WO2019079540A1 - AMINO-SUBSTITUTED HETEROCYCLIC COMPOUNDS AS INHIBITORS OF EHMT2, SALTS THEREOF, AND METHODS OF SYNTHESIS THEREOF - Google Patents
AMINO-SUBSTITUTED HETEROCYCLIC COMPOUNDS AS INHIBITORS OF EHMT2, SALTS THEREOF, AND METHODS OF SYNTHESIS THEREOF Download PDFInfo
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- WO2019079540A1 WO2019079540A1 PCT/US2018/056428 US2018056428W WO2019079540A1 WO 2019079540 A1 WO2019079540 A1 WO 2019079540A1 US 2018056428 W US2018056428 W US 2018056428W WO 2019079540 A1 WO2019079540 A1 WO 2019079540A1
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- 0 CCCc(cc1)c(CC[C@](CN2CCC2)C=N)cc1N(C)C1=*=CC(C)=CC(C(C)=C)=I1 Chemical compound CCCc(cc1)c(CC[C@](CN2CCC2)C=N)cc1N(C)C1=*=CC(C)=CC(C(C)=C)=I1 0.000 description 6
- HLNRRPIYRBBHSQ-UHFFFAOYSA-N CCCN1CCCC1 Chemical compound CCCN1CCCC1 HLNRRPIYRBBHSQ-UHFFFAOYSA-N 0.000 description 2
Classifications
-
- 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
- C07D401/14—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 three or more hetero rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- 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
- A61K31/4709—Non-condensed quinolines and containing further heterocyclic rings
-
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/06—Antianaemics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom
-
- 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
- C07D405/14—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 three or more hetero rings
Definitions
- Methylation of protein lysine residues is an important signaling mechanism in eukaryotic ceils, and the methylation state of histone lysines encodes signals that are recognized by a multitude of proteins and protein complexes in the context of epi genetic gene regulation.
- Histone methylation is catalyzed by histone methyltransterases (HMTs), and HMTs have been implicated in various human diseases, HMTs can play a role in either activating or repressing gene expression, and certain HMTs (e.g., Vietnamese histone-lysine N- methyltransferase 2 or EHMT2, also called G9a) may methylate many nonhistone proteins, such as tumor suppressor proteins (see, e.g., Liu ei al. Journal of Medicinal Chemistry 56:893 -8942, 2013 and Krivega ei al, Blood 126(5):665-672, 2015).
- HMTs histone methyltransterases
- EHMTl and EHMT2 Two related HMTs, EHMTl and EHMT2, are overexpressed or play a role in diseases and disorders such as sickle ceil anemia (see, e.g., Rennevilie ei al,, Blood 126(16): 1930-1939, 2015) and proliferative disorders (e.g., cancers), and other blood disorders.
- diseases and disorders such as sickle ceil anemia (see, e.g., Rennevilie ei al,, Blood 126(16): 1930-1939, 2015) and proliferative disorders (e.g., cancers), and other blood disorders.
- the present disclosure provides, inter alia, compounds selected from the group consisting of
- the present disclosure features pharmaceutical compositions comprising one or more pharmaceutically acceptable carriers and one or more of the compounds of the present disclosure.
- the present disclosure features a method of inhibiting one or more HMTs (e.g., EHMTl and/or EHMT2).
- the method includes administering to a subject in need thereof a therapeutically effective amount of a compound of the present disclosure, or a tautomer thereof, or a pharmaceutically acceptable salt of the compound or the tautomer.
- the subject has one or more disorders associated with the activity of one or more HMTs (e.g., EHMTl and/or EHMT2), thereby benifiting from the inhibition of one or more HMTs (e.g., EHMTl and/or EHMT2).
- the subject has an EHMT-mediated disorder.
- the subject has a disease, disorder, or condition that is mediated at least in part by the activity of one or both of EHMTl and EHMT2.
- the present disclosure features a method of preventing or treating an EHMT-mediated disorder.
- the method includes administering to a subject in need thereof a therapeutically effective amount of a compound of the present disclosure, or a tautomer thereof, or a pharmaceutically acceptable salt of the compound or the tautomer.
- the EHMT-mediated disorder is a disease, disorder, or condition that is mediated at least in part by the activity of EHMTl or EHMT2 or both.
- the EHMT-mediated disorder is a blood disease or disorder.
- the EHMT-mediated disorder is selected from proliferative disorders (e.g., cancers such as leukemia, hepatocellular carcinoma, prostate carcinoma, and lung cancer), addiction (e.g., cocaine addiction), and mental retardation.
- the EHMT-mediated disease or disorder comprises a di sorder that is associated with gene silencing by one or more HMTs (e.g., EHMT 1 and/or EHMT2).
- EHMT-mediated disease or disorder is a blood disease or disorder associated with gene silencing by EHMT2.
- the method comprises the step of administering to a subject having a disease or disorder associated with gene silencing by one or more HMTs (e.g., EHMT1 and/or EHMT2) a therapeutically effective amount of one or more compounds of the present disclosure, wherein the compound(s) inhibits histone methyltransferase activity of one or more HMTs (e.g., EHMTl and/or EHMT2), thereby treating the disease or disorder.
- HMTs e.g., EHMT1 and/or EHMT2
- the blood disease or disorder is selected from the group consisting of sickle ceil anemia and beta-thalassemia.
- the blood disease or disorder is hematological cancer.
- the hematological cancer is acute myeloid leukemia (AML) or chronic lymphocytic leukemia (CLL).
- AML acute myeloid leukemia
- CLL chronic lymphocytic leukemia
- the method further comprises the steps of performing an assay to detect the degree of histone methylation by one or more HMTs (e.g., EHMT l and/or EHMT2) in a sample comprising blood cells from a subject in need thereof.
- performing the assay to detect methylation of H3-K9 in the histone substrate comprises measuring
- performing the assay to detect methylation of H3-K9 in the histone substrate comprises contacting the histone substrate with an antibody that binds specifically to dimethylated H3-K9.
- any description of a method of treatment includes use of the compounds to provide such treatment or prophylaxis as i s described herein, as wel l as use of the compounds to prepare a medicament to treat or prevent such condition.
- the treatment includes treatment of human or non-human animals including rodents and other disease models. Methods described herein may be used to identify suitable candidates for treating or preventing EHMT- mediated disorders. For example, the disclosure also provides methods of identifying an inhibitor of EHMTl or EHMT2 or both. [016] In some aspects, the present disclosure features a method of inhibiting conversion of H3-
- the method comprises the step of contacting a mutant EHMT, the wild-type EHMT, or both, with a histone substrate comprising H3-K9 and an effective amount of a compound of the present disclosure, wherein the compound inhibits histone methyl transferase activity of EHMT, thereby inhibiting conversion of H3-K9 to dimethylated H3-K9.
- the present disclosure features compounds disclosed herein for use in inhibiting one or both of EHMT 1 and EHMT2 in a subject in need thereof.
- the present disclosure features compounds disclosed herein for use in preventing or treating an EHMT-mediated disorder in a subject in need thereof.
- the present disclosure features compounds disclosed herein for use in preventing or treating a blood disorder in a subject in need thereof.
- the present disclosure features compounds disclosed herein for use in preventing or treating a cancer in a subject in need thereof.
- the present disclosure features use of a compound of the present disclosure in the manufacture of a medicament for inhibiting one or both of EHMT 1 and EHMT2 in a subject in need thereof.
- the present disclosure features use of a compound of the present disclosure in the manufacture of a medicament for preventing or treating an EHMT-mediated disorder in a subject in need thereof.
- the present disclosure features use of a compound of the present disclosure in the manufacture of a medicament for preventing or treating a blood disorder in a subject in need thereof,
- the present disclosure features use of a compound of the present disclosure in the manufacture of a medicament for preventing or treating a cancer in a subject in need thereof.
- the compounds or methods described herein can be used for research (e.g., studying epi genetic enzymes) and other non-therapeutic purposes.
- the compounds of the present disclosure do not show significant inhibitory activity towards a kinase. Absence of significant kinase inhibition can be determined by measuring IC50 values for one or more kinases of interest, wherein IC50 values greater than a certain reference value are indicative of low or no inhibitory activity towards a given kinase.
- the compounds of the present disclosure inhibit a kinase with an enzyme inhibition ICso value of about 100 nM or greater, 1 ⁇ or greater, 10 ⁇ or greater, 100 ⁇ , ⁇ or greater, or 1000 ⁇ or greater.
- one or more of the compounds of the present disclosure inhibit a kinase with an enzyme inhibition ICso value of about 1 mM or greater,
- one or more of the compounds of the present disclosure inhibit a kinase with an enzyme inhibition ICso value of 1 ⁇ or greater, 2 ⁇ or greater, 5 ⁇ or greater, or 10 ⁇ or greater, wherein the kinase is one or more of the following: Abl, AurA, CHK1, MAP4K, IRA 4, JAK3, EphA2, FGFR3, KDR, Lck, MARK1 , MNK2, PKCb2, SIK, and Src.
- Figure 1A shows XRPD pattern of Compound 1R freebase Type A.
- Figure IB shows XRPD pattern of Compound 1R freebase Type B .
- Figure 2A shows XRPD pattern of Compound 2 freebase Type A.
- Figure 2B shows XRPD overlay of Compound 2 freebase Type A before and after DVS
- Figure 3 shows XRPD pattern of Compound 3 freebase Type A.
- Figure 4A shows XRPD pattern of Compound 4R freebase Type A
- Figure 4B shows XRPD pattern of Compound 4R freebase Type B .
- Figure 5A shows XRPD pattern of Compound 5R freebase Type A.
- Figure SB shows XRPD of Compound 5R freebase Type A, and XRPD of the compound after heating to 130 °C (freebase Type B).
- Figure 51 shows XRPD overlay of Compound 5R freebase Type B before and after DVS.
- Figure 6 shows XRPD pattern of Compound 6 freebase Type A.
- the present disclosure provides novel amine-substituted heterocyclic compounds, synthetic methods for making the compounds, pharmaceutical compositions containing them various uses of the compounds.
- the present disclosure provides a compound selected from the group consisti
- the compound is selected from the compounds listed in Table I, pharmaceutically acceptable salts thereof, and phannaceutically acceptable salts of the tautomer
- the compound is selected from the compounds listed in Table I .
- the compound is a crystalline form of any one of the compounds listed in Table 1.
- the compound e.g., the crystalline form of any one of the compounds listed in Table 1
- the compound is an anhydrate (e.g., an anhydrate of any one of the compounds listed in Table 1).
- the compound is selected from pharmaceutically acceptable salts of the compounds listed in Table I .
- the compound is a crystalline form of any one of the pharmaceutically acceptable salts of the compounds listed in Table 1.
- the compound e.g., the crystalline form of any one of the pharmaceutically acceptable salts of the compounds listed in Table 1
- is an anhydrate e.g., an anhydrate of any one of the pharmaceutically acceptable salts of the compounds listed in Table 1).
- the compound is selected from hydrochloride salts, sulfate salts, glycolate salts, adipate salts, succinate salts, oxalate salts, phosphate salts, fumarate salts, hippurate salts, gentisate salts, and benzoate salts of the compounds listed in Table 1.
- the compound is selected from hydrochloride salts of the compounds listed in Table 1.
- the compound is a crystalline form of any one of the hydrochloride salts of the compounds listed in Table 1.
- the compound is selected from sulfate salts of the compounds listed in Table 1.
- the compound is a crystalline form of any one of the sulfate salts of the compounds listed in Table 1.
- the compound is selected from glycolate salts of the compounds listed in Table 1.
- the compound is a crystalline form of any one of the adipate salts of the compounds listed in Table 1.
- the compound is selected from succinate salts of the compounds listed in Table I .
- the compound is selected from oxalate salts of the compounds listed in Table 1.
- the compound is a crystalline form of any one of the oxalate salts of the compounds listed in Table 1.
- the compound is selected from phosphate salts of the compounds listed in Table 1.
- the compound is selected from fumarate salts of the compounds listed in Table 1.
- the compound is a crystalline form of any one of the fumarate salts of the compounds listed in Table I ,
- the compound is selected from hippurate salts of the compounds listed in Table 1.
- the compound is a crystalline form of any one of the hippurate salts of the compounds listed in Table 1.
- the compound is a crystalline form of any one of the gentisate salts of the compounds listed in Table 1.
- the compound is selected from benzoate salts of the compounds listed in Table 1.
- the compound is N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(075] in some embodiments, the compound is N-[075]
- the compound is Compound I . [077] In some embodiments, the compound is Compound I .
- the compound is Compound 1R or Compound I S.
- the compound is Compound 1R, a tautomer thereof, a
- the crystalline form of Compound 1R is an anhydrate.
- the compound is a phannaceutically acceptable salt of Compound 1R.
- the compound is a crystalline form of a pharmaceutically acceptable salt of Compound 1R.
- the crystalline form of the pharmaceutically acceptable salt of Compound 1R is an anhydrate.
- the compound is a hydrochloride salt, sulfate salt, glycoiate salt, adipate salt, succinate salt, oxalate salt, phosphate salt, fumarate salt, hippurate salt, gentisate salt, or benzoate salt of Compound 1R.
- the compound is Compound IR.
- the compound is a crystalline form of Compound IR.
- the compound e.g., the crystalline form of Compound IR
- DSC differential scanning calorimeter
- the compound e.g., the crystalline form of Compound 1R
- the compound e.g., the crystalline form of Compound 1R
- mDSC modulated differential scanning calorimeter
- the compound is Compound 1R.
- the compound is a crystalline form of Compound 1R.
- the compound e.g., the crystalline form of the hydrochloride salt of Compound 1R
- the compound is characterized by an XRPD pattern having at least two peaks selected from 6.4 ⁇ 0.2, 11.8.0.2, 14.2:02, 18.21+0.2, 19.2.0.2, 25.7:02, 264 ⁇ 0.2. and 293 ⁇ 0.2 °2 ⁇ (e.g., 6.4:0.1, 11.8-0.1.1-1.2:0.1.18.21+0.1, 19.2+0.1, 25.7+0.1, 26.4+0.1, and 29.3+0.1 °2 ⁇ ) using Cu Ka radiation,
- the compound e.g., the crystalline form of the hydrochloride salt of Compound 1R
- the compound is characterized by an XRPD pattern having at least three peaks selected from ⁇ ,4 ⁇ 0.2, II.8+0.2, 14.2:02, 1821 -0.2.19.2+0.2, 25.7-02, 26,4+0.2, and 293-0.2 °2 ⁇ (e.g., 64 : 0.1.11.8.0.1, 14.2:01, 18.21+0.1, 19.2.0.1, 25.7:0 !, 2 4-0.1. and 293-0.1 °2 ⁇ ) using Cu Kct radiation.
- the compound e.g., the crystalline form of the hydrochloride salt of Compound IR
- the compound is characterized by an XRPD pattern having at least five peaks selected from 6.4:0.2.11.8:0.2, 14.2:0.2, 18.21 ⁇ 0.2, 19.2:0.2, 25.7:0.2, 26.4+0.2, and 29.3+0.2 °2 ⁇ (e.g., 64 -0.1. i 1.8.0.1, 14.2 01, 1821- .1..19.2.0.1, 25.7-01, 264-0.1. and 293-0.1 °2 ⁇ ) using Cu Ka radiation.
- the compound e.g., the crystalline form of the hydrochloride salt of Compound IR
- the compound is characterized by an XRPD pattern having at least six peaks selected from 6.4 ⁇ 0.2, 11.8.0.2, 14.2:02, 18.21+0.2, 19.2.0.2, 25.7:02, 264 ⁇ 0.2. and 293 ⁇ 0.2 °2 ⁇ (e.g., 6.4:0.1, 11.8-0.1.1-1.2:0.1.18.21+0.1, 19.2+0.1, 25.7+0.1, 26.4+0.1, and 29.3+0.1 °2 ⁇ ) using Cu Ka radiation,
- the compound e.g., the crystalline form of the hydrochloride salt of Compound IR
- the compound is characterized by an XRPD pattern having at least seven peaks selected from 6.4+0.2, 11.8+0,2, 14,2+0.2, 18.21+0.2, 19.2+0,2, 25,7+0.2, 26.4+0.2, and 29.3+0.2 °2 ⁇ (e.g., 6.4+0.1, 11.8+0.1, 14.2+0.1, 18.21+0.1, 19.2+0.1, 25.7+0.1, 26.4+0.1, and 29.3+0.1 °2 ⁇ ) using Cu Ka radiation.
