KR100814269B1 - 고나도트로핀-분비 호르몬 수용체 길항제 및 이를 포함하는 약제학적 조성물 - Google Patents

고나도트로핀-분비 호르몬 수용체 길항제 및 이를 포함하는 약제학적 조성물 Download PDF

Info

Publication number
KR100814269B1
KR100814269B1 KR1020027009582A KR20027009582A KR100814269B1 KR 100814269 B1 KR100814269 B1 KR 100814269B1 KR 1020027009582 A KR1020027009582 A KR 1020027009582A KR 20027009582 A KR20027009582 A KR 20027009582A KR 100814269 B1 KR100814269 B1 KR 100814269B1
Authority
KR
South Korea
Prior art keywords
alkyl
compound
substituted
hydrogen
halogen
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
KR1020027009582A
Other languages
English (en)
Korean (ko)
Other versions
KR20030012846A (ko
Inventor
주윤페이
첸첸
투씨파비오씨
구오지퀴앙
그로쓰티모티디
로우보텀마틴
스트루터스알스코트
Original Assignee
뉴로크린 바이오사이언시즈 인코퍼레이티드
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 뉴로크린 바이오사이언시즈 인코퍼레이티드 filed Critical 뉴로크린 바이오사이언시즈 인코퍼레이티드
Publication of KR20030012846A publication Critical patent/KR20030012846A/ko
Application granted granted Critical
Publication of KR100814269B1 publication Critical patent/KR100814269B1/ko
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D239/00Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24Heterocyclic 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
    • C07D239/28Heterocyclic 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
    • C07D239/46Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/60Three or more oxygen or sulfur atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D239/00Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24Heterocyclic 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
    • C07D239/28Heterocyclic 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
    • C07D239/46Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/52Two oxygen atoms
    • C07D239/54Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495Heterocyclic 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
    • A61K31/505Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/513Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim having oxo groups directly attached to the heterocyclic ring, e.g. cytosine
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/04Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00Drugs for disorders of the urinary system
    • A61P13/08Drugs for disorders of the urinary system of the prostate
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00Drugs for genital or sexual disorders; Contraceptives
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00Drugs for genital or sexual disorders; Contraceptives
    • A61P15/08Drugs for genital or sexual disorders; Contraceptives for gonadal disorders or for enhancing fertility, e.g. inducers of ovulation or of spermatogenesis
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00Drugs for genital or sexual disorders; Contraceptives
    • A61P15/18Feminine contraceptives
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/20Hypnotics; Sedatives
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00Antineoplastic agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00Drugs for immunological or allergic disorders
    • A61P37/02Immunomodulators
    • A61P37/06Immunosuppressants, e.g. drugs for graft rejection
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P5/00Drugs for disorders of the endocrine system
    • A61P5/02Drugs for disorders of the endocrine system of the hypothalamic hormones, e.g. TRH, GnRH, CRH, GRH, somatostatin
    • A61P5/04Drugs for disorders of the endocrine system of the hypothalamic hormones, e.g. TRH, GnRH, CRH, GRH, somatostatin for decreasing, blocking or antagonising the activity of the hypothalamic hormones
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P5/00Drugs for disorders of the endocrine system
    • A61P5/24Drugs for disorders of the endocrine system of the sex hormones
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D401/00Heterocyclic 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
    • C07D401/02Heterocyclic 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
    • C07D401/04Heterocyclic 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D401/00Heterocyclic 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
    • C07D401/02Heterocyclic 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
    • C07D401/06Heterocyclic 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D401/00Heterocyclic 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
    • C07D401/02Heterocyclic 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
    • C07D401/12Heterocyclic 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D401/00Heterocyclic 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
    • C07D401/14Heterocyclic 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D403/00Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02Heterocyclic 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
    • C07D403/04Heterocyclic 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 directly linked by a ring-member-to-ring-member bond
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D403/00Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02Heterocyclic 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
    • C07D403/06Heterocyclic 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D403/00Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02Heterocyclic 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
    • C07D403/12Heterocyclic 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D405/00Heterocyclic 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
    • C07D405/02Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D405/00Heterocyclic 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
    • C07D405/02Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/06Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D405/00Heterocyclic 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
    • C07D405/02Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D405/00Heterocyclic 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
    • C07D405/14Heterocyclic 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D409/00Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/04Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D409/00Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/06Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D409/00Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D409/00Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D413/00Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/04Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D413/00Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/06Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D413/00Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14Heterocyclic 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D417/00Heterocyclic 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
    • C07D417/02Heterocyclic 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
    • C07D417/04Heterocyclic 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 directly linked by a ring-member-to-ring-member bond
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D417/00Heterocyclic 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
    • C07D417/02Heterocyclic 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
    • C07D417/06Heterocyclic 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 carbon chain containing only aliphatic carbon atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D417/00Heterocyclic 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
    • C07D417/02Heterocyclic 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
    • C07D417/12Heterocyclic 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D471/00Heterocyclic 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
    • C07D471/02Heterocyclic 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
    • C07D471/04Ortho-condensed systems
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D487/00Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04Ortho-condensed systems
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D491/00Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/08Bridged systems
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D498/00Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D498/02Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D498/08Bridged systems
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D513/00Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
    • C07D513/02Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
    • C07D513/04Ortho-condensed systems

