AU2017231860C1 - Indole derivatives and their use as protein kinase inhibitors - Google Patents
Indole derivatives and their use as protein kinase inhibitors Download PDFInfo
- Publication number
- AU2017231860C1 AU2017231860C1 AU2017231860A AU2017231860A AU2017231860C1 AU 2017231860 C1 AU2017231860 C1 AU 2017231860C1 AU 2017231860 A AU2017231860 A AU 2017231860A AU 2017231860 A AU2017231860 A AU 2017231860A AU 2017231860 C1 AU2017231860 C1 AU 2017231860C1
- Authority
- AU
- Australia
- Prior art keywords
- methyl
- phenyl
- amino
- carboxylate
- methylene
- 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.)
- Ceased
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/32—Oxygen atoms
- C07D209/34—Oxygen atoms in position 2
-
- 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
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
- A61K31/404—Indoles, e.g. pindolol
- A61K31/4045—Indole-alkylamines; Amides thereof, e.g. serotonin, melatonin
-
- 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
- A61K31/445—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
- 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
- A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
-
- 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
- A61K31/527—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim spiro-condensed
-
- 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
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5375—1,4-Oxazines, e.g. morpholine
- A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
-
- 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
- A61K31/54—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
- A61K31/541—Non-condensed thiazines containing further heterocyclic 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
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
- A61K31/551—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having two nitrogen atoms, e.g. dilazep
-
- 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
- A61K31/63—Compounds containing para-N-benzenesulfonyl-N-groups, e.g. sulfanilamide, p-nitrobenzenesulfonyl hydrazide
- A61K31/635—Compounds containing para-N-benzenesulfonyl-N-groups, e.g. sulfanilamide, p-nitrobenzenesulfonyl hydrazide having a heterocyclic ring, e.g. sulfadiazine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
- C07C205/57—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/14—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D295/145—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
-
- 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
-
- 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
- C07D403/12—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 chain containing hetero atoms as chain links
-
- 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
- C07D405/12—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 chain containing hetero atoms as chain links
-
- 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
- C07D471/10—Spiro-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Pulmonology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Indole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP16159231 | 2016-03-08 | ||
| EP16159231.6 | 2016-03-08 | ||
| PCT/GB2017/050619 WO2017153748A1 (en) | 2016-03-08 | 2017-03-08 | Indole derivatives and their use as protein kinase inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| AU2017231860A1 AU2017231860A1 (en) | 2018-09-27 |
| AU2017231860B2 AU2017231860B2 (en) | 2021-06-10 |
| AU2017231860C1 true AU2017231860C1 (en) | 2022-01-20 |
Family
ID=55521584
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2017231860A Ceased AU2017231860C1 (en) | 2016-03-08 | 2017-03-08 | Indole derivatives and their use as protein kinase inhibitors |
Country Status (10)
| Country | Link |
|---|---|
| US (2) | US10669235B2 (https=) |
| EP (1) | EP3426649B1 (https=) |
| JP (1) | JP7039480B2 (https=) |
| CN (1) | CN109153666B (https=) |
| AU (1) | AU2017231860C1 (https=) |
| BR (1) | BR112018068213A2 (https=) |
| CA (1) | CA3017308A1 (https=) |
| EA (1) | EA038773B1 (https=) |
| ES (1) | ES2836255T3 (https=) |
| WO (1) | WO2017153748A1 (https=) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PL3722291T3 (pl) | 2015-12-24 | 2023-11-27 | Respivert Limited | Związki indolinonowe i ich zastosowanie w leczeniu chorób zwłóknieniowych |
| CN109153666B (zh) | 2016-03-08 | 2021-07-16 | 莱斯彼维特有限公司 | 吲哚衍生物及其作为蛋白激酶抑制剂的用途 |