- the compound e.g., the crystalline form of the hydrochloride salt of Compound 1R
- the compound is characterized by an XRPD pattern having three peaks selected from 6.4+0.2, i 1.8:0.2, 14.2.0.2.18.21 -0.2, 19.2:0.2, 25.7.0.2.26.4-02, and 29.3+0.2 °2 ⁇ (e.g., 6.4:01, 11.8:0.1.14.2+0.1, 18.21 -0.1. I9.2+0.I, 25.7+0.1, 26.4 ⁇ 0.1, and 29.3 ⁇ 0.1 °2 ⁇ ) using Cu Ka radiation.
- the compound e.g., the crystalline form of the hydrochloride salt of Compound 1R
- the compound is characterized by an XRPD pattern having six peaks selected from 6.4+0,2, 11.8+0.2, 14.2+0.2, 18.21+0.2, 19.2+0.2, 25.7+0.2, 26.4+0.2, and 29.3+0.2 °2 ⁇ (e.g., 6.4+0.1, 11,8+0.1, 14.2+0.1, 18.21+0,1, 19,2+0.1, 25.7+0.1, 26.4+0,1, and 29.3+0.1 °2 ⁇ ) using Cu Ka radiation.
- the compound e.g., the crystalline form of the hydrochloride salt of Compound 1R
- the compound is characterized by an XRPD pattern having seven peaks selected from 6.4+0.2, 1.8+0.2, 14.2+0.2, 18.21+0.2, 19.2+0.2, 25.7+0.2, 26.4+0.2, and 29.3+0.2 °2 ⁇ (e.g., 6.4+0.1, 11.8+0.1, 14.2+0,1, 18.23+0.1, 19.2+0.1, 25,7+0.1, 26.4+0.1, and 29,3+0.1 °2 ⁇ ) using Cu Ka radiation.
- the compound e.g., the crystalline form of the hydrochloride salt of Compound 1R
- the compound is characterized by an XRPD pattern having a peak at from about 6.2 to about 6.6, from about 25.5 to about 25.9, and from about 26.2 to about 26.6 °2 ⁇ using Cu Ka radiation.
- the compound e.g., the crystalline form of the hydrochloride salt of Compound 1R
- the compound is characterized by an XRPD pattern having a peak at from about 6.2 to about 6.6, from about 14.0 to about 14.4, from about 25.5 to about 25.9, and from about 26.2 to about 26,6 °2 ⁇ using Cu Kot radiation.
- the compound e.g., the crystalline form of the hydrochloride salt of Compound 1R
- the compound is characterized by an XRPD pattern having a peak at from about 6.2 to about 6.6, from about 14.0 to about 14.4, from about 18.0 to about 18.4, from about 19.0 to about 19.4, from about 25.5 to about 25.9, and from about 26.2 to about 26.6 °2 ⁇ using Cu Ka radiation.
- the compound e.g., the crystalline form of the hydrochloride salt of Compound 1 R
- the compound is characterized by an XRPD pattern having a peak at from about 6,2 to about 6.6, from about 11.6 to about 12.0, from about 14.0 to about 14.4, from about 18.0 to about 18.4, from about 19.0 to about 19.4, from about 25.5 to about 25.9, and from about 26,2 to about 26.6 °2 ⁇ using Cu Ka radiation.
- the compound e.g., the crystalline form of the hydrochloride salt of Compound 1R
- the compound is characterized by an XRPD pattern having a peak at from about 6.2 to about 6.6, from about 11.6 to about 12.0, from about 14.0 to about 14.4, from about 18.0 to about 18.4, from about 19.0 to about 19.4, from about 25.5 to about 25.9, from about 26.2 to about 26.6, and from about 29.1 to about 29.5 °2 ⁇ using Cu Ka radiation.
- the compound e.g., the crystalline form of the hydrochloride salt of Compound 1R
- the compound is characterized by an XRPD pattern having a peak at from about 6.3 to about 6.5, from about 1 1 .7 to about 11.9, from about 14.1 to about 14.3, from about 18.1 to about 18.3, from about 19.1 to about 19.3, from about 25.6 to about 25.8, from about 26.3 to about 26.5, and from about 29.2 to about 29,4 °2 ⁇ using Cu Ka radiation.
- the compound e.g., the crystalline form of the hydrochloride salt of Compound 1R
- the compound is characterized by an XRPD pattern having a peak at about 6.39, about 11.80, about 14.20, about 18.21, about 19.15, about 25.67, about 26.41, and about 29.31 °2 ⁇ using Cu K radiation.
- the compound e.g., the crystalline form of Compound IR
- the compound is a hydrochloride salt of Compound IR.
- the compound e.g., the crystalline form of the hydrochloride salt of Compound IR
- the compound is characterized by an XRPD pattern having at least one peak selected from 6.2:0.2, 7.2:0.2.8.0-0.2.8.8:0.2.12.4:0.2, 13.3:0.2.17.7 - 0.2. and 20.2-0.2 20 (e.g., 0.2-0.1. 72 : 0.1.8.0:0.1, 8.8.0.1, ! 2.4:0 !, 1 - 0.1.17.7.0.1, and26,2 ⁇ 0.1 °2 ⁇ ) using Cu Ka radiation,
- the compound e.g., the crystalline form of the hydrochloride salt of Compound IR
- the compound is characterized by an XRPD pattern having at least two peaks selected from 6.2:0.2.7.2:0.2.8.0:0.2, 8.8:0.2, 12.4-0.2.13.3:0.2.17.7:0.2, and 26.2:0.2 °2 ⁇ (e.g., 6.2:0.1, 7.2:0.1.8.0:01, 88-0.1, 12.4:0.1, 13.3.0.1.17.7-01, and 26.2:01 °2 ⁇ ) using CuK radiation.
- the compound e.g., the crystalline form of the hydrochloride salt of Compound IR
- the compound is characterized by an XRPD pattern having at least three peaks selected from 6.2:0.2, 7.2 ⁇ 0.2, 8.0+0.2, 8.8 ⁇ 0.2, 12.4:0.2, 13.3 ⁇ 0.2, 17.7+0.2, and 26.2+0.2 °2 ⁇ (e.g., 6.2+0.1, 7,2+0.1, 8,0+0.1, 8.8+0.1, 12.4+0.1, 13,3+0.1, 17.7.0.1, and 26,2+0.1 °2 ⁇ ) using Cu Ka radiation
- the compound e.g., the crystalline form of the hydrochloride salt of Compound IR
- the compound is characterized by an XRPD pattern having at least four peaks selected from 6.2:0.2, 7.2:0.2.8.0-0.2.8.8:0.2.12.4:0.2, 13.3:0.2.17.7 - 0.2. and 20.2-0.2 20 (e.g.,
- the compound e.g., the crystalline form of the hydrochloride salt of Compound IR
- the compound is characterized by an XRPD pattern having at least five peaks selected from 6.2 ⁇ 0.2, 7.2 ⁇ 0.2, 8.0:0.2, 8.8 ⁇ 0.2, 12.4+0.2, 13.3 ⁇ 0.2, 17.7 ⁇ 0.2, and 26.2:0.2 °2 ⁇ (e.g., 6.2 ⁇ 0.1, 7.2 0.1, 8.0-0 i, 88-0.1.12.4:0.1, 13.3.0.1, 17.7-01. and 26.2-01 °2 ⁇ ⁇ using Cu Ka radiation.
- the compound e.g., the crystalline form of the hydrochloride salt of Compound IR
- the compound is characterized by an XRPD pattern having one peak selected from 6.2 ⁇ 0.2, 7.2 ⁇ 0.2, 8.0:0.2, 8.8.0.2, 12.4-02, 133-0.2.17.7.0.2, and 26.2 0.2 °2 ⁇ (e.g., 6.2:0.1, 7.2.0.1, 8.0 ⁇ 0.1, 8.8 ⁇ 0.1, 12.4 ⁇ 0.1, 13.3+0.1, 17.7+0.1, and 26.2+0.1 °2 ⁇ ) using CuKa radiation.
- the compound e.g., the crystalline form of the hydrochloride salt of Compound IR
- the compound is characterized by an XRPD pattern having two peaks selected from 6.2+0.2, 7,2+0.2, 8,0+0.2, 8.8+0.2, 12.4+0.2, 133- 0.2.17.7.0.2, and 26,2+0.2 °2 ⁇ (e.g., 6.2+0.1, 7.2.0.1. 8.0+0.1, 8.8+0.1, 12.4+0.1, 13.3+0.1, 17.7+0.1, and 26.2+0.1 °2 ⁇ ) using Cu Ka radiation.
- the compound e.g., the crystalline form of the hydrochloride salt of Compound IR
- the compound is characterized by an XRPD pattern having four peaks selected from 6.2+0.2, 7,2 ⁇ 0.2, 8.0 : 0.2 , 8.8 . 0.2, ! 2.4 : 0 2, 1 3 - 0.2. 1 7.7 . 0.2, and 26,2 ⁇ 0.2 °2 ⁇ (e.g., 6.2 ⁇ 0.1, 7.2 . 0. 1 . 8.0 ⁇ 0.1, 8.8+0.1, 1 2,-h O. L 13.3+0.1, 17.7+0.1, and 26.2 ⁇ 0.1 °2 ⁇ ) using Cu Ka radiation.
- the compound e.g., the crystalline form of the hydrochloride salt of Compound IR
- the compound is characterized by an XRPD pattern having five peaks selected from 6,2+0.2, 7.2 ⁇ 0.2, 8.0 ⁇ 0.2, 8.8+0.2, 12.4 ⁇ 0.2, 13.3 ⁇ 0.2, 17.7+0.2, and 26.2 ⁇ 0.2 °2 ⁇ (e.g., 6.2 ⁇ 0.1, 7.2+0.1, 8,0+0.1, 8.8 : 0. 1 , 12.4+0.1, 13.3+0, 1, 17,7+0.1, and 26,2+0.1 °2 ⁇ ) using Cu Ka radiation.
- the compound e.g., the crystalline form of the hydrochloride salt of Compound I R
- the compound is characterized by an XRPD pattern having a peak at 6,2+0,2, 7,2+0.2, 8.0+0.2, 8.8+0.2, 12.4+0.2, 13.3+0.2, 17.7+0.2, and 26.2+0.2 °2 ⁇ (e.g., 6.2+0.1, 7.2+0.1, 8.0+0.1, 8.8+0.1, 12.4+0. 1 , 13.3+0, 1, 17.7+0.1, and 26,2+0.1 °2 ⁇ ) using Cu Ka radiation.
- the compound e.g., the crystalline form of the hydrochloride salt of Compound IR
- the compound is characterized by an XRPD pattern having a peak at from about 6.0 to about 6,4, from about 7,8 to about 8.2, from about 8.6 to about 9.0, from from about 12.2 to about 12,6, and from about 26.0 to about 26.4 °2 ⁇ using Cu Ka radiation.
- the compound e.g., the crystalline form of the hydrochloride salt of Compound 111 is characterized by an XRPD pattern having a peak at from about 6.0 to about 6,4, from about 7.0 to about 7.4, from about 7.8 to about 8.2, from about 8.6 to about 9.0, from from about 12.2 to about 12.6, and from about 26.0 to about 26.4 °2 ⁇ using Cu Ka radiation.
- the compound is a crystalline form of Compound S.
- the compound is a hydrochloride salt, sulfate salt, glycoiate salt, adipate salt, succinate salt, oxalate salt, phosphate salt, fumarate salt, hippurate salt, geiitisate salt, or benzoate salt of Compound I S.
- the compound is Compound 2
- the compound is a crystalline form of a pharmaceutically acceptable salt of Compound 2.
- the compound is a crystalline form of Compound 2,
- the compound e.g., the crystalline form of Compound 2 is characterized by an XRPD pattern having a peak at from about 7.9 to about 8, 1, from about 9.5 to about 9.7, from about 12.5 to about 12.7, from about 15.6 to about 15.8, from about 15.9 to about 16.1 , from about 18.5 to about 18.7, from about 19.1 to about 19.3, from about 19,5 to about 19.7, from about 23.1 to about 23.3, and from about 29.9 to about 30.1 °2 ⁇ using Cu Kct radiation.
- the compound e.g., the crystalline form of Compound 2
- DSC differential scanning calorimeter
- the compound is a hydrochloride salt of Compound 2,
- the compound e.g., the crystalline form of the hydrochloride salt of Compound 2 is characterized by an XRPD pattern having at least one peak selected from 5.3 ⁇ 0.2, 8.3 ⁇ 0.2, 9,9 : 0.2, 16.7 ⁇ 0.2, 17.5+0.2, 20.3 : 0.2, 25.1 ⁇ 0.2, and 27.0 ⁇ 0.2 °2 ⁇ (e.g., 5.3 ⁇ 0.1, 8.3 . 0, 1 , 9.9 - 0 ! , 16.7 ⁇ 0.1, 17.5 ⁇ 0.1, 20. 0 1 , 25. H0.1, and 27.0 - 0 I °2 ⁇ ) using Cu a radiation.
- an XRPD pattern having at least one peak selected from 5.3 ⁇ 0.2, 8.3 ⁇ 0.2, 9,9 : 0.2, 16.7 ⁇ 0.2, 17.5+0.2, 20.3 : 0.2, 25.1 ⁇ 0.2, and 27.0 ⁇ 0.2 °2 ⁇ (e.g., 5.3 ⁇ 0.1, 8.3 . 0, 1 , 9.9 - 0 ! , 16.7 ⁇ 0.1
- the compound e.g., the crystalline form of the hydrochloride salt of Compound 2 is characterized by an XRPD pattern having at least five peaks selected from 5.3 ⁇ 0.2, 8.3:0.2, 9.9.0.2, 1 .7:02, 175- 0.2.20.3.0.2, 25.1 ⁇ 0.2, and 27.0.0.2 °2 ⁇ (e.g., 5.3.0.1. 8.3:0.1.9.9:0.1.16.7:0.1, 17.5-0.1.20.3:0.1.25.1 : 0.1, and 27. : 0.1 °2 ⁇ ) using Cu Ka radiation.
- the compound e.g., the crystalline form of the hydrochloride salt of Compound 2 is characterized by an XRPD pattern having two peaks selected from 5.3+0.2,
- the compound e.g., the crystalline form of the hydrochloride salt of Compound 2 is characterized by an XRPD pattern having four peaks selected from 5.3+0.2, 8.3+0.2, 9.9+0.2, 16,7+0.2, ⁇ 7.5+ ⁇ .2, 20.3+0.2, 25.1+0,2, and 27.0+0,2 °2 ⁇ (e.g., 5.3+0,1, 8,3+0.1, 9.9+0.1, 16.7+0.1, 17.5+0.1, 20.3+0.1, 25.1+0.1, and 27.0+0.1 °2 ⁇ ) using CuKa radiation.
- the compound e.g., the crystalline form of the hydrochloride salt of Compound 2 is characterized by an XRPD pattern having a peak at from about 5.1 to about 5.4, from about 8.1 to about 8.5, from about 9,7 to about 10.1, from about 17.3 to about 17.7, and from about about 20.1 to about 20.5 °2 ⁇ using Cu Ka radiation.
- the compound e.g., the crystalline form of the hydrochloride salt of Compound 2 is characterized by an XRPD pattern having a peak at from about 5.1 to about 5.4, from about 8.1 to about 8.5, from about 9,7 to about 10.1, from about 16.5 to about 16.9, from about 17.3 to about 17.7, and from about about 20.1 to about 20.5 °2 ⁇ using Cu Ka radiation.
- the compound e.g., the crystalline form of the hydrochloride salt of Compound 2 is characterized by an XRPD pattern having a peak at from about 5.1 to about 5.4, from about 8.1 to about 8.5, from about 9.7 to about 10.1, from about 16.5 to about 16.9, from about 17.3 to about 17.7, from about about 20.1 to about 20.5, from about 24.9 to about 25.3, and from about 26.8 to about 27.2 °2 ⁇ using Cu Ka radiation.
