1 GAHLXGAQEUNMBN-UHFFFAOYSA-N 0.000 claims description 2
- 238000007796 conventional method Methods 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- ZSRNFXQWCQXPSR-UHFFFAOYSA-N [4-(2-phenylphenyl)-2-(2h-tetrazol-5-yl)phenyl]urea Chemical compound NC(=O)NC1=CC=C(C=2C(=CC=CC=2)C=2C=CC=CC=2)C=C1C1=NN=NN1 ZSRNFXQWCQXPSR-UHFFFAOYSA-N 0.000 claims 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 33
- 239000000243 solution Substances 0.000 description 29
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 15
- 150000003536 tetrazoles Chemical class 0.000 description 14
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- 230000003389 potentiating effect Effects 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
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- SIAVMDKGVRXFAX-UHFFFAOYSA-N 4-carboxyphenylboronic acid Chemical compound OB(O)C1=CC=C(C(O)=O)C=C1 SIAVMDKGVRXFAX-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 108010010803 Gelatin Proteins 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
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- SYVZTFRUMHJQIR-UHFFFAOYSA-N 1-[2-(4-hydroxy-1,2,4-triazol-3-yl)phenyl]-1-[3-(trifluoromethyl)phenyl]urea Chemical compound C=1C=CC=C(C=2N(C=NN=2)O)C=1N(C(=O)N)C1=CC=CC(C(F)(F)F)=C1 SYVZTFRUMHJQIR-UHFFFAOYSA-N 0.000 description 2
- AVGUGCMPZHFFFN-UHFFFAOYSA-N 1-[4-naphthalen-1-yl-2-(2h-tetrazol-5-yl)phenyl]-1-[3-(trifluoromethyl)phenyl]urea Chemical compound C=1C=C(C=2C3=CC=CC=C3C=CC=2)C=C(C=2NN=NN=2)C=1N(C(=O)N)C1=CC=CC(C(F)(F)F)=C1 AVGUGCMPZHFFFN-UHFFFAOYSA-N 0.000 description 2
- HSKRHNHJEOBQPN-UHFFFAOYSA-N 2-[n-carbamoyl-3-(trifluoromethyl)anilino]benzoic acid Chemical compound C=1C=CC=C(C(O)=O)C=1N(C(=O)N)C1=CC=CC(C(F)(F)F)=C1 HSKRHNHJEOBQPN-UHFFFAOYSA-N 0.000 description 2
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 2
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Classifications
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- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C275/42—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by carboxyl groups
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/45—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
- C07C233/53—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
- C07C233/55—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring having the carbon atom of the carboxamide group bound to a carbon atom of an unsaturated carbon skeleton
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- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
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- C07C271/40—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of six-membered aromatic rings
- C07C271/58—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of six-membered aromatic rings with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C275/40—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by nitrogen atoms not being part of nitro or nitroso groups
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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
- C07C309/45—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton
- C07C309/51—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton at least one of the nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom
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- C—CHEMISTRY; METALLURGY
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- 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
- C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
- C07C311/02—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C311/08—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
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- 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
- C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
- C07C311/21—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
-
- 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
-
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- 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