| KR102460040B1 (ko) | 2016-04-27 | 2022-11-01 | 애브비 인코포레이티드 | 항-il-13 항체를 이용한 il-13 활성이 유해한 질환의 치료 방법 |
| CN112574094B (zh) * | 2020-12-14 | 2022-07-01 | 成都大学 | 吲哚酮衍生物及其制药用途 |
| WO2023043473A1 (en) * | 2021-09-14 | 2023-03-23 | R-Pharm Overseas, Inc. | TGF-β INHIBITOR COMPOSITION AND USE THEREOF |
| CN117624014A (zh) * | 2022-11-02 | 2024-03-01 | 徐诺药业(南京)有限公司 | 3-(吲哚氨基)亚甲基吲哚啉类衍生物及其制备方法和应用 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002081445A1 (de) * | 2001-04-06 | 2002-10-17 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | In 6-stellung substituierte indoline und ihre verwendung als kinase-inhibitoren |
| WO2006067168A1 (en) * | 2004-12-24 | 2006-06-29 | Boehringer Ingelheim International Gmbh | Medicaments for the treatment or prevention of fibrotic diseases |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| UA75054C2 (uk) | 1999-10-13 | 2006-03-15 | Бьорінгер Інгельхайм Фарма Гмбх & Ко. Кг | Заміщені в положенні 6 індолінони, їх одержання та їх застосування як лікарського засобу |
| JP2004182726A (ja) | 2002-11-22 | 2004-07-02 | Yamanouchi Pharmaceut Co Ltd | 2−オキソインドリン誘導体 |
| JP2005145928A (ja) * | 2003-11-19 | 2005-06-09 | Yamanouchi Pharmaceut Co Ltd | 3−キノリン−2(1h)−イリデンインドリン−2−オン誘導体を有効成分とする医薬組成物 |
| PE20060777A1 (es) | 2004-12-24 | 2006-10-06 | Boehringer Ingelheim Int | Derivados de indolinona para el tratamiento o la prevencion de enfermedades fibroticas |
| EP1902025A1 (en) | 2005-07-13 | 2008-03-26 | Allergan, Inc. | Kinase inhibitors |
| WO2010009166A1 (en) * | 2008-07-14 | 2010-01-21 | Gilead Colorado, Inc. | Oxindolyl inhibitor compounds |
| JP6152389B2 (ja) * | 2012-01-26 | 2017-06-21 | アンジオン バイオメディカ コーポレーション | 抗線維化化合物及びその使用 |
| WO2015179436A1 (en) * | 2014-05-19 | 2015-11-26 | Sanford-Burnham Medical Research Institute | Inflammation therapy using mekk3 inhibitors or blocking peptides |
| PL3722291T3 (pl) | 2015-12-24 | 2023-11-27 | Respivert Limited | Związki indolinonowe i ich zastosowanie w leczeniu chorób zwłóknieniowych |
| CN109153666B (zh) | 2016-03-08 | 2021-07-16 | 莱斯彼维特有限公司 | 吲哚衍生物及其作为蛋白激酶抑制剂的用途 |
-
2017
- 2017-03-08 CN CN201780023315.XA patent/CN109153666B/zh not_active Expired - Fee Related
- 2017-03-08 JP JP2018547928A patent/JP7039480B2/ja not_active Expired - Fee Related
- 2017-03-08 ES ES17711736T patent/ES2836255T3/es active Active
- 2017-03-08 EP EP17711736.3A patent/EP3426649B1/en not_active Not-in-force
- 2017-03-08 BR BR112018068213A patent/BR112018068213A2/pt not_active IP Right Cessation
- 2017-03-08 AU AU2017231860A patent/AU2017231860C1/en not_active Ceased
- 2017-03-08 EA EA201892020A patent/EA038773B1/ru unknown
- 2017-03-08 US US16/083,886 patent/US10669235B2/en active Active
- 2017-03-08 WO PCT/GB2017/050619 patent/WO2017153748A1/en not_active Ceased
- 2017-03-08 CA CA3017308A patent/CA3017308A1/en not_active Abandoned
-
2020
- 2020-06-01 US US16/889,780 patent/US11208381B2/en not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002081445A1 (de) * | 2001-04-06 | 2002-10-17 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | In 6-stellung substituierte indoline und ihre verwendung als kinase-inhibitoren |
| WO2006067168A1 (en) * | 2004-12-24 | 2006-06-29 | Boehringer Ingelheim International Gmbh | Medicaments for the treatment or prevention of fibrotic diseases |
Non-Patent Citations (1)
| Title |
|---|
| Roth et al, J. Med. Chem., 2009, 52, 4466-4480 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN109153666A (zh) | 2019-01-04 |
| EA038773B1 (ru) | 2021-10-18 |
| CN109153666B (zh) | 2021-07-16 |
| WO2017153748A1 (en) | 2017-09-14 |
| US20210114982A1 (en) | 2021-04-22 |
| US11208381B2 (en) | 2021-12-28 |
| US10669235B2 (en) | 2020-06-02 |
| JP2019509294A (ja) | 2019-04-04 |
| BR112018068213A2 (pt) | 2019-01-29 |
| EA201892020A1 (ru) | 2019-02-28 |
| AU2017231860A1 (en) | 2018-09-27 |
| CA3017308A1 (en) | 2017-09-14 |
| EP3426649B1 (en) | 2020-07-22 |
| JP7039480B2 (ja) | 2022-03-22 |
| EP3426649A1 (en) | 2019-01-16 |
| AU2017231860B2 (en) | 2021-06-10 |
| US20190071399A1 (en) | 2019-03-07 |
| ES2836255T3 (es) | 2021-06-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| DA2 | Applications for amendment section 104 |
Free format text: THE NATURE OF THE AMENDMENT IS AS SHOWN IN THE STATEMENT(S) FILED 09 SEP 2021 |
|
| DA3 | Amendments made section 104 |
Free format text: THE NATURE OF THE AMENDMENT IS AS SHOWN IN THE STATEMENT(S) FILED 09 SEP 2021 |
|
| FGA | Letters patent sealed or granted (standard patent) | ||
| MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |