AU2017380282B2 - Pyran derivatives as cyp11a1 (cytochrome p450 monooxygenase 11a1) inhibitors - Google Patents

Pyran derivatives as cyp11a1 (cytochrome p450 monooxygenase 11a1) inhibitors Download PDF

Info

Publication number
AU2017380282B2
AU2017380282B2 AU2017380282A AU2017380282A AU2017380282B2 AU 2017380282 B2 AU2017380282 B2 AU 2017380282B2 AU 2017380282 A AU2017380282 A AU 2017380282A AU 2017380282 A AU2017380282 A AU 2017380282A AU 2017380282 B2 AU2017380282 B2 AU 2017380282B2
Authority
AU
Australia
Prior art keywords
alkyl
pyran
compound
methyl
isoindolin
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.)
Active
Application number
AU2017380282A
Other languages
English (en)
Other versions
AU2017380282A1 (en
Inventor
David Din Belle
Mikko MÄKELÄ
Mikko PASSINIEMI
Pekka PIETIKÄINEN
Petteri Rummakko
Eija Tiainen
Matti VAISMAA
Gerd Wohlfahrt
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Orion Oyj
Original Assignee
Orion Oyj
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 Orion Oyj filed Critical Orion Oyj
Publication of AU2017380282A1 publication Critical patent/AU2017380282A1/en
Priority to AU2021203497A priority Critical patent/AU2021203497B2/en
Application granted granted Critical
Publication of AU2017380282B2 publication Critical patent/AU2017380282B2/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • 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
    • C07D405/02—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 two hetero rings
    • C07D405/06—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 two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • 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
    • 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
    • A61K31/445—Non condensed piperidines, e.g. piperocaine
    • A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
    • A61K31/454—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. pimozide, domperidone
    • 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
    • A61P35/00—Antineoplastic agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic 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
    • 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
    • C07D417/14—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
    • C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
    • C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic 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
    • C07D491/02—Heterocyclic 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
    • C07D491/04—Ortho-condensed systems
    • C07D491/056—Ortho-condensed systems with two or more oxygen atoms as ring hetero atoms in the oxygen-containing ring
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2300/00—Mixtures or combinations of active ingredients, wherein at least one active ingredient is fully defined in groups A61K31/00 - A61K41/00
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
    • Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
    • Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Steroid Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Pyrane Compounds (AREA)
AU2017380282A 2016-12-22 2017-12-21 Pyran derivatives as cyp11a1 (cytochrome p450 monooxygenase 11a1) inhibitors Active AU2017380282B2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2021203497A AU2021203497B2 (en) 2016-12-22 2021-05-28 Pyran derivatives as cyp11a1 (cytochrome p450 monooxygenase 11a1) inhibitors

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
FI20166024 2016-12-22
FI20166024 2016-12-22
PCT/FI2017/050926 WO2018115591A1 (en) 2016-12-22 2017-12-21 Pyran dervatives as cyp11a1 (cytochrome p450 monooxygenase 11a1) inhibitors

Related Child Applications (1)

Application Number Title Priority Date Filing Date
AU2021203497A Division AU2021203497B2 (en) 2016-12-22 2021-05-28 Pyran derivatives as cyp11a1 (cytochrome p450 monooxygenase 11a1) inhibitors

Publications (2)

Publication Number Publication Date
AU2017380282A1 AU2017380282A1 (en) 2019-08-01
AU2017380282B2 true AU2017380282B2 (en) 2021-06-24

Family

ID=61005837

Family Applications (2)

Application Number Title Priority Date Filing Date
AU2017380282A Active AU2017380282B2 (en) 2016-12-22 2017-12-21 Pyran derivatives as cyp11a1 (cytochrome p450 monooxygenase 11a1) inhibitors
AU2021203497A Active AU2021203497B2 (en) 2016-12-22 2021-05-28 Pyran derivatives as cyp11a1 (cytochrome p450 monooxygenase 11a1) inhibitors

Family Applications After (1)

