WO2004058720A2 - Compound libraries of 1,3,5-substitute indazole derivatives as compounds for targetting compounds capable of binding to the g-protein coupled receptor - Google Patents
Compound libraries of 1,3,5-substitute indazole derivatives as compounds for targetting compounds capable of binding to the g-protein coupled receptor Download PDFInfo
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- WO2004058720A2 WO2004058720A2 PCT/GB2003/005650 GB0305650W WO2004058720A2 WO 2004058720 A2 WO2004058720 A2 WO 2004058720A2 GB 0305650 W GB0305650 W GB 0305650W WO 2004058720 A2 WO2004058720 A2 WO 2004058720A2
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- 0 CS(c1ccc2nc(*)[s]c2c1)(=O)=O Chemical compound CS(c1ccc2nc(*)[s]c2c1)(=O)=O 0.000 description 37
- IYSAOZFRXQYCDR-UHFFFAOYSA-N CCC(Nc(cc1)ccc1Oc1ccccc1)=O Chemical compound CCC(Nc(cc1)ccc1Oc1ccccc1)=O IYSAOZFRXQYCDR-UHFFFAOYSA-N 0.000 description 1
- FVUFTABOJFRHSU-UHFFFAOYSA-N COc(cc1)cc([s]2)c1nc2Cl Chemical compound COc(cc1)cc([s]2)c1nc2Cl FVUFTABOJFRHSU-UHFFFAOYSA-N 0.000 description 1
- LVFRCHIUUKWBLR-UHFFFAOYSA-N COc1cc(OC)nc(N)n1 Chemical compound COc1cc(OC)nc(N)n1 LVFRCHIUUKWBLR-UHFFFAOYSA-N 0.000 description 1
- SMDXMKNQGRCNRE-UHFFFAOYSA-N CS(c(cc1)cc([s]2)c1nc2Cl)(=O)=O Chemical compound CS(c(cc1)cc([s]2)c1nc2Cl)(=O)=O SMDXMKNQGRCNRE-UHFFFAOYSA-N 0.000 description 1
- UENBBJXGCWILBM-UHFFFAOYSA-N Cc(nc1)ccc1N Chemical compound Cc(nc1)ccc1N UENBBJXGCWILBM-UHFFFAOYSA-N 0.000 description 1
- KNDOFJFSHZCKGT-UHFFFAOYSA-N Clc1ccnc2ccccc12 Chemical compound Clc1ccnc2ccccc12 KNDOFJFSHZCKGT-UHFFFAOYSA-N 0.000 description 1
- KLEYVGWAORGTIT-UHFFFAOYSA-N Clc1ncc[s]1 Chemical compound Clc1ncc[s]1 KLEYVGWAORGTIT-UHFFFAOYSA-N 0.000 description 1
- RWDRRVXXFFXKMM-UHFFFAOYSA-N NC(Nc(cc1)cc2c1OCO2)=O Chemical compound NC(Nc(cc1)cc2c1OCO2)=O RWDRRVXXFFXKMM-UHFFFAOYSA-N 0.000 description 1
- NAHHNSMHYCLMON-UHFFFAOYSA-N NCCc1cnccc1 Chemical compound NCCc1cnccc1 NAHHNSMHYCLMON-UHFFFAOYSA-N 0.000 description 1
- DDRPCXLAQZKBJP-UHFFFAOYSA-N NCc1ccc[o]1 Chemical compound NCc1ccc[o]1 DDRPCXLAQZKBJP-UHFFFAOYSA-N 0.000 description 1
- TVOSOIXYPHKEAR-UHFFFAOYSA-N Nc(cc1)ccc1N1CCCCC1 Chemical compound Nc(cc1)ccc1N1CCCCC1 TVOSOIXYPHKEAR-UHFFFAOYSA-N 0.000 description 1
- ICSNLGPSRYBMBD-UHFFFAOYSA-N Nc1ccccn1 Chemical compound Nc1ccccn1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 1
- UHGULLIUJBCTEF-UHFFFAOYSA-N Nc1nc2ccccc2[s]1 Chemical compound Nc1nc2ccccc2[s]1 UHGULLIUJBCTEF-UHFFFAOYSA-N 0.000 description 1
- UZXIGICHRPRUAI-UHFFFAOYSA-N O=C(c1n[n](Cc(cc2)ccc2OCc2ccccc2)c2ccccc12)Nc1ccc(C(F)(F)F)cc1 Chemical compound O=C(c1n[n](Cc(cc2)ccc2OCc2ccccc2)c2ccccc12)Nc1ccc(C(F)(F)F)cc1 UZXIGICHRPRUAI-UHFFFAOYSA-N 0.000 description 1
Classifications
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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
- A61K31/41—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
- A61K31/4164—1,3-Diazoles
- A61K31/4184—1,3-Diazoles condensed with carbocyclic rings, e.g. benzimidazoles
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/438—The ring being spiro-condensed with carbocyclic or heterocyclic ring systems
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4747—Quinolines; Isoquinolines spiro-condensed
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having 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
- C07D241/20—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having 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
- C07D241/24—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/10—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing aromatic rings
