SG11201809559UA - Substituted pyridines as inhibitors of dnmt1 - Google Patents

Substituted pyridines as inhibitors of dnmt1

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Publication number
SG11201809559UA
SG11201809559UA SG11201809559UA SG11201809559UA SG11201809559UA SG 11201809559U A SG11201809559U A SG 11201809559UA SG 11201809559U A SG11201809559U A SG 11201809559UA SG 11201809559U A SG11201809559U A SG 11201809559UA SG 11201809559U A SG11201809559U A SG 11201809559UA
Authority
SG
Singapore
Prior art keywords
collegeville
road
south
pennsylvania
manchester
Prior art date
Application number
SG11201809559UA
Inventor
Nicholas David Adams
Andrew B Benowitz
Benede Maria Lourdes Rueda
Karen Anderson Evans
David T Fosbenner
Bryan Wayne King
Mei Li
Juan Ignacio Luengo
William Henry Miller
Alexander Joseph Reif
Stuart Paul Romeril
Stanley J Schmidt
Roger J Butlin
Kristin M Goldberg
Allan M Jordan
Christopher S Kershaw
Ali Raoof
Bohdan Waszkowycz
Original Assignee
Glaxosmithkline Ip Dev Ltd
Cancer Research Tech Ltd
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 Glaxosmithkline Ip Dev Ltd, Cancer Research Tech Ltd filed Critical Glaxosmithkline Ip Dev Ltd
Publication of SG11201809559UA publication Critical patent/SG11201809559UA/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
    • C07D401/02—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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/4412—Non condensed pyridines; Hydrogenated derivatives thereof having oxo groups directly attached to the heterocyclic ring
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
    • 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
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/72—Nitrogen atoms
    • C07D213/73—Unsubstituted amino or imino radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/72—Nitrogen atoms
    • C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
    • 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
    • C07D401/04—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 directly linked by a ring-member-to-ring-member bond
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