- C07C311/50—Compounds containing any of the groups, X being a hetero atom, Y being any atom
- C07C311/52—Y being a hetero atom
- C07C311/54—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea
- C07C311/57—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea having sulfur atoms of the sulfonylurea groups bound to carbon atoms of six-membered aromatic rings
- C07C311/60—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea having sulfur atoms of the sulfonylurea groups bound to carbon atoms of six-membered aromatic rings having nitrogen atoms of the sulfonylurea groups bound to carbon atoms of six-membered aromatic rings
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- 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
- C07C335/22—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 carboxyl groups
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- Veterinary Medicine (AREA)
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- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
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- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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DK45297 | 1997-04-22 | ||
PCT/DK1998/000162 WO1998047879A1 (en) | 1997-04-22 | 1998-04-21 | Substituted phenyl derivatives, their preparation and use |
Publications (2)
Publication Number | Publication Date |
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IL132107A0 IL132107A0 (en) | 2001-03-19 |
IL132107A true IL132107A (en) | 2004-09-27 |
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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IL13210798A IL132107A (en) | 1997-04-22 | 1998-04-21 | Substituted phenyl derivatives, their preparation and use |
Country Status (19)
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US (1) | US6297261B1 (cs) |
EP (1) | EP0977741B1 (cs) |
JP (1) | JP2001521532A (cs) |
CN (1) | CN1118462C (cs) |
AT (1) | ATE248824T1 (cs) |
AU (1) | AU728520B2 (cs) |
BR (1) | BR9808938A (cs) |
CA (1) | CA2285424A1 (cs) |
CZ (1) | CZ295822B6 (cs) |
DE (1) | DE69817802T2 (cs) |
DK (1) | DK0977741T3 (cs) |
ES (1) | ES2205472T3 (cs) |
IL (1) | IL132107A (cs) |
NZ (1) | NZ337976A (cs) |
PT (1) | PT977741E (cs) |
RU (1) | RU2197482C2 (cs) |
SK (1) | SK282818B6 (cs) |
TR (1) | TR199902593T2 (cs) |
WO (1) | WO1998047879A1 (cs) |
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US6696475B2 (en) | 1997-04-22 | 2004-02-24 | Neurosearch A/S | Substituted phenyl derivatives, their preparation and use |
CN1213022C (zh) * | 1997-12-22 | 2005-08-03 | 拜尔有限公司 | 用对称和不对称的取代二苯脲抑制raf激酶 |
EE04849B1 (et) * | 1998-10-22 | 2007-06-15 | Neurosearch A/S | Asendatud fenüülderivaadid, nende valmistamine jakasutamine |
US20050080112A1 (en) * | 2001-06-22 | 2005-04-14 | Madsen Lars Siim | Compounds for use in disorders associated with mast cell or basophil acitvity |
US7087631B2 (en) * | 2002-07-18 | 2006-08-08 | Inotek Pharmaceuticals Corporation | Aryltetrazole compounds, and compositions thereof |
US7078423B2 (en) * | 2002-07-18 | 2006-07-18 | Inotek Pharmaceuticals Corporation | 5-Aryltetrazole compounds, compositions thereof, and uses therefor |
JP2005537336A (ja) * | 2002-08-01 | 2005-12-08 | ニューロサーチ、アクティーゼルスカブ | 抗血管新生治療に応答する疾患の治療に有用な化合物 |
WO2004022525A1 (en) * | 2002-09-05 | 2004-03-18 | Neurosearch A/S | Amide derivatives and their use as chloride channel blockers |
MXPA05002493A (es) * | 2002-09-05 | 2005-05-27 | Neurosearch As | Derivados de diarilurea y su uso como bloqueadores del canal del cloro. |
AU2003282920A1 (en) * | 2002-10-04 | 2004-05-04 | Bristol-Myers Squibb Company | Hydantoin derivatives as inhibitors of matrix metalloproteinases and/or tnf-alpha converting enzyme (tace) |
US7521480B2 (en) | 2002-11-21 | 2009-04-21 | Neurosearch | Aryl ureido benzoic acid derivatives and their use |
WO2004058722A1 (en) * | 2002-12-24 | 2004-07-15 | Arena Pharmaceuticals, Inc. | Diarylamine and arylheteroarylamine pyrazole derivatives as modulators of 5ht2a |