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Endocrinology (AREA)
  • Reproductive Health (AREA)
  • Immunology (AREA)
  • Diabetes (AREA)
  • Gynecology & Obstetrics (AREA)
  • Epidemiology (AREA)
  • Anesthesiology (AREA)
  • Neurosurgery (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Pregnancy & Childbirth (AREA)
  • Transplantation (AREA)
  • Urology & Nephrology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Investigating Or Analysing Biological Materials (AREA)
KR1020027009582A 2000-01-25 2001-01-25 고나도트로핀-분비 호르몬 수용체 길항제 및 이를 포함하는 약제학적 조성물 Expired - Lifetime KR100814269B1 (ko)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US17793300P 2000-01-25 2000-01-25
US60/177,933 2000-01-25
US23968300P 2000-10-11 2000-10-11
US60/239,683 2000-10-11
PCT/US2001/002740 WO2001055119A2 (en) 2000-01-25 2001-01-25 Gonadotropin-releasing hormone receptor antagonists and methods relating thereto

Publications (2)

Publication Number Publication Date
KR20030012846A KR20030012846A (ko) 2003-02-12
KR100814269B1 true KR100814269B1 (ko) 2008-03-18

Family

ID=26873790

Family Applications (1)

Application Number Title Priority Date Filing Date
KR1020027009582A Expired - Lifetime KR100814269B1 (ko) 2000-01-25 2001-01-25 고나도트로핀-분비 호르몬 수용체 길항제 및 이를 포함하는 약제학적 조성물

Country Status (14)

Country Link
US (4) US6608197B2 (https=)
EP (1) EP1255738B1 (https=)
JP (1) JP4931314B2 (https=)
KR (1) KR100814269B1 (https=)
AT (1) ATE548357T1 (https=)
AU (1) AU767585B2 (https=)
CA (1) CA2398018C (https=)
CY (1) CY1112815T1 (https=)
DK (1) DK1255738T3 (https=)
ES (1) ES2383954T3 (https=)
MX (1) MXPA02006848A (https=)
NO (1) NO20023525L (https=)
PT (1) PT1255738E (https=)
WO (1) WO2001055119A2 (https=)