- the compound e.g., the crystalline form of the hydrochloride salt of Compound 2 is characterized by an XRPD pattern having a peak at from about 5.2 to about 5.3, from about 8.2 to about 8.4, from about 9,8 to about 10.0, from about 16.6 to about 16,8, from about 17.4 to about 17,6, from about about 20.2 to about 20,4, from about 25,0 to about 25.2, and from about 26.9 to about 27.1 °2 ⁇ using Cu a radiation.
- the compound is a crystalline form of Compound 3.
- the compound is a crystalline form of Compound 3.
- the compound e.g., the crystalline form of Compound 3 is characterized by an XRPD pattern having seven peaks selected from 6.3 ⁇ 0.2, 8.3 ⁇ 0.2, 12.4 ⁇ 0.2, 14.7-02, 159-0.2.17.3.0.2, 23.1+0.2, 256-0.2. and 32.7-02 °2 ⁇ (e.g., 6.3-01.83-0.1.
- the compound e.g., the crystalline form of Compound 3 is characterized by an XRPD pattern having a peak at from about 6.2 to about 6.4, from about 8.33 to about 8.35, from about 14.6 to about 14.8, from about 25.5 to about 25.7, and from about 32.6 to about 32.8 °2 ⁇ using Cu a radiation.
- the compound e.g., the crystalline form of the hydrochloride salt of Compound 3 is characterized by an XRPD pattern having at least five peaks selected from ⁇ ,8 ⁇ 0.2, 9.0:0.2, ! 1.8.0.2, 16.3 ⁇ 0,2, 25,1 ⁇ 0.2, 25.6.0.2, 26.3 ⁇ 0,2, and 27.6-02 °2 ⁇ (e.g.,
- the compound e.g., the crystalline form of the hydrochloride salt of Compound 3 is characterized by an XRPD pattern having one peak selected from 6.8+0.2, 90 : 0.2.11.8.0.2, 16.3:02, 25.1 ⁇ 0,2, 25.6:0.2, 26.3:0.2, and 27.6.0.2 °2 ⁇ (e.g., 6.8.0.1. 9.0:0.1. i 1.8:0.1, 16.3:0.1, 25.1 -0.1.25.6+0.1, 26.3:0.1, and 27.6:0.1 °2 ⁇ ) using Cu Ka radiation.
- the compound e.g., the crystalline form of the hydrochloride salt of Compound 3 is characterized by an XRPD pattern having a peak at 6.8+0.2, 9.0+0.2, 11.8+0,2, 16.3+0.2, 25.1+0.2, 25.6+0.2, 26.3+0.2, and 27.6+0.2 °2 ⁇ (e.g., 6.8+0.1, 9.0+0.1, 11.8+0.1, 16,3+0.1, 25.1.0.1, 25.6+0,1, 26,3+0.1, and 27,6+0.1 20) using Cu Ka radiation.
- the compound e.g., the crystalline form of the hydrochloride salt of Compound 3 is characterized by an XRPD pattern having a peak at from about 6.6 to about 7,0, from about 8,8 to about 9.2, from about 24.9 to about 25,3, from about 25,4 to about 25.8, from about 26.1 to about 26.5, and from about 27.4 to about 27.8 °2 ⁇ using Cu Ka radiation.
- the compound e.g., the crystalline form of the hydrochloride salt of Compound 3 has an endothermic peak top temperature in differential scanning calorimeter (DSC) analy sis at between about 75 °C and about 115 °C, between about 80 °C and about 100 °C, between about 85 °C and about 105 °C, between about 90 °C and about 100 C 'C, or between about 95 °C and about 96 °C.
- the compound e.g., the crystalline form of the hydrochloride salt of Compound 3 has an endothermic peak top temperature in differential scanning calorimeter (DSC) analysis at about 95.5 °C.
- the compound e.g., the crystalline form of the hydrochloride salt of Compound 3 is characterized by an XRPD pattern having at least three peaks selected from 11.8:0.2.12.3:0.2, 16.9:02.22.3:0.2.23.R0.2, 23.6:0.2.2x3-0.2.27.5+ .2, 28.U0.2, and 30.U0.2 °20(e.g., 11.8.0.1, 12.3:01, 16.9 ⁇ 0.1, 22.3 ⁇ 0.1, 23.1+0.1, 23.6 ⁇ 0.1, 25,3 ⁇ 0.1, 27.5:0.1.28.1 :0.1, and 30.1 ⁇ 0.1 °2 ⁇ ) using CuKa radiation.
- the compound e.g., the crystalline form of the hydrochloride salt of Compound 3 is characterized by an XRPD pattern having at least four peaks selected from ! 1.8:0.2, 12.3-0.2.16.9:0.2.22.3 ⁇ 0.2, 23 ! -0.2.23.6:0.2.25.3:0.2, 27.5-0.2.28.1 : 0.2. and 30.1 ⁇ 02 °2 ⁇ (e.g., 11.8-01.12.3-0.1.16.9.0.1, 22.3-01, 231-0.1.23.6.0.1, 25.3 01, 27.5 ⁇ 0.1, 28.1+0.1, and 30.1 ⁇ 0.1 °2 ⁇ ) using Cu Ka radiation.
- the compound e.g., the crystalline form of the hydrochloride salt of Compound 3 is characterized by an XRPD pattern having seven peaks selected from H.8 ⁇ 0.2, 12.3 ⁇ 0.2, 16.9:0.2, 22.3 ⁇ 0.2, 23.1 ⁇ 0.2, 23.6:0.2, 25.3 ⁇ 0.2, 27.5+0.2, 28.1 ⁇ 0.2, and 3Q.1 ⁇ 0.2 °2 ⁇ (e.g., 11.8:0.1, 12.3:0.1.16.9+0.1, 22.3:0.1, 23.1 ⁇ 0.1, 23.6+0.1, 25.3 ⁇ 0.I, 27.5 ⁇ 0.1, 28.1+0.1, and 30.1 ⁇ 0.1 °2 ⁇ ) using Cu Ka. radiation,
- the compound e.g., the crystalline form of the hydrochloride salt of Compound 3 is characterized by an XRPD pattern having nine peaks selected from 1 ⁇ .8+ .2, 12.3:0.2, 16.9.0.2.22.3:02, 23.U0.2, 23.6+0.2, 25.3:02, 27.5 ⁇ 0.2, 28.1+0.2, and 30,1 ⁇ 0.2 °2 ⁇ (e.g., 11.8-0.1.12.3:0.1.16.9+-0.1, 22.3+0.1, 23.1 ⁇ 0.I, 23.6:0.1, 25.3:0.1.27.5:0.1.28.I+ .L and 30.1 ⁇ 0.1 °2 ⁇ ) using Cu Ka radiation.
- the compound e.g., the crystalline form of the hydrochloride salt of Compound 3 is characterized by an XRPD pattern having a peak at from about 12.1 to about 12.5, from about 16.7 to about 17.0, and from about 25.1 to about 25.5 °2 ⁇ using Cu Ka radiation.
- the compound e.g., the crystalline form of the hydrochloride salt of Compound 3
- the compound e.g., the crystalline form of the sulfate salt of Compound 3 is characterized by an XRPD pattern having at least five peaks selected from 5.2 ⁇ 0.2, 10.9+0.2, 14.6:02, 18.3+0,2, 19.6+0.2, 20.9+0.2, 225 ⁇ 0.2.24.2:0.2, 25.6.0.2, and 28.0:0.2 °2 ⁇ (e.g., 5.2:0.1, 10.9.0.1.14.6-0 I, 18.3:0.1, 19.6.0.1.20.9:01, 22,5 ⁇ ().l, 24.2.0.1, 25.6+0.1, and 28.0+0.1 °26) using Cu K radiation.
- the compound e.g., the crystalline form of the sulfate salt of Compound 3 is characterized by an XRPD pattern having at least six peaks selected from 5.2 ⁇ 0.2, 10.9:02, 14.6-0.2.18.3:0.2.19.6:0.2, 20.9-0.2.22.5:0.2.24.2:0.2, 25.6-0.2. and 28.0:0.2 °2 ⁇ (e.g., 5.2 ⁇ 0,1, 10,9 ⁇ ().l, 14.6.0.1, 18.3:01, 196- 0.1.20.9 : 0.1 , 22.5 : 0. L 242 ⁇ 0. L 25. : 0.1 , and 28.0 ⁇ 0.1 °2 ⁇ ) using Cu Ka radiation.
- the compound e.g., the crystalline form of the sulfate salt of Compound 3 is characterized by an XRPD pattern having one peak selected from 5.2+0.2, 10.9+0.2, 14.6+0.2, 18.3+0.2, 19.6+0.2, 20.9+0.2, 22.5+0.2, 24.2+0.2, 25.6+0.2, and 28.0+0.2 20 (e.g., 5.2+0.1, 10.9+0.1, 14.6+0,1, 18,3+0.1, 19.6+0.1, 20.9+0,1, 22,5+0.1, 24.2+0.1, 25.6+0.1, and 28.0+0.1 °2 ⁇ ) using Cu Ka radiation.
- 5.2+0.1, 10.9+0.1, 14.6+0,1, 18,3+0.1, 19.6+0.1, 20.9+0,1, 22,5+0.1, 24.2+0.1, 25.6+0.1, and 28.0+0.1 °2 ⁇ using Cu Ka radiation.
- the compound e.g., the crystalline form of the sulfate salt of Compound 3 is characterized by an XRPD pattern having two peaks selected from 5.2+0,2, 10.9+0.2, 14.6+0.2, 18.3+0.2, 19.6+0.2, 20.9+0.2, 22.5+0.2, 24.2+0.2, 25.6+0.2, and 28.0+0.2 °2 ⁇ (e.g., 5.2:0.1, 10.0:01, 14.6+ ⁇ , ⁇ , 18.3 O.K.19.6.0.1, 20.9-0 I.22.5-0.!..24.2.0.1, 25.6-0 i, and 28.0 ⁇ 0.1 °2 ⁇ ) using Cu Ka radiation.
- 5.2:0.1, 10.0:01, 14.6+ ⁇ , ⁇ , 18.3 O.K.19.6.0.1, 20.9-0 I.22.5-0.!..24.2.0.1, 25.6-0 i, and 28.0 ⁇ 0.1 °2 ⁇ using Cu Ka radiation.
- the compound e.g., the crystalline form of the sulfate salt of Compound 3 is characterized by an XRPD pattern having three peaks selected from 5.2+0.2, 10,9 ⁇ 0.2, 14.6.0.2.18.3:02, 196:0.2, 20.9.0.2, 22.5:02, 24.2 ⁇ 0.2, 25.6.0.2, and 28.0:0.2 °2 ⁇ (e.g., 5.2:0.1.10.9:0.1.14.6 ⁇ 0.1, 18.3:0.1, 19.6-0.1.20.9:0.1, 22.5 ⁇ 0.1, 24.2-0.1.25.0:0. L and 28. : 01 °2 ⁇ ) using Cu Ka radiation.
- the compound e.g., the crystalline form of the sulfate salt of Compound 3 is characterized by an XRPD pattern having eight peaks selected from 5.2+0.2, 10.9:0.2, 14.6.0.2.18.3:02, 196:0.2, 20.9.0.2, 22.5:02, 24.2 ⁇ 0.2, 25.6.0.2, and 28,0+0.2 °2 ⁇ (e.g., 5.2:0.1, i 0.9:0.1, 14.6 ⁇ 0,1, 18,3 ⁇ 0.1, 19.6.0.1, 20.9-01.22.5-0.!..24.2.0.1, 25.6-01, and 28.0 ⁇ 0.1 °2 ⁇ ) using Cu Ka radiation.
- the compound e.g., the crystalline form of the sulfate salt of Compound 3 is characterized by an XRPD pattern having a peak at from about 5.0 to about 5.4, from about 10.7 to about 1 1 .0, from about 14.4 to about 14.8, from about 18.1 to about 18.4, from about 19.4 to about 19.8, from about 20.7 to about 21.0, from about 25.4 to about 25.8, and from about 27.8 to about 28,2 °2 ⁇ using Cu K radiation.
- an XRPD pattern having a peak at from about 5.0 to about 5.4, from about 10.7 to about 1 1 .0, from about 14.4 to about 14.8, from about 18.1 to about 18.4, from about 19.4 to about 19.8, from about 20.7 to about 21.0, from about 25.4 to about 25.8, and from about 27.8 to about 28,2 °2 ⁇ using Cu K radiation.
- the compound e.g., the crystalline form of the sulfate salt of Compound 3 is characterized by an XRPD pattern having a peak at from about 5.0 to about 5.4, from about 10.7 to about 11.0, from about 14.4 to about 14.8, from about 18.1 to about 18.4, from about 19.4 to about 19,8, from about 20,7 to about 21.0, from about 22.3 to about 22,7, from about
- the compound is a glycolate salt of Compound 3.
- the compound is a crystalline form of a glycolate salt of
- the compound e.g., the crystalline form of the glycolate salt of Compound 3 is characterized by an XRPD pattern having at least five peaks selected from 68 : 0.2.9.0:0.2, 11.8.0.2.13.2-02, 16.3:0.2, 20.4.0.2.23.6:02, 250:0.2, 25.5.0.2, and 27.6:0.2 °2 ⁇ (e.g., 6.8:0.1.9. -0.1. 11.8:0.1.13.2:0.1, 16.3-0. i.20.4:0.1.23.6:0.1, 25.0:0.1. 25.5 ⁇ 0.1, and 27.6 ⁇ 0.1 °2 ⁇ ) using Cu Ka radiation,
- the compound e.g., the crystalline form of the glycolate salt of Compound 3 is characterized by an XRPD pattern having at least seven peaks selected from 6.8:0.2.9.0:0.2.11.8:0.2, 13.2-0.2. 16.3 : 0.2.20.4:0.2, 23.6:0.2.2x0:0.2.25.5+0.2, and 27.6:0.2 °2 ⁇ (e.g., 6.8:0.1, 9.0.0.1, 11.8:01, 132- 0.1. 16.3.0.1, 20.4:01, 236-0.1.25.0:0.1, 25.5+0.1, and 27.6 ⁇ 0.1 °26) using Cu Ka radiation.
- the compound e.g., the crystalline form of the glycolate salt of Compound 3 is characterized by an XRPD pattern having a peak at from about 6.7 to about 6.9, from about 8.9 to about 9.1 , from about 1 1.7 to about 1 1.9, from about 13.0 to about 13.2, from about 16.2 to about 16.4, from about 20.3 to about 20.5, from about 23.5 to about 23.7, from about
- the compound e.g., the crystalline form of the glycolate salt of Compound 3 is characterized by an XRPD pattern having a peak at about 6,81 , about 9.00, about 1 1.77, about 13. 15, about 16.28, about 20.44, about 23.63, about 25.02, about 25.52, and about 27,59 °2 ⁇ using Cu Ka radiation.
- the compound e.g., the crystalline form of the glycolate salt of Compound 3 has an endothermic peak top temperature in differential scanning calorimeter (DSC) analysis at about 103.9 °C, at about 132.6 °C, and/or at about 231.9 °C.
- DSC differential scanning calorimeter
- the compound e.g., the crystalline form of the succinate salt of Compound 3 is characterized by an XRPD pattern having at least six peaks selected from 6.8+0.2, 7.6+0.2, 9.0+0,2, 11 ,8+0.2, 14.8+0.2, 22.1+0,2, 23,3+0.2, 25.7+0.2, 27.3+0.2, and 32.7+0.2 °2 ⁇ (e.g., 6.8:0.1, 7.6.0.1, 9.0:01, II 8-0.1.14.8:0.1, 22.1+0.1, 23.3+0,1, 25,7 ⁇ 0.1, 27.3.0.1, and 32.7 ⁇ 0.1 °2 ⁇ ) using Cu Ka radiation.
