DK74282A - Fremgangsmaade til fremstilling af imidazodiazepiner eller farmaceutisk acceptable syreadditionssalte deraf - Google Patents
Fremgangsmaade til fremstilling af imidazodiazepiner eller farmaceutisk acceptable syreadditionssalte deraf Download PDFInfo
- Publication number
- DK74282A DK74282A DK74282A DK74282A DK74282A DK 74282 A DK74282 A DK 74282A DK 74282 A DK74282 A DK 74282A DK 74282 A DK74282 A DK 74282A DK 74282 A DK74282 A DK 74282A
- Authority
- DK
- Denmark
- Prior art keywords
- imidazodiazepins
- preparing
- procedure
- acid addition
- addition salts
- Prior art date
Links
- 239000002253 acid Substances 0.000 title 1
- 150000003839 salts Chemical class 0.000 title 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
- C07D265/12—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems
- C07D265/14—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D265/24—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with hetero atoms directly attached in positions 2 and 4
- C07D265/26—Two oxygen atoms, e.g. isatoic anhydride
-
- 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
- C07D209/38—Oxygen atoms in positions 2 and 3, e.g. isatin
-
- 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
- C07D471/12—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 three hetero rings
- C07D471/14—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic 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
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/12—Heterocyclic 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 three hetero rings
- C07D487/14—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D495/14—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (12)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH134281 | 1981-02-27 | ||
| CH133881 | 1981-02-27 | ||
| CH133881 | 1981-02-27 | ||
| CH134181 | 1981-02-27 | ||
| CH134281 | 1981-02-27 | ||
| CH133981 | 1981-02-27 | ||
| CH133981 | 1981-02-27 | ||
| CH134181 | 1981-02-27 | ||
| CH367581 | 1981-06-04 | ||
| CH367581 | 1981-06-04 | ||
| CH793481 | 1981-12-11 | ||
| CH793481 | 1981-12-11 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DK74282A true DK74282A (da) | 1982-08-28 |
| DK168073B1 DK168073B1 (da) | 1994-01-31 |
Family
ID=27543637
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK074282A DK168073B1 (da) | 1981-02-27 | 1982-02-19 | Analogifremgangsmaade til fremstilling af imidazodiazepiner eller farmaceutisk acceptable syreadditionssalte deraf |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US4353827A (da) |
| EP (1) | EP0059391B1 (da) |
| KR (1) | KR890002624B1 (da) |
| AU (1) | AU551891B2 (da) |
| BR (1) | BR8201024A (da) |
| CA (1) | CA1185602A (da) |
| CS (1) | CS247064B2 (da) |
| DE (1) | DE3263633D1 (da) |
| DK (1) | DK168073B1 (da) |
| FI (1) | FI73430C (da) |
| HK (1) | HK23288A (da) |
| IE (1) | IE52543B1 (da) |
| IL (1) | IL65056A0 (da) |
| MC (1) | MC1442A1 (da) |
| NO (1) | NO157620C (da) |
| NZ (1) | NZ199793A (da) |
| PH (1) | PH19881A (da) |
| PT (1) | PT74504B (da) |
| YU (1) | YU45860B (da) |
