US20150141433A1 - N-arylmethyl sulfonamide negative modulators of nr2a - Google Patents
N-arylmethyl sulfonamide negative modulators of nr2a Download PDFInfo
- Publication number
- US20150141433A1 US20150141433A1 US14/498,466 US201414498466A US2015141433A1 US 20150141433 A1 US20150141433 A1 US 20150141433A1 US 201414498466 A US201414498466 A US 201414498466A US 2015141433 A1 US2015141433 A1 US 2015141433A1
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- United States
- Prior art keywords
- methyl
- carboxamide
- chloro
- fluorobenzene
- sulfonamidomethyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
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- YAOQMFAHUHDJOE-UHFFFAOYSA-N O=C(c1ncc(CNS(c(cc2)cc(Cl)c2F)(=O)=O)nc1)NCc1c[o]cn1 Chemical compound O=C(c1ncc(CNS(c(cc2)cc(Cl)c2F)(=O)=O)nc1)NCc1c[o]cn1 YAOQMFAHUHDJOE-UHFFFAOYSA-N 0.000 description 1
- BZNOMUOJUFPNBS-UHFFFAOYSA-N O=C(c1ncc(CNS(c(cc2)cc(Cl)c2F)(=O)=O)nc1)NCc1cncnc1 Chemical compound O=C(c1ncc(CNS(c(cc2)cc(Cl)c2F)(=O)=O)nc1)NCc1cncnc1 BZNOMUOJUFPNBS-UHFFFAOYSA-N 0.000 description 1
- BMTNDPQKBCSHJW-UHFFFAOYSA-N O=C(c1nnc(CNS(c(cc2)cc(Cl)c2F)(=O)=O)cc1)NCc1ccc[o]1 Chemical compound O=C(c1nnc(CNS(c(cc2)cc(Cl)c2F)(=O)=O)cc1)NCc1ccc[o]1 BMTNDPQKBCSHJW-UHFFFAOYSA-N 0.000 description 1
- XIOSVEOOUVWCDM-UHFFFAOYSA-N O=C(c1nnc(CNS(c(cc2)cc(Cl)c2F)(=O)=O)cc1)NCc1ccncn1 Chemical compound O=C(c1nnc(CNS(c(cc2)cc(Cl)c2F)(=O)=O)cc1)NCc1ccncn1 XIOSVEOOUVWCDM-UHFFFAOYSA-N 0.000 description 1
- PPMDBYFJRDPBPJ-UHFFFAOYSA-N O=C(c1nnc(CNS(c(cc2)cc(Cl)c2F)(=O)=O)cc1)NCc1cnc[s]1 Chemical compound O=C(c1nnc(CNS(c(cc2)cc(Cl)c2F)(=O)=O)cc1)NCc1cnc[s]1 PPMDBYFJRDPBPJ-UHFFFAOYSA-N 0.000 description 1
- XYFZBGNHKKFGQX-UHFFFAOYSA-N O=C(c1nnc(CNS(c(cc2)cc(Cl)c2F)(=O)=O)cc1)NCc1ncccn1 Chemical compound O=C(c1nnc(CNS(c(cc2)cc(Cl)c2F)(=O)=O)cc1)NCc1ncccn1 XYFZBGNHKKFGQX-UHFFFAOYSA-N 0.000 description 1
- DXFXNSNBZNELII-UHFFFAOYSA-N O=S(c(cc1Cl)ccc1F)(Cl)=O Chemical compound O=S(c(cc1Cl)ccc1F)(Cl)=O DXFXNSNBZNELII-UHFFFAOYSA-N 0.000 description 1
- QCQSNDYZDJHKAT-UHFFFAOYSA-N [C-]#[N+]C1=C(C)N=C(C(=O)CCC2=CN=C(C)S2)C=N1 Chemical compound [C-]#[N+]C1=C(C)N=C(C(=O)CCC2=CN=C(C)S2)C=N1 QCQSNDYZDJHKAT-UHFFFAOYSA-N 0.000 description 1
- WGIRLPQDCZBKLT-UHFFFAOYSA-N [C-]#[N+]C1=CN=C(C(=O)OC)C=C1 Chemical compound [C-]#[N+]C1=CN=C(C(=O)OC)C=C1 WGIRLPQDCZBKLT-UHFFFAOYSA-N 0.000 description 1
- QLZWHLJTIBSFDP-UHFFFAOYSA-N [N-]=[N+]=NCC1=CN=C(C(=O)O)C=N1 Chemical compound [N-]=[N+]=NCC1=CN=C(C(=O)O)C=N1 QLZWHLJTIBSFDP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
-
- 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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
- C07D213/82—Amides; Imides in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-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
- C07D237/24—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- C07D403/12—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 chain containing hetero atoms as chain links
-
- 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
- C07D405/12—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 chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur 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
- 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
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
Definitions
- the present disclosure relates to compounds and compositions that negatively modulate the activity of an NR2A receptor, as well as methods of using these compounds and compositions for treating patients suffering from diseases associated with NR2A receptors.
- the NMDA receptor is arguably an important signaling mechanism in the human brain.
- the brain processes a complex array of information to allow humans to function, storing information from the past and analyzing this information in the context of the present to respond and plan for the future.
- These incredibly complex computations are mediated at the molecular level by the continual adjustment of the strength of synapses, the nodes for communication between nerve cells (estimated at about 60 trillion in the human brain).
- NMDA receptors are one of three classes that mediate synaptic transmission using glutamate. NMDA receptors play a critical role in regulating the strength of synapses, that is, in regulating synaptic plasticity. Thus, the NMDA receptor is at the molecular core of brain function, and in particular the cognitive functions of learning and memory. These facts underlie the tremendous therapeutic utility of modulating NMDA receptor function with new drugs to treat a broad range of neuropsychiatric disease and cognitive dysfunction.
- NMDA receptor comprises four protein subunits: two NR1 subunits and two NR2 subunits.
- An NR1 subunit derived from a single gene is ubiquitously expressed throughout the brain and is common to all NMDA receptors.
- four different NR2 subunits, NR2A-D are derived from separate genes that are differentially expressed in different brain regions and by distinct populations of neurons within a particular region.