Abstract

INTERNATIONAL APPLICATION PUBLISHED UNDER THE PATENT COOPERATION TREATY (PCT) (19) World Intellectual Property 1 MEM 0 11101 HOE 010 1111 1 0 013 011110011111010 1111 1111011110111111 Organization International Bureau (10) International Publication Number (43) International Publication Date ......0\"\" WO 2017/216727 Al 21 December 2017 (21.12.2017) WIP0 I PCT (51) International Patent Classification: Road, Collegeville, Pennsylvania 19426 (US). BUTLIN, CO7D 213/73 (2006.01) A61K 31/4412 (2006.01) Roger J.; Wilmslow Road, Manchester Greater Manches- CO7D 213/74 (2006.01) A61P 37/00 (2006.01) ter M20 4BX (GB). GOLDBERG, Kristen M.; Wilmslow (21) International Application Number: Road, Manchester Greater Manchester M20 4BX (GB). PCT/IB2017/053511 JORDAN, Allan M.; Wilmslow Road, Manchester Greater Manchester M20 4BX (GB). KERSHAW, Christopher S.; (22) International Filing Date: Wilmslow Road, Manchester Greater Manchester M20 4BX 13 June 2017 (13.06.2017) (GB). RAOOF, Ali; Wilmslow Road, Manchester Greater (25) Filing Language: English Manchester M20 4BX (GB). WASZKOWYCS, Bohdan; Wilmslow Road, Manchester Greater Manchester M20 4BX (26) Publication Language: English (GB). (30) Priority Data: (81) Designated States (unless otherwise indicated, for every 62/349,227 13 June 2016 (13.06.2016) US kind of national protection available): AE, AG, AL, AM, 62/393,256 12 September 2016 (12.09.2016) US AO, AT, AU, AZ, BA, BB, BG, BH, BN, BR, BW, BY, BZ, 62/412,343 25 October 2016 (25.10.2016) US CA, CH, CL, CN, CO, CR, CU, CZ, DE, DJ, DK, DM, DO, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, HN, (71) Applicants: GLAXOSMITHKLINE INTELLECTUAL HR, HU, ID, IL, IN, IR, IS, JO, JP, KE, KG, KH, KN, KP, PROPERTY DEVELOPMENT LIMITED [GB/GB]; KR, KW, KZ, LA, LC, LK, LR, LS, LU, LY, MA, MD, ME, 980 Great West Road, Brentford Middlesex TW89GS MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, (GB). CANCER RESEARCH TECHNOLOGY LTD. OM, PA, PE, PG, PH, PL, PT, QA, RO, RS, RU, RW, SA, [GB/GB]; Sardinia House, Sardinia Street, London Greater SC, SD, SE, SG, SK, SL, SM, ST, SV, SY, TH, TJ, TM, TN, London WC2A 3NL (GB). TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, ZW. = _ (72) Inventors: ADAMS, Nicholas David; 1250 South Col-(84) Designated States (unless otherwise indicated, for every legeville Road, Collegeville, Pennsylvania 19426 (US). kind of regional protection available): ARIPO (BW, GH, BENOWITZ, Andrew B.; 1250 South Collegeville GM, KE, LR, LS, MW, MZ, NA, RW, SD, SL, ST, SZ, TZ, = _ Road, Collegeville, Pennsylvania 19426 (US). RUEDA UG, ZM, ZW), Eurasian (AM, AZ, BY, KG, KZ, RU, TJ, BENEDE, Maria Lourdes; 1250 South Collegeville Road, TM), European (AL, AT, BE, BG, CH, CY, CZ, DE, DK, Collegeville, Pennsylvania 19426 (US). EVANS, Karen EE, ES, FI, FR, GB, GR, HR, HU, IE, IS, IT, LT, LU, LV, Anderson; 1250 South Collegeville Road, Collegeville, MC, MK, MT, NL, NO, PL, PT, RO, RS, SE, SI, SK, SM, Pennsylvania 19426 (US). FOSBENNER, David T.; 1250 TR), OAPI (BF, BJ, CF, CG, CI, CM, GA, GN, GQ, GW, South Collegeville Road, Collegeville, Pennsylvania 19426 KM, ML, MR, NE, SN, TD, TG). (US). KING, Bryan Wayne; 1250 South Collegeville _ — = = = _ = Road, Collegeville, Pennsylvania 19426 (US). LI, Mei; Published: 1250 South Collegeville Road, Collegeville, Pennsylva- — = = = 21(3)) 19426 LUENGO, Juan Ignacio; 1250 South with international search report (Art. nia (US). Collegeville Road, Collegeville, Pennsylvania 19426 (US). = = MILLER, William Henry; 1250 South Collegeville Road, Collegeville, Pennsylvania 19426 (US). REIF, Alexan- = der Joseph; 1250 South Collegeville Road, Collegeville, Pennsylvania 19426 (US). ROMERIL, Stuart Paul; 1250 = = — South Collegeville Road, Collegeville, Pennsylvania 19426 = (US). SCHMIDT, Stanley J.; 1250 South Collegeville = (54) Title: SUBSTITUTED PYRIDINES AS INHIBITORS OF DNMT1 11 R lar (57) : The invention is directed to substituted pyridine derivatives. Specifically, the invention .4 N ei arR2ar * 3. , is directed to compounds according to Formula (Iar): (Iar) wherein Y ar , Xlar, x2ar, Rear, R 2ar , R 3ar , R oar R R5'r N ya r R oar and R 5 ar are as defined herein; or a pharmaceutically acceptable salt or prodrug thereof. The compounds IN of the invention are selective inhibitors of DNMT1 and can be useful in the treatment of cancer, pre- 1-1 (Iar) cancerous syndromes, beta hemoglobinopathy disorders, sickle cell disease, sickle cell anemia, and ei beta thalassemia, and diseases associated with DNMT1 inhibition. Accordingly, the invention is further IN directed to pharmaceutical compositions comprising a compound of the invention. The invention is 1-1 still further directed to methods of inhibiting DNMT1 activity and treatment of disorders associated 0 ei therewith using a compound of the invention or a pharmaceutical composition comprising a compound of the invention. O
SG11201809559UA 2016-06-13 2017-06-13 Substituted pyridines as inhibitors of dnmt1 SG11201809559UA (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US201662349227P 2016-06-13 2016-06-13
US201662393256P 2016-09-12 2016-09-12
US201662412343P 2016-10-25 2016-10-25
PCT/IB2017/053511 WO2017216727A1 (en) 2016-06-13 2017-06-13 Substituted pyridines as inhibitors of dnmt1

Publications (1)

Publication Number Publication Date
SG11201809559UA true SG11201809559UA (en) 2018-12-28

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SG11201809559UA SG11201809559UA (en) 2016-06-13 2017-06-13 Substituted pyridines as inhibitors of dnmt1

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US (1) US10975056B2 (en)
EP (1) EP3468953A1 (en)
JP (1) JP7051829B2 (en)
KR (1) KR20190017030A (en)
CN (1) CN109563043B (en)
AU (1) AU2017283790B2 (en)
BR (1) BR112018075992A2 (en)
CA (2) CA3026211A1 (en)
CL (1) CL2018003577A1 (en)
CO (1) CO2018013717A2 (en)
CR (1) CR20180580A (en)
DO (1) DOP2018000273A (en)
IL (1) IL263163B (en)
JO (1) JOP20180120A1 (en)
MA (1) MA45244A (en)
MX (1) MX2018015483A (en)
PE (1) PE20190971A1 (en)
PH (1) PH12018502633A1 (en)
SG (1) SG11201809559UA (en)
WO (2) WO2017216727A1 (en)

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