SG11201808163WA - 6-hydroxy-4-oxo-1,4-dihydropyrimidine-5-carboxamides as apj agonists - Google Patents

6-hydroxy-4-oxo-1,4-dihydropyrimidine-5-carboxamides as apj agonists

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Publication number
SG11201808163WA
SG11201808163WA SG11201808163WA SG11201808163WA SG11201808163WA SG 11201808163W A SG11201808163W A SG 11201808163WA SG 11201808163W A SG11201808163W A SG 11201808163WA SG 11201808163W A SG11201808163W A SG 11201808163WA SG 11201808163W A SG11201808163W A SG 11201808163WA
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Singapore
Prior art keywords
pennington
bristol
new jersey
rocky hill
myers
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Application number
SG11201808163WA
Inventor
Zulan Pi
Donna M Bilder
Robert Paul Brigance
Heather Finlay
Wen Jiang
James A Johnson
R Michael Lawrence
Wei Meng
Michael C Myers
Monique Phillips
George O Tora
Xiaojun Zhang
Original Assignee
Bristol Myers Squibb Co
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Publication of SG11201808163WA publication Critical patent/SG11201808163WA/en

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    • 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
    • C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
    • 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
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • 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
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/52—Two oxygen atoms
    • C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
    • 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
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/52—Two oxygen atoms
    • C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
    • C07D239/545—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other 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
    • 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
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/52—Two oxygen atoms
    • C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
    • C07D239/545—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other 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
    • C07D239/557—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other 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 with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms, e.g. orotic acid
    • 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
    • C07D401/06—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 carbon chain containing only aliphatic carbon atoms
    • 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
    • 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
    • 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
    • C07D403/14—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 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
    • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Epidemiology (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Diabetes (AREA)
  • Vascular Medicine (AREA)
  • Emergency Medicine (AREA)
  • Endocrinology (AREA)
  • Hematology (AREA)
  • Obesity (AREA)
  • Hospice & Palliative Care (AREA)
  • Urology & Nephrology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