Families Citing this family (39)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001055119A2 (en) 2000-01-25 2001-08-02 Neurocrine Biosciences, Inc. Gonadotropin-releasing hormone receptor antagonists and methods relating thereto
SE0100567D0 (sv) * 2001-02-20 2001-02-20 Astrazeneca Ab Compounds
US6939883B2 (en) 2001-08-02 2005-09-06 Neurocrine Biosciences, Inc. Gonadotropin-releasing hormone receptor antagonists and methods relating thereto
EP1411941A2 (en) 2001-08-02 2004-04-28 Neurocrine Biosciences, Inc. Pyridinone and pyridazinone derivatives as gonadotropin-releasing hormone receptor antagonists
EP1495768A4 (en) * 2002-04-12 2007-12-05 Takeda Pharmaceutical MEANS FOR THE PREVENTION / TREATMENT OF HITZEWALLUNGEN
ES2387495T3 (es) * 2003-07-07 2012-09-25 Neurocrine Biosciences, Inc. Arilpirimidinas útiles en el tratamiento de trastornos relacionados con las hormonas sexuales, tales como endometriosis, cáncer de próstata y similares
DE602004020638D1 (de) 2003-07-07 2009-05-28 Neurocrine Biosciences Inc Pyrimidin-2,4-dion-derivate als gonadotropin freisetzende hormon-rezeptor-antagonisten
AU2004257639B2 (en) * 2003-07-07 2011-01-06 Neurocrine Biosciences, Inc. Pyrimidine-2, 4-dione derivatives as gonadotropin-releasing hormone receptor antagonists
KR20060041309A (ko) 2003-08-13 2006-05-11 다케다 야쿠힌 고교 가부시키가이샤 4-피리미돈 유도체 및 펩티딜 펩티다제 저해제로서의 그의용도
UA85871C2 (uk) * 2004-03-15 2009-03-10 Такеда Фармасьютікал Компані Лімітед Інгібітори дипептидилпептидази
WO2005113516A1 (en) * 2004-05-14 2005-12-01 Neurocrine Biosciences, Inc. Uracil-type gonadotropin-releasing hormone receptor antagonists and methods related thereto
EP1655288A1 (en) * 2004-11-05 2006-05-10 Institut Pasteur Aryl pyrimidyl compounds, pharmaceutical compositions comprising them, their use as antimicrobial agents
MY147393A (en) 2005-09-14 2012-11-30 Takeda Pharmaceutical Administration of dipeptidyl peptidase inhibitors
CA2622642C (en) 2005-09-16 2013-12-31 Takeda Pharmaceutical Company Limited Dipeptidyl peptidase inhibitors
WO2007122634A2 (en) * 2006-04-24 2007-11-01 Jubilant Biosys Limited Pyrimidinediones as tyrosine kinase inhibitors
TW200838536A (en) 2006-11-29 2008-10-01 Takeda Pharmaceutical Polymorphs of succinate salt of 2-[6-(3-amino-piperidin-1-yl)-3-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-ylmethy]-4-fluor-benzonitrile and methods of use therefor
EP2155194B1 (en) 2007-04-06 2015-01-21 Neurocrine Biosciences, Inc. Gonadotropin-releasing hormone receptor antagonists and methods relating thereto