- individual neurons may express more than one NR2 subunit and individual NMDA receptors expressed by such neurons may contain two of the same NR2 subunits (for example, 2 NR2A subunits) or two different subunits (one NR2A and one NR2B subunit). Therefore, a drug that selectively modulates the activity of one NR2 subunit may do so at receptors that express either one or two of the targeted subunits. Thus, there is a need for new treatments for diseases related to the NR2A receptor.
- A, B, C, and D are independently CR or N provided that at least one of A, B, C or D is N;
- each R is independently selected from the group consisting of H, halogen, C 1 -C 5 alkyl, C 1 -C 5 haloalkyl, CN and O-alkyl; or
- the R groups on A and B may form, with A and B, a fused 5,6 or 6,6 bicyclic aryl group or heteroaryl group;
- R 1 is aryl or heteroaryl both of which are optionally substituted with one or more substitutents selected from the group consisting of halogen, C 1 -C 5 alkyl, C(O)C 1 -C 5 alkyl, haloalklyl, CN, O-aryl, O-alkyl, aryl, and heteroaryl; or
- R 1 is selected from the group consisting of optionally substituted alkyl, optionally substituted cycloalkyl, or optionally substituted heterocycloalkyl;
- R 2 and R 2′ are independently selected from the group consisting of H, and C 1 -C 5 alkyl; or R 2 and R 2′ may form, with the carbon to which they are connected, a cycloalkane;
- X is C ⁇ O or SO 2 ;
- Y is selected from the group consisting of H, C 1 -C 5 alkyl, and a group —CHP 1 P 2
- P 1 is selected from the group consisting of H, and C 1 -C 5 alkyl
- P 2 is O(C 1 -C 5 )alkyl optionally substituted by one or more alkoxy and/or hydroxy groups;
- P 2 is selected from the group consisting of OC(O)R 4 , OC(O)OR 4 , OC(O)NHR 4 , OC(O)NR 4 R 5 , OC(O)-alkyl-NR 4 R 5 , and O(PO)O 2 ⁇ 2 ; or P 1 and P 2 , form a cycloalkyl or a heterocycle;
- R 4 and R 5 are independently selected from the group consisting of H, and C 1 -C 5 alkyl with the proviso that when P 2 is OC(O)OR 4 , R 4 is not hydrogen;
- R 3 is -L 1 -Ar 1 , L 1 -N(C 1 -C 6 alkyl) 2 , or
- L 1 is straight or branched C 1 -C 5 alkyl, optionally substituted with —OH, —OC 1 -C 6 alkyl, or ( ⁇ O);
- Z is selected from the group consisting of H and C 1 -C 5 alkyl; or Z and R 3 , with the nitrogen to which they are connected, may form a heterocycle;
- Ar 1 is aryl optionally substituted with one or more substitutents selected from the group consisting of C 1 -C 5 alkyl, halogen, C 1 -C 6 haloalkyl, CN, and O-alkyl; or
- Ar 1 is heteroaryl optionally substituted with one or more substitutents selected from the group consisting of C 1 -C 5 alkyl, halogen, C 1 -C 6 haloalkyl, CN, and O-alkyl; and
- n is 1 or 2.
- the present disclosure relates to and provides compounds that selectively modulate NMDA receptors that contain an NR2A subunit, which encompasses receptors containing two NR2A subunits or one NR2A subunit in combination with one other NR2 subunit (ie, NR2A/NR2B, NR2A/NR2C, or NR2A/NR2D receptors).
- NR2A subunit which encompasses receptors containing two NR2A subunits or one NR2A subunit in combination with one other NR2 subunit (ie, NR2A/NR2B, NR2A/NR2C, or NR2A/NR2D receptors).
- Such compounds may either increase or decrease the activity of NR2A-containing NMDA receptors.
- the present disclosure also relates to the therapeutic uses of such compounds.
- pharmaceutical formulations comprising at least one disclosed compound.
- compositions that comprise an effective amount of a disclosed compound and a pharmaceutically acceptable carrier.
- the compositions are useful for treating or preventing a disease or disorder.
- the invention includes a disclosed compound provided as a pharmaceutically acceptable prodrug, hydrate, salt, stereoisomer, or mixtures thereof
- diseases include, without limitation, neurological dysfunction such as Parkinson's disease, Huntington's disease, amyotrophic lateral sclerosis, multiple sclerosis, and seizure disorders; emotional disorders; depression; bipolar disorder; obsessive-compulsive disorder; and other anxiety disorders.
- the compounds described may be useful in the treatment of diseases in which NMDA receptors containing the NR2A subunit are expressed outside the central nervous system contribute to pathophysiology. This may include, but is not limited to, diseases such as cancer, and particularly including melanomas, diseases of the lung or injury to the lung caused by toxins, diseases involving the peripheral nervous system. These compounds may also be useful in the treatment of autoimmune conditions in which antibodies develop that interact with NMDA receptors.
- compositions that comprise an effective amount of a disclosed compound and a pharmaceutically acceptable carrier.
- the compositions are useful for treating or preventing a disease or disorder.
- the invention includes a disclosed compound provided as a pharmaceutically acceptable prodrug, hydrate, salt, stereoisomer, or mixtures thereof
- an element means one element or more than one element.
- an alkyl group that is optionally substituted can be a fully saturated alkyl chain (i.e. a pure hydrocarbon).
- the same optionally substituted alkyl group can have substituents different from hydrogen. For instance, it can, at any point along the chain be bounded to a halogen atom, a hydroxyl group, or any other substituent described herein.
- optionally substituted means that a given chemical moiety has the potential to contain other functional groups, but does not necessarily have any further functional groups.
- aryl refers to cyclic, aromatic hydrocarbon groups that have 1 to 2 aromatic rings, including monocyclic or bicyclic groups such as phenyl, biphenyl or naphthyl. Where containing two aromatic rings (bicyclic, etc.), the aromatic rings of the aryl group may be joined at a single point (e.g., biphenyl), or fused (e.g., naphthyl).
- the aryl group may be optionally substituted by one or more substituents, e.g., 1 to 5 substituents, at any point of attachment.