Application Number Title Priority Date Filing Date
AU2021203497A Active AU2021203497B2 (en) 2016-12-22 2021-05-28 Pyran derivatives as cyp11a1 (cytochrome p450 monooxygenase 11a1) inhibitors

Country Status (30)

Country Link
US (4) US10717726B2 (enExample)
EP (2) EP3558981B1 (enExample)
JP (2) JP7025432B2 (enExample)
KR (3) KR102826021B1 (enExample)
CN (2) CN116162084B (enExample)
AR (1) AR110412A1 (enExample)
AU (2) AU2017380282B2 (enExample)
CA (1) CA3047370A1 (enExample)
CL (1) CL2019001728A1 (enExample)
CO (1) CO2019007321A2 (enExample)
CY (1) CY1124461T1 (enExample)
DK (1) DK3558981T3 (enExample)
EA (1) EA039309B1 (enExample)
ES (1) ES2880151T3 (enExample)
HR (1) HRP20211255T1 (enExample)
HU (1) HUE056540T2 (enExample)
IL (2) IL267484B (enExample)
LT (1) LT3558981T (enExample)
MA (2) MA55983A (enExample)
MX (1) MX388538B (enExample)
PE (1) PE20191137A1 (enExample)
PH (1) PH12019550111A1 (enExample)
PL (1) PL3558981T3 (enExample)
PT (1) PT3558981T (enExample)
RS (1) RS62198B1 (enExample)
SI (1) SI3558981T1 (enExample)
TN (1) TN2019000189A1 (enExample)
TW (2) TWI762544B (enExample)
UA (1) UA124640C2 (enExample)
WO (1) WO2018115591A1 (enExample)

Families Citing this family (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AR110412A1 (es) * 2016-12-22 2019-03-27 Orion Corp Inhibidores de la cyp11a1
CN115551831A (zh) * 2020-05-14 2022-12-30 奥赖恩公司 Cyp11a1抑制剂
CN116724034B (zh) * 2020-12-01 2026-06-05 奥赖恩公司 作为用于治疗前列腺癌的cyp11a1抑制剂的2,3-二氢-4h-苯并[b][1,4]噁嗪-4-基)(5-(苯基)-吡啶-3-基)甲酮衍生物和类似化合物
CN117279893A (zh) 2021-03-01 2023-12-22 奥仁公司 用于制备cyp11a1抑制剂及其中间体的方法
AR124985A1 (es) 2021-03-01 2023-05-24 Orion Corp Nuevas formas de sal de un inhibidor de cyp11a1 estructurado en 4h-piran-4-ona
CN117242070A (zh) * 2021-03-01 2023-12-15 奥仁公司 4h-吡喃-4-酮结构化cyp11a1抑制剂的固体形式
AU2022297768A1 (en) 2021-06-23 2024-01-18 Orion Corporation Process for the preparation of a cyp11a1 inhibitor and intermediates thereof
EP4408426A1 (en) * 2021-09-28 2024-08-07 Orion Corporation Cyp11a1 inhibitor for use in the treatment of prostate cancer
WO2023073285A1 (en) 2021-10-28 2023-05-04 Orion Corporation Salt forms of a 4h-pyran-4-one structured cyp11 at inhibitor
EP4430027A1 (en) 2021-11-10 2024-09-18 Orion Corporation Cyp11a1 inhibitors
KR20240130101A (ko) 2022-01-20 2024-08-28 오리온 코포레이션 Cyp11a1 억제제의 약제 조성물
CN118307519A (zh) * 2023-01-06 2024-07-09 上海闻耐医药科技有限公司 一类cyp11a1抑制剂化合物及其制备方法和用途
KR20240126916A (ko) 2023-02-14 2024-08-22 경북대학교 산학협력단 Asm 단백질 또는 이의 단편을 포함하는 퇴행성 신경질환 또는 우울증 예방 또는 치료용 조성물
TW202440557A (zh) 2023-03-29 2024-10-16 大陸商西藏海思科製藥有限公司 Cyp11a1抑制劑及其用途
JP2026514915A (ja) 2023-04-21 2026-05-13 シーザン ハイスーク ファーマシューティカル カンパニー リミテッド Cyp11a1阻害剤及びその用途
KR20260040160A (ko) * 2023-05-11 2026-03-24 셴젠 이오노바 라이프 사이언스 시오., 엘티디. Cyp11a1 억제제로서의 신규 화합물 및 그 용도
EP4746854A1 (en) 2023-07-19 2026-05-27 Orion Corporation Stable pharmaceutical compositions of a cyp11a1 inhibitor
WO2025021182A1 (en) * 2023-07-27 2025-01-30 Acerand Therapeutics (Hong Kong) Limited Cyp11a1 inhibitors
CN121889383A (zh) * 2023-09-08 2026-04-17 深圳众格生物科技有限公司 一种cyp11a1抑制剂、其制备方法及其应用
WO2025168117A1 (zh) * 2024-02-08 2025-08-14 盛睿泽华医药科技(苏州)有限公司 一种多环化合物及其制备方法和应用
WO2025237211A1 (zh) * 2024-05-11 2025-11-20 辽宁海思科制药有限公司 一种cyp11a1抑制剂的晶型物及其制备方法和应用
TW202613102A (zh) * 2024-05-27 2026-04-01 大陸商遼寧海思科製藥有限公司 Cyp11a1抑制劑的鹽及其晶型、其製備方法和應用
WO2026021515A1 (zh) * 2024-07-25 2026-01-29 海思科制药(眉山)有限公司 一种cyp11a1抑制剂的制备方法
WO2026040949A1 (zh) * 2024-08-19 2026-02-26 辽宁海思科制药有限公司 一种cyp11a1抑制剂的药物组合物及其制备方法和用途