- the compound e.g., the crystalline form of the succinate salt of Compound 3 is characterized by an XRPD pattern having two peaks selected from 6.8+0.2, 7.6 ⁇ 0.2, 9.0 ⁇ 0.2, 11.8 ⁇ 0.2, 14.8+0.2, 22.1 ⁇ 0.2, 23.3:0.2, 25.7 ⁇ 0.2, 27.3 ⁇ 0.2, and 32.7+0.2 °2 ⁇ (e.g., 6.8:0.1.7.6:0.1, 9.0:0.1, i 1.8-0.1.14.8:0.1.22.1+0.1, 23.3+0.1, 25.7+0.1, 27.3+0.1, and 32,7+0.1 °2 ⁇ ) using Cu Ka radiation.
- the compound e.g., the crystalline form of the succinate salt of Compound 3 is characterized by an XRPD pattern having seven peaks selected from 6.8+0.2, 7.6 ⁇ 0.2, 9.0 ⁇ 0.2, 11.8+0.2, 14.8:0.2, 22.1 ⁇ 0.2, 23.3+0.2, 25.7 ⁇ 0.2, 27.3 ⁇ 0.2, and 32.7 ⁇ 0.2 °2 ⁇ (e.g., 6.8-01, 76-0.1.9.0-0.1.11.8+0.1, 14.8-01, 22 I ⁇ 0.1.23.3+0.1, 25.7-01, 273-0.1. and 32.7 ⁇ 0.1 °2 ⁇ ) using Cu Ka radiation.
- the compound e.g., the crystalline form of the succinate salt of Compound 3 is characterized by an XRPD pattern having nine peaks selected from 6.8 ⁇ 0.2, 7.6 ⁇ 0.2, 9.0:0.2, 11.8+0.2, 14.8-02, 22.1 : 0.2, 23.3+0.2, 25.7+0,2, 27,3 ⁇ 0.2, and 327-0.2 °2 ⁇ (e.g., 6.8:0.1, 7.6.0.1, 9.0:0 !, II 8-0.1.14.8:0.1, 22.1 ⁇ 0.1, 23.3 ⁇ 0.1, 25,7 ⁇ 0.1, 27.3.0.1, and 32.7 ⁇ 0.1 °2 ⁇ ) using Cu Ka radiation.
- XRPD pattern having nine peaks selected from 6.8 ⁇ 0.2, 7.6 ⁇ 0.2, 9.0:0.2, 11.8+0.2, 14.8-02, 22.1 : 0.2, 23.3+0.2, 25.7+0,2, 27,3 ⁇ 0.2, and 327-0.2 °2 ⁇ (e.g., 6.8:0.1, 7.6.0.1, 9.0:0 !, II
- the compound e.g., the crystalline form of the succinate salt of Compound 3 is characterized by an XRPD pattern having a peak at from about 6.6 to about 7.0, from about 7.4 to about 7.8, and from about 25.5 to about 25.9 °2 ⁇ using Cu Ka radiation.
- the compound e.g., the crystalline form of the succinate salt of Compound 3 is characterized by an XRPD pattern having a peak at from about 6.6 to about 7.0, from about 7.4 to about 7.8, from about 11.6 to about 12.0, from about 25.5 to about 25,9, and from about 32.5 to about 32.9 °2 ⁇ using Cu Ka radiation.
- the compound e.g., the crystalline form of the succinate salt of Compound 3 is characterized by an XRPD pattern having a peak at from about 6.6 to about 7.0, from about 7,4 to about 7.8, from about 8.8 to about 9.2, from about 11.6 to about 12.0, from about 14.6 to about 15.0, from about 23.1 to about 23.5, from about 25.5 to about 25.9, from about 27, 1 to about 27.5, and from about 32.5 to about 32.9 °2 ⁇ using Cu Ka radiation.
- the compound e.g., the crystalline form of the succinate salt of Compound 3
- DSC differential scanning calorimeter
- the compound is Compound 4R or Compound 4S.
- the compound is 4R.
- the compound is a pharmaceutically acceptable salt of Compound
- the compound is a crystalline form of a pharmaceutically acceptable salt of Compound 4R.
- the crystalline form of the pharmaceutically acceptable salt of Compound 4R is an anhydrate.
- the compound is a crystalline form of Compound 4R.
- the compound e.g., the crystalline form of Compound 4R
- the compound is characterized by an XRPD pattern having at least one peak selected from 6.4 ⁇ 0.2, 7.2 ⁇ 0.2, 9.0:0.2, 13.3-0.2.15.7 ⁇ 0.2, and 26. ! : 0.2 °26 (e.g., 6.4:0.1.7.2 :().!.9.9 ⁇ 0.1, 13.3:0.!.15.7 ⁇ 0.1, and 26.1 ⁇ 0.1 °2 ⁇ ) using Cu K radiation.
- the compound e.g., the crystalline form of Compound 4R
- the compound is characterized by an XRPD pattern having at least two peaks selected from 6.4 ⁇ 0.2, 7.2+0.2, 9.9 ⁇ 0,2, 13.3 -02.15,7 ⁇ 0.2, and 261 ⁇ 0.2 °2 ⁇ (e.g., 64 ⁇ 0. i ..7.2 ⁇ 0.1, 9.9.0.1, 13.3-01, 15.7 ⁇ 0.1, and 26.1 ⁇ 0.1 °2 ⁇ ) using Cu Ka radiation.
- the compound e.g., the crystalline form of Compound 4R
- the compound is characterized by an XRPD pattern having a peak at from about 6.2 to about 6.6, from about 7.0 to about 7,4, from about 13.1 to about 13.5, and from about 25.9 to about 26.3 °2 ⁇ using Cu Ka radiation.
- the compound e.g., the crystalline form of Compound 4R
- the compound is characterized by an XRPD pattern having at least three peaks selected from 6.3+0,2, 6.7+0,2, 9.2 ⁇ 0.2, 12.7+0.2, 13.1 ⁇ 0.2, 14.4+0.2, 20.1+0.2, 22.0 ⁇ 0.2, 26.2+0.2, and 27.1+0.2 °2 ⁇ (e.g., 6.3:0.1.6.7:0.1.9.2 : 0.1 , 12.7:0 !.13.1+0.1, 1 .4:0.1, 20.1+0.1, 22.0+0.1, 26.2+0.1, and 27.1+0.1 °2 ⁇ ) using Cu Ka radiation.
- the compound e.g., the crystalline form of Compound 4R
- an XRPD pattern having at least four peaks selected from 6.3+0.2, 6.7+0.2, 9,2+0.2, 12.7+0.2, 13.1+0.2, 14.4+0,2, 20.1+0.2, 22.0+0.2, 26.2+0,2, and 27.1+0,2 °2 ⁇ (e.g., 6.3+0.1, 6.7+0.1, 9.2+0.1, 12.7+0.1, 13.1+0.1, 14.4+0.1, 20.1+0.1, 22.0+0.1, 26.2+0.1, and 27,1+0.1 °2 ⁇ ) using Cu Ka radiation,
- the compound e.g., the crystalline form of Compound 4R
- the compound is characterized by an XRPD pattern having six peaks selected from 6.3+0.2, 6.7 ⁇ 0.2, 9.2+0.2, ! .7:02, 13 ! -0.2.14.4:0.2, 20.1 ⁇ 0.2, 220-0.2, 26.2:0.2, anil 27 I : 0.2 °2 ⁇ (e.g., 6.3:0.1, 6.7+0.1,9.2+0.1, 12.7 ⁇ 0.1, 13.1 ⁇ 0.1, 14.4 ⁇ 0.1, 20.1 ⁇ 0.1, 22.0 ⁇ 0.1, 26.2 ⁇ 0.1, and 27.1+0.1 °2 ⁇ ) using Cu Ka radiation.
- the compound e.g., the crystalline form of Compound 4R
- the compound e.g., the crystalline form of Compound 4R
- the compound e.g., the crystalline form of Compound 4R
- the compound is characterized by an XRPD pattern having at least one peak selected from 7.3+0.2, 8.0 ⁇ 0.2, 8.8 ⁇ 0.2, 9.8 ⁇ 0.2, 12.4+0.2, 13.3+0.2, and 26.2 : 0.2 °2 ⁇ (e.g., 7.3+0.1, 8.0+0.1, 8.8+0.1, 9.8+0.1, 12.4+0.1 , 13.3+0, 1, and 26.2+0, 1 : 20 ⁇ using Cu a radiation.
- the compound e.g., the crystalline form of Compound 4R
- the compound is characterized by an XRPD pattern having at least two peaks selected from 7.3+0.2, 8.0+0.2, 8,8+0.2, 9,8+0.2, 12.4+0.2, 13.3+0,2, and 26.2+0.2 °2 ⁇ (e.g., 7.3+0.1 , 8.0+0, 1 , 8,8+0.1, 9.8+0.1, 12.4+0.1, 13.3+0.1, and 26.2+0.1 °2 ⁇ ) using Cu K radiation.
- the compound e.g., the crystalline form of Compound 4R
- the compound is characterized by an XRPD pattern having two peaks selected from 7.3 ⁇ 0.2, 8.0 ⁇ 0.2, 8.8 ⁇ 0.2, 9.8:0.2.12.4-02, 13.3 : 0.2, and26,2 ⁇ 0.2 °2 ⁇ (e.g., 7,3 ⁇ ().l, 8.0:0.1, 8.8.0.1.9.8:0
- the compound e.g., the crystalline form of Compound 4R
- the compound is characterized by an XRPD pattern having five peaks selected from 7.3 ⁇ 0.2, 8.0 ⁇ 0.2, 8.8 ⁇ 0.2, 98 : 0.2. 12.4.0.2, 13.3:02, and 26.2 ⁇ 0.2 °2 ⁇ (e.g., 7.3:0.1, 8.0:01, 88-0.1.9.8:0.1, 12.4.0.1. 13.3:0.1. and 26.2 ⁇ 0.1 °2 ⁇ ) using Cu Ka radiation.
- the compound e.g., the crystalline form of Compound 4R
- an XRPD pattern having a peak at from about 7.1 to about 7.5, from about about 13,1 to about 13.5, and from about 26.0 to about 26.4 °2 ⁇ using Cu K radiation.
- the compound e.g., the crystalline form of Compound 4R
- an XRPD pattern having a peak at from about 7. 1 to about 7,5, from about 9,6 to about 10.0, from about about 13.1 to about 13.5, and from about 26.0 to about 26.4 °2 ⁇ using Cu K radiation
- the compound is a hydrochloride salt of Compound 4R.
- the compound e.g., the crystalline form of the hydrochloride salt of Compound 4R
- the compound is characterized by an XRPD pattern having a peak at from about 6.1 to about 6.5, from about 14.3 to about 14.7, and from about 25.3 to about 25.7 °2 ⁇ using Cu Ka radiation.
- the compound e.g., the crystalline form of the hydrochloride salt of Compound 4R
- the compound is characterized by an XRPD pattern having a peak at from about 6.1 to about 6.5, from about 1 1 .6 to about 12,0, from about 14.3 to about 14.7, from about 15.3 to about 15.7, from about 25.3 to about 25.7, and from about 26.1 to about 26.5 °2 ⁇ using Cu Ka radiation.
- the compound e.g., the crystalline form of the hydrochloride salt of Compound 4R
- the compound is characterized by an XRPD pattern having a peak at from about 6.1 to about 6,5, from about 11.6 to about 12,0, from about 14.3 to about 14.7, from about 15.3 to about 15.7, from about 19.2 to about 19.6, from about 25.3 to about 25.7, from about 26.1 to about 26.5, and from about 29.2 to about 29.6 °2 ⁇ using Cu Ka radiation.
- the compound e.g., the crystalline form of the hydrochloride salt of Compound 4R
- the compound is characterized by an XRPD pattern having a peak at from about 6.2 to about 6.4, from about 1 1.7 to about 11.9, from about 14.4 to about 14.6, from about 15.4 to about 15.6, from about 19.3 to about 19.5, from about 25.4 to about 25.6, from about 26.2 to about 26.4, and from about 29.3 to about 29.5 °2 ⁇ using Cu Ka radiation.
- the compound e.g., the crystalline form of the hydrochloride salt of Compound 4R
- DSC differential scanning calorimeter
- the compound is a hydrochloride salt of Compound 4R.
- the compound e.g., the crystalline form of the hydrochloride salt of Compound 4R
- the compound e.g., the crystalline form of the hydrochloride salt of Compound 4R
- the compound is characterized by an XRPD pattern having seven peaks selected from 7.2+0.2, 8.0+0.2, 8.8+0.2, 9.8+0.2, 12.4+0.2, 13.3+0.2, 14.4+0.2, 17.6+0.2, and 26.2+0.2 °2 ⁇ (e.g., 7.2+0.1, 8.0:0.1, 8.8+0.1, 9.8+0,1, 12,4+0.1, 13.3+0.1, 14.4+0,1, 17,6+0.1, and 26,2+0.1 °2 ⁇ ) using Cu Ka radiation.
- the compound e.g., the crystalline form of the hydrochloride salt of Compound 4R
- the compound is characterized by an XRPD pattern having eight peaks selected from 7.2+0.2, 8,0+0.2, 8,8+0.2, 9.8+0.2, 12.4+0.2, 133- 0.2.14.4+0.2, 17.6+0.2, and 26.2+0.2 °2 ⁇ (e.g., 7.2+0.1, 8.0:0.1, 8.8-0 !, 98-0.1. 12.4:0.1, 1 .3.0.1, 14.4-0 I.17,6 ⁇ 0.1, and26.2 ⁇ 0.1 °2 ⁇ ) using Cu Ka radiation.
- the compound e.g., the crystalline form of the succinate salt of Compound 4R
- the compound is characterized by an XRPD pattern having at least six peaks selected from 6.3+0.2, 6.8+0.2, 9.2+0.2, 12.7+0.2, 13.1+0.2, 14.4+0.2, 20.1+0.2, 22.0+0.2, 26.2+0.2, and 27.1+0.2 °2 ⁇ (e.g., 6.3+0.1 , 6.8+0, 1 , 9,2+0.1, 12.7+0.1, 13.1+0.1 , 14,4+0, 1, 20.1+0.1, 22.0+0. 1 , 26.2+0.1, and 27.1+0.1 °2 ⁇ ) using Cu Ka radiation.
- the compound e.g., the crystalline form of the succinate salt of Compound 4R
- the compound is characterized by an XRPD pattern having eight peaks selected from 6.3 ⁇ 0.2, 68 ⁇ 0.2.9.2:0.2, 12.7+0.2, 1 .1 -02.1 .4-0.2.20.1+0.2, 22.0-02, 262 ⁇ 0.2. and 271 -0.2 °2 ⁇ (e.g., 6.3:0.1, 6.8.0.1.9.2:01, 127-0.1.13.1 ⁇ 0.1, 14.4:0.1, 201-01, 22.0:0.1, 26.2.0.1. and 27.1 ⁇ 0.1 °2 ⁇ ) using Cu Ka radiation.
- the compound e.g., the crystalline form of the succinate salt of Compound 4R
- the compound is characterized by an XRPD pattern having a peak at from about 6.1 to about 6.5, from about 6.6 to about 7.0, from about 9.0 to about 9.4, and from about 12.9 to about 13.3 °2 ⁇ using Cu Ka radiation.
- the compound e.g., the crystalline form of the succinate salt of Compound 4R
- the compound is characterized by an XRPD pattern having a peak at from about 6.1 to about 6.5, from about 6.6 to about 7.0, from about 9,0 to about 9.4, from about 12.5 to about 12.9, from about 12.9 to about 13.3, from about 14.2 to about 14.6, from about 19.9 to about 20.3, and from about 26,0 to about 26.4 °2 ⁇ using Cu Ka radiation.
- the compound e.g., the crystalline form of the succinate salt of Compound 4R
- the compound is characterized by an XRPD pattern having a peak at from about 6.2 to about 6,4, from about 6.7 to about 6.9, from about 9.1 to about 9.3, from about 12.6 to about 12.8, from about 13 ,0 to about 13.2, from about 14.3 to about 14,5, from about 20.0 to about 20.2, from about
- the compound e.g., the crystalline form of the succinate salt of Compound 4R
- DSC differential scanning calorimeter
- the compound is Compound 5R or Compound 5S.
- the compound is Compound 5R.
- the compound is a crystalline form of Compound 5R.