Families Citing this family (52)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MC1528A1 (fr) * | 1982-07-21 | 1984-04-13 | Hoffmann La Roche | Imidazobenzodiazepines |
| DE3587913D1 (de) * | 1984-01-19 | 1994-10-06 | Hoffmann La Roche | Imidazodiazepin-Derivate. |
| DK174086D0 (da) * | 1986-04-16 | 1986-04-16 | Ferrosan As | Nye benzodiazepinderivater samt fremgangsmaade til fremstilling af samme |
| CA1327008C (en) * | 1988-01-15 | 1994-02-15 | Walter Merz | Anti-psychotic imidazobenzodiazepine |
| CA1312825C (en) * | 1988-01-27 | 1993-01-19 | F. Hoffmann-La Roche Ag | Prevention or interruption of panic states with an imidazobenzodiazepine |
| CA2015336A1 (en) * | 1989-05-19 | 1990-11-19 | F. Hoffmann-La Roche Ag | Imidazodiazepines for the treatment of neurological symptoms |
| CA2055308A1 (en) * | 1990-11-29 | 1992-05-30 | F. Hoffmann-La Roche Ag | Imidazobenzodiazepine for the treatment of sleep disorders |
| JO2259B1 (en) * | 1999-05-12 | 2004-10-07 | اف. هوفمان- لاروش أيه جي | Method for the manufacture of diazapine derivatives |
| US7678818B2 (en) * | 2006-02-07 | 2010-03-16 | Hoffmann-La Roche Inc. | Anthranilamide and 2-amino-heteroarene-carboxamide compounds |
| US20090054412A1 (en) * | 2007-08-20 | 2009-02-26 | John Alan Kemp | Treatment of Sleep Disorders |
| CA2696703C (en) | 2007-08-20 | 2016-07-26 | Evotec Neurosciences Gmbh | Treatment of sleep disorders |
| KR101772354B1 (ko) | 2010-04-15 | 2017-08-28 | 시애틀 지네틱스, 인크. | 표적화된 피롤로벤조디아제핀 접합체 |
| ES2623057T3 (es) | 2010-04-15 | 2017-07-10 | Medimmune Limited | Pirrolobenzodiazepinas usadas para tratar enfermedades proliferativas |
| WO2013041606A1 (en) | 2011-09-20 | 2013-03-28 | Spirogen Sàrl | Pyrrolobenzodiazepines as unsymmetrical dimeric pbd compounds for inclusion in targeted conjugates |
| US9526798B2 (en) | 2011-10-14 | 2016-12-27 | Seattle Genetics, Inc. | Pyrrolobenzodiazepines and targeted conjugates |
| MX358757B (es) | 2011-10-14 | 2018-09-03 | Seattle Genetics Inc | Pirrolobenzodiazepinas y conjugados dirigidos. |
| US9388187B2 (en) | 2011-10-14 | 2016-07-12 | Medimmune Limited | Pyrrolobenzodiazepines |
| BR112014008888A2 (pt) | 2011-10-14 | 2017-04-18 | Seattle Genetics Inc | pirrolobenzodiazepinas |
| CN103374000B (zh) * | 2012-04-13 | 2015-11-11 | 中国科学院广州生物医药与健康研究院 | 嘧啶并二氮杂卓类化合物及其药用组合物和应用 |
| WO2014057117A1 (en) | 2012-10-12 | 2014-04-17 | Adc Therapeutics Sàrl | Pyrrolobenzodiazepine-antibody conjugates |
| HRP20190366T1 (hr) | 2012-10-12 | 2019-04-19 | Medimmune Limited | Pirolobenzodiazepini i njihovi konjugati |
| ES2680153T3 (es) | 2012-10-12 | 2018-09-04 | Adc Therapeutics Sa | Conjugados de anticuerpos anti-PSMA-pirrolobenzodiazepinas |
| PL2906251T3 (pl) | 2012-10-12 | 2018-02-28 | Adc Therapeutics Sa | Koniugaty pirolobenzodiazepina-przeciwciało anty-CD22 |
| WO2014057120A1 (en) | 2012-10-12 | 2014-04-17 | Adc Therapeutics Sàrl | Pyrrolobenzodiazepine-antibody conjugates |
| MX364328B (es) | 2012-10-12 | 2019-04-23 | Medimmune Ltd | Conjugados del anticuerpo pirrolobenzodiazepina. |
| AU2013328673B2 (en) | 2012-10-12 | 2017-07-13 | Medimmune Limited | Synthesis and intermediates of pyrrolobenzodiazepine derivatives for conjugation |