- substituents include, but are not limited to, —H, -halogen, —O—C 1 -C 6 alkyl, C 1 -C 6 alkyl, —OC 1 -C 6 alkenyl, —OC 1 -C 6 alkynyl, —C 1 -C 6 alkenyl, —C 1 -C 6 alkynyl, —OH, —OP(O)(OH) 2 , —OC(O)C 1 -C 6 alkyl, —C(O)C 1 -C 6 alkyl, —OC(O)OC 1 -C 6 alkyl, NH 2 , NH(C 1 -C 6 alkyl), N(C 1 -C 6 alkyl) 2 , —S(O) 2 —C 1 -C 6 alkyl, —S(O)NHC 1 -C 6 alkyl, and S(O)N(C 1 -C 6 alkyl) 2 .
- aryl groups herein defined may have an unsaturated or partially saturated ring fused with a fully saturated ring.
- Exemplary ring systems of these aryl groups include indanyl, indenyl, tetrahydronaphthalenyl, and tetrahydrobenzoannulenyl.
- heteroaryl means a monovalent monocyclic or bicyclic aromatic radical of 5 to 10 ring atoms or a polycyclic aromatic radical, containing one or more ring heteroatoms selected from N, O, or S, the remaining ring atoms being C.
- Heteroaryl as herein defined also means a bicyclic heteroaromatic group wherein the heteroatom is selected from N, O, or S.
- the aromatic radical is optionally substituted independently with one or more substituents described herein.
- Examples include, but are not limited to, furyl, thienyl, pyrrolyl, pyridyl, pyrazolyl, pyrimidinyl, imidazolyl, pyrazinyl, indolyl, thiophen-2-yl, quinolyl, benzopyranyl, thiazolyl, and derivatives thereof.
- the aryl groups herein defined may have an unsaturated or partially saturated ring fused with a fully saturated ring.
- Exemplary ring systems of these heteroaryl groups include indolinyl, indolinonyl, dihydrobenzothiophenyl, dihydrobenzofuran, chromanyl, thiochromanyl, tetrahydroquinolinyl, dihydrobenzothiazine, and dihydrobenzoxanyl.
- C 1 -C 3 alkyl refers to a straight or branched chain saturated hydrocarbon containing 1-3 carbon atoms. Examples of a C 1 -C 3 alkyl group include, but are not limited to, methyl, ethyl, propyl and isopropyl.
- C 1 -C 5 alkyl refers to a straight or branched chain saturated hydrocarbon containing 1-5 carbon atoms.
- Examples of a C 1 -C 5 alkyl group include, but are not limited to, methyl, ethyl, propyl, butyl, pentyl, isopropyl, isobutyl, sec-butyl and tert-butyl, isopentyl and neopentyl.
- Alkyl is generally lower alkyl, or C 1 -C 6 alkyl.
- Examples of a C 1 -C 6 alkyl group include, but are not limited to, methyl, ethyl, propyl, butyl, pentyl, hexyl, isopropyl, isobutyl, sec-butyl, tert-butyl, isopentyl, neopentyl, and isohexyl.
- Alkylenyl refers to groups of general formula (CH 2 ) where n is an integer from 1 to 6. Suitable examples of alkylenyl groups include methylenyl, ethylenyl, and propylenyl.
- haloalkyl refers to straight or branched saturated hydrocarbon chains containing 1-5 carbon atoms which are substituted at least one of the carbon with halogen groups such fluorine, chlorine, bromine, iodide.
- haloalkyl groups as herein defined include without limitation trifluoromethyl, tribromomethyl, and 1,1,1-trifluoroethyl.
- Cycloalkyl means monocyclic saturated carbon rings containing 3-18 carbon atoms.
- Examples of cycloalkyl groups include, without limitations, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptanyl, cyclooctanyl, norboranyl, norborenyl, bicyclo[2.2.2]octanyl, or bicyclo[2.2.2]octenyl.
- Heterocyclyl or “heterocycloalkyl” or” heterocycle” means monocyclic rings containing carbon and heteroatoms taken from oxygen, nitrogen, or sulfur and wherein there is not delocalized ⁇ electrons (aromaticity) shared among the ring carbon or heteroatoms; heterocyclyl rings include, but are not limited to, oxetanyl, azetadinyl, tetrahydrofuranyl, pyrrolidinyl, oxazolinyl, oxazolidinyl, thiazolinyl, thiazolidinyl, pyranyl, thiopyranyl, tetrahydropyranyl, dioxalinyl, piperidinyl, morpholinyl, thiomorpholinyl, thiomorpholinyl S-oxide, thiomorpholinyl S-dioxide, piperazinyl, azepinyl, oxepinyl, dia
- “Spirocycle” means bicyclic ring systems with both rings connected through a single atom.
- the ring can be different in size and nature, or identical in size and nature. Examples include spiropentane, spriohexane, spiroheptane, spirooctane, spirononane, or spirodecane.
- compositions comprising an effective amount of a disclosed compound and a pharmaceutically acceptable carrier.
- pharmaceutically acceptable salts include, e.g., water-soluble and water-insoluble salts, such as the acetate, amsonate (4,4-diaminostilbene-2,2-disulfonate), benzenesulfonate, benzonate, bicarbonate, bisulfate, bitartrate, borate, bromide, butyrate, calcium, calcium edetate, camsylate, carbonate, chloride, citrate, clavulariate, dihydrochloride, edetate, edisylate, estolate, esylate, fiunarate, gluceptate, gluconate, glutamate, glycollylarsanilate, hexafluorophosphate, hexylresorcinate, hydrabamine, hydrobromide, hydrochloride, hydroxynaphthoate, i
- stereoisomers refers to the set of compounds which have the same number and type of atoms and share the same bond connectivity between those atoms, but differ in three dimensional structure.
- stereoisomer refers to any member of this set of compounds.
- diasteromers refers to the set of stereoisomers which cannot be made superimposable by rotation around single bonds. For example, cis- and trans-double bonds, endo- and exo-substitution on bicyclic ring systems, and compounds containing multiple stereogenic centers with different relative configurations are considered to be diasteromers.
- the term “diasteromer” refers to any member of this set of compounds.
- the synthetic route may produce a single diateromer or a mixture of diasteromers. In some cases these diateromers were separated and in other cases a wavy bond is used to indicate the structural element where configuration is variable.