- the compound e.g., the crystalline form of Compound 5R
- the compound is characterized by an XRPD pattern having at least two peaks selected from 12.8+0.2, 13.4 ⁇ 0.2, 14.6 02, 176-0.2.20.9 ⁇ 0.2, and 23,9 ⁇ 0.2 °2 ⁇ (e.g., 12.8.0.1, 13.4:0.1, 146-0.1.17.6:0.1, 20.9 ⁇ 0.1, and 23.9 ⁇ 0.1 °2 ⁇ ) using Cu Ka radiation.
- the compound e.g., the crystalline form of Compound 5R
- the compound is characterized by an XRPD pattern having at least four peaks selected from 12.8-1-0,2, 13,4 ⁇ 0.2, 14.6 ⁇ 0.2, 17.6:0.2, 20.9 ⁇ 0.2, and 23.9 ⁇ 0.2 °2 ⁇ (e.g., 12.8 ⁇ 0.1, 13.4 ⁇ 0.1, 14.6:0.1, 17.6 ⁇ 0.1, 20.9-0 !, and 23.9+0.1 °2 ⁇ ) using Cu Ka radiation.
- the compound e.g., the crystalline form of Compound 5R
- the compound is characterized by an XRPD pattern having at least five peaks selected from 12.8 ⁇ 0.2, 13.4+0.2, 14,6 ⁇ 0.2, 17.6.0.2, 20.9-02, and 23.9:02 °2 ⁇ (e.g., 12.8-01.13.4-0.1..14.6.0.1, 17.6-01, 20.9 ⁇ 0.1, and 23.9 ⁇ 0.1 °2 ⁇ ) using Cu Ka radiation.
- the compound e.g., the crystalline form of Compound 5R
- the compound is characterized by an XRPD pattern having one peak selected from 12.8+0.2, 13.4 ⁇ 0.2, 14.6 ⁇ 0.2, 17.6:0.2, 20.9.0.2. and 23.9.0.2 °2 ⁇ (e.g., 12.8.0.1.13.4-01, 14.6:0.1, 17.6.0.1, 20.9:01, and 23.9 ⁇ 0.1 °2 ⁇ ) using Cu Ka radiation.
- the compound e.g., the crystalline form of Compound 5R
- the compound is characterized by an XRPD pattern having a peak at from about 12.6 to about 13.0, from about 13.1 to about 13.6, from about 17.4 to about 17.8, and from about 20.7 to about 30.1 °2 ⁇ using Cu Ka radiation.
- the compound e.g., the crystalline form of Compound 5R
- the compound is characterized by an XRPD pattern having a peak at from about 12.7 to about 12.9, from about 13.3 to about 13,5, from about 14.5 to about 14.7, from about 17.5 to about 17.7, from about 20.8 to about 30.0, and from about 23.7 to about 24.1 °2 ⁇ using Cu Koc radiation.
- the compound e.g., the crystalline form of Compound 5R
- DSC differential scanning calorimeter
- the compound e.g., the crystalline form of Compound 5R
- an XRPD pattern having at least one peak selected from 10.2 ⁇ 0.2, 12.5+0.2
- the compound e.g., the crystalline form of Compound 5R.
- the compound is characterized by an XRPD pattern having at least five peaks selected from 10.2 ⁇ 0.2, 12.5+0.2,
- the compound e.g., the crystalline form of Compound 5R
- the compound is characterized by an XRPD pattern having three peaks selected from 10.2+0.2, 12.5+0.2, 14.0+0,2, 17,8+0.2, 18.8.0.2.19.3+0,2, and 24.6+0.2 °2 ⁇ (e.g., 10.2+0,1, 12,5+0.1, 14.0.0.1, 17.8+0.1, 18.8+0.1, 19.3+0.1, and 24.6+0.1 °2 ⁇ ) using CuKa radiation.
- the compound e.g., the crystalline form of Compound 5R
- the compound is characterized by an XRPD pattern having a peak at from about 13.8 to about 14.2, from about 17.6 to about 18.0, and from about 18.6 to about 19.0 °2 ⁇ using Cu Ka radiation.
- the compound e.g., the crystalline form of Compound 5R
- the compound is characterized by an XRPD pattern having a peak at from about 12.3 to about 12.7, from about 13.8 to about 14.2, from about 17.6 to about 18,0, and from about 18,6 to about 19.0 °2 ⁇ using Cu Ka radiation.
- the compound e.g., the crystalline form of Compound 5R
- the compound is characterized by an XRPD pattern having a peak at from about 12,3 to about 12.7, from about 13.8 to about 14.2, from about 17.6 to about 18.0, from about 18.6 to about 19.0, from about 19.1 to about 19.5, and from about 24.4 to about 24.8 °2 ⁇ using Cu Ka radiation.
- the compound e.g., the crystalline form of Compound 5R
- the compound is characterized by an XRPD pattern having a peak at from about 10,0 to about 10.4, from about 12,3 to about 12.7, from about 13.8 to about 14.2, from about 17.6 to about 18.0, from about 18.6 to about 19.0, from about 19. 1 to about 19,5, and from about 24,4 to about 24.8 °2 ⁇ using Cu Koc radiation
- the compound e.g., the crystalline form of Compound 5R
- the compound is characterized by an XRPD pattern having a peak at from about 10.1 to about 10,3, from about 12,4 to about 12.6, from about 13.9 to about 14.1, from about 17.7 to about 17.9, from about 18,7 to about 18.9, from about 19.2 to about 19.4, and from about 24.5 to about 24.7 °2 ⁇ using Cu Kcx radiation.
- the compound e.g., the crystalline form of Compound 5R
- the compound is characterized by an XRPD pattern having a peak at about 10.17, about 12.49, about 13.97, about 17.75, about 18.82, about 19.34, and about 24.56 °2 ⁇ using Cu Kcx radiation.
- the compound e.g., the crystalline form of Compound 5R
- DSC differential scanning calorimeter
- the compound e.g., the crystalline form of Compound 5R
- an XRPD pattern having at least two peaks selected from 8,5 ⁇ 0.2, 12.9 ⁇ 0.2, 13,6 ⁇ 0.2, 15.4.0.2, 16.0 ⁇ 0,2, 181 - .2..21.3+0.2, 21.6-02, 22,9+0.2, and 248 ⁇ 0.2 °2 ⁇ (e.g., 85 : 0.1. 12.9.0.1, 1 .6:0 I, 154-0.1. 16.0:0.1, 18.1 ⁇ 0.1, 21.3 ⁇ 0.1, 21.6 ⁇ 0.1, 22.9 ⁇ 0.1, and 24.8+0.1 °2 ⁇ ) using Cu K radiation.
- the compound e.g., the crystalline form of Compound 5R
- the compound is characterized by an XRPD pattern having at least three peaks selected from 8.5 ⁇ 0.2, 12.9 ⁇ 0.2, 13.6:0.2, 15.4-0.2. 16.0:0.2.18.1+0.2, 21.3-0.2.21.0:0.2.22.9:0.2, and 24.8+0.2 °2 ⁇ (e.g., 8.5:0.1. 12.9-01, 13.6:0.1, 15.4.0.1. 16.0:01, 18,l ⁇ ().l, 21.3.0.1, 21.6:01, 229 ⁇ 0. j . and 24.8 ⁇ 0.1 °2 ⁇ ) using Cu Ka radiation.
- the compound e.g., the crystalline form of Compound 5R
- the compound is characterized by an XRPD pattern having at least six peaks selected from 8.5+0.2, 12.9+0.2, 13.6+0.2, 15.4+0,2, 16.0+0.2, 18.1+0.2, 21.3+0,2, 21,6+0.2, 22.9.0.2, and 24.8+0.2 °2 ⁇ (e.g., 8.5+0.1, 12.9+0.1, 13.6+0.1, 15.4+0.1, 16.0+0.1, 18.1+0.1, 21.3+0.1, 21.6+0.1, 22.9+0.1, and 24.8-01 °2 ⁇ ) using Cu Ka radiation.
- the compound e.g., the crystalline form of Compound 5R
- the compound e.g., the crystalline form of Compound 5R
- the compound is characterized by an XRPD pattern having five peaks selected from 8.5+0.2, 12.9+0.2, 13.6+0.2, 15,4+0.2, 16.0+0.2, 18.1+0,2, 21,3+0.2, 21.6+0.2, 22.9+0.2, and 24.8+0.2 °2 ⁇ (e.g., 8.5+0.1, 12.9 0.1..1 .6.0.1, 15.4-01, 1 0 ⁇ 0.1..18.1.0.1, 21.3-01, 216-0.1.22.9.0.1, and 24,8+0.1 °2 ⁇ ) using Cu Ka radiation.
- the compound e.g., the crystalline form of Compound 5R
- the compound is characterized by an XRPD pattern having eight peaks selected from 8.5+0.2, 12.9+0.2, 13.6+0.2, 15.4+0.2, 16.0+0.2, 18.1+0.2, 21.3+0.2, 21.6+0.2, 22.9+0.2, and 24.8+0.2 °2 ⁇ (e.g., 8.5+0.1, 12,9+0.1, 13.6.0.1.15.4+0,1, 16,0+0.1, 18.1+0.1, 21.3+0.1, 21,6+0.1, 22.9+0.1, and 24.8:0.1 °2 ⁇ ) using Cu Ka radiation.
- the compound e.g., the crystalline form of Compound 5R
- the compound is characterized by an XRPD pattern having a peak at from about 8.3 to about 8.7, from about 12.7 to about 13.1, from about 13.4 to about 13.8, from about 15.2 to about 15.6, from about 15.8 to about 16.2, from about 17.9 to about 18.3, from about 21.1 to about 21.5, from about 21.4 to about 21.8, and from about 22.7 to about 23.1 °2 ⁇ using Cu Ka radiation.
- the compound e.g., the crystalline form of the sulfate salt of Compound 5R
- the compound is characterized by an XRPD pattern having at least five peaks selected from 6.8:0.2, 8.7:0.2.1 .0:0.2, i 0. -0.2.23.5:0.2.25.3+0.2, and 26.5+0.2 °2 ⁇ (e.g., 6.8:0.1, 87 : 0.1.14.0.0.1, ! 6.4:0 !, 235-0.1.25.3:0.1, and 26.5:0.1 °2 ⁇ ) using Cu Ka.
- the compound e.g., the crystalline form of the sulfate salt of Compound 5R
- an XRPD pattern having one peak selected from 6.8 ⁇ 0,2, 8.7 ⁇ 0.2, 14.0:0.2, 16.4 ⁇ 0.2, 23.5+0.2, 25.3 ⁇ 0.2, and 26.5 ⁇ 0.2 °2 ⁇ (e.g., 6.8+0.1, 8.7+0.1, 14.0-01, 164- .L 23.5 0.1, 25.3.0.1, and 26.5+0.1 °2 ⁇ ) using CuKa radiation.
- the compound e.g., the crystalline form of the sulfate salt of Compound 5R
- the compound is characterized by an XRPD pattern having two peaks selected from 6.8 ⁇ 0.2, 8.7:0.2.14.0:0.2, 16.4:0.2, 23.5+0.2, 25.3+0.2, and 26.5+0.2 20 (e.g., 6.8+0.1, 8.7+0.1, 14.0+0.1, 16.4+0,1, 23.5+0.1, 25.3+0.1, and 26.5+0.1 °2 ⁇ ) using Cu Ka radiation.
- the compound e.g., the crystalline form of the sulfate salt of Compound 5R
- the compound is characterized by an XRPD pattern having five peaks selected from 6.8+0.2. 8.7+0.2, 14.0+0.2, 16.4+0.2, 23.5+0.2, 25.3+0.2, and 26.5+0.2 °2 ⁇ (e.g., 6.8+0.1, 8.7+0.1, 14,0+0.1, 16.4.0.1.23.5+0,1, 25,3+0.1, and 26,5+0.1 °2 ⁇ ) using Cu Ka radiation.
- the compound e.g., the crystalline form of the sulfate salt of Compound 5R
- the compound is characterized by an XRPD pattern having six peaks selected from 6.8+0.2, 8 7 - 0.2. 14.0 ⁇ 0.2, 16.4 ⁇ 0.2, 5 ⁇ 0.2. 25.3 . 0.2, and 26.5 ⁇ 0.2 °2 ⁇ (e.g., 6.8 : 0. 1 , 8 7 - 0. 1.
- the compound e.g., the crystalline form of the sulfate salt of Compound 5R
- the compound is characterized by an XRPD pattern having a peak at from about 8.5 to about 8.9, from about 13.8 to about 14.2, from about 16.2 to about 16.6, from about 25.1 to about 25.5, and from about 26.3 to about 26.7 °2 ⁇ using Cu K radiation.
- the compound e.g., the crystalline form of the sulfate salt of Compound 5R
- the compound is characterized by an XRPD pattern having a peak at from about 6.6 to about 7.0, from about 8.5 to about 8.9, from about 13 ,8 to about 14.2, from about 16.2 to about 16,6, from about 25.1 to about 25.5, and from about 26.3 to about 26.7 °2 ⁇ using Cu Ka radiation.
- the compound is a glycoiate salt of Compound 5R.
- the compound is a crystalline form of a glycoiate salt of
- the compound e.g., the crystalline form of the glycoiate salt of Compound 5R
- an XRPD pattern having at least one peak selected from 6.5:0.2, ⁇ 4.f ⁇ () 2. 17.8-0.2..18.9.0.2, 24.7-02, 7-0.2.. and 265 ⁇ 0.2 °2 ⁇ (e.g., 65 ⁇ 0. L 14.U0.1, 17.8+0.1, 18.9:0.1, 24.7 ⁇ 0.1, 25.7 ⁇ 0.1, and 26.5 ⁇ 0.1 °2 ⁇ ) using Cu Ka radiation.
- the compound e.g., the crystalline form of the glycoiate salt of Compound 5R
- the compound is characterized by an XRPD pattern having at least two peaks selected from 6.5:0.2.14.1 -02, 17.8:0.2, 18.9.0.2.24.7:02, 25 ,7 ⁇ 0.2, and 265-0.2 °2 ⁇ (e.g., 65 ⁇ 0.1. 14.1 ⁇ 0.1, 17.8 ⁇ 0.1, 18.9 ⁇ 0.1,24.7 ⁇ 0.1, 25.7+0.1, and 26.5 ⁇ 0.1 °2 ⁇ ) using Cu Ka radiation.
- the compound e.g., the crystalline form of the glycoiate salt of Compound 5R
- an XKPD pattern having at least three peaks selected from 6.5 ⁇ 0.2, 14.1 :0.2, 17.8 ⁇ 0.2, 18.9+0.2, 24.7 ⁇ 0.2, 25.7 ⁇ 0.2, and 26.5:0.2 °2 ⁇ (e.g., 6.5 ⁇ 0.1, 14.1 -01, !78-0.1. 18.9:0.1, 24.7.0.1, 257-0.1. and 26.5-01 °2 ⁇ ) using Cu Ka radiation.
- the compound e.g., the crystalline form of the glycoiate salt of Compound 5R
- the compound is characterized by an XRPD pattern having at least four peaks selected from 65 ⁇ 0.2. 14.1.0.2, 17.8. ⁇ 02, 189 02.24.7:0.2, 25.7+0.2, and 26.5.0.2 °2 ⁇ (e.g., 6.5+0.1, 14.1+0.1, 17.8:0.1, 18.9 ⁇ 0.1, 24.7 ⁇ 0.1, 25.7:0.1, and 26.5:0.1 °2 ⁇ ) using Cu radiation.
- the compound e.g., the crystalline form of the glycoiate salt of Compound 5R
- the compound is characterized by an XRPD pattern having at least five peaks selected from 65 : 0.2. 14.1.0.2, 17.8:02, 189-0.2.24.7:0.2, 25.7:0.2, d 26.5.0.2 °2 ⁇ (e.g., 6.5.0.1. 14.1+0.1, 17.8+0.1, 18.9 ⁇ 0.1, 24.7+0.1, 25.7+0.1, and 26.5+0.1 °2 ⁇ ) using CuKa radiation.