| HRP20181646T2 (hr) | 2012-10-12 | 2019-08-09 | Adc Therapeutics Sa | Konjugati pirolobenzodiazepin - anti-psma protutijela |
| KR101645905B1 (ko) | 2012-10-12 | 2016-08-04 | 스피로즌 살 | 피롤로벤조디아제핀 및 그의 컨주게이트 |
| EP3054986B1 (en) | 2013-10-11 | 2019-03-20 | Medimmune Limited | Pyrrolobenzodiazepine-antibody conjugates |
| US9950078B2 (en) | 2013-10-11 | 2018-04-24 | Medimmune Limited | Pyrrolobenzodiazepine-antibody conjugates |
| GB201317982D0 (en) | 2013-10-11 | 2013-11-27 | Spirogen Sarl | Pyrrolobenzodiazepines and conjugates thereof |
| GB201317981D0 (en) | 2013-10-11 | 2013-11-27 | Spirogen Sarl | Pyrrolobenzodiazepines and conjugates thereof |
| US10010624B2 (en) | 2013-10-11 | 2018-07-03 | Medimmune Limited | Pyrrolobenzodiazepine-antibody conjugates |
| GB201416112D0 (en) | 2014-09-12 | 2014-10-29 | Medimmune Ltd | Pyrrolobenzodiazepines and conjugates thereof |
| US10780096B2 (en) | 2014-11-25 | 2020-09-22 | Adc Therapeutics Sa | Pyrrolobenzodiazepine-antibody conjugates |
| GB201506411D0 (en) | 2015-04-15 | 2015-05-27 | Bergenbio As | Humanized anti-axl antibodies |
| GB201506402D0 (en) | 2015-04-15 | 2015-05-27 | Berkel Patricius H C Van And Howard Philip W | Site-specific antibody-drug conjugates |
| GB201601431D0 (en) | 2016-01-26 | 2016-03-09 | Medimmune Ltd | Pyrrolobenzodiazepines |
| GB201602359D0 (en) | 2016-02-10 | 2016-03-23 | Medimmune Ltd | Pyrrolobenzodiazepine Conjugates |
| GB201602356D0 (en) | 2016-02-10 | 2016-03-23 | Medimmune Ltd | Pyrrolobenzodiazepine Conjugates |
| GB201607478D0 (en) | 2016-04-29 | 2016-06-15 | Medimmune Ltd | Pyrrolobenzodiazepine Conjugates |
| GB201617466D0 (en) | 2016-10-14 | 2016-11-30 | Medimmune Ltd | Pyrrolobenzodiazepine conjugates |
| UA125198C2 (uk) | 2017-02-08 | 2022-01-26 | Ейдісі Терапьютікс Са | Кон'югати піролобензодіазепін-антитіло |
| GB201702031D0 (en) | 2017-02-08 | 2017-03-22 | Medlmmune Ltd | Pyrrolobenzodiazepine-antibody conjugates |
| SI3612537T1 (sl) | 2017-04-18 | 2022-10-28 | Medimmune Limited | Konjugati pirolobenzodiazepina |
| WO2018193102A1 (en) | 2017-04-20 | 2018-10-25 | Adc Therapeutics Sa | Combination therapy with an anti-axl antibody-drug conjugate |
| JP7145891B2 (ja) | 2017-06-14 | 2022-10-03 | アーデーセー セラピューティクス ソシエテ アノニム | 抗ｃｄ１９ ａｄｃを投与するための投与レジメ |
| BR112020003003A2 (pt) | 2017-08-18 | 2020-08-11 | Medimmune Limited | conjugados de pirrolobenzodiazepina |
| GB201803342D0 (en) | 2018-03-01 | 2018-04-18 | Medimmune Ltd | Methods |
| GB201806022D0 (en) | 2018-04-12 | 2018-05-30 | Medimmune Ltd | Pyrrolobenzodiazepines and conjugates thereof |
| MX2021010477A (es) | 2019-03-15 | 2021-10-01 | Medimmune Ltd | Dimeros de azetidobenzodiazepina y conjugados que los comprenden para uso en el tratamiento de cancer. |
| WO2021113492A1 (en) * | 2019-12-06 | 2021-06-10 | Schrödinger, Inc. | Cyclic compounds and methods of using same |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3933794A (en) * | 1971-08-04 | 1976-01-20 | The Upjohn Company | 2-(2-Alkynylamino)-3H-1,4-benzodiazepines |
| GB1600600A (en) * | 1977-03-10 | 1981-10-21 | Diamond Shamrock Chem | Plasticiser compositions for use with synthetic resin polymers |