- enantiomers refers to a pair of stereoisomers which are non-superimposable mirror images of one another.
- enantiomer refers to a single member of this pair of stereoisomers.
- racemic refers to a 1:1 mixture of a pair of enantiomers.
- tautomers refers to a set of compounds that have the same number and type of atoms, but differ in bond connectivity and are in equilibrium with one another.
- a “tautomer” is a single member of this set of compounds. Typically a single tautomer is drawn but it is understood that this single structure is meant to represent all possible tautomers that might exist. Examples include enol-ketone tautomerism. When a ketone is drawn it is understood that both the enol and ketone forms are part of the invention.
- a “subject” is a mammal, e.g., a human, mouse, rat, guinea pig, dog, cat, horse, cow, pig, or non-human primate, such as a monkey, chimpanzee, baboon or rhesus.
- an “effective amount” when used in connection with a compound is an amount effective for treating or preventing a disease in a subject as described herein.
- carrier encompasses carriers, excipients, and diluents and means a material, composition or vehicle, such as a liquid or solid filler, diluent, excipient, solvent or encapsulating material, involved in carrying or transporting a pharmaceutical agent from one organ, or portion of the body, to another organ, or portion of the body of a subject.
- treating refers to improving at least one symptom of the subject's disorder. Treating includes curing, improving, or at least partially ameliorating the disorder.
- disorder is used in this disclosure to mean, and is used interchangeably with, the terms disease, condition, or illness, unless otherwised indicated.
- administer refers to either directly administering a disclosed compound or pharmaceutically acceptable salt of the disclosed compound or a composition to a subject, or administering a prodrug derivative or analog of the compound or pharmaceutically acceptable salt of the compound or composition to the subject, which can form an equivalent amount of active compound within the subject's body.
- prodrug means a compound which is convertible in vivo by metabolic means (e.g., by hydrolysis) to a disclosed compound.
- a prodrug is a drug which is inactive in the body, but is transformed in the body typically either during absorption or after absorption from the gastrointestinal tract into the active compound.
- the conversion of the prodrug into the active compound in the body may be done chemically or biologically (i.e., using an enzyme).
- A, B, C, D, R 1 , R 2 , R 2′ , X, Y, R 3 , Z and n are defined as above.
- R 1 is aryl substituted with one or more substitutents selected from the group consisting of halogen, C 1 -C 5 alkyl, CN and O-alkyl.
- R 1 is heteroaryl substituted with one or more substitutents selected from the group consisting of halogen, C 1 -C 5 alkyl, CN and O-alkyl.
- R 1 is aryl substituted by one or more halogen.
- R 1 is heteroaryl substituted by one or more halogen.
- R 1 is aryl wherein the aryl is phenyl substituted by one or more halogen.
- R 1 is aryl wherein the aryl is phenyl substituted by two halogens.
- R 1 is aryl wherein the aryl is
- X is SO 2 .
- Y is H.
- n 1
- R 2 is H.
- R 2′ is H.
- At least two of A, B, C, and D are N.
- A, B, C, D and the carbons to which they are attached is
- Z is H.
- L 1 is C 1 -C 3 .
- L 1 is CH 2 .
- Ar 1 is heteroaryl substituted with one or more of C 1 -C 5 alkyl, CN, and O-alkyl.
- Ar 1 is heteroaryl wherein the heteroaryl is pyridyl substituted with one or more of C 1 -C 5 alkyl, CN, and O-alkyl.
- Ar 1 is pyridinazyl substituted with one or more of C 1 -C 5 alkyl, CN, and O-alkyl.
- Ar 1 is thiazolyl substituted with one or more of C 1 -C 5 alkyl, CN, and O-alkyl.
- thiazolyl is bonded to L 1 at the 5 position of the thiazolyl ring:
- the present disclosure includes Formula I compounds where any hydrogen atom may be replaced with a deuterium atom.
- Formula I tautomers are also provided.
- A, B, C, and D are independently CR or N provided that at least one of A, B, C or D is N;
- R is independently selected from the group consisting of H, halogen, C 1 -C 5 alkyl, CN and O-alkyl;
- R 3 is -L 1 -Ar 1 ;
- L 1 is straight or branched C 1 -C 5 alkyl; Z is H or C 1 -C 5 alkyl; or Z and R 3 , with the nitrogen to which they are connected, form a heterocycle;
- Ar 1 is aryl optionally substituted with one or more substitutents selected from the group consisting of: C 1 -C 5 alkyl, CN, and O-alkyl; or Ar 1 is a heteroaryl group substituted with one or more substitutents selected from the group consisting of C 1 -C 5 alkyl, CN, and O-alkyl.
- At least two of A, B, C, and D are N.
- A, B, C, D and the carbons to which they are attached is
- Z is H.
- L 1 is C 1 -C 3 .
- L 1 is CH 2 .
- Ar 1 is heteroaryl substituted with one or more substitutents selected from the group consisting of C 1 -C 5 alkyl, CN, and O-alkyl.
- Ar 1 is pyridyl substituted with one or more substitutents selected from the group consisting of C 1 -C 5 alkyl, CN, and O-alkyl.
- Ar 1 is pyridinazyl substituted with one or more of the following features: C 1 -C 5 alkyl, CN, and O-alkyl.
- Ar 1 is thiazolyl substituted with one or more of the following features: C 1 -C 5 alkyl, CN, and O-alkyl.
- a compound of Formula I may be:
- the present disclosure relates to and provides compounds that selectively modulate NMDA receptors that contain an NR2A subunit, which encompasses receptors containing two NR2A subunits or one NR2A subunit in combination with one other NR2 subunit (ie, NR2A/NR2B, NR2A/NR2C, or NRSA/NRSD receptors).
- NR2A subunit which encompasses receptors containing two NR2A subunits or one NR2A subunit in combination with one other NR2 subunit (ie, NR2A/NR2B, NR2A/NR2C, or NRSA/NRSD receptors).
- the present disclosure also relates to the therapeutic uses of such compounds.
- One therapeutic use of a compound of the present invention that modulates the activity of NR2A-containing NMDA receptors is to treat patients suffering from Major Depressive Disorder (MDD, or depression).