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003074450A2 (en) * 2002-02-28 2003-09-12 The University Of Tennessee Research Corporation Radiolabeled selective androgen receptor modulators and their use in prostate cancer imaging and therapy
WO2004076445A2 (en) * 2003-02-28 2004-09-10 Exonhit Therapeutics Sa Compounds and methods of treating cell proliferative diseases, retinopathies and arthritis
US20140005181A1 (en) * 2012-06-21 2014-01-02 Sanford-Burnham Medical Research Institute Small molecule antagonists of the apelin receptor for the treatment of disease
WO2014202827A1 (en) * 2013-06-11 2014-12-24 Orion Corporation Novel cyp17 inhibitors/antiandrogens

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6176485A (ja) * 1984-09-20 1986-04-18 Ss Pharmaceut Co Ltd 新規なγ−ピラン誘導体
AR110412A1 (es) 2016-12-22 2019-03-27 Orion Corp Inhibidores de la cyp11a1

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003074450A2 (en) * 2002-02-28 2003-09-12 The University Of Tennessee Research Corporation Radiolabeled selective androgen receptor modulators and their use in prostate cancer imaging and therapy
WO2004076445A2 (en) * 2003-02-28 2004-09-10 Exonhit Therapeutics Sa Compounds and methods of treating cell proliferative diseases, retinopathies and arthritis
US20140005181A1 (en) * 2012-06-21 2014-01-02 Sanford-Burnham Medical Research Institute Small molecule antagonists of the apelin receptor for the treatment of disease
WO2014202827A1 (en) * 2013-06-11 2014-12-24 Orion Corporation Novel cyp17 inhibitors/antiandrogens