BRPI0410576A (pt) * | 2003-06-17 | 2006-06-20 | Neurosearch As | composto quìmico, composição farmacêutica, uso de um composto ou um sal farmaceuticamente aceitável do mesmo, e, método para o tratamento, prevenção ou alìvio de uma doença ou um distúrbio ou condição de um corpo de animal vivo |
JP4198733B2 (ja) | 2003-07-22 | 2008-12-17 | アリーナ ファーマシューティカルズ, インコーポレイテッド | 関連性障害の予防および処置に有用な、5−ht2aセロトニンレセプターのモジュレーターとしてのジアリールおよびアリールへテロアリールウレア誘導体 |
US7202363B2 (en) | 2003-07-24 | 2007-04-10 | Abbott Laboratories | Thienopyridine and furopyridine kinase inhibitors |
WO2005023238A1 (en) * | 2003-09-04 | 2005-03-17 | Poseidon Pharmaceuticals A/S | Erg channel openers for the treatment of hyperexcitability-related neuronal diseases |
ATE415959T1 (de) | 2003-09-04 | 2008-12-15 | Neurosearch As | Herg1-kanal-öffner zur behandlung von herzarrythmien |
US20080045546A1 (en) * | 2003-10-15 | 2008-02-21 | Axel Bouchon | Tetradydro-Naphthalene And Urea Derivatives |
US20090253908A1 (en) * | 2004-03-11 | 2009-10-08 | Glaxo Group Limited | Novel m3 muscarinic acetylchoine receptor antagonists |
ATE548353T1 (de) * | 2004-03-23 | 2012-03-15 | Arena Pharm Inc | Verfahren zur herstellung von substituierte n- aryl-n'-ä3-(1h-pyrazol-5-yl)phenylü-harnstoffe and intermediate davon. |
PE20061130A1 (es) | 2004-11-19 | 2007-01-05 | Arena Pharm Inc | Derivados de 3-fenil-pirazol como moduladores del receptor de serotonina 5-ht2a |
AU2005321946B2 (en) * | 2004-12-23 | 2012-08-16 | Deciphera Pharmaceuticals, Llc | Enzyme modulators and treatments |
EA016675B1 (ru) | 2006-05-18 | 2012-06-29 | Арена Фармасьютикалз, Инк. | Способы получения фенилпиразолов и кристаллическая форма производного фенилпиразола |
EP2018371B1 (en) | 2006-05-18 | 2015-03-04 | Arena Pharmaceuticals, Inc. | Primary amines and derivatives thereof as modulators of the 5-ht2a serotonin receptor useful for the treatment of disorders related thereto |
US8148418B2 (en) | 2006-05-18 | 2012-04-03 | Arena Pharmaceuticals, Inc. | Ethers, secondary amines and derivatives thereof as modulators of the 5-HT2A serotonin receptor useful for the treatment of disorders related thereto |
TWI415845B (zh) | 2006-10-03 | 2013-11-21 | Arena Pharm Inc | 用於治療與5-ht2a血清素受體相關聯病症之作為5-ht2a血清素受體之調節劑的吡唑衍生物 |
US7790756B2 (en) * | 2006-10-11 | 2010-09-07 | Deciphera Pharmaceuticals, Llc | Kinase inhibitors useful for the treatment of myleoproliferative diseases and other proliferative diseases |
EP2152677A1 (en) | 2007-05-03 | 2010-02-17 | NeuroSearch A/S | Acetamide derivatives as potassium channel modulators |
EP2190844B3 (en) | 2007-08-15 | 2013-07-17 | Arena Pharmaceuticals, Inc. | Imidazo[1,2-a]pyridine derivatives as modulators of the 5-ht2a serotonin receptor useful for the treatment of disorders related thereto |
US20110021538A1 (en) | 2008-04-02 | 2011-01-27 | Arena Pharmaceuticals, Inc. | Processes for the preparation of pyrazole derivatives useful as modulators of the 5-ht2a serotonin receptor |
RS57110B1 (sr) | 2008-10-28 | 2018-06-29 | Arena Pharm Inc | Sastavi modulatora 5-ht2a serotoninskog receptora korisni za tretiranje poremećaja povezanih sa njim |
WO2010062321A1 (en) | 2008-10-28 | 2010-06-03 | Arena Pharmaceuticals, Inc. | Processes useful for the preparation of 1-[3-(4-bromo-2-methyl-2h-pyrazol-3-yl)-4-methoxy-phenyl]-3-(2,4-difluoro-phenyl)-urea and crystalline forms related thereto |
CN102239171B (zh) | 2008-12-05 | 2014-06-11 | 艾伯维巴哈马有限公司 | 作为激酶抑制剂用于治疗癌症的噻吩并[3,2-c]吡啶衍生物 |
WO2011075596A1 (en) | 2009-12-18 | 2011-06-23 | Arena Pharmaceuticals, Inc. | Crystalline forms of certain 3-phenyl-pyrazole derivatives as modulators of the 5-ht2a serotonin receptor useful for the treatment of disorders related thereto |
US8436179B2 (en) | 2011-07-20 | 2013-05-07 | Abbvie Inc. | Kinase inhibitor with improved solubility profile |
CN103709185A (zh) * | 2013-12-30 | 2014-04-09 | 大连联化医药技术有限公司 | 一种4-(n-甲基甲酰氨)苯基硼酸的制备方法 |
RU2017145976A (ru) | 2015-06-12 | 2019-07-15 | Аксовант Сайенсиз Гмбх | Производные диарил- и арилгетероарилмочевины, применимые для профилактики и лечения нарушения поведения во время REM-фазы сна |
CA2992518A1 (en) | 2015-07-15 | 2017-01-19 | Axovant Sciences Gmbh | Diaryl and arylheteroaryl urea derivatives as modulators of the 5-ht2a serotonin receptor useful for the prophylaxis and treatment of hallucinations associated with a neurodegenerative disease |