- Depression is the prolonged experience of sadness, hopelessness, or worthlessness to a degree that significantly impairs quality of life and the ability to function Major Depressive Disorder is now commonly treated with Selective Serotonin Reuptake Inhibitors (SSRIs) such as Prozac, Zoloft and newer variants, but these agents are of limited effectiveness.
- SSRIs Selective Serotonin Reuptake Inhibitors
- Prozac Prozac
- Zoloft newer variants
- Schizophrenia is a debilitating mental disorder encompassing three symptom domains: positive (hallucination, delusions), negative (withdrawal), and cognitive (pervasive reduction in cognitive ability). Schizophrenia typically strikes in early adulthood with the emergence of positive symptoms; however, it is the chronic cognitive deficits that prevent patients from resuming normal activities after the initial onset of symptoms and largely accounts for a lifetime disability.
- NR2A containing NMDA receptors in brain function (vide supra), there are many other therapeutic uses for compounds of the present invention that modulate the activity of NR2A-containing NMDA receptors.
- Compounds of the present invention may improve cognitive function in individuals suffering from cognitive deficits in addition to schizophrenia, including but not limited to those suffering from Alzheimer's disease. Such compounds may also be used in the treatment of post-traumatic stress syndrome.
- Compounds of the present invention may be used to treat individuals suffering from neurological dysfunction, including but not limited to those suffering from Parkinson's disease, Huntington's disease, amyotrophic lateral sclerosis, multiple sclerosis, and seizure disorders.
- Compounds of the present invention may be used to treat individuals suffering from emotional disorders in addition to depression, including but not limited to those suffering from bipolar disorder, obsessive-compulsive disorder and other anxiety disorders.
- Compounds of the present invention may be used to treat individuals that experience dysfunction caused by abnormal brain development, including but not limited to those suffering from autism and autism spectrum disorders, Fragile X syndrome, tuberous sclerosis, Down's syndrome and other forms of mental retardation.
- Such compounds may also be used to treat abnormal brain function that results from infections of the central nervous system, exposure to toxic agents or other xenobiotics or naturally occurring toxins.
- the disclosure includes methods for treating diseases including but not limited to Alzheimer's disease, Parkinson's disease, epilepsy, schizophrenia, depression, manic depression, neurodevelopmental disorder, autism, Huntington's disease, stroke, cerebral palsy, traumatic brain injury, dementia, progressive muscular atrophy, amyotrophic lateral sclerosis, post-polio syndrome, tabes dorsalis, multiple sclerosis, arm peripheral nerve disease, leg peripheral nerve disease, facial nerve palsy, Guillian-Barre's syndrome, Friedreich's ataxia, Charcot-Marie-Tooth disease, spina bifida, hydrocephalus, Down's syndrome, Rett syndrome, Fragile X syndrome Attention deficit/hyperactivity disorder (ADHD), Tourette's syndrome, tuberous sclerosis and chorea.
- diseases including but not limited to Alzheimer's disease, Parkinson's disease, epilepsy, schizophrenia, depression, manic depression, neurodevelopmental disorder, autism, Huntington's disease, stroke, cerebral palsy, traumatic brain injury, dementia, progressive muscular
- Stroke is the focal loss of blood supply to the brain, caused by clots or hemorrhage that results in brain ischemia. In the US, approximately 800,000 people suffer a stroke each year and stroke is the leading cause of long-term disability. The estimated economic burden from stroke is projected to exceed $45B per year through 2050. Head trauma causes both mechanical damage to the brain and ischemia.
- Traumatic brain injury may be treated with the compounds of the present disclosure.
- TBI necessitates acute intensive medical support that affects approximately 200,000 people in the US annually.
- the total costs to society of the resultant disabilities may exceed $60B per year.
- TBI has also become recognized as the ‘signature injury’ of soldiers returning from Iraq and Afghanistan, affecting as many as 18% of the veterans of these wars. It is estimated that the care for these veterans may approach $1.0B annually.
- tPA The only available therapy, tPA, which reduces brain tissue loss by restoring brain perfusion after embolic stroke, is appropriate for only 2-3% of stroke patients.
- Other approaches to prevent or reduce brain tissue loss after injury have failed, largely because brain damage occurs rapidly and neuroprotectant treatment cannot be administered in a time frame to be effective.
- a new approach to reduce disability and improve longterm outcomes for brain injury survivors is to promote the natural process of recovery after brain injury by treating such patients with the compounds of the present disclosure that selectively inhibit NMDA receptors containing the NR2A subunit.
- brain injury survivors often partially recover lost function resulting from reorganization of surviving brain tissue to assume the function of damaged tissue. This process is mechanistically similar to brain organization during development, which includes synapse formation and strengthening.
- NR2B-containing NMDA receptors predominate to mediate initial synapse formation and strengthening.
- NR2A receptors subsequently predominate to stabilize synapses in the adult brain.
- NR2A receptors limit synapse reformation between surviving neurons.
- inhibiting NR2A receptors will reduce this limitation, thereby promoting brain reorganization to facilitate the natural process of recovery after injury.
- the therapeutic window for initiating treatment is days after brain injury, not minutes to hours as is the case for neuroprotective therapies.
- one therapeutic use of a compound of the present disclosure that inhibits NR2A-containing NMDA receptors is to facilitate recovery of function after brain injury. Damage to the brain can result in lifelong disability.
- RTT Rett Syndrome
- MECP2 X-linked transcriptional repressor
- NMDA receptors are a target of high interest in the development of new treatments for RTT.
- manipulations that decrease the level of NR2A receptor expression in mice for which the MeCP2 gene has been deleted remediates the cortical dysfunction caused by MeCP2 lesion.
- NR2A-containing NMDA receptors in brain function (vide supra), there may be many other therapeutic uses for compounds of the present disclosure that inhibit the activity of NR2A-containing NMDA receptors.
- compounds of the present disclosure may improve cognitive function in individuals suffering from cognitive deficits, including but not limited to those suffering from Alzheimer's disease and schizophrenia.
- Compounds of the present disclosure may be used to treat individuals suffering from neurological dysfunction, including but not limited to those suffering from Parkinson's disease, Huntington's disease, amyotrophic lateral sclerosis, multiple sclerosis, and seizure disorders.