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/10—Spiro-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C40—COMBINATORIAL TECHNOLOGY
- C40B—COMBINATORIAL CHEMISTRY; LIBRARIES, e.g. CHEMICAL LIBRARIES
- C40B40/00—Libraries per se, e.g. arrays, mixtures
- C40B40/04—Libraries containing only organic compounds
-
- C—CHEMISTRY; METALLURGY
- C40—COMBINATORIAL TECHNOLOGY
- C40B—COMBINATORIAL CHEMISTRY; LIBRARIES, e.g. CHEMICAL LIBRARIES
- C40B50/00—Methods of creating libraries, e.g. combinatorial synthesis
- C40B50/08—Liquid phase synthesis, i.e. wherein all library building blocks are in liquid phase or in solution during library creation; Particular methods of cleavage from the liquid support
Definitions
- the present invention relates to compounds capable of binding to G-protein coupled receptors.
- a library of compounds is provided for use in screening programmes against GPCR targets as well as the individual compounds for use in hit to lead and lead optimisation projects and similar stages in the drug discovery process.
- the method also provides methods for making compounds and libraries.
- Screening libraries are commonly collections of compounds from several sources. As a result, they typically contain compounds synthesised as a part of previous projects in the history of a company. With regard to drug discovery, these collections will be drug-like but are likely to be limited in scope and will be directed to certain areas of a particular project. It has been the common practice of many pharmaceutical companies in recent times to augment the collections by purchasing either single compounds from vendors or by contracting the synthesis of combinatorial libraries of compounds. The singly purchased compounds may have been selected to fill in areas of compound space poorly ' represented in ' the compound collections. Combinatorial libraries are typically synthesised around well- performing chemistries with some design based on producing iversity' in compound space.
- a complementary approach, and one that is increasingly preferred, is to screen focused libraries against the target of choice. Focused libraries are becoming of increasing importance in their ability to generate hits capable of rapid expansion in many areas including GPCRs . Such libraries are slightly more expensive to prepare but have attributes of reliability, reproducibility and provide a considerably higher hit rate: typically 10-100 fold and above compared with random screening. They are, however, very difficult to design and their efficiency relates directly to the amount of effort that has gone into the design. Using focused libraries, it is usually possible to get a number of hits in the low micromolar and below range. As there is a defined set of compounds there is the potential to observe indications of SAR in a chemical series and progress the chemistry efficiently.
- GPCRs G-protein-coupled receptors
- the rhodopsin receptor is somewhat unusual in its interactions with its ligand and is not used as a drug target. Nevertheless the overall three dimensional arrangement can be deduced from the X-ray and is in accordance with previous work based upon bacteriorhodopsin receptor which is not G-protein-coupled.
- GPCRs are most often characterised by sequence homology as being comprised of several sub-families. Most attention currently is directed towards Family A receptors as being the most tractable class historically and also the one with the most potential targets.
- Family A comprises about 300 receptors that are potential drug targets, approximately half of which have known ligands and the rest, the so-called orphan receptors.