- the compound e.g., the crystalline form of the glycoiate salt of Compound 5R
- the compound is characterized by an XRPD pattern having at least six peaks selected from ⁇ ,5 ⁇ 0.2, 14.1+0.2, 17.8+0.2, 18.9+0,2, 24.7:0.2, 25.7+0.2, and 26.5.0.2 °2 ⁇ (e.g., 6.5+0.1,
- the compound e.g., the crystalline form of the glycolate salt of
- Compound 5R is characterized by an XRPD pattern having one peak selected from 6.5 ⁇ 0.2,
- Compound 5R is characterized by an XRPD pattern having three peaks selected from 6.5 ⁇ 0.2,
- the compound e.g., the crystalline form of the glycolate salt of Compound 5R
- the compound is characterized by an XRPD pattern having a peak at from about 6.3 to about 6,7, from about 17.6 to about 18.0, from about 18.7 to about 19.1, and from about 26.3 to about 26.7 °2 ⁇ using Cu Koc radiation.
- the compound e.g., the crystalline form of the glycolate salt of Compound 5R
- the compound is characterized by an XRPD pattern having a peak at from about 6.3 to about 6.7, from about 17.6 to about 18.0, from about 18.7 to about 19.1, from about 25.5 to about 25.9, and from about 26.3 to about 26.7 °2 ⁇ using Cu Koc radiation.
- the compound e.g., the crystalline form of the glycolate salt of Compound 5R
- the compound is characterized by an XRPD pattern having a peak at from about 6.3 to about 6.7, from about 17.6 to about 18.0, from about 18.7 to about 19.1, from about 24.5 to about 24.9, from about 25,5 to about 25.9, and from about 26.3 to about 26.7 °2 ⁇ using Cu Koc radiation.
- the compound is a fumarate salt of Compound 5R, [0762] In some embodiments, the compound is a crystalline form of a fumarate salt of Compound 5R.
- the compound e.g., the crystalline form of the fumarate salt of Compound 5R
- an XRPD pattern having at least one peak selected from 5.9 ⁇ 0.2, 7.7:0.2.11.3+0.2, 11.9+0.2, I 5. : 0.2.18.4+0.2, 25.8:0.2. and 26.5 ⁇ 0.2 °2 ⁇ (e.g., 5,9 ⁇ 0.1, 7.7 ⁇ 0.1, 11.3+0.1, ! 1.9-0 I.15,4 ⁇ 0.1, 18.4.0.1, 25.8-0 i, and 26.5:0 ! °2 ⁇ ) using Cu Koc radiation.
- the compound e.g., the crystalline form of the fumarate salt of Compound 5R
- an XRPD pattern having at least two peaks selected from 5.9 ⁇ 0.2, 7.7:0.2, 11.3+0.2, 11.9:02, 15.4 ⁇ 0.2, 18.4+0.2, 25.8:0.2, and 26.5:0.2 °2 ⁇ (e.g., 5.9:01, 7.7-01, I I 3-0.1. i 1.9.0.1, 15.4:01, 184-0.1.25.8:0.1, and 26.5 ⁇ 0.1 °2 ⁇ ) using Cu Ka radiation.
- the compound e.g., the crystalline form of the fumarate salt of Compound 5R
- an XRPD pattern having at least six peaks selected from 5.9+0.2, 7.7+0.2, 11.3+0.2, 11.9+0.2, 15.4+0.2, 18.4+0.2, 25.8+0.2, and 26.5+0.2 °2 ⁇ (e.g., 5,9 ⁇ 0.1, 7.7 ⁇ 0.1, 11.3+0.1, 11.9+0,1, 15,4 ⁇ 0.1, 18.4+0.1, 25.8 ⁇ 0.1, and 26.5+0.1 °2 ⁇ ) using Cu Koc radiation.
- the compound e.g., the crystalline form of the fumarate salt of Compound 5R
- the compound is characterized by an XRPD pattern having two peaks selected from 5.9 ⁇ 0.2, 7.7 ⁇ 0.2, 11.3:0.2, 11.9 ⁇ 0.2, 15.4 ⁇ 0.2, 18.4:0.2.25.8 ⁇ 0.2, and 26.5+0.2 °2 ⁇ (e.g., 5.9 ⁇ 0.1, 7.7:0.1.11.3-0 I, 11.9:0.1, 15.4.0.1.18.4:01, 258:0.1, and 265-0.1 °2 ⁇ ) using Cu Ka radiation.
- the compound e.g., the crystalline form of the fumarate salt of Compound 5R
- the compound is characterized by an XRPD pattern having six peaks selected from 5.9+0.2, 7 ,7 ⁇ 0.2, 11.3.0.2, ! 1.9:02, 15.4 ⁇ 0.2, 18.4:0.2, 25.8 ⁇ 0.2, nd 26.5.0.2 °2 ⁇ (e.g., 5.9.0.1.
- the compound e.g., the crystalline form of the fumarate salt of Compound 5R
- the compound is characterized by an XRPD pattern having a peak at from about 5.7 to about 6.1, from about 7.5 to about 7.9, from about 15.2 to about 15.6, from about 25.6 to about 26.0, and from about 26.3 to about 26.7 °2 ⁇ using Cu Ka radiation.
- the compound e.g., the crystalline form of the fumarate salt of Compound 5R
- the compound is characterized by an XRPD pattern having a peak at from about 5.7 to about 6,1, from about 7.5 to about 7.9, from about 15.2 to about 15.6, from about 18.2 to about 18.6, from about 25.6 to about 26,0, and from about 26.3 to about 26,7 °2 ⁇ using Cu Ka radiation.
- the compound e.g., the crystalline form of the fumarate salt of Compound 5R
- the compound is characterized by an XRPD pattern having a peak at from about 5.7 to about 6.1 , from about 7.5 to about 7.9, from about 11.7 to about 12.1, from about 15.2 to about 15.6, from about 18.2 to about 18.6, from about 25.6 to about 26,0, and from about 26.3 to about 26.7 °2 ⁇ using Cu Ka radiation.
- the compound e.g., the crystalline form of the fumarate salt of Compound 5R
- the compound is characterized by an XKPD pattern having a peak at from about 5.7 to about 6.1, from about 7.5 to about 7.9, from about 11. 1 to about 11.5, from about 1 1 .7 to about 12.1, from about 15.2 to about 15.6, from about 18.2 to about 18.6, from about 25.6 to about 26.0, and from about 26.3 to about 26.7 °2 ⁇ using Cu Ka radiation.
- the compound e.g., the crystalline form of the fumarate salt of Compound 5R
- the compound is characterized by an XRPD pattern having a peak at from about 5.8 to about 6.0, from about 7,6 to about 7.8, from about 1 1 .2 to about 1 ,4, from about 11.8 to about 12,0, from about 15.3 to about 15.5, from about 18.3 to about 18.5, from about 25.7 to about 25.9, and from about 26.4 to about 26,6 °2 ⁇ using Cu Ka radiation.
- the compound e.g., the crystalline form of the fumarate salt of Compound 5R
- the compound is characterized by an XRPD pattern having a peak at about 5.94, about 7.66, about 1 1 .31 , about 11.88, about 15.40, about 18.41, about 25,84, and about 26.47 °2 ⁇ using Cu Ka radiation.
- the compound is a hippurate salt of Compound 5R.
- the compound is a crystalline form of a hippurate salt of
- the compound e.g., the crystalline form of the hippurate salt of
- Compound 5R is characterized by an XRPD pattern having at least three peaks selected from
- the compound e.g., the crystalline form of the hippurate salt of
- Compound 5R is characterized by an XRPD pattern having at least six peaks selected from
- the compound e.g., the crystalline form of the hippurate salt of
- Compound 5R is characterized by an XRPD pattern having one peak selected from 6.5+0,2,
- the compound e.g., the crystalline form of the hippurate salt of
- Compound 5R is characterized by an XRPD pattern having two peaks selected from 6.5+0.2,
- Compound 5R is characterized by an XRPD pattern having three peaks selected from 6.5+0.2,
- the compound e.g., the crystalline form of the hippurate salt of
- Compound 5R is characterized by an XRPD pattern having four peaks selected from 6,5 ⁇ 0.2,
- the compound e.g., the crystalline form of the hippurate salt of
- Compound 5R is characterized by an XRPD pattern having five peaks selected from 6.5+0.2,
- the compound e.g., the crystalline form of the hippurate salt of
- Compound 5R is characterized by an XRPD pattern having six peaks selected from 6.5 ⁇ 0.2,
- the compound e.g., the crystalline form of the hippurate salt of
- Compound 5R is characterized by an XRPD pattern having a peak at 6.5 ⁇ 0.2, 9.7 ⁇ 0.2, 1.0 ⁇ 0.2,
- the compound e.g., the crystalline form of the hippurate salt of Compound 5R
- the compound is characterized by an XRPD pattern having a peak at from about 6.3 to about 6.7, from about 12.8 to about 13,2, and from about 25,9 to about 26.3 °2 ⁇ using Cu Ka radiation.
- the compound e.g., the crystalline form of the hippurate salt of Compound 5R
- the compound is characterized by an XRPD pattern having a peak at from about 6.3 to about 6.7, from about 12.8 to about 13.2, from about 19.2 to about 19.6, from about 23.4 to about 23.8, and from about 25.9 to about 26.3 °2 ⁇ using Cu Ka radiation.
- the compound e.g., the crystalline form of the hippurate salt of Compound 5R
- the compound is characterized by an XRPD pattern having a peak at from about 6.3 to about 6,7, from about 9.5 to about 9.9, from about 10.8 to about 1 1.2, from about 12.8 to about 13.2, from about 19.2 to about 19.6, from about 23.4 to about 23,8, and from about 25.9 to about 26.3 °2 ⁇ using Cu Ka radiation.
- the compound e.g., the crystalline form of the hippurate salt of Compound 5R
- the compound is characterized by an XKPD pattern having a peak at from about 6.4 to about 6.6, from about 9.6 to about 9.8, from about 10.9 to about 1 .1, from about 12.9 to about 13.1, from about 19.3 to about 19,5, from about 23.5 to about 23.7, and from about 26.0 to about 26.2 °2 ⁇ using Cu Ka radiation.
- the compound e.g., the crystalline form of the hippurate salt of Compound 5R
- the compound is characterized by an XRPD pattern having a peak at about 6.49, about 9.70, about 10.98, about 12.96, about 19.44, about 23.62, and about 26.07 °2 ⁇ using Cu Ka radiation.
- the compound is an adipate salt of Compound 5R.
- the compound is a crystalline form of an adipate salt of Compound
- the compound e.g., the crystalline form of the adipate salt of Compound 5R
- an XRPD pattern having at least one peak selected from 10.7 ⁇ 0.2, 13.1+0.2, ! 7.8 : 0.2, 18.8 ⁇ 0.2, 21.6+0.2, 22.9 ⁇ 0.2, 24.6+0.2, and 25.5+0.2 °2 ⁇ (e.g., 10.7 - 0 1 , 1 1 - 0. 1. 1 .8 : 0. 1 , 18.8 : 0. 1 , ! 6 0. ] . 22.9 : 0. 1 , 24. . 0. 1 , and 25.5+0.1 °2 ⁇ ) using Cu Ka radiation.
- the compound e.g., the crystalline form of the adipate salt of Compound 5R
- the compound is characterized by an XRPD pattern having at least two peaks selected from 1 .7 : 0 2, 1 1 - 0.2. 1 7.8 : 0.2, 18.8 : 0.2, 2 1 6 - 0.2, 22.9 : 0.2, 24.6 . 0.2. and 25.5 . 0.2 °2 ⁇ (e.g., 10.7+0.1, 13.1+0.1, 17.8 ⁇ 0.1, 18.8+0.1, 21.6+0.1, 22.9 ⁇ 0.1, 24.6+0.1, and 25.5+0.1 °2 ⁇ ) using Cu Ka radiation.
- the compound e.g., the crystalline form of the adipate salt of Compound 5R
- an XRPD pattern having at least four peaks selected from 10.7:0.2, 13.1.0.2.17.8:02, 188:0.2, 21.6+0.2, 22.9:02, 246 ⁇ 0.2. and 255 ⁇ 0.2 °2 ⁇ (e.g., 10.7:0.1, 13.1 -0.1.17.8:0.1.18.8 ⁇ 0.1, 21.6 ⁇ 0.1, 22.9 ⁇ 0.1, 24.6 ⁇ 0.1, and 25.5 ⁇ 0.1 °2 ⁇ ) using Cu Ka. radiation,
- the compound e.g., the crystalline form of the adipate salt of Compound 5R
- an XRPD pattern having at least five peaks selected from 10.7-02, 131 -0.2.17.8.0.2, 18.8:0.2, 216-0.2.22.9:0.2, 24.6.0.2, and 25.5.0.2 °2 ⁇ (e.g., 10.7 ⁇ 0.1, 13.1 ⁇ 0.1, 17.8 ⁇ 0.1, 18.8 ⁇ 0.1, 21.6 ⁇ 0.1, 22.9 ⁇ 0.1, 24.6+0.1, and 25.5 ⁇ 0.1 °2 ⁇ ) using Cu Ka radiation.
- the compound e.g., the crystalline form of the adipate salt of Compound 5R
- the compound is characterized by an XRPD pattern having at least seven peaks selected from 10.7 ⁇ 0.2, 13.1+0.2, 17.8:0.2, 18.8+ ⁇ .2, 21.6+0.2, 22.9 ⁇ 0.2, 24.6+ .2, and 25.5 ⁇ 0.2 °2 ⁇ (e.g., 10.7-01, 131-0.1.17.8:0.1, 18.8 0.1, 216-0.1.22.9:0.1, 24.6+0.1, and 25.5+0.1 °2 ⁇ ) using Cu Ka radiation.
- the compound e.g., the crystalline form of the adipate salt of Compound 5R
- an XRPD pattern having one peak selected from 10.7 ⁇ 0.2, 13.1 ⁇ 0.2, 17.8:0.2, 18.8 ⁇ 0.2, 21.6 ⁇ 0.2, 22.9:0.2, 24.6 ⁇ 0.2, and25.5 ⁇ 0.2 °2 ⁇ (e.g., 10.7 ⁇ 0.1, 13.1 -01, 178-0.1.18.8:0.1, 21.6 0.1, 229-0.1.24.6:0.1, and 5-0.1 °2 ⁇ ) using Cu Ka radiation.
- the compound e.g., the crystalline form of the adipate salt of Compound 5R
- the compound is characterized by an XRPD pattern having three peaks seiected from 10.7 ⁇ 0.2, 13,1 ⁇ 0.2, 17.8.0.2.18.8:0 , 216:0.2, 22.9.0.2, 24.6:02, and 25.5:0.2 °2 ⁇ (e.g., 10.7:0 !, 13.1 :().!.17.8:0.1, 18.8 ⁇ 0.1, 21.6:0.1.22.9:0.1, 24.6 ⁇ 0.1, and25.5 ⁇ 0.1 °2 ⁇ ) using Cu Ka radiation.
- the compound e.g., the crystalline form of the adipate salt of Compound 5R
- the compound is characterized by an XRPD pattern having four peaks selected from 10.7 ⁇ 0.2, 1 .1 -02, 178-0.2.18.8 0.2, 21.6:0.2, 229-0.2.24.6:0.2, and 5-0.2 20 (e.g., 10.7:0.1, 13.1+0.1, 17.8+0.1, 18.8 ⁇ 0.1, 21.6 ⁇ 0.1, 22.9 ⁇ 0.1, 24.6 ⁇ 0.1, and 25.5 ⁇ 0.1 °2 ⁇ ) using Cu Ka radiation.
- the compound e.g., the crystalline form of the adipate salt of Compound 5R
- the compound is characterized by an XRPD pattern having five peaks selected from 10.7 ⁇ 0.2, 13.1+0.2, 17.8:0.2, 18.8:0.2.21.6:0.2.22.9:0.2, 24.6:0.2. and 25.5 ⁇ 0.2 °2 ⁇ (e.g., 10.7:0.1. 13.1 :01, 178-0.1.18.8:0.1, 21.6:0.1, 229-0.1, 24.6:0.1, and25,5 ⁇ ().l °2 ⁇ ) using Cu Ka radiation.