- Compounds of the present disclosure may be used to treat individuals suffering from emotional disorders, including but not limited to those suffering from depression, bipolar disorder, obsessive compulsive disorder and other anxiety disorders.
- Compounds of the present disclosure may be used to treat individuals that experience dysfunction caused by abnormal brain development, including but not limited to those suffering from autism and autism spectrum disorders, Fragile X syndrome, tuberous sclerosis, Down's syndrome and other forms of mental retardation.
- Such compounds may also be used to treat abnormal brain function that results from infections of the central nervous system, exposure to toxic agents or other xenobiotics or naturally occurring toxins.
- another therapeutic use of a compound of the present disclosure that inhibits NR2A-containing NMDA receptors is to treat patients suffering from cancer such as melanoma.
- the compounds described may be useful in the treatment of diseases in which NMDA receptors containing the NR2A subunit are expressed outside the central nervous system and contribute to pathophysiology. This may include, but is not limited to, diseases such as cancer, and particularly including melanomas.
- the disclosed compound can be administered in effective amounts to treat or prevent a disorder and/or prevent the development thereof in subjects.
- Administration of the disclosed compounds can be accomplished via any mode of administration for therapeutic agents. These modes include systemic or local administration such as oral, nasal, parenteral, transdermal, subcutaneous, vaginal, buccal, rectal or topical administration modes.
- compositions can be in solid, semi-solid or liquid dosage form, such as, for example, injectables, tablets, suppositories, pills, time-release capsules, elixirs, tinctures, emulsions, syrups, powders, liquids, suspensions, or the like, sometimes in unit dosages and consistent with conventional pharmaceutical practices.
- injectables tablets, suppositories, pills, time-release capsules, elixirs, tinctures, emulsions, syrups, powders, liquids, suspensions, or the like, sometimes in unit dosages and consistent with conventional pharmaceutical practices.
- they can also be administered in intravenous (both bolus and infusion), intraperitoneal, subcutaneous or intramuscular form, all using forms well known to those skilled in the pharmaceutical arts.
- Illustrative pharmaceutical compositions are tablets and gelatin capsules comprising a Compound of the Invention and a pharmaceutically acceptable carrier, such as a) a diluent, e.g., purified water, triglyceride oils, such as hydrogenated or partially hydrogenated vegetable oil, or mixtures thereof, corn oil, olive oil, sunflower oil, safflower oil, fish oils, such as EPA or DHA, or their esters or triglycerides or mixtures thereof, omega-3 fatty acids or derivatives thereof, lactose, dextrose, sucrose, mannitol, sorbitol, cellulose, sodium, saccharin, glucose and/or glycine; b) a lubricant, e.g., silica, talcum, stearic acid, its magnesium or calcium salt, sodium oleate, sodium stearate, magnesium stearate, sodium benzoate, sodium acetate, sodium chloride and/or polyethylene glycol; for tablets also;
- Liquid, particularly injectable, compositions can, for example, be prepared by dissolution, dispersion, etc.
- the disclosed compound is dissolved in or mixed with a pharmaceutically acceptable solvent such as, for example, water, saline, aqueous dextrose, glycerol, ethanol, and the like, to thereby form an injectable isotonic solution or suspension.
- a pharmaceutically acceptable solvent such as, for example, water, saline, aqueous dextrose, glycerol, ethanol, and the like.
- Proteins such as albumin, chylomicron particles, or serum proteins can be used to solubilize the disclosed compounds.
- the disclosed compounds can be also formulated as a suppository that can be prepared from fatty emulsions or suspensions; using polyalkylene glycols such as propylene glycol, as the carrier.
- the disclosed compounds can also be administered in the form of liposome delivery systems, such as small unilamellar vesicles, large unilamellar vesicles and multilamellar vesicles.
- Liposomes can be formed from a variety of phospholipids, containing cholesterol, stearylamine or phosphatidylcholines.
- a film of lipid components is hydrated with an aqueous solution of drug to a form lipid layer encapsulating the drug, as described in U.S. Pat. No. 5,262,564.
- Disclosed compounds can also be delivered by the use of monoclonal antibodies as individual carriers to which the disclosed compounds are coupled.
- the disclosed compounds can also be coupled with soluble polymers as targetable drug carriers.
- Such polymers can include polyvinylpyrrolidone, pyran copolymer, polyhydroxypropylmethacrylamide-phenol, polyhydroxyethylaspanamidephenol, or polyethyleneoxidepolylysine substituted with palmitoyl residues.
- the disclosed compounds can be coupled to a class of biodegradable polymers useful in achieving controlled release of a drug, for example, polylactic acid, polyepsilon caprolactone, polyhydroxy butyric acid, polyorthoesters, polyacetals, polydihydropyrans, polycyanoacrylates and cross-linked or amphipathic block copolymers of hydrogels.
- a polymer e.g., a polycarboxylic acid polymer, or a polyacrylate.
- Parenteral injectable administration is generally used for subcutaneous, intramuscular or intravenous injections and infusions.
- Injectables can be prepared in conventional forms, either as liquid solutions or suspensions or solid forms suitable for dissolving in liquid prior to injection.
- compositions can be prepared according to conventional mixing, granulating or coating methods, respectively, and the present pharmaceutical compositions can contain from about 0.1% to about 99%, from about 5% to about 90%, or from about 1% to about 20% of the disclosed compound by weight or volume.
- the dosage regimen utilizing the disclosed compound is selected in accordance with a variety of factors including type, species, age, weight, sex and medical condition of the patient; the severity of the condition to be treated; the route of administration; the renal or hepatic function of the patient; and the particular disclosed compound employed.
- a physician or veterinarian of ordinary skill in the art can readily determine and prescribe the effective amount of the drug required to prevent, counter or arrest the progress of the condition.
- effective dosage amounts of the disclosed compounds when used for the indicated effects, range from about 0.5 mg to about 5000 mg of the disclosed compound per day, or as needed per episode of the disorder.
- Compositions for in vivo or in vitro use can contain about 0.5, 5, 20, 50, 75, 100, 150, 250, 500, 750, 1000, 1250, 2500, 3500, or 5000 mg of the disclosed compound, or, in a range of from one amount to another amount in the list of doses.
- the compositions are in the form of a tablet that can be scored.