CL2008000986A1 (es) 2007-04-06 2008-10-17 Neurocrine Biosciences Inc COMPUESTO DERIVADO DE HETEROCICLOS DE NITROGENO, AGONISTAS DEL RECEPTOR GnRH; COMPOSICION FARMACEUTICA QUE COMPRENDE A DICHO COMPUESTO; Y USO PARA TRATAR UNA AFECCION RELACIONADA CON LAS HORMONAS SEXUALES, ENDOMETRIOSIS, DISMENORREA, ENFERMEDAD DE OV
EP2147922B1 (en) * 2007-04-18 2017-08-02 Kissei Pharmaceutical Co., Ltd. Fused heterocyclic derivative, pharmaceutical composition comprising the derivative, and use of the composition for medical purposes
EP2145889A4 (en) * 2007-04-18 2012-04-18 Kissei Pharmaceutical HETEROCYCLIC FUSED CORE DERIVATIVE, PHARMACEUTICAL COMPOSITION COMPRISING THE DERIVATIVE, AND USE OF THE COMPOSITION FOR MEDICAL PURPOSES
US8765948B2 (en) 2007-11-07 2014-07-01 Neurocrine Biosciences, Inc. Processes for the preparation of uracil derivatives
DE102008030091B4 (de) * 2008-06-25 2011-03-03 Resprotect Gmbh Uracilderivate und deren Verwendung
WO2010029299A1 (en) * 2008-09-12 2010-03-18 Biolipox Ab Pyrimidinone derivaties for use as medicaments
JP5757956B2 (ja) * 2009-11-20 2015-08-05 エスケー ケミカルス シーオー., エルティーディー.Sk Chemicals Co., Ltd. ゴナドトロピン放出ホルモン受容体拮抗剤、その製造方法及びそれを含む医薬組成物
TW201130854A (en) 2009-12-22 2011-09-16 Bayer Schering Pharma Ag Pyridinone derivatives and pharmaceutical compositions thereof
WO2012175514A1 (en) 2011-06-21 2012-12-27 Bayer Intellectual Property Gmbh Pyridinone derivatives and pharmaceutical compositions thereof
IL241595B2 (en) 2013-03-15 2025-10-01 Abbvie Inc Composition for use in methods of treating heavy menstrual bleeding associated with uterine fibroids
US20200113901A1 (en) * 2017-03-31 2020-04-16 Epizyme, Inc. Methods of using ehmt2 inhibitors
CN110621316B (zh) 2017-04-21 2024-01-26 Epizyme股份有限公司 用ehmt2抑制剂进行的组合疗法
US20190054088A1 (en) 2017-08-18 2019-02-21 Abbvie Inc. Pharmaceutical Formulations for Treating Endometriosis, Uterine Fibroids, Polycystic Ovary Syndrome or Adenomyosis
TW201912157A (zh) 2017-08-18 2019-04-01 美商艾伯維有限公司 治療子宮內膜異位症、子宮纖維瘤、多囊性卵巢症候群及子宮腺肌症之固體醫藥調配物
CN111698992A (zh) 2017-08-18 2020-09-22 艾伯维公司 用于治疗子宫内膜异位症、子宫肌瘤、多囊卵巢综合症或子宫腺肌症的药物配制物
AU2018419533A1 (en) 2018-04-19 2020-11-12 Abbvie Inc. Methods of treating heavy menstrual bleeding
BR112021000973A2 (pt) 2018-07-23 2021-04-20 Abbvie Inc. composições e processos de sódio de elagolix
PH12021551685A1 (en) 2019-01-15 2022-05-16 Lupin Inc Deuterated elagolix-like compositions and methods
CN111333586A (zh) * 2020-02-19 2020-06-26 诚达药业股份有限公司 一种含有6-甲基尿嘧啶结构化合物的制备方法
CN111333587B (zh) * 2020-04-11 2023-04-07 东莞市东阳光新药研发有限公司 取代的嘧啶-2,4(1h,3h)-二酮衍生物及其用途
CN113527213B (zh) * 2020-04-20 2023-01-03 上海英诺富成生物科技有限公司 促性激素释放激素受体拮抗剂及其用途
LT4122926T (lt) * 2021-04-14 2025-07-25 Shionogi & Co., Ltd. Triazino dariniai, turintys virusų replikaciją slopinantį poveikį, ir juos apimanti farmacinė kompozicija