| US4118386A (en) * | 1977-04-04 | 1978-10-03 | Hoffmann-La Roche Inc. | Synthesis of imidazo[1,5-a]diazepine-3-carboxylates |
| CA1143728A (en) * | 1979-10-04 | 1983-03-29 | Max Gerecke | Imidazodiazepine derivatives |
-
1982
- 1982-01-21 CA CA000394685A patent/CA1185602A/en not_active Expired
- 1982-02-10 PH PH26851A patent/PH19881A/en unknown
- 1982-02-17 CS CS821081A patent/CS247064B2/cs unknown
- 1982-02-18 US US06/349,801 patent/US4353827A/en not_active Expired - Lifetime
- 1982-02-19 IL IL65056A patent/IL65056A0/xx not_active IP Right Cessation
- 1982-02-19 DE DE8282101273T patent/DE3263633D1/de not_active Expired
- 1982-02-19 DK DK074282A patent/DK168073B1/da not_active IP Right Cessation
- 1982-02-19 EP EP82101273A patent/EP0059391B1/de not_active Expired
- 1982-02-22 AU AU80669/82A patent/AU551891B2/en not_active Expired
- 1982-02-22 NZ NZ199793A patent/NZ199793A/en unknown
- 1982-02-25 MC MC821577A patent/MC1442A1/fr unknown
- 1982-02-25 FI FI820647A patent/FI73430C/fi not_active IP Right Cessation
- 1982-02-26 YU YU43682A patent/YU45860B/sh unknown
- 1982-02-26 NO NO820622A patent/NO157620C/no unknown
- 1982-02-26 IE IE421/82A patent/IE52543B1/en not_active IP Right Cessation
- 1982-02-26 PT PT74504A patent/PT74504B/pt unknown
- 1982-02-26 KR KR8200862A patent/KR890002624B1/ko not_active Expired
- 1982-02-26 BR BR8201024A patent/BR8201024A/pt unknown
-
1988
- 1988-03-30 HK HK232/88A patent/HK23288A/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CS247064B2 (en) | 1986-11-13 |
| BR8201024A (pt) | 1983-01-04 |
| NO820622L (no) | 1982-08-30 |
| FI820647L (fi) | 1982-08-28 |
| US4353827A (en) | 1982-10-12 |
| YU43682A (en) | 1988-08-31 |
| DK168073B1 (da) | 1994-01-31 |
| PH19881A (en) | 1986-08-13 |
| NO157620C (no) | 1988-04-20 |
| AU551891B2 (en) | 1986-05-15 |
| IE52543B1 (en) | 1987-12-09 |
| NZ199793A (en) | 1985-08-30 |
| IL65056A0 (en) | 1982-04-30 |
| HK23288A (en) | 1988-04-08 |
| AU8066982A (en) | 1982-09-02 |
| DE3263633D1 (en) | 1985-06-13 |
| PT74504A (en) | 1982-03-01 |
| EP0059391B1 (de) | 1985-05-08 |
| YU45860B (sh) | 1992-09-07 |
| FI73430C (fi) | 1987-10-09 |
| PT74504B (en) | 1984-11-26 |
| KR890002624B1 (ko) | 1989-07-20 |
| MC1442A1 (fr) | 1982-12-06 |
| KR830009105A (ko) | 1983-12-17 |
| CA1185602A (en) | 1985-04-16 |
| EP0059391A1 (de) | 1982-09-08 |
| FI73430B (fi) | 1987-06-30 |
| NO157620B (no) | 1988-01-11 |
| IE820421L (en) | 1982-08-27 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DK74282A (da) | Fremgangsmaade til fremstilling af imidazodiazepiner eller farmaceutisk acceptable syreadditionssalte deraf | |
| DK149895C (da) | Fremgangsmaade til fremstilling af alfa-aminoacylprolyl-ng-carboxy-argininaldehydderivater eller farmaceutisk acceptable syreadditionssalte deraf | |
| DK148795C (da) | Anologifremgangsmaade til fremstilling af 3-(2-morpholino-ethyl-amino)-5-phenyl-pyridazin eller farmaceutisk acceptable syreadditionssalte deraf | |
| DK552581A (da) | Fremgangsmaade til fremstilling af 3-pyridylaklyl-indol-forbindelser eller farmaceutisk acceptable salte deraf | |
| DK157862C (da) | Analogifremgangsmaade til fremstilling af imidazolylphenylamidiner eller farmaceutisk acceptable syreadditionssalte deraf | |