- substitutents R 1 , X, Y, R 2 , R 2′ , n, A, B, C, and D have the meanings as understood in formula I, by reaction of the compound of formula II with an amine of formula III
- the compound of formula II may be prepared from a compound of formula IV:
- substitutents R 1 , X, Y, R 2 , R 2′ , n, A, B, C, and D have the meanings as understood in formula I, by basic hydrolysis of the compound of formula IV.
- the compound of formula II may be prepared by reaction of a compound of formula V:
- substitutents Y, R 2 , R 2′ , n, A, B, C, and D have the meanings as understood in formula I, with an acyl halide or sulfonyl halide of formula VI:
- substitutents R 1 and X have the have the meanings as understood in formula I, in the presence of a base, e.g., triethylamine.
- Step-2 Preparation of methyl 5-(aminomethyl)picolinate hydrochloride
- Step-3 Preparation of methyl 5-((3-chloro-4-fluorophenylsulfonamido)methyl)picolinate
- Step-4 Preparation of 5-((3-chloro-4-fluorophenylsulfonamido)methyl)picolinic acid
- Step-5 Preparation of 5-[(3-chloro-4-fluorobenzene)sulfonamidomethyl]-N-[2-(4-methoxyphenyl)ethyl]pyridine-2-carboxamide
- Step-1 Preparation of methyl 6-(bromomethyl)nicotinate
- Step-2 Preparation of methyl 6-(aminomethyl)nicotinate hydrochloride
- Step-3 Preparation of methyl 6-((3-chloro-4-fluorophenylsulfonamido)methyl)nicotinate
- Step-4 Preparation of 6-((3-chloro-4-fluorophenylsulfonamido)methyl)nicotinic acid
- Step-5 Preparation of 6-[(3-chloro-4-fluorobenzene)sulfonamidomethyl]-N-(1,3-thiazol-5-ylmethyl)pyridine-3-carboxamide
- Step-1 Preparation of methyl 5-(bromomethyl)pyrazine-2-carboxylate
- Step-2 Preparation of methyl 5-(aminomethyl)pyrazine-2-carboxylate hydrochloride
- Step-3 Preparation of methyl 5-((3-chloro-4-fluorophenylsulfonamido)methyl)pyrazine-2-carboxylate
- Step-4 Preparation of 5-((3-chloro-4-fluorophenylsulfonamido)methyl)pyrazine-2-carboxylic acid
- Step-5 Preparation of 5-[(3-chloro-4-fluorobenzene)sulfonamidomethyl]-N-(1,3-thiazol-5-ylmethyl)pyrazine-2-carboxamide
- Step-1 Preparation of methyl 6-(bromomethyl)pyridazine-3-carboxylate
- Step-2 Preparation of methyl 6-(aminomethyl)pyridazine-3-carboxylate hydrochloride
- Step-3 Preparation of methyl 6-((3-chloro-4-fluorophenylsulfonamido)methyl)pyridazine-3-carboxylate
- Step-4 Preparation of 6-((3-chloro-4-fluorophenylsulfonamido)methyl)pyridazine-3-carboxylic acid
- Step-5 Preparation of 6-[(3-chloro-4-fluorobenzene)sulfonamidomethyl]-N-(1,3-thiazol-5-ylmethyl)pyridazine-3-carboxamide
- Step-1 Preparation of methyl 5-cyanopyrimidine-2-carboxylate
- Step-4 Preparation of 5-[(3-chloro-4-fluorobenzene)sulfonamidomethyl]-N-(pyridin-3-ylmethyl)pyrimidine-2-carboxamide
- Step-4 Preparation of methyl 5-((3,5-difluorobenzamido)methyl)picolinate
- Step-6 Preparation of 5-((3,5-difluorobenzamido)methyl)-N-(thiazol-5-ylmethyl)picolinamide
- Step-1 Preparation of methyl 5-(((4-fluorophenyl)sulfonamido)methyl)picolinate
- Step-3 Preparation of 5-((4-fluorophenylsulfonamido)methyl)-N-((2-methylthiazol-5-yl)methyl)picolinamide
- Step-1 Preparation of methyl 5-(bromomethyl)pyrazine-2-carboxylate
- Step-4 Preparation of 5-(azidomethyl)-N-((2-methylthiazol-5-yl)methyl)pyrazine-2-carboxamide
- Step-6 Preparation of 5-((5-chloro-2-fluorobenzamido)methyl)-N-((2-methylthiazol-5-yl)methyl)pyrazine-2-carboxamide
- reaction mixture was poured into ice-cold water (20 mL) and extracted with ethyl acetate (10 mL ⁇ 3).
- the combined organic extract was washed with brine (20 mL), dried over sodium sulfate and concentrated under vacuum to obtain the crude material which was purified by preparative HPLC (analytical conditions: column: Xbridge C18 (19 mm ⁇ 250 mm ⁇ 5 ⁇ m), mobile phase (A): 5 mM ammonium acetate in water, mobile phase (B): HPLC grade acetonitrile.
