SG11201804664XA - Salt forms and polymorphs of (r)-1-(4-(6-(2-(4-(3,3-difluorocyclobutoxy)-6-methylpyridin-2-yl) acetamido) pyridazin-3-yl)-2-fluorobutyl)-n-methyl-1h-1,2,3-triazole-4-carboxamide - Google Patents

Salt forms and polymorphs of (r)-1-(4-(6-(2-(4-(3,3-difluorocyclobutoxy)-6-methylpyridin-2-yl) acetamido) pyridazin-3-yl)-2-fluorobutyl)-n-methyl-1h-1,2,3-triazole-4-carboxamide

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Publication number
SG11201804664XA
SG11201804664XA SG11201804664XA SG11201804664XA SG11201804664XA SG 11201804664X A SG11201804664X A SG 11201804664XA SG 11201804664X A SG11201804664X A SG 11201804664XA SG 11201804664X A SG11201804664X A SG 11201804664XA SG 11201804664X A SG11201804664X A SG 11201804664XA
Authority
SG
Singapore
Prior art keywords
international
difluorocyclobutoxy
pyridazin
polymorphs
acetamido
Prior art date
Application number
SG11201804664XA
Inventor
Philip Jones
Michael Soth
Jason Burke
Kang Le
Gang Liu
Original Assignee
Univ Texas
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Univ Texas filed Critical Univ Texas
Publication of SG11201804664XA publication Critical patent/SG11201804664XA/en

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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
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/337—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having four-membered rings, e.g. taxol
    • 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
    • A61K31/50—Pyridazines; Hydrogenated pyridazines
    • A61K31/501—Pyridazines; Hydrogenated pyridazines not condensed and containing further heterocyclic rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • 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
    • A61P37/00—Drugs for immunological or allergic disorders
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/13—Crystalline forms, e.g. polymorphs

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Epidemiology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Biomedical Technology (AREA)
  • Neurosurgery (AREA)
  • Immunology (AREA)
  • Neurology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Pathology (AREA)
  • Radiology & Medical Imaging (AREA)
  • Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)

Abstract

INTERNATIONAL APPLICATION PUBLISHED UNDER THE PATENT COOPERATION TREATY (PCT) (19) World Intellectual Property , Organization MD 1111101110101011111 HO 11111011101 01110111111011 IDIOM III International Bureau .. .... ..Yejd (10) International Publication Number (43) International Publication Date ..... ...r .....1 WO 2017/112831 Al 29 June 2017(29.06.2017) WIPO I PCT (51) International Patent Classification: (81) Designated States (unless otherwise indicated, for every C07D 249/08 (2006.01) A61K 31/41 (2006.01) kind of national protection available): AE, AG, AL, AM, C07D 235/00 (2006.01) AO, AT, AU, AZ, BA, BB, BG, BH, BN, BR, BW, BY, BZ, CA, CH, CL, CN, CO, CR, CU, CZ, DE, DJ, DK, DM, (21) International Application Number: DO, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, PCT/US2016/068149 HN, HR, HU, ID, IL, IN, IR, IS, JP, KE, KG, KH, KN, (22) International Filing Date: KP, KR, KW, KZ, LA, LC, LK, LR, LS, LU, LY, MA, 21 December 2016 (21.12.2016) MD, ME, MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, OM, PA, PE, PG, PH, PL, PT, QA, RO, RS, (25) Filing Language: English RU, RW, SA, SC, SD, SE, SG, SK, SL, SM, ST, SV, SY, (26) Publication Language: English TH, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, ZW. (30) Priority Data: 62/271,018 22 December 2015 (22.12.2015) US (84) Designated States (unless otherwise indicated, for every kind of regional protection available): ARIPO (BW, GH, (71) Applicant: BOARD OF REGENTS, THE UNIVER- GM, KE, LR, LS, MW, MZ, NA, RW, SD, SL, ST, SZ, SITY OF TEXAS SYSTEM [US/US]; 201 W. 7th Street, TZ, UG, ZM, ZW), Eurasian (AM, AZ, BY, KG, KZ, RU, Austin, TX 78701 (US). TJ, TM), European (AL, AT, BE, BG, CH, CY, CZ, DE, (72) Inventors: JONES, Philip; 2727 Carolina Way, Houston, DK, EE, ES, FI, FR, GB, GR, HR, HU, IE, IS, IT, LT, LU, TX 77005 (US). SOTH, Michael, J.; 18 Thetford Street, LV, MC, MK, MT, NL, NO, PL, PT, RO, RS, SE, SI, SK, Sugar Land, TX 77479 (US). BURKE, Jason, B.; 4301 SM, TR), OAPI (BF, BJ, CF, CG, CI, CM, GA, GN, GQ, — Hazelton St., Houston, TX 77035 (US). KANG, Le; 5103 GW, KM, ML, MR, NE, SN, TD, TG). — Manzanilla View Lane, Sugar Land, TX 77479 (US). LIU, Published: _ Gang; 4807 Whitby Circle, Sugar Land, TX 77479 (US). with international search report (Art. 21(3)) (74) Agent: HATHAWAY, Cynthia; Global Patent Group, LLC, 17014 New College Avenue, Ste 201, St. Louis, MO 63040 (US). = = = = = = = = = Il 11 M GC ei ,-1 ,-1 IN 1-1 (54) Title: SALT FORMS AND POLYMORPHS OF (R)-1-(4-(6-(2-(4-(3,3-DIFLUOROCYCLOBUTOXY)-6-METHYLPYRID- © IN-2-YL) ACETAMIDO) PYRIDAZIN-3-YL)-2-FLUOROBUTYL)-N-METHYL-1H-1,2,3-TRIAZOLE-4-CARBOXAMIDE ei 0 (57) : Disclosed herein is the compound (R)-1-(4-(6-(2-(4-(3,3-difluorocyclobutoxy)-6- methylpyridin-2-yl)acetamido) pyridazin-3-y1)-2-fluorobuty1)-N-methyl-1H-1,2,3-triazole-4- carboxamide, and salt forms and polymorphs thereof demonstrating im- proved exposure after oral dosing. Methods of inhibition GLS1 activity in a human or animal subject are also provided.
SG11201804664XA 2015-12-22 2016-12-21 Salt forms and polymorphs of (r)-1-(4-(6-(2-(4-(3,3-difluorocyclobutoxy)-6-methylpyridin-2-yl) acetamido) pyridazin-3-yl)-2-fluorobutyl)-n-methyl-1h-1,2,3-triazole-4-carboxamide SG11201804664XA (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US201562271018P 2015-12-22 2015-12-22
PCT/US2016/068149 WO2017112831A1 (en) 2015-12-22 2016-12-21 Salt forms and polymorphs of (r)-1-(4-(6-(2-(4-(3,3-difluorocyclobutoxy)-6-methylpyridin-2-yl) acetamido) pyridazin-3-yl)-2-fluorobutyl)-n-methyl-1h-1,2,3-triazole-4-carboxamide