- the compound e.g., the crystalline form of the adipate salt of Compound 5R
- the compound is characterized by an XRPD pattern having six peaks selected from 10,7+0.2, 13.1+0.2, 17.8+0.2, 18.8 ⁇ 0.2, 21.6 ⁇ 0.2, 22.9+0.2, 24.6 ⁇ 0.2, and25.5 ⁇ 0.2 °2 ⁇ (e.g., 10.7:0.1, 1 .1.0.1.17.8.0.1, 18.8-01, 216-0.1..22.9.0.1, 24.6-01, and 25.5:0.1 °2 ⁇ ) using Cu Ka radiation.
- the compound e.g., the crystalline form of the adipate salt of Compound 5R
- the compound is characterized by an XRPD pattern having seven peaks seiected from 10.7+0.2, 13.1+0.2, 17.8:0.2, 18.8 ⁇ 0.2, 21.6 ⁇ 0.2, 22.9:0.2, 24.6 ⁇ 0.2, and25.5 ⁇ 0.2 °2 ⁇ (e.g., 10.7 ⁇ 0.1, 13.1 -01, 178-0.1.18.8:0.1, 21.6.0.1, 229-0.1.24.6:0.1, and 5-0.1 °2 ⁇ ) using Cu Ka radiation.
- the compound e.g., the crystalline form of the adipate salt of Compound 5R
- the compound is characterized by an XRPD pattern having a peak at from about 12.9 to about 13.3, from about 17.6 to about 18.0, from about 21.4 to about 21.8, from about 22.7 to about 23.1, and from about 25.3 to about 25.7 °2 ⁇ using Cu Ka radiation.
- the compound e.g., the crystalline form of the adipate salt of Compound 5R
- the compound is characterized by an XRPD pattern having a peak at from about 10.5 to about
- the compound e.g., the crystalline form of the adipate salt of Compound 5R
- the compound is characterized by an XRPD pattern having a peak at from about 10.5 to about 10.9, from about 12.9 to about 13.3, from about 17.6 to about 18.0, from about 18.6 to about 19.0, from about 21.4 to about 21 .8, from about 22.7 to about 23.1, and from about 25,3 to about 25.7 °2 ⁇ using Cu Ka radiation.
- the compound e.g., the crystalline form of the adipate salt of Compound 5R
- the compound is characterized by an XRPD pattern having a peak at from about 10.5 to about 10.9, from about 12.9 to about 13.3, from about 1 7.6 to about 18.0, from about 18.6 to about 19.0, from ab out 21.4 to ab out 21.8, from ab out 22.7 to ab out 23.1, from ab out 24.4 t o ab out 24.8, an d from about 25.3 to about 25.7 °2 ⁇ using Cu Ka radiation.
- the compound e.g., the crystalline form of the adipate salt of Compound 5R
- the compound is characterized by an XRPD pattern having a peak at from about 10.6 to about 10.8, from about 13.0 to about 13.2, from about 17.7 to about 17.9, from about 18,7 to about 18.9, from about 21.5 to about 21.7, from about 22.8 to about 23.0, from about 24.5 to about 24.7, and from about 25.4 to about 25,6 °2 ⁇ using Cu Ka radiation.
- the compound is a gentisate salt of Compound 5R,
- the compound is a crystalline form of a gentisate salt of Compound
- the compound e.g., the crystalline form of the gentisate salt of Compound 5R
- an XRPD pattern having at least one peak selected from 5.3:0.2.7.7:0 , 88 ⁇ 0.2, 9,3 ⁇ 0.2, 15.0+0.2, 16.2 ⁇ 0.2, 172- 0.2.21.2:0.2, and 25.3: 0.2 °2 ⁇ (e.g., 5.3 ⁇ 0.1, 7.7:0.1.8.8:0.1, 9.3:0.1, 15.0+0.1, 16.2:0.1.17.2:0.1, 21.2-0.1. and 25.3:0.1 °2 ⁇ ) using Cu Ka radiation.
- the compound e.g., the crystalline form of the gentisate salt of Compound 5R
- the compound is characterized by an XRPD pattern having at least two peaks selected from 5,3 ⁇ 0.2, 7.7:0.2, 8.8.0.2, 9.3:0.2, 150-0.2.1 .2 0.2, 17.2.0.2, 21.2 ⁇ 0,2, and 25.3-02 °2 ⁇ (e.g., 5.3 ⁇ 0.1, 7.7 ⁇ 0.1, 8.8 ⁇ 0.1, 9.3 ⁇ 0.1, 1 .0:0.1, 16.2 ⁇ 0.1, 17.2+0.1, 21.2:0.1, and25.3 ⁇ 0.1 °2 ⁇ ) using Cu Ka radiation.
- the compound e.g., the crystalline form of the gentisate salt of Compound 5R
- the compound is characterized by an XRPD pattern having at least three peaks selected from 5.3 ⁇ 0,2, 7.7-02, 88 ⁇ 0.2.93 ⁇ 0.2..15.0.0.2, 16.2-02, 172-0.2, 21.2:0.2, and 2x3:0.2 °2 ⁇ (e.g., 5.3:0.1.7.7:01, 88-0.1, 9,3 ⁇ ().l, 15.0.0.1, 1 .2:01, 172- 0.1.21.2.0.1, and 25.3: 0.1 °2 ⁇ ) using Cu Ka radiation.
- the compound e.g., the crystalline form of the gentisate salt of Compound 5R
- the compound is characterized by an XRPD pattern having at least four peaks selected from 5.3 ⁇ 0.2, 7.7:0.2.8.8:0.2, 9.3:0.2, 15.0+0.2, 16.2:0.2.17.2:0.2, 21.2:0.2. and 25.3:0.2 °2 ⁇ (e.g., 53 : 0.1.7.7:0.1, 8.8+0.1, 9.3+0.1, 150-0.1, 1 .2:0.1, 17.2+0.1, 21.2-01, and 25.3:01 °2 ⁇ ) using Cu Ka radiation.
- the compound e.g., the crystalline form of the gentisate salt of Compound 5R
- the compound is characterized by an XRPD pattern having at least five peaks selected from 5.3 ⁇ 0.2, 7.7 ⁇ 0.2, 8.8+0.2, 9.3 ⁇ 0.2, 15.0+-0.2, 16.2 ⁇ 0.2, 17.2+0.2, 21.2 ⁇ 0.2, and25.3 ⁇ 0.2 °2 ⁇ (e.g., 5,3 ⁇ 0.1, 77:0.1, 8.8- ⁇ . ⁇ , 9.3 ⁇ 0.1, 150-0.1.16,2 ⁇ 0.I, 17.2.0.!, 21.2-01, and 25.3-01 °2 ⁇ ) using Cu Ka radiation.
- the compound e.g., the crystalline form of the gentisate salt of Compound 5R
- the compound is characterized by an XRPD pattern having at least seven peaks selected from 5.3 ⁇ 0,2, 7.7-02, 88 ⁇ 0.2.93 ⁇ O.2..15.0.0.2, 16.2-02, 172-0.2.21.2:0.2, and 2x3:0.2 °2 ⁇ (e.g., 5.3 ⁇ 0.1, 7.7 ⁇ 0.1, 8.8:0.1, 9.3 ⁇ 0.1, 15.0:0.1.16.2 ⁇ 0.1, 17.2 ⁇ 0.1, 21.2+0.1, and 25.3 ⁇ 0.1 °2 ⁇ ) using Cu Ka radiation.
- the compound e.g., the crystalline form of the gentisate salt of Compound 5R
- the compound is characterized by an XRPD pattern having at least eight peaks selected from 5.3 ⁇ 0.2, 7.7:0.2.8.8:0.2, 9.3:0.2, 15.0-0.2.16.2:0.2.17.2:0.2, 21.2:0.2. and 25.3:0.2 °2 ⁇ (e.g., 53 : 0.1.7.7:0.1, 8.8.0.1, 9.3:0.1, 150-0.1, 16.2:0.1, 17.2.0.1.21.2-01, and 25.3:01 20 ⁇ using Cu Ka radiation.
- the compound e.g., the crystalline form of the gentisate salt of Compound 5R
- the compound is characterized by an XRPD pattern having one peak selected from 5.3 ⁇ 0.2, 7.7+ ⁇ .2, 8.8 ⁇ 0.2, 9.3+0.2, 15.0 ⁇ 0.2, 16.2+ .2, 17.2+0.2, 21.2 ⁇ 0.2, and 25.3+0.2 °2 ⁇ (e.g., 5.3+0.1, 77-0.1.8.8:0.1, 9.3.0.1, 15.0-01, 1 2-0.1.17.2+0.1, 21.2:01, and 25.3.0.1 °2 ⁇ ) using Cu Ka radiation.
- the compound e.g., the crystalline form of the gentisate salt of Compound 5R
- the compound is characterized by an XRPD pattern having two peaks selected from 5.3+ ⁇ .2,
- the compound e.g., the crystalline form of the gentisate salt of Compound 5R
- the compound is characterized by an XRPD pattern having three peaks selected from 5.3 ⁇ 0.2
- the compound e.g., the crystalline form of the gentisate salt of Compound 5R
- the compound is characterized by an XRPD pattern having four peaks selected from 5.3 ⁇ 0.2, 7.7 ⁇ 0.2, 8.8:0.2, 9.3+0.2, 15.0:02, 1 2- 0.2.17.2.0.2, 21.2 ⁇ 0.2, and 25.3+0.2 °2 ⁇ (e.g., 5.3+0.1, 7.7:0.1.8.8:0.1.9.3:0.1, 1 .0:0.1.16.2+0.1, ⁇ 7.2+ .1, 21.2 ⁇ 0.1, and 25.3+ .1 °2 ⁇ ) using Cu Ka radiation.
- the compound e.g., the crystalline form of the gentisate salt of Compound 5R
- the compound is characterized by an XRPD pattern having five peaks selected from 5.3+0.2, 7.7:0.2, 8.8-02, 93 ⁇ 0.2.15,0 ⁇ 0.2, 16.2+0.2, 17.2 ⁇ 0.2, 21.2- .2.. and 25.3+ .2 °2 ⁇ (e.g., 5.3 ⁇ 0.1, 7.7+ ⁇ .1, 8.8 ⁇ 0.1, 9.3+0.1, 15.0 ⁇ 0.1, 16.2 ⁇ 0.1, 17.2+0.1, 21.2 ⁇ 0.1, and 25.3+0.1 °2 ⁇ ) using Cu Ka radiation.
- the compound e.g., the crystalline form of the gentisate salt of Compound 5R
- the compound is characterized by an XRPD pattern having six peaks selected from 5.3+0.2, 7.7+ .2, 8.8 ⁇ 0.2, 9.3:0.2, 15.0 ⁇ 0.2, 16.2+0.2, 17.2:0.2, 21.2 ⁇ 0.2, and 25.3:0.2 °2 ⁇ (e.g., 5.3:0.1, 7.7:0.1.8.8:01, 9 -0.1, 1 .0:0.1, 16.2+0.1, 17.2-01, 21.2:0.1, and 253 ⁇ 0.1 °2 ⁇ ) using Cu Ka radiation.
- the compound e.g., the crystalline form of the gentisate salt of Compound 5R
- the compound is characterized by an XRPD pattern having seven peaks selected from 5.3 ⁇ 0.2, 7.7+ ⁇ .2, 8.8 ⁇ 0.2, 9.3+0.2, 5.0 ⁇ 0.2, 16.2+ .2, 17.2+0.2, 21.2 ⁇ 0.2, and 25.3+0.2 °2 ⁇ (e.g., 5.3+0.1, 77-0.1.8.8:0.1, 9.3+0.1, 15.0-01, 16 - .1.17.2+0.1, 21.2:01, and 25.3+0.1 °2 ⁇ ) using Cu Ka radiation.
- the compound e.g., the crystalline form of the gentisate salt of Compound 5R
- the compound is characterized by an XRPD pattern having a peak at 5.3+ .2, 7.7+0.2, 8.8 ⁇ 0.2
- the compound e.g., the crystalline form of the gentisate salt of Compound 5R
- the compound is characterized by an XRPD pattern having a peak at from about 5.1 to about 5 ,5, from about 9.1 to about 9.5, and from about 25.1 to about 25.5 °2 ⁇ using Cu K radiation.
- the compound e.g., the crystalline form of the gentisate salt of Compound 5R
- the compound is characterized by an XRPD pattern having a peak at from about 5.1 to about 5.5, from about 7.5 to about 7.9, from about 8,6 to about 9.0, from about 9.1 to about 9.5, and from about 25.1 to about 25.5 °2 ⁇ using Cu Ka radiation.
- the compound e.g., the crystalline form of the gentisate salt of Compound 5R
- i characterized by an XRPD pattern having a peak at from about 5.1 to about 5.5, from about 7.5 to about 7.9, from about 8.6 to about 9.0, from about 9.1 to about 9.5, from about
- the compound e.g., the crystalline form of the gentisate salt of Compound 5R
- the compound is characterized by an XRPD pattern having a peak at from about 5.1 to about 5 ,5, from about 7.5 to about 7.9, from about 8.6 to about 9.0, from about 9.1 to about 9.5, from about 14.8 to about 15,2, from about 16.0 to about 16.4, from about 17.0 to about 17.4, and from about
- the compound e.g., the crystalline form of the gentisate salt of Compound 5R
- the compound is characterized by an XRPD pattern having a peak at from about 5.1 to about 5.5, from about 7.5 to about 7.9, from about 8,6 to about 9.0, from about 9.1 to about 9.5, from about 14.8 to about 15.2, from about 16.0 to about 16.4, from about 17.0 to about 17.4, from about 21.1 to about 21 .5, and from about 25.1 to about 25.5 °2 ⁇ using Cu Ka radiation.
- the compound e.g., the crystalline form of the gentisate salt of Compound 5R
- the compound is characterized by an XRPD pattern having a peak at about 5.25, about 7,66, about 8,84, about 9.34, about 14.97, about 16.22, about 17.15, about 21,25, and about 25.26 °2 ⁇ using Cu Ka radiation.
- the compound is a crystalline form of a gentisate salt of Compound
- the compound e.g., the crystalline form of the gentisate salt of Compound 5R
- an XRPD pattern having at least one peak selected from 6,0 ⁇ 0.2, 9,1 ⁇ 0.2, 15.0.0,2, ! 7,7-0.?..18,4-0.2,.20.7.0.2, 23,8-02, 25,8 ⁇ 0.2, and 266-0,2 °2 ⁇ (e.g., 6.0 ⁇ 0.1, 9.1+0.1, 15.0:0.!, 17.7 ⁇ 0.1, 18.4 ⁇ 0.1, 20.7+0.1, 23.8+0.1, 25.8 ⁇ 0.1, and 26.6 ⁇ 0.1 °2 ⁇ ) using Cu Ka radiation.
- the compound e.g., the crystalline form of the gentisate salt of Compound 5R
- the compound is characterized by an XRPD pattern having at least two peaks selected from 6.0:0.2, 9.1+0.2, 1 0 ⁇ 0.2.17.7.0.2, 18.4:02, 207-0.2.23.8.0.2, 25.8+0.2, and 26.6.0.2 °2 ⁇ (e.g., 6.0:0 !, 9 ! - 0.1.1 .0:0.1, 17.7:0 ⁇ .!, 184-0.1, 20.7:0.1, 23.8.0.1.25.8:0 !, and 26.6:0 ! °2 ⁇ ) using Cu Ka radiation.
- the compound e.g., the crystalline form of the gentisate salt of Compound 5R
- the compound is characterized by an XRPD pattern having at least three peaks selected from 6.0:0.2.0.1 : 0.2.1 .0:0.2, 17.7+0.2, 18.4:0.2.20.7:0.2, 23.8:0.2.2x8:0.2. and 26.6+0.2 20 (e.g., 6.0:0.1, 9.1+0.1, 15.0+0,1, 17,7+0.1, 18.4+0.1, 20.7+0.1, 238-0.1.25.8+0.1, and 26,6+0.1 °2 ⁇ ) using Cu Ka radiation.