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000029386A1 (en) * 1998-11-12 2000-05-25 Merck & Co., Inc. Pyrimidinedione derivatives useful as alpha 1a adrenoceptor antagonists
WO2000069833A1 (en) * 1999-05-19 2000-11-23 Pharmacia Corporation Substituted polycyclic aryl and heteroaryl uracils as anticoagulative agents

Family Cites Families (34)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2631625B1 (fr) * 1988-05-17 1992-10-16 Synthelabo Derives de phenyl-6 piperazinylalkyl-3 1h,3h-pyrimidinedione-2,4, leur preparation et leur application en therapeutique
US5140029A (en) 1989-01-09 1992-08-18 Janssen Pharmaceutica N.V. 2-aminopyrimidinone derivatives
US5476855A (en) * 1993-11-02 1995-12-19 Mahmoud H. el Kouni Enzyme inhibitors, their synthesis and methods for use
UY23948A1 (es) * 1995-02-08 2001-10-25 Takeda Chemical Industries Ltd Derivados de anillos condensados de tiofeno su producción y uso.
AU5844896A (en) 1995-06-01 1996-12-18 Takeda Chemical Industries Ltd. Tricyclic diazepines useful as gnrh receptor antagonists
US5859014A (en) * 1995-06-09 1999-01-12 Syntex (U.S.A.) Inc. Pyrimidinedione, pyrimidinetrione, triazinedione and tetrahydroquinazolinedione derivatives as α1 -adrenergic receptor antagonists
ATE201016T1 (de) * 1995-06-09 2001-05-15 Hoffmann La Roche Pyrimidindion-, pyrimidintrion-, triazindion- derivate als alpha-1-adrenergische rezeptorantagonisten
CN1063446C (zh) 1995-10-19 2001-03-21 武田药品工业株式会社 作为促性腺激素释放激素拮抗剂的噻吩并吡啶衍生物
CN1200114A (zh) 1995-10-19 1998-11-25 武田药品工业株式会社 作为gnrh拮抗剂的喹啉衍生物
JP3092946B2 (ja) 1995-12-14 2000-09-25 メルク エンド カンパニー インコーポレーテッド ゴナドトロピン放出ホルモン拮抗剤
SK77598A3 (en) 1995-12-14 1999-01-11 Merck & Co Inc Nonpeptide derivatives, pharmaceutical composition containing them and their use
WO1997021435A1 (en) 1995-12-14 1997-06-19 Merck & Co., Inc. Antagonists of gonadotropin releasing hormone
CN1208412A (zh) 1995-12-14 1999-02-17 麦克公司 促性腺激素释放激素拮抗剂
US5780437A (en) 1995-12-14 1998-07-14 Merck & Co., Inc. Antagonists of gonadotropin releasing hormone
US5849764A (en) 1995-12-14 1998-12-15 Merck & Co., Inc. Antagonists of gonadotropin releasing hormone
JPH09286786A (ja) * 1996-04-18 1997-11-04 Nippon Paper Ind Co Ltd ピリミジン誘導体及びその抗腫瘍剤としての用途
WO1997044041A1 (en) 1996-05-20 1997-11-27 Merck & Co., Inc. Antagonists of gonadotropin releasing hormone
JP2000511533A (ja) 1996-05-20 2000-09-05 メルク エンド カンパニー インコーポレーテッド ゴナドトロピン放出ホルモン拮抗薬
AU710926B2 (en) 1996-05-20 1999-09-30 Merck & Co., Inc. Antagonists of gonadotropin releasing hormone
AU3071397A (en) 1996-05-20 1997-12-09 Merck & Co., Inc. Antagonists of gonadotropin releasing hormone
EP0986385A4 (en) 1997-06-05 2001-05-16 Merck & Co Inc GONADORELIN ANTAGONISTS
AU729752B2 (en) 1997-06-05 2001-02-08 Merck & Co., Inc. Antagonists of gonadotropin releasing hormone
AU7806998A (en) 1997-06-05 1998-12-21 Merck & Co., Inc. Antagonists of gonadotropin releasing hormone
WO1998055479A1 (en) 1997-06-05 1998-12-10 Merck & Co., Inc. Antagonists of gonadotropin releasing hormone
US6313301B1 (en) 1997-08-13 2001-11-06 Takeda Chemical Industries, Ltd. Thienopyridine derivatives, their intermediates and production thereof
US6194419B1 (en) 1997-12-26 2001-02-27 Takeda Chemical Industries, Ltd. Nitrogen-containing heterocyclic compounds, their production and use
CA2326143A1 (en) 1998-04-02 1999-10-14 Merck & Co., Inc. Antagonists of gonadotropin releasing hormone
CA2372044A1 (en) 1999-05-14 2000-11-23 Neurocrine Biosciences, Inc. Imidazo- and pyrrolo[1,2-a]pyrimid-4-ones as gonadotropin-releasing hormone receptor antagonists
ES1043085Y (es) * 1999-06-03 2001-02-01 Nueva Ceramica Arb Sa Teja planoconvexa
MXPA02003614A (es) 1999-10-15 2002-10-23 Neurocrine Biosciences Inc Antagonistas del receptor de la hormona liberadora de ganadotropina y metodos relacionados con los mismos..
WO2001055119A2 (en) * 2000-01-25 2001-08-02 Neurocrine Biosciences, Inc. Gonadotropin-releasing hormone receptor antagonists and methods relating thereto
ES2387495T3 (es) * 2003-07-07 2012-09-25 Neurocrine Biosciences, Inc. Arilpirimidinas útiles en el tratamiento de trastornos relacionados con las hormonas sexuales, tales como endometriosis, cáncer de próstata y similares
DE602004020638D1 (de) * 2003-07-07 2009-05-28 Neurocrine Biosciences Inc Pyrimidin-2,4-dion-derivate als gonadotropin freisetzende hormon-rezeptor-antagonisten
AU2004257639B2 (en) * 2003-07-07 2011-01-06 Neurocrine Biosciences, Inc. Pyrimidine-2, 4-dione derivatives as gonadotropin-releasing hormone receptor antagonists