Publications (1)

Publication Number Publication Date
SG11201804664XA true SG11201804664XA (en) 2018-07-30

Family

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SG11201804664XA SG11201804664XA (en) 2015-12-22 2016-12-21 Salt forms and polymorphs of (r)-1-(4-(6-(2-(4-(3,3-difluorocyclobutoxy)-6-methylpyridin-2-yl) acetamido) pyridazin-3-yl)-2-fluorobutyl)-n-methyl-1h-1,2,3-triazole-4-carboxamide

Country Status (14)

Country Link
US (4) US10150753B2 (en)
EP (1) EP3394039A4 (en)
JP (1) JP6976248B2 (en)
KR (1) KR20180095677A (en)
CN (1) CN108602782B (en)
AU (1) AU2016378746B2 (en)
BR (1) BR112018012660B1 (en)
CA (1) CA3009355A1 (en)
IL (1) IL260178B2 (en)
MX (1) MX2018007143A (en)
RU (1) RU2018124266A (en)
SG (1) SG11201804664XA (en)
WO (1) WO2017112831A1 (en)
ZA (1) ZA201804843B (en)

Families Citing this family (5)

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Publication number Priority date Publication date Assignee Title
HUE049600T2 (en) 2014-07-03 2020-10-28 Univ Texas Gls1 inhibitors for treating diseases
ES2794868T3 (en) 2015-06-30 2020-11-19 Univ Texas GLS1 inhibitors for the treatment of diseases
RU2018124266A (en) 2015-12-22 2020-01-23 Боард Оф Реджентс, Де Юниверсити Оф Техас Систем Salt forms and polymorphs (R) -1- (4- (6- (2- (4- (3,3-difluorocyclobutoxy) -6-methylpyridin-2-yl) acetamido) pyridazin-3-yl) -2-fluorobutyl ) -N-methyl-1H-1,2,3-triazole-4-carboxamide
US10722487B2 (en) 2017-10-18 2020-07-28 Board Of Regents, The University Of Texas System Glutaminase inhibitor therapy
CN116023375A (en) * 2021-10-25 2023-04-28 成都苑东生物制药股份有限公司 Heterocyclic derivative, preparation method and application thereof

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US10722487B2 (en) 2017-10-18 2020-07-28 Board Of Regents, The University Of Texas System Glutaminase inhibitor therapy

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Publication number Publication date
US20230250081A1 (en) 2023-08-10
BR112018012660B1 (en) 2023-12-19
KR20180095677A (en) 2018-08-27
JP2019502663A (en) 2019-01-31
US20170174661A1 (en) 2017-06-22
ZA201804843B (en) 2019-09-25
BR112018012660A2 (en) 2018-12-04
MX2018007143A (en) 2018-11-29
WO2017112831A1 (en) 2017-06-29
AU2016378746A1 (en) 2018-06-28
IL260178A (en) 2018-07-31
US11603365B2 (en) 2023-03-14
US10150753B2 (en) 2018-12-11
RU2018124266A (en) 2020-01-23
JP6976248B2 (en) 2021-12-08
AU2016378746B2 (en) 2021-05-20
EP3394039A4 (en) 2019-06-12
IL260178B2 (en) 2023-05-01
RU2018124266A3 (en) 2020-03-25
CN108602782A (en) 2018-09-28
US20210206745A1 (en) 2021-07-08
IL260178B1 (en) 2023-01-01
US20190144425A1 (en) 2019-05-16
US10899740B2 (en) 2021-01-26
EP3394039A1 (en) 2018-10-31
CA3009355A1 (en) 2017-06-29
CN108602782B (en) 2022-06-17

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