- Step-2 Preparation of 5-chloro-6-methyl-N-((2-methylthiazol-5-yl)methyl)pyrazine-2-carboxamide
- Step-4 Preparation of 5-(aminomethyl)-6-methyl-N-((2-methylthiazol-5-yl)methyl)pyrazine-2-carboxamide hydrochloride
- Step-5 Preparation of 5-((3-chloro-2-methylbenzamido)methyl)-6-methyl-N-((2-methylthiazol-5-yl)methyl)pyrazine-2-carboxamide
- Step-1 Preparation of 5-ethyl-6-oxo-1,6-dihydropyrazine-2,3-dicarbonitrile
- Step-2 Preparation of 6-ethyl-5-oxo-4,5-dihydropyrazine-2-carboxylic acid hydrochloride
- Step-3 Preparation of methyl 6-ethyl-5-oxo-4,5-dihydropyrazine-2-carboxylate
- Step-4 Preparation of methyl 5-chloro-6-ethylpyrazine-2-carboxylate
- Step-6 Preparation of 5-chloro-6-ethyl-N-((2-methylthiazol-5-yl)methyl)pyrazine-2-carboxamide
- Step-7 Preparation of 5-cyano-6-ethyl-N-((2-methylthiazol-5-yl)methyl)pyrazine-2-carboxamide
- Step-8 Preparation of 5-(aminomethyl)-6-ethyl-N-((2-methylthiazol-5-yl)methyl)pyrazine-2-carboxamide
- Step-9 Preparation of 5-((3-chloro-4-fluorophenylsulfonamido)methyl)-6-ethyl-N-((2-methylthiazol-5-yl)methyl)pyrazine-2-carboxamide
- Step-1 Preparation of 6-oxo-5-(trifluoromethyl)-1,6-dihydropyrazine-2,3-dicarbonitrile
- Step-2 Preparation of 5-oxo-6-(trifluoromethyl)-4,5-dihydropyrazine-2-carboxylic acid hydrochloride
- Step-3 Preparation of methyl 5-oxo-6-(trifluoromethyl)-4,5-dihydropyrazine-2-carboxylate
- Step-4 Preparation of methyl 5-chloro-6-(trifluoromethyl)pyrazine-2-carboxylate
- Step-5 Preparation of methyl 5-methyl-6-(trifluoromethyl)pyrazine-2-carboxylate
- Step-6 Preparation of methyl 5-(bromomethyl)-6-(trifluoromethyl)pyrazine-2-carboxylate
- Step-7 Preparation of methyl 5-(aminomethyl)-6-(trifluoromethyl)pyrazine-2-carboxylate dihydrochloride
- Step-8 Preparation of methyl 5-((3-chloro-4-fluorophenylsulfonamido)methyl)-6-(trifluoromethyl)pyrazine-2-carboxylate
- Step-9 Preparation of 5-((3-chloro-4-fluorophenylsulfonamido)methyl)-6-(trifluoromethyl)pyrazine-2-carboxylic acid
- Step-10 Preparation of 5-((3-chloro-4-fluorophenylsulfonamido)methyl)-N-((2-methylthiazol-5-yl)methyl)-6-(trifluoromethyl)pyrazine-2-carboxamide
- HEK293 cells expressing NR1/NR2A (Chantest, Cleveland, Ohio) were grown to 70-80% confluency as an adherent monolayer in standard tissue culture flasks at 37° C., 5% CO 2 per supplier's instructions.
- NR2A expression was induced by incubation with 0.3-0.4 ⁇ g/ml tetracycline in the presence of 4 mM ARL-15896 for 18-24 hours under the same growth conditions, then transferred to 30° C. for another 3-5 hours.
- cell culture medium was removed and cells were rinsed once with Ca 2+ and Mg 2+ -free Dulbecco's phosphate buffered saline. Cells were then removed from the flask using TrypLETM Express (Life Technologies) according to the manufacturer's instructions and collected to 50 ml centrifuge tubes. Following two washes in Ca 2 7 Mg 2 ′-free HBSS with 20 mM HEPES (HHnoCa), cells were counted and viability assessed using trypan blue.
- TrypLETM Express Life Technologies
- FDSS Assay To each well of the plate, 10 ⁇ Ltest compound, control (MK801) or HHnoCa buffer was added to a final concentration of 10 ⁇ M with a final concentration of DMSO of 0.1%. Following 10 minutes pre-incubation in the dark, plates are loaded onto the Hamamatsu FDSS 6000. After collecting baseline fluorescence images, 3 ⁇ M glutamate, 3 ⁇ M glycine, and 1 mM Ca 2+ in HHnoCa buffer is added to each well, and Ca 2+ is recorded for 3 minutes. Data were processed by computing ratio of fluorescence at the end of data collection to baseline fluorescence to assess degree of Ca 2+ influx inhibition relative to that observed in MK801.
- Table 14 provides activity of each compound according to the legend that “++++” indicates inhibition at a concentration ⁇ 100 nM; “+++” indicates inhibition at a concentration between 100 nM and 1 ⁇ M of the disclosed compound; “++” indicates inhibition at a concentration of from 1 ⁇ M to 10 ⁇ M; and “+” indicates inhibition at a concentration >10 ⁇ M.
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EP4006038A1 (fr) | 2015-12-09 | 2022-06-01 | Cadent Therapeutics, Inc. | Modulateurs des récepteurs nmda à base de thiénopyrimidinone et leurs utilisations |
WO2018119374A1 (fr) | 2016-12-22 | 2018-06-28 | Cadent Therapeutics | Modulateurs des récepteurs nmda et utilisations de ceux-ci |
CR20210125A (es) | 2018-08-03 | 2021-06-30 | Cadent Therapeutics Inc | Moduladores del receptor nmda heteroaromático y usos de los mismos |
CN114539169A (zh) * | 2020-11-18 | 2022-05-27 | 江苏恒盛药业有限公司 | 一种含有取代基的吡嗪环合成方法 |
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WO2003024955A2 (fr) | 2001-09-18 | 2003-03-27 | Sunesis Pharmaceuticals, Inc. | Inhibiteurs a petites molecules de caspases |
MX2007000468A (es) * | 2004-07-13 | 2007-03-08 | Hoffmann La Roche | Derivados de sulfonamida. |
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2014
- 2014-09-26 US US14/498,466 patent/US20150141433A1/en not_active Abandoned
- 2014-09-26 TW TW103133693A patent/TW201609656A/zh unknown
- 2014-09-26 UY UY0001035751A patent/UY35751A/es not_active Application Discontinuation
- 2014-09-26 US US15/024,870 patent/US9963434B2/en active Active
- 2014-09-26 AR ARP140103585A patent/AR097795A1/es unknown
- 2014-09-26 WO PCT/US2014/057795 patent/WO2015048503A2/fr active Application Filing
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WO2023011144A1 (fr) * | 2021-08-06 | 2023-02-09 | 中国科学院上海有机化学研究所 | Application de glun2a et du récepteur nmda contenant le glun2a comme cibles dans le criblage de médicaments pour le traitement de la dépression |
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US20160311782A1 (en) | 2016-10-27 |
WO2015048503A2 (fr) | 2015-04-02 |
TW201609656A (zh) | 2016-03-16 |
US9963434B2 (en) | 2018-05-08 |
UY35751A (es) | 2015-04-30 |
WO2015048503A3 (fr) | 2015-11-19 |
AR097795A1 (es) | 2016-04-13 |
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