Also Published As

Publication number Publication date
EP3868756A1 (en) 2021-08-25
IL285729B (en) 2022-02-01
MA55983A (fr) 2022-03-23
TWI762544B (zh) 2022-05-01
JP2022078068A (ja) 2022-05-24
TW202229264A (zh) 2022-08-01
AU2021203497A1 (en) 2021-07-01
US20210347765A1 (en) 2021-11-11
MA47102B1 (fr) 2021-09-30
IL267484B (en) 2021-09-30
MX2019007373A (es) 2019-09-18
EA201991513A1 (ru) 2019-11-29
PE20191137A1 (es) 2019-09-02
JP7025432B2 (ja) 2022-02-24
KR20250097993A (ko) 2025-06-30
EP3558981B1 (en) 2021-05-26
CO2019007321A2 (es) 2019-07-31
KR102491308B1 (ko) 2023-01-27
TWI796205B (zh) 2023-03-11
HRP20211255T1 (hr) 2021-11-12
JP7286825B2 (ja) 2023-06-05
TW201835072A (zh) 2018-10-01
AU2017380282A1 (en) 2019-08-01
PL3558981T3 (pl) 2021-12-06
MX388538B (es) 2025-03-20
US11098032B2 (en) 2021-08-24
AU2021203497B2 (en) 2022-11-10
HUE056540T2 (hu) 2022-02-28
KR20190095950A (ko) 2019-08-16
NZ755395A (en) 2025-10-31
LT3558981T (lt) 2021-08-25
US10717726B2 (en) 2020-07-21
KR102826021B1 (ko) 2025-06-30
WO2018115591A1 (en) 2018-06-28
CN110139861B (zh) 2022-12-30
JP2020502229A (ja) 2020-01-23
CA3047370A1 (en) 2018-06-28
CN110139861A (zh) 2019-08-16
PT3558981T (pt) 2021-07-06
PH12019550111A1 (en) 2020-03-09
SI3558981T1 (sl) 2021-09-30
UA124640C2 (uk) 2021-10-20
EP3558981A1 (en) 2019-10-30
CL2019001728A1 (es) 2019-09-27
RS62198B1 (sr) 2021-08-31
IL267484A (en) 2019-08-29
CY1124461T1 (el) 2022-07-22
BR112019012906A2 (pt) 2019-12-03
CN116162084A (zh) 2023-05-26
KR20230019496A (ko) 2023-02-08
ES2880151T3 (es) 2021-11-23
CN116162084B (zh) 2025-12-09
IL285729A (en) 2021-09-30
US12030871B2 (en) 2024-07-09
US20240308989A1 (en) 2024-09-19
DK3558981T3 (da) 2021-07-26
AR110412A1 (es) 2019-03-27
US20190359601A1 (en) 2019-11-28
EA039309B1 (ru) 2022-01-12
US20200299280A1 (en) 2020-09-24
TN2019000189A1 (en) 2020-10-05

Similar Documents

Publication Publication Date Title
AU2021203497B2 (en) Pyran derivatives as cyp11a1 (cytochrome p450 monooxygenase 11a1) inhibitors
US20250154148A1 (en) Kras inhibitors
AU2007315955B2 (en) Pyridine carboxamides as 11-beta-HSD1 inhibitors
TWI386405B (zh) 咪唑衍生物
CA3178067A1 (en) Cyp11a1 inhibitors
JP2020530446A (ja) 化合物、組成物、及び、方法
CA2758210A1 (en) Proline derivatives as cathepsin inhibitors
CN101370806A (zh) 取代的4-苯基哌啶
HK40016600A (en) Pyran derivatives as cyp11a1 (cytochrome p450 monooxygenase 11a1) inhibitors
HK40016600B (en) Pyran derivatives as cyp11a1 (cytochrome p450 monooxygenase 11a1) inhibitors
BR122024021737A2 (pt) Compostos derivados de pirano como inibidores de cyp11a1, uso dos mesmos para o tratamento de doenças dependentes de receptor esteroide, particularmente, receptor androgênico e composição e combinação farmacêuticas que compreendem os ditos compostos
BR112019012906B1 (pt) Compostos derivados de pirano como inibidores de cyp11a1, uso dos mesmos para o tratamento de doenças dependentes de receptor esteroide, particularmente, receptor androgênico e composição e combinação farmacêuticas que compreendem os ditos compostos

Legal Events

Date Code Title Description
DA3 Amendments made section 104

Free format text: THE NATURE OF THE AMENDMENT IS: AMEND THE INVENTION TITLE TO READ PYRAN DERIVATIVES AS CYP11A1 (CYTOCHROME P450 MONOOXYGENASE 11A1) INHIBITORS

FGA Letters patent sealed or granted (standard patent)