- the group of druggable receptors is composed essentially of two types: those whose natural ligand interacts wholly within the transmembrane domain, such as the aminergic, nucleotide-like, prostaglandin receptors, etc. and those peptide liganded receptors, which have a large part of their interactions in the extracellular region and which may insert a peptide loop or tail into the transmembrane region to effect signal transduction. Examples of this class are angiotensin, cholecystokinin and opioid receptors.
- the focused library provided herein is designed to interact with a range of the family A receptors.
- Each library is a defined set of compounds that will enhance the probability of finding a small molecule that will interact with one or more type of GPCR receptor.
- focused libraries can be provided having compounds which will interact with aminergic GPCRs, and peptidic GPCRs requiring an obligatory positive charge in ligands, or other types or groups of GPCRs.
- Focused libraries according to this invention can provide hit rates of 1-13% or more for the requisite predicted GPCRs from both amine- and peptide-liganded classes and with agonists and antagonists .
- library means a group of compounds which are structurally related by virtue of a core chemical structure (or “scaffold”) but which differ from each other by virtue of permutation of specific substituent groups attached to the scaffold.
- such a library will consist of or comprise a number of compounds, e.g. as many as about 100, 1000,2000, 3000 or indeed 10,000 compounds.
- the number of compounds should be sufficient to provide an adequate diversity of related compounds without being so large as to be unduly complex/expensive to produce.
- the substituent may appear in the compound exactly as shown (i.e. simply covalently bonded to the scaffold) or may be a derivative of the shown chemical formula of the substituent by virtue of use of a reactive group to couple the substituent to the scaffold.
- the total number of permutations created by the permitted substituents may be a very large number, far greater in magnitude than the actual number of compounds in an actual library.
- the number of possible compounds for any "virtual" library may well greatly exceed the number of synthesised compounds making up an embodiment of the "real" library.
- the invention is intended to encompass libraries having all, and a number, which is less than all, of the permitted substitutions represented by compounds therein.
- the present invention provides a novel focused library of compounds. Most of the compounds defined by the permitted substitutions on the scaffolds are also novel compounds per se and the invention is intended to encompass each individual novel compound.
- WO 03/028720 discloses 3- aminoindazole derivatives or salts thereof for treatment of diseases caused by and/or associated with an altered protein kinase activity.
- the compound library of the present invention may include the compounds disclosed in WO 03/028720, but the compound library is not identical to the class of compounds claimed in WO 03/028720. where compounds per se are generally claimed by the present invention, any compounds specifically discloses in WO 03/028720 are hereby disclaimed per se.
- Library 06 is a library that is targeted against a group of peptide liganded receptors, which can be characterised broadly as requiring an interaction with an amide or acid function interacting largely by hydrogen bonding. In addition the library picks up interactions for electron-rich aromatic rings and other interactions. Receptors that fall into the broad scope for this library include receptors like bombesin, endothelin A, galanin, and the prolactin releasing peptide receptor GPRA amongst others.
- the invention provides a compound ' library comprising or consisting of a set of structurally related compounds of the following general formulae A, B and C:
- the permitted substituents for Rl are derived from List 12 and from List 13; the permitted substituents for R2 are R9RION-# and R8S02NH-#, wherein the permitted substituents for R9R10N-# are as defined in List 14; the permitted substituents for R8S02NH-# are as defined in List 15 the permitted substituents for R3 are derived from List 12; the permitted substituents' for R5 are RllS0 2 -#, R12NHC0-#,
- R13CO-#,R140CO-#, and R15S0 2 NHCO-# wherein the permitted substituents for Rll are derived from List 16; the permitted substituents for R12 are derived from List 17; the permitted substituents for R13 are derived from List 18; the permitted substituents for R14 are derived from List 19; the permitted substituents for R15 are derived ' from
- the permitted substituents for R6 is R16S0 2 -#, wherein the permitted substituent for R16 is derived from List 21; the permitted substituent for R7 is R17CO-#, wherein the permitted substituent for R17 is derived from List 22;
- X can be hydrogen, methyl, methoxy, trifluoromethyl, nitro, chloro or fluoro; and # is the point of attachment
- the known compounds have one of four aryl groups (unsubstituted phenyl; 4-C1; 4-F; 2,4-diN02). All of the compounds of the library 6 have a more complex pattern based on a substituted amine in the 4 position.