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000029386A1 (en) * 1998-11-12 2000-05-25 Merck & Co., Inc. Pyrimidinedione derivatives useful as alpha 1a adrenoceptor antagonists
WO2000069833A1 (en) * 1999-05-19 2000-11-23 Pharmacia Corporation Substituted polycyclic aryl and heteroaryl uracils as anticoagulative agents

Also Published As

Publication number Publication date
US20050234082A1 (en) 2005-10-20
US20040048884A1 (en) 2004-03-11
US6608197B2 (en) 2003-08-19
EP1255738B1 (en) 2012-03-07
US20070208049A1 (en) 2007-09-06
ATE548357T1 (de) 2012-03-15
AU767585B2 (en) 2003-11-20
KR20030012846A (ko) 2003-02-12
DK1255738T3 (da) 2012-06-25
JP2003520856A (ja) 2003-07-08
NO20023525D0 (no) 2002-07-24
EP1255738A2 (en) 2002-11-13
PT1255738E (pt) 2012-06-19
US7179815B2 (en) 2007-02-20
WO2001055119A2 (en) 2001-08-02
NO20023525L (no) 2002-07-24
MXPA02006848A (es) 2002-12-13
CY1112815T1 (el) 2016-02-10
ES2383954T3 (es) 2012-06-27
US7462625B2 (en) 2008-12-09
CA2398018C (en) 2011-10-18
US20020132820A1 (en) 2002-09-19
JP4931314B2 (ja) 2012-05-16
US6872728B2 (en) 2005-03-29
HK1051042A1 (en) 2003-07-18
AU3797501A (en) 2001-08-07
WO2001055119A3 (en) 2002-02-14
CA2398018A1 (en) 2001-08-02

Similar Documents

Publication Publication Date Title
KR100814269B1 (ko) 고나도트로핀-분비 호르몬 수용체 길항제 및 이를 포함하는 약제학적 조성물
KR101139148B1 (ko) 고나도트로핀-방출 호르몬 수용체 길항제로서의피리미딘-2,4-디온 유도체
JP2011079857A (ja) 性腺刺激ホルモン放出ホルモンレセプターアンタゴニストおよびそれに関連する方法
EP1411941A2 (en) Pyridinone and pyridazinone derivatives as gonadotropin-releasing hormone receptor antagonists
KR20020045609A (ko) 고나도트로핀-분비 호르몬 수용체 길항제 및 이와 관련된방법
EP1412338B1 (en) 1,3,5-triazine-2,4,6-triones, preparation and use as gonadotropin-releasing hormone receptor antagonists
KR20040030893A (ko) 치환된 피리딘-4-온 및 고나도트로핀 분비 호르몬 수용체길항제로서의 이의 용도
AU2002324586A1 (en) 1,3,5-triazine-2,4,6-triones, preparation and use as gonadotropin-releasing hormone receptor antagonists
AU2012261077A1 (en) 2-amino-3-(imidazol-2-yl)-pyridin-4-one derivatives and their use as VEGF receptor kinase inhibitors
KR20020039266A (ko) 고나도트로핀 방출 호르몬 수용체 길항제로서의 이미다조-및 피롤로[1,2-a]피리미드-4-온
KR20040023712A (ko) 고나도트로핀 분비 호르몬 수용체(gnrh) 길항제로서의1,2,4-트리아진-3,5-디온
US6740656B2 (en) Gonadotropin-releasing hormone receptor antagonists and methods relating thereto
AU2002321864A1 (en) 1,2,4-triazin-3,5-diones as gonadotropin-releasing hormone receptor (GNRH) antagonists
HK1051042B (en) Gonadotropin-releasing hormone receptor antagonists and methods relating thereto