| DK151017C (da) | Analogifremgangsmaade til fremstilling af substituerede n-(4-indolyl-piperidino-alkyl)-benzimidazoloner eller fysiologisk acceptable syreadditionssalte deraf | |
| DK413783A (da) | Fremgangsmaade til fremstilling af 20-amino-macrolidderivater eller syreadditionssalte deraf | |
| DK323780A (da) | Fremgangsmaade til fremstilling af substituerede 3-amino-sydnonimider eller farmakologisk acceptable syreadditionssalte deraf | |
| DK148596C (da) | Analogifremgangsmaade til fremstilling af 3-aminosubstituerede pyridaziner eller farmaceutisk acceptable syreadditionssalte deraf | |
| DK321482A (da) | Fremgangsmaade til fremstilling af 1-imidazolyl-2-phenyl-8-piperazinylphenoxy-octan-2-ol-forbindelser eller farmaceutisk acceptable syreadditionssalte deraf | |
| DK165790C (da) | Fremgangsmaade til fremstilling af adriamycin-4'-o-derivater eller syreadditionssalte deraf | |
| DK160498C (da) | Analogifremgangsmaade til fremstilling af 3-methyl-flavon-8-carboxylsyreestere eller farmaceutisk acceptable syreadditionssalte deraf | |
| DK98383D0 (da) | Fremgangsmade til fremstilling af 1,2,4-triazol-forbindelser eller farmaceutisk acceptable syreadditionssalte deraf | |
| DK438482A (da) | Fremgangsmaade til fremstilling af indanderivater eller syreadditionssalte deraf | |
| DK319982A (da) | Fremgangsmaade til fremstilling af bicykliske forbindelser eller farmaceutisk acceptable syreadditionssalte deraf | |
| DK152427C (da) | Analogifremgangsmaade til fremstilling af 4-thiomethylpyridinforbindelser eller farmaceutisk acceptable syreadditionssalte deraf | |
| DK157023C (da) | Analogifremgangsmaade til fremstilling af imidazodiazepiner eller farmaceutisk acceptable syreadditionssalte deraf | |
| DK411982A (da) | Fremgangsmaade til fremstilling af polycycliske polyazaheterocycliske forbindelser eller syreadditionssalte deraf | |
| DK160874C (da) | Analogifremgangsmaade til fremstilling af ergol-8-en- eller ergolinforbindelser eller farmaceutisk acceptable syreadditionssalte deraf | |
| DK160043C (da) | Analogifremgangsmaade til fremstilling af n-alk-2-en-4-yn-yl-benzothienylalkylaminer eller syreadditionssalte deraf | |
| DK553982A (da) | Fremgangsmaade til fremstilling af omt-esterderivater eller syreadditionssalte deraf | |
| DK398283D0 (da) | Fremgangsmade til fremstilling af 1,4-dihydropyridinderivater eller farmaceutisk acceptable syreadditionssalte deraf | |
| DK151021C (da) | Analogifremgangsmaade til fremstilling af 17,18-dehydro-apovincaminol-3',4',5'-trimethoxybenzoat eller farmaceutisk acceptable syreadditionssalte deraf | |
| DK163660C (da) | Fremgangsmaade til fremstilling af benzylalkoholderivater eller farmaceutisk acceptable syreadditionssalte deraf | |
| DK156652C (da) | Analogifremgangsmaade til fremstilling af pyridinyloxypropanolamin-derivater eller farmaceutiske acceptable syreadditionssalte deraf |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| AHS | Application shelved for other reasons than non-payment | ||
| AHB | Application shelved due to non-payment | ||
| B1 | Patent granted (law 1993) | ||
| PUP | Patent expired |