- the compounds of formulae (B) and (C) may be obtained by applying synthetic procedures, some of which are illustrated in the scheme 1, 2 and 3.
- the synthesis provided for in these schemes is applicable for producing compounds of formulae (B) and (C) below, having a variety of different R3, R4, R5, R6, R7 and X groups .
- reaction mixture was poured into water (500cm 3 ) and stirred for 30 minutes. Ethyl acetate (150cm 3 ) was added, the layers separated and the aqueous phase was extracted with ethyl acetate (2x150cm 3 ) . The organic layers were combined, washed with brine (150cm 3 ) , dried over magnesium sulphate, filtered and concentrated in vacuo .
- IH Indazole-3-carboxylic acid (1.2g, 0.0075M) was .dis-solved in 25ml dimethyl formamide under nitrogen.
- Sodium hydride (0.6g of 40% in oil, 0.015M) was added portionwise. Stirred at room temperature for 30 minutes, a solution of 4-benzyloxy-benzyl chloride (1.74g, 0.0075M) in dimethyl formamide (10ml) was added dropwise and the mixture was stirred at room temperature overnight.
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
PCT/GB2003/005650 WO2004058720A2 (en) | 2002-12-24 | 2003-12-24 | Compound libraries of 1,3,5-substitute indazole derivatives as compounds for targetting compounds capable of binding to the g-protein coupled receptor |
AU2003295158A AU2003295158A1 (en) | 2002-12-24 | 2003-12-24 | Compound libraries of 1,3,5-substitute indazole derivatives as compounds for targetting compounds capable of binding to the g-protein coupled receptor |
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB0230195.0 | 2002-12-24 | ||
GB0230195A GB0230195D0 (en) | 2002-12-24 | 2002-12-24 | Compound Libraries |
PCT/GB2003/005650 WO2004058720A2 (en) | 2002-12-24 | 2003-12-24 | Compound libraries of 1,3,5-substitute indazole derivatives as compounds for targetting compounds capable of binding to the g-protein coupled receptor |
Publications (2)
Publication Number | Publication Date |
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WO2004058720A2 true WO2004058720A2 (en) | 2004-07-15 |
WO2004058720A3 WO2004058720A3 (en) | 2004-08-19 |
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Application Number | Title | Priority Date | Filing Date |
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PCT/GB2003/005650 WO2004058720A2 (en) | 2002-12-24 | 2003-12-24 | Compound libraries of 1,3,5-substitute indazole derivatives as compounds for targetting compounds capable of binding to the g-protein coupled receptor |
Country Status (2)
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AU (1) | AU2003295158A1 (ja) |
WO (1) | WO2004058720A2 (ja) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7868184B2 (en) * | 2004-06-08 | 2011-01-11 | The University of the University of St. Andrews | Multicore indazolinone library |
US10239838B2 (en) * | 2014-12-19 | 2019-03-26 | Merck Sharp & Dohme Corp. | Heteroaryl orexin receptor antagonists |
CN110392686A (zh) * | 2016-12-30 | 2019-10-29 | 频率治疗公司 | 1h-吡咯-2,5-二酮化合物以及使用它们来诱导干/祖支持细胞自我更新的方法 |
WO2021226003A1 (en) * | 2020-05-06 | 2021-11-11 | Merck Sharp & Dohme Corp. | Il4i1 inhibitors and methods of use |
Citations (2)
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WO1998054116A1 (en) * | 1997-05-28 | 1998-12-03 | Cadus Pharmaceutical Corporation | Synthesis and use of thiophene- and pyrrole-based heteroaromatic compounds |