Legal Events

Date Code Title Description
PA0105 International application

Patent event date: 20020725

Patent event code: PA01051R01D

Comment text: International Patent Application

PG1501 Laying open of application
A201 Request for examination
PA0201 Request for examination

Patent event code: PA02012R01D

Patent event date: 20060124

Comment text: Request for Examination of Application

E902 Notification of reason for refusal
PE0902 Notice of grounds for rejection

Comment text: Notification of reason for refusal

Patent event date: 20061207

Patent event code: PE09021S01D

E902 Notification of reason for refusal
PE0902 Notice of grounds for rejection

Comment text: Notification of reason for refusal

Patent event date: 20070705

Patent event code: PE09021S01D

E701 Decision to grant or registration of patent right
PE0701 Decision of registration

Patent event code: PE07011S01D

Comment text: Decision to Grant Registration

Patent event date: 20071221

GRNT Written decision to grant
PR0701 Registration of establishment

Comment text: Registration of Establishment

Patent event date: 20080311

Patent event code: PR07011E01D

PR1002 Payment of registration fee

Payment date: 20080312

End annual number: 3

Start annual number: 1

PG1601 Publication of registration
G170 Re-publication after modification of scope of protection [patent]
PG1701 Publication of correction
PR1001 Payment of annual fee

Payment date: 20110228

Start annual number: 4

End annual number: 4

PR1001 Payment of annual fee

Payment date: 20120228

Start annual number: 5

End annual number: 5

FPAY Annual fee payment

Payment date: 20130226

Year of fee payment: 6

PR1001 Payment of annual fee

Payment date: 20130226

Start annual number: 6

End annual number: 6

FPAY Annual fee payment

Payment date: 20140226

Year of fee payment: 7

PR1001 Payment of annual fee

Payment date: 20140226

Start annual number: 7

End annual number: 7

FPAY Annual fee payment

Payment date: 20150226

Year of fee payment: 8

PR1001 Payment of annual fee

Payment date: 20150226

Start annual number: 8

End annual number: 8

FPAY Annual fee payment

Payment date: 20160224

Year of fee payment: 9

PR1001 Payment of annual fee

Payment date: 20160224

Start annual number: 9

End annual number: 9

FPAY Annual fee payment

Payment date: 20170307

Year of fee payment: 10

PR1001 Payment of annual fee

Payment date: 20170307

Start annual number: 10

End annual number: 10

FPAY Annual fee payment

Payment date: 20180228

Year of fee payment: 11

PR1001 Payment of annual fee

Payment date: 20180228

Start annual number: 11

End annual number: 11

FPAY Annual fee payment

Payment date: 20190227

Year of fee payment: 12

PR1001 Payment of annual fee

Payment date: 20190227

Start annual number: 12

End annual number: 12

FPAY Annual fee payment

Payment date: 20200227

Year of fee payment: 13

PR1001 Payment of annual fee

Payment date: 20200227

Start annual number: 13

End annual number: 13

PC1801 Expiration of term

Termination date: 20210725

Termination category: Expiration of duration