- the compound e.g., the crystalline form of the gentisate salt of Compound 5R
- the compound is characterized by an XRPD pattern having at least five peaks selected from 6 : 0.2.9,1 ⁇ 0.2, 15.0+0.2, 17.7 - 02, S 8.4 : 0.2, 20.7+0.2, 23.8 ⁇ 0,2, 258 : 0.2, and 266-0.2 °2 ⁇ (e.g., 6.0:0.1.9.1+0.1, 15.0 ⁇ 0.1, 17.7:0.1, 18.4-0.!.20.7:0.1.23.8:0.1, 25.8:0.1. and 26.6:0.1 °2 ⁇ ) using Cu Ka radiation.
- the compound e.g., the crystalline form of the gentisate salt of Compound 5R
- the compound is characterized by an XRPD pattern having at least six peaks selected from 6.0:0.2, 9.1 ⁇ 02, 1 0 ⁇ 0.2. 17.7.0.2, 18.4:02, 207-0.2.23.8 0.2, 25.8 ⁇ 0,2, and 26.6.0.2 °2 ⁇ (e.g., 6.0:0.1, 9.1+XU, 15.0 ⁇ 0.1, 17.7 ⁇ 0.1, 18.4:0.1, 20.7 ⁇ 0.1, 23.8+0.1, 25.8 ⁇ 0.1, and 26.6: 0.1 °2 ⁇ ) using Cu Ka radiation.
- the compound e.g., the crystalline form of the gentisate salt of Compound 5R
- the compound is characterized by an XRPD pattern having at least seven peaks selected from 6.0:0.2.9.1 ⁇ 0.2, 1 .0:0.2, 17.7+0.2, 18.4:0.2.20.7:0.2, 23.8:0.2.2x8:0.2. and 26.6+0.2 20 (e.g., 6.0:0.1, 9.1+0.1, 15.0+0,1, 17 ,7 ⁇ 0.1, 18.4+0.1, 20.7:01, 238-0.1.25.8:0.1, and 26.6:0.1 °2 ⁇ ) using Cu Ka radiation.
- the compound e.g., the crystalline form of the gentisate salt of Compound 5R
- the compound is characterized by an XRPD pattern having at least eight peaks selected from 6.0 ⁇ 0.2, 9.H0.2, 15.0+0.2, 17.7 ⁇ 0.2, 18.4 ⁇ 0.2, 20.7+0.2, 23.8 ⁇ 0.2, 25.8 ⁇ 0.2, and26.6 ⁇ 0.2 °2 ⁇ (e.g., 6.0-01, 91 - 0.1. 15.0:0.1, 17.7.0.1, 184-0.1.20.7:0.1, 23.8+0.1, 25.8-01, and 26.6-01 °2 ⁇ ) using Cu Ka radiation.
- the compound e.g., the crystalline form of the gentisate salt of Compound 5R
- the compound is characterized by an XRPD pattern having three peaks selected from 6.0 ⁇ 0.2, 9.1 ⁇ 0.2, 15.0+0.2, 17.7:02, 184-0.2.20.7:0.2, 23.8:0.2, 258-0.2, and 26.6:02 °2 ⁇ (e.g., 6.0:0.1, 9.1 ⁇ 0.1, 15.0+0.1, 17.7:0.1, 18.4:0.1, 20.7-0.1.23.8:0.1.25.8:0.1, and 26.6:0.1 °2 ⁇ ) using Cu Ka. radiation,
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Priority Applications (18)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2020521599A JP2021500334A (ja) | 2017-10-18 | 2018-10-18 | Ehmt2阻害剤としてのアミン置換複素環化合物、その塩、及びそれらの合成方法 |
| MX2020007152A MX2020007152A (es) | 2017-10-18 | 2018-10-18 | Compuestos heterociclicos sustituidos con amina como inhibidores de ehmt2, sales de los mismos, y metodos de sintesis de los mismos. |
| EP18869308.9A EP3697762A4 (en) | 2017-10-18 | 2018-10-18 | AMINE SUBSTITUTED HETEROCYCLIC COMPOUNDS, USED AS EHMT2 INHIBITORS, SALTS THEREOF, AND THEIR METHODS OF SYNTHESIS |
| IL301746A IL301746B2 (en) | 2017-10-18 | 2018-10-18 | Amine-modified heterocyclic compounds as EHMT2 inhibitors, their salts and a method for their synthesis |
| AU2018353122A AU2018353122B2 (en) | 2017-10-18 | 2018-10-18 | Amine-substituted heterocyclic compounds as EHMT2 inhibitors, salts thereof, and methods of synthesis thereof |
| KR1020207013781A KR20200101330A (ko) | 2017-10-18 | 2018-10-18 | Ehmt2 저해제로서의 아민-치환된 헤테로사이클릭 화합물, 이의 염, 및 이들의 합성 방법 |
| CA3079273A CA3079273A1 (en) | 2017-10-18 | 2018-10-18 | Amine-substituted heterocyclic compounds as ehmt2 inhibitors, salts thereof, and methods of synthesis thereof |
| CN201880077022.4A CN111417628A (zh) | 2017-10-18 | 2018-10-18 | 作为ehmt2抑制剂的胺取代的杂环化合物、其盐及其合成方法 |
| US16/756,565 US20200247790A1 (en) | 2017-10-18 | 2018-10-18 | Amine-substituted heterocyclic compounds as ehmt2 inhibitors, salts thereof, and methods of synthesis thereof |
| BR112020007632-5A BR112020007632A2 (pt) | 2017-10-18 | 2018-10-18 | composto, composição farmacêutica, método para inibir um dentre ou tanto ehmt1 quanto ehmt2, método para prevenir ou tratar um distúrbio sanguíneo, método para prevenir ou tratar um câncer e uso do composto |
| SG11202003225YA SG11202003225YA (en) | 2017-10-18 | 2018-10-18 | Amine-substituted heterocyclic compounds as ehmt2 inhibitors, salts thereof, and methods of synthesis thereof |
| EA202090959A EA202090959A1 (ru) | 2017-10-18 | 2018-10-18 | Аминзамещенные гетероциклические соединения в качестве ингибиторов ehmt2, их соли и способы их синтеза |
| IL273974A IL273974B2 (en) | 2017-10-18 | 2020-04-16 | Amine-disubstituted heterocyclic compounds as ehmt2 inhibitors, salts thereof and method for their synthesis |
| CONC2020/0005944A CO2020005944A2 (es) | 2017-10-18 | 2020-05-15 | Compuestos heterocíclicos sustituidos con amina como inhibidores de ehmt2, sales de los mismos, y métodos de síntesis de los mismos |
| MX2024012124A MX2024012124A (es) | 2017-10-18 | 2020-07-13 | Compuestos heterociclicos sustituidos con amina como inhibidores de ehmt2, sales de los mismos, y metodos de sintesis de los mismos. |
| US17/703,155 US20220324851A1 (en) | 2017-10-18 | 2022-03-24 | Amine-substituted heterocyclic compounds as ehmt2 inhibitors, salts thereof, and methods of synthesis thereof |
| JP2023002371A JP2023036991A (ja) | 2017-10-18 | 2023-01-11 | Ehmt2阻害剤としてのアミン置換複素環化合物、その塩、及びそれらの合成方法 |
| AU2024201165A AU2024201165A1 (en) | 2017-10-18 | 2024-02-22 | Amine-substituted heterocyclic compounds as ehmt2 inhibitors, salts thereof, and methods of synthesis thereof |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201762573917P | 2017-10-18 | 2017-10-18 | |
| US62/573,917 | 2017-10-18 |
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| US16/756,565 A-371-Of-International US20200247790A1 (en) | 2017-10-18 | 2018-10-18 | Amine-substituted heterocyclic compounds as ehmt2 inhibitors, salts thereof, and methods of synthesis thereof |
| US17/703,155 Continuation US20220324851A1 (en) | 2017-10-18 | 2022-03-24 | Amine-substituted heterocyclic compounds as ehmt2 inhibitors, salts thereof, and methods of synthesis thereof |
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| WO2019079540A1 true WO2019079540A1 (en) | 2019-04-25 |
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| PCT/US2018/056428 Ceased WO2019079540A1 (en) | 2017-10-18 | 2018-10-18 | AMINO-SUBSTITUTED HETEROCYCLIC COMPOUNDS AS INHIBITORS OF EHMT2, SALTS THEREOF, AND METHODS OF SYNTHESIS THEREOF |
Country Status (16)
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| US (2) | US20200247790A1 (enExample) |
| EP (1) | EP3697762A4 (enExample) |
| JP (2) | JP2021500334A (enExample) |
| KR (1) | KR20200101330A (enExample) |
| CN (1) | CN111417628A (enExample) |
| AU (2) | AU2018353122B2 (enExample) |
| BR (1) | BR112020007632A2 (enExample) |
| CA (1) | CA3079273A1 (enExample) |
| CL (1) | CL2020001009A1 (enExample) |
| CO (1) | CO2020005944A2 (enExample) |
| EA (1) | EA202090959A1 (enExample) |
| IL (2) | IL301746B2 (enExample) |
| MA (1) | MA50418A (enExample) |
| MX (2) | MX2020007152A (enExample) |
| SG (1) | SG11202003225YA (enExample) |
| WO (1) | WO2019079540A1 (enExample) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2022093904A1 (en) * | 2020-10-27 | 2022-05-05 | Trevena, Inc. | Crystalline and amorphous forms of a delta-opioid modulator |
| US11672800B2 (en) | 2017-04-21 | 2023-06-13 | Epizyme, Inc. | Combination therapies with EHMT2 inhibitors |
| US11912713B2 (en) | 2017-02-17 | 2024-02-27 | Trevena, Inc. | 7-membered aza-heterocyclic containing delta-opioid receptor modulating compounds, methods of using and making the same |
| WO2025240956A1 (en) * | 2024-05-17 | 2025-11-20 | Yale University | G9a/ehmt2 inhibitor use for prader-willi syndrome |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MX2020003862A (es) | 2017-10-18 | 2020-08-13 | Incyte Corp | Derivados condensados de imidazol sustituidos por grupos hidroxi terciarios como inhibidores de fosfoinositido 3-cinasas gamma (pi3k-gamma). |
| CR20250050A (es) | 2018-09-05 | 2025-03-19 | Incyte Corp | Formas cristalinas de un inhibidor de fosfoinositida 3–quinasa (pi3k) (divisional 2021-0165) |
| CN114249785B (zh) * | 2020-09-23 | 2024-04-05 | 常州方圆制药有限公司 | 一种2-腺苷n-吡唑的衍生物瑞加德松的制备方法 |
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| US8604042B2 (en) * | 2005-11-01 | 2013-12-10 | Targegen, Inc. | Bi-aryl meta-pyrimidine inhibitors of kinases |
| US9284272B2 (en) * | 2014-03-28 | 2016-03-15 | Abbvie Inc. | Inhibitors of histone methyltransferase G9a |
| US20170121316A1 (en) * | 2014-06-16 | 2017-05-04 | Fundación Para La Investigación Médica Aplicada | Novel compounds as dual inhibitors of histone methyltransferases and dna methyltransferases |
| US20170209444A1 (en) * | 2014-06-23 | 2017-07-27 | Genentech Inc. | Methods of treating cancer and preventing cancer drug resistance |
| WO2017181177A1 (en) * | 2016-04-15 | 2017-10-19 | Epizyme, Inc. | Amine-substituted aryl or heteroaryl compounds as ehmt1 and ehmt2 inhibitors |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2538413A1 (en) * | 2003-09-18 | 2005-03-24 | Novartis Ag | 2,4-di (phenylamino) pyrimidines useful in the treatment of proliferative disorders |
| MY167260A (en) * | 2005-11-01 | 2018-08-14 | Targegen Inc | Bi-aryl meta-pyrimidine inhibitors of kinases |
| EP3555070B1 (en) * | 2016-12-19 | 2023-08-09 | Epizyme, Inc. | Amine-substituted heterocyclic compounds as ehmt2 inhibitors and methods of use thereof |
| US20200113901A1 (en) * | 2017-03-31 | 2020-04-16 | Epizyme, Inc. | Methods of using ehmt2 inhibitors |
| CA3079412A1 (en) * | 2017-10-18 | 2019-04-25 | Epizyme, Inc. | Methods of using ehmt2 inhibitors in immunotherapies |
-
2018
- 2018-10-18 MA MA050418A patent/MA50418A/fr unknown
- 2018-10-18 BR BR112020007632-5A patent/BR112020007632A2/pt unknown
- 2018-10-18 JP JP2020521599A patent/JP2021500334A/ja not_active Withdrawn
- 2018-10-18 CA CA3079273A patent/CA3079273A1/en active Pending
- 2018-10-18 KR KR1020207013781A patent/KR20200101330A/ko not_active Ceased
- 2018-10-18 US US16/756,565 patent/US20200247790A1/en not_active Abandoned
- 2018-10-18 WO PCT/US2018/056428 patent/WO2019079540A1/en not_active Ceased
- 2018-10-18 EP EP18869308.9A patent/EP3697762A4/en not_active Withdrawn
- 2018-10-18 EA EA202090959A patent/EA202090959A1/ru unknown
- 2018-10-18 SG SG11202003225YA patent/SG11202003225YA/en unknown
- 2018-10-18 MX MX2020007152A patent/MX2020007152A/es unknown
- 2018-10-18 AU AU2018353122A patent/AU2018353122B2/en active Active
- 2018-10-18 IL IL301746A patent/IL301746B2/en unknown
- 2018-10-18 CN CN201880077022.4A patent/CN111417628A/zh active Pending
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2020
- 2020-04-15 CL CL2020001009A patent/CL2020001009A1/es unknown
- 2020-04-16 IL IL273974A patent/IL273974B2/en unknown
- 2020-05-15 CO CONC2020/0005944A patent/CO2020005944A2/es unknown
- 2020-07-13 MX MX2024012124A patent/MX2024012124A/es unknown
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2022
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2023
- 2023-01-11 JP JP2023002371A patent/JP2023036991A/ja active Pending
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2024
- 2024-02-22 AU AU2024201165A patent/AU2024201165A1/en active Pending
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| US8604042B2 (en) * | 2005-11-01 | 2013-12-10 | Targegen, Inc. | Bi-aryl meta-pyrimidine inhibitors of kinases |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US11912713B2 (en) | 2017-02-17 | 2024-02-27 | Trevena, Inc. | 7-membered aza-heterocyclic containing delta-opioid receptor modulating compounds, methods of using and making the same |
| US11672800B2 (en) | 2017-04-21 | 2023-06-13 | Epizyme, Inc. | Combination therapies with EHMT2 inhibitors |
| WO2022093904A1 (en) * | 2020-10-27 | 2022-05-05 | Trevena, Inc. | Crystalline and amorphous forms of a delta-opioid modulator |
| WO2025240956A1 (en) * | 2024-05-17 | 2025-11-20 | Yale University | G9a/ehmt2 inhibitor use for prader-willi syndrome |
Also Published As
| Publication number | Publication date |
|---|---|
| CN111417628A (zh) | 2020-07-14 |
| CA3079273A1 (en) | 2019-04-25 |
| EA202090959A1 (ru) | 2020-07-13 |
| IL301746B2 (en) | 2025-01-01 |
| IL273974B2 (en) | 2023-08-01 |
| AU2018353122A1 (en) | 2020-06-04 |
| MA50418A (fr) | 2021-04-07 |
| JP2023036991A (ja) | 2023-03-14 |
| IL273974A (en) | 2020-05-31 |
| CO2020005944A2 (es) | 2020-07-31 |
| IL301746B1 (en) | 2024-09-01 |
| AU2018353122B2 (en) | 2023-11-23 |
| AU2024201165A1 (en) | 2024-03-14 |
| CL2020001009A1 (es) | 2020-12-18 |
| IL301746A (en) | 2023-05-01 |
| US20220324851A1 (en) | 2022-10-13 |
| EP3697762A1 (en) | 2020-08-26 |
| BR112020007632A2 (pt) | 2020-09-29 |
| MX2024012124A (es) | 2025-02-10 |
| IL273974B1 (en) | 2023-04-01 |
| JP2021500334A (ja) | 2021-01-07 |
| KR20200101330A (ko) | 2020-08-27 |
| MX2020007152A (es) | 2020-12-10 |
| SG11202003225YA (en) | 2020-05-28 |
| EP3697762A4 (en) | 2021-04-07 |
| US20200247790A1 (en) | 2020-08-06 |
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