INTERNATIONAL APPLICATION PUBLISHED UNDER THE PATENT COOPERATION TREATY (PCT) (19) World Intellectual Property -, Organization 11M1111101110101011111 HO 1111101110111101111011001110110111110111011# International Bureau ... .... ..)d .... ..... (10) International Publication Number (43) International Publication Date WO 2017/165640 Al 28 September 2017 (28.09.2017) WIP0 I PCT (51) International Patent Classification: Rocky Hill Road, Pennington, New Jersey 08534 (US). CO7D 401/14 (2006.01) CO7D 417/14 (2006.01) LAWRENCE, R. Michael; c/o Bristol-Myers Squibb CO7D 401/06 (2006.01) CO7D 471/04 (2006.01) Company, 311 Pennington Rocky Hill Road, Pennington, CO7D 403/06 (2006.01) A61K 31/505 (2006.01) New Jersey 08534 (US). MENG, Wei; c/o Bristol-Myers C07D 403/14 (2006.01) A61K 31/506 (2006.01) Squibb Company, 311 Pennington Rocky Hill Road, Pen- C07D 239/557 (2006.01) A61P 35/00 (2006.01) nington, New Jersey 08534 (US). MYERS, Michael C.; c/o Bristol-Myers Squibb Company, 311 Pennington (21) International Application Number: Rocky Hill Road, Pennington, New Jersey 08534 (US). PCT/US2017/023801 PHILLIPS, Monique; c/o Bristol-Myers Squibb Com- (22) International Filing Date: pany, Route 206 and Province Line Road, Princeton, New 23 March 2017 (23.03.2017) Jersey 08543 (US). TORA, George 0.; c/o Bristol-Myers Squibb Company, 311 Pennington Rocky Hill Road, Pen- (25) Filing Language: English nington, New Jersey 08534 (US). ZHANG, Xiaojun; c/o (26) Publication Language: English Bristol-Myers Squibb Company, 311 Pennington Rocky Hill Road, Pennington, New Jersey 08534 (US). (30) Priority Data: 62/312,780 24 March 2016 (24.03.2016) US (74) Agents: LIU, Hong et al.; Bristol-Myers Squibb Company, Route 206 and Province Line Road, Princeton, New Jersey (71) Applicant: BRISTOL-MYERS SQUIBB COMPANY 08543 (US). [US/US]; Route 206 and Province Line Road, Princeton, New Jersey 08543 (US). (81) Designated States (unless otherwise indicated, for every kind of national protection available): AE, AG, AL, AM, (72) Inventors: PI, Zulan; c/o Bristol-Myers Squibb Company, AO, AT, AU, AZ, BA, BB, BG, BH, BN, BR, BW, BY, — 311 Pennington Rocky Hill Road, Pennington, New Jersey BZ, CA, CH, CL, CN, CO, CR, CU, CZ, DE, DJ, DK, DM, _ 08534 (US). BILDER, Donna M; c/o Bristol-Myers DO, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, Squibb Company, 311 Pennington Rocky Hill Road, Pen- HN, HR, HU, ID, IL, IN, IR, IS, JP, KE, KG, KH, KN, = nington, New Jersey 08534 (US). BRIGANCE, Robert KP, KR, KW, KZ, LA, LC, LK, LR, LS, LU, LY, MA, Paul; 28 Lakeside Drive, Levittown, Pennsylvania 19054 MD, ME, MG, MK, MN, MW, MX, MY, MZ, NA, NG, = (US). FINLAY, Heather; c/o Bristol-Myers Squibb Com- NI, NO, NZ, OM, PA, PE, PG, PH, PL, PT, QA, RO, RS, = pany, 311 Pennington Rocky Hill Road, Pennington, New RU, RW, SA, SC, SD, SE, SG, SK, SL, SM, ST, SV, SY, = Jersey 08534 (US). JIANG, Wen; c/o Bristol-Myers TH, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, = Squibb Company, 311 Pennington Rocky Hill Road, Pen- ZA, ZM, ZW. nington, New Jersey 08534 (US). JOHNSON, James A.; c/o Bristol-Myers Squibb Company, 311 Pennington (84) Designated States (unless otherwise indicated, for every = kind of regional protection available): ARIPO (BW, GH, = [Continued on next page] = (54) Title: 6-HYDROXY-4-0X0-1,4-DIHYDROPYRIMIDINE-5-CARBOXAMIDES = = = = = — R2 _ ,—, © 7r N A (alk)0.2 0 N I I I OH AS APJ AGONISTS NR 3 R 4 ir) 1— 1 IN 1-1 (57) : The present invention provides 0 and compositions comprising any of such \" ments. i ED compounds novel compounds. (R 1 )1-4 (I) of Formula (I) wherein all variables are as defined in the specification, These compounds are APJ agonists which may be used as medico - O WO 2017/165640 Al MIDEDIMOMOIDEIR010130HinlINIMEMOVOIMIE GM, KE, LR, LS, MW, MZ, NA, RW, SD, SL, ST, SZ, — as to the applicant's entitlement to claim the priority of TZ, UG, ZM, ZW), Eurasian (AM, AZ, BY, KG, KZ, RU, TJ, TM), European (AL, AT, BE, BG, CH, CY, CZ, DE, DK, EE, ES, FI, FR, GB, GR, HR, HU, IE, IS, IT, LT, — the earlier application (Rule 4.17(iii)) of inventorship (Rule 4.17(iv)) LU, LV, MC, MK, MT, NL, NO, PL, PT, RO, RS, SE, Published: SI, SK, SM, TR), OAPI (BF, BJ, CF, CG, CI, CM, GA, GN, GQ, GW, KM, ML, MR, NE, SN, TD, TG). — with international search report (Art. 21(3)) Declarations under Rule 4.17: — as to applicant's entitlement to apply for and be granted a patent (Rule 4.17(ii))
SG11201808163WA 2016-03-24 2017-03-23 6-hydroxy-4-oxo-1,4-dihydropyrimidine-5-carboxamides as apj agonists SG11201808163WA (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US201662312780P 2016-03-24 2016-03-24
PCT/US2017/023801 WO2017165640A1 (en) 2016-03-24 2017-03-23 6-hydroxy-4-oxo-1,4-dihydropyrimidine-5-carboxamides as apj agonists

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US (2) US10106528B2 (en)
EP (1) EP3433247B1 (en)
JP (1) JP6716711B2 (en)
KR (1) KR102433280B1 (en)
CN (1) CN109195963B (en)
AR (1) AR107973A1 (en)
AU (1) AU2017238504B2 (en)
BR (1) BR112018068341A2 (en)
CA (1) CA3018346A1 (en)
CL (1) CL2018002671A1 (en)
CO (1) CO2018011105A2 (en)
EA (1) EA037162B1 (en)
ES (1) ES2895124T3 (en)
IL (1) IL261904B (en)
MA (1) MA43761A (en)
MX (1) MX2018011194A (en)
MY (1) MY189454A (en)
SG (1) SG11201808163WA (en)
TW (1) TWI744301B (en)
UY (1) UY37169A (en)
WO (1) WO2017165640A1 (en)
ZA (1) ZA201806356B (en)

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