HK1057213A1 - Tetrahydroquinoline derivatives having selective activity for retinoid x receptors - Google Patents
Tetrahydroquinoline derivatives having selective activity for retinoid x receptorsInfo
- Publication number
- HK1057213A1 HK1057213A1 HK04100089A HK04100089A HK1057213A1 HK 1057213 A1 HK1057213 A1 HK 1057213A1 HK 04100089 A HK04100089 A HK 04100089A HK 04100089 A HK04100089 A HK 04100089A HK 1057213 A1 HK1057213 A1 HK 1057213A1
- Authority
- HK
- Hong Kong
- Prior art keywords
- carbons
- retinoid
- receptors
- alkyl
- selective activity
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/14—Drugs for dermatological disorders for baldness or alopecia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
- A61P39/02—Antidotes
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/10—Drugs for disorders of the endocrine system of the posterior pituitary hormones, e.g. oxytocin, ADH
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
- C07D215/22—Oxygen atoms attached in position 2 or 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/36—Sulfur 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
- C07D405/02—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
- C07D405/04—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 directly linked by a ring-member-to-ring-member bond
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US09/164,949 US6048873A (en) | 1998-10-01 | 1998-10-01 | Tetrahdroquinolin-2-one 6 or 7-yl, tetrahdroquinilin-2-thione 6 or 7-yl pentadienoic acid and related derivatives having retinoid-like biological activity |
Publications (1)
Publication Number | Publication Date |
---|---|
HK1057213A1 true HK1057213A1 (en) | 2004-03-19 |
Family
ID=22596785
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
HK02100562A HK1039121A1 (en) | 1998-10-01 | 2002-01-24 | Tetrahydroquinoline derivatives having selective activity for retinoid x receptors |
HK04100089A HK1057213A1 (en) | 1998-10-01 | 2004-01-06 | Tetrahydroquinoline derivatives having selective activity for retinoid x receptors |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
HK02100562A HK1039121A1 (en) | 1998-10-01 | 2002-01-24 | Tetrahydroquinoline derivatives having selective activity for retinoid x receptors |
Country Status (11)
Country | Link |
---|---|
US (1) | US6048873A (xx) |
EP (2) | EP1117648B1 (xx) |
JP (1) | JP2002526534A (xx) |
AT (2) | ATE246676T1 (xx) |
AU (1) | AU763108B2 (xx) |
CA (1) | CA2346037A1 (xx) |
DE (2) | DE69910231T2 (xx) |
DK (1) | DK1117648T3 (xx) |
ES (1) | ES2201835T3 (xx) |
HK (2) | HK1039121A1 (xx) |
WO (1) | WO2000020397A1 (xx) |
Families Citing this family (30)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB2335335A (en) * | 1998-03-13 | 1999-09-15 | Northern Telecom Ltd | Carrying speech-band signals over power lines |
US6313107B1 (en) | 2000-08-29 | 2001-11-06 | Allergan Sales, Inc. | Methods of providing and using compounds having activity as inhibitors of cytochrome P450RAI |
US6291677B1 (en) | 2000-08-29 | 2001-09-18 | Allergan Sales, Inc. | Compounds having activity as inhibitors of cytochrome P450RAI |
US6388105B1 (en) * | 2001-09-27 | 2002-05-14 | Allergan Sales, Inc. | Benzofuran, indole or benzothiophene 2,4-pentadienoic acid derivatives having selective activity for retinoid X (RXR) receptors |
US6720423B2 (en) | 2002-04-30 | 2004-04-13 | Allergan, Inc. | Dihydrobenzofuran and dihydrobenzothiophene 2,4-pentadienoic acid derivatives having selective activity for retinoid X (RXR) receptors |
MXPA05003456A (es) * | 2002-10-04 | 2005-07-05 | Millennium Pharm Inc | Antagonistas del receptor de pgd2 para el tratamiento de enfermedades inflamatorias. |
US7504508B2 (en) * | 2002-10-04 | 2009-03-17 | Millennium Pharmaceuticals, Inc. | PGD2 receptor antagonists for the treatment of inflammatory diseases |
US20090181966A1 (en) * | 2002-10-04 | 2009-07-16 | Millennium Pharmaceuticals, Inc. | PGD2 receptor