WO1999009024A1 (en) * | 1997-08-14 | 1999-02-25 | Smithkline Beecham Plc | Phenyl urea and phenyl thiourea derivatives as hfgan72 antagonists |
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2003
- 2003-12-24 WO PCT/GB2003/005650 patent/WO2004058720A2/en not_active Application Discontinuation
- 2003-12-24 AU AU2003295158A patent/AU2003295158A1/en not_active Abandoned
Patent Citations (2)
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---|---|---|---|---|
WO1998054116A1 (en) * | 1997-05-28 | 1998-12-03 | Cadus Pharmaceutical Corporation | Synthesis and use of thiophene- and pyrrole-based heteroaromatic compounds |
WO1999009024A1 (en) * | 1997-08-14 | 1999-02-25 | Smithkline Beecham Plc | Phenyl urea and phenyl thiourea derivatives as hfgan72 antagonists |
Non-Patent Citations (9)
Title |
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DATABASE BEILSTEIN BEILSTEIN INSTITUTE FOR ORGANIC CHEMISTRY, FRANKFURT-MAIN, DE; 27 June 1988 (1988-06-27), XP002279667 Database accession no. BRN 6354 * |
DATABASE BEILSTEIN BEILSTEIN INSTITUTE FOR ORGANIC CHEMISTRY, FRANKFURT-MAIN, DE; 27 June 1988 (1988-06-27), XP002279668 Database accession no. BRN 9068 * |
DATABASE BEILSTEIN BEILSTEIN INSTITUTE FOR ORGANIC CHEMISTRY, FRANKFURT-MAIN, DE; 27 June 1988 (1988-06-27), XP002279673 Database accession no. BRN 3706 * |
DATABASE BEILSTEIN BEILSTEIN INSTITUTE FOR ORGANIC CHEMISTRY, FRANKFURT-MAIN, DE; 28 November 1988 (1988-11-28), XP002279669 Database accession no. BRN 518679 * |
DATABASE BEILSTEIN BEILSTEIN INSTITUTE FOR ORGANIC CHEMISTRY, FRANKFURT-MAIN, DE; 28 November 1988 (1988-11-28), XP002279670 Database accession no. BRN 518680 * |
DATABASE BEILSTEIN BEILSTEIN INSTITUTE FOR ORGANIC CHEMISTRY, FRANKFURT-MAIN, DE; 28 November 1988 (1988-11-28), XP002279671 Database accession no. BRN 519491 * |
DATABASE BEILSTEIN BEILSTEIN INSTITUTE FOR ORGANIC CHEMISTRY, FRANKFURT-MAIN, DE; 28 November 1988 (1988-11-28), XP002279672 Database accession no. BRN 531661 * |
PARNELL E W: "2-Cyano-4-nitrophenylhydrazine and 3-Amino-5-nitroindazole" JOURNAL OF THE CHEMICAL SOCIETY, CHEMICAL SOCIETY. LETCHWORTH, GB, 1959, pages 2363-2365, XP002185285 ISSN: 0368-1769 cited in the application * |
ZHANG ET AL.: "Discovery and Optimization of a Novel Series of Thrombin Receptor (PAR-1) Antagonists: Potent, Selective Peptide Mimetics Based on Indole and Indazole Templates" J. MED. CHEM., vol. 44, 22 March 2001 (2001-03-22), pages 1021-1024, XP002279666 * |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7868184B2 (en) * | 2004-06-08 | 2011-01-11 | The University of the University of St. Andrews | Multicore indazolinone library |
US10239838B2 (en) * | 2014-12-19 | 2019-03-26 | Merck Sharp & Dohme Corp. | Heteroaryl orexin receptor antagonists |
CN110392686A (zh) * | 2016-12-30 | 2019-10-29 | 频率治疗公司 | 1h-吡咯-2,5-二酮化合物以及使用它们来诱导干/祖支持细胞自我更新的方法 |
WO2021226003A1 (en) * | 2020-05-06 | 2021-11-11 | Merck Sharp & Dohme Corp. | Il4i1 inhibitors and methods of use |
Also Published As
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AU2003295158A1 (en) | 2004-07-22 |
WO2004058720A3 (en) | 2004-08-19 |
AU2003295158A8 (en) | 2004-07-22 |
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