ES2770374T3 (es) | 2016-05-17 | 2020-07-01 | Scandion Oncology As | Tratamiento combinado de cáncer |
EP3651752B1 (en) | 2017-07-11 | 2024-11-20 | Vertex Pharmaceuticals Incorporated | Carboxamides as modulators of sodium channels |
CN117229258B (zh) * | 2022-06-07 | 2024-07-19 | 杭州壹瑞医药科技有限公司 | N-四唑基芳基脲类衍生物及其制备方法和应用 |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3682136D1 (de) | 1985-07-31 | 1991-11-28 | Hoechst Ag | N-substituierte 5-nitroanthranilsaeuren, verfahren zu ihrer herstellung, ihre verwendung sowie pharmazeutische praeparate auf basis dieser verbindungen. |
US4889612A (en) | 1987-05-22 | 1989-12-26 | Abbott Laboratories | Ion-selective electrode having a non-metal sensing element |
US5489612A (en) | 1991-08-23 | 1996-02-06 | The University Of Alabama At Birmingham Research Foundation | Calixarene chloride-channel blockers |
US5273992A (en) | 1992-11-02 | 1993-12-28 | Beth Israel Hospital Assoc. Inc. | Method for reducing sickle erythrocyte dehydration and delaying the occurrence of erythrocyte sickling in-situ |
DK41193D0 (da) * | 1993-04-07 | 1993-04-07 | Neurosearch As | Ionkanalaabnere |
US5362744A (en) | 1993-11-22 | 1994-11-08 | Warner-Lambert Company | Tetrazole-substituted urea acat inhibitors |
US5559151A (en) | 1994-11-30 | 1996-09-24 | Allergan | Method for reducing intraocular pressure in the mammalian eye by administration of chloride channel blockers |
US6417393B1 (en) * | 1996-05-24 | 2002-07-09 | Neurosearch A/S | Phenyl derivatives containing an acidic group, their preparation and their use as chloride channel blockers |
JP2000510862A (ja) | 1996-05-24 | 2000-08-22 | ニューロサーチ・アクティーゼルスカブ | クロライドチャンネル遮断剤として有用なフエニル誘導体 |
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1998
- 1998-04-21 CN CN98804446A patent/CN1118462C/zh not_active Expired - Fee Related
- 1998-04-21 NZ NZ337976A patent/NZ337976A/en unknown
- 1998-04-21 SK SK1447-99A patent/SK282818B6/sk not_active IP Right Cessation
- 1998-04-21 US US09/402,165 patent/US6297261B1/en not_active Expired - Fee Related
- 1998-04-21 IL IL13210798A patent/IL132107A/en not_active IP Right Cessation
- 1998-04-21 TR TR1999/02593T patent/TR199902593T2/xx unknown
- 1998-04-21 JP JP54475998A patent/JP2001521532A/ja not_active Abandoned
- 1998-04-21 DK DK98914851T patent/DK0977741T3/da active
- 1998-04-21 EP EP98914851A patent/EP0977741B1/en not_active Expired - Lifetime
- 1998-04-21 PT PT98914851T patent/PT977741E/pt unknown
- 1998-04-21 DE DE69817802T patent/DE69817802T2/de not_active Expired - Lifetime
- 1998-04-21 ES ES98914851T patent/ES2205472T3/es not_active Expired - Lifetime
- 1998-04-21 RU RU99124188/04A patent/RU2197482C2/ru not_active IP Right Cessation
- 1998-04-21 WO PCT/DK1998/000162 patent/WO1998047879A1/en active IP Right Grant
- 1998-04-21 CZ CZ19993699A patent/CZ295822B6/cs not_active IP Right Cessation
- 1998-04-21 BR BR9808938-2A patent/BR9808938A/pt not_active Application Discontinuation
- 1998-04-21 CA CA002285424A patent/CA2285424A1/en not_active Abandoned
- 1998-04-21 AU AU69196/98A patent/AU728520B2/en not_active Ceased
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DK0977741T3 (da) | 2003-12-01 |
DE69817802D1 (de) | 2003-10-09 |
NZ337976A (en) | 2001-05-25 |
RU2197482C2 (ru) | 2003-01-27 |
CN1253553A (zh) | 2000-05-17 |
EP0977741B1 (en) | 2003-09-03 |
SK282818B6 (sk) | 2002-12-03 |
US6297261B1 (en) | 2001-10-02 |
EP0977741A1 (en) | 2000-02-09 |
DE69817802T2 (de) | 2004-04-08 |
IL132107A0 (en) | 2001-03-19 |
AU728520B2 (en) | 2001-01-11 |
CZ295822B6 (cs) | 2005-11-16 |
PT977741E (pt) | 2004-01-30 |
SK144799A3 (en) | 2000-05-16 |
CN1118462C (zh) | 2003-08-20 |
TR199902593T2 (xx) | 2000-03-21 |
WO1998047879A1 (en) | 1998-10-29 |
BR9808938A (pt) | 2000-08-01 |
HK1026909A1 (en) | 2000-12-29 |
CZ369999A3 (cs) | 2000-02-16 |
ATE248824T1 (de) | 2003-09-15 |
AU6919698A (en) | 1998-11-13 |
ES2205472T3 (es) | 2004-05-01 |
CA2285424A1 (en) | 1998-10-29 |
JP2001521532A (ja) | 2001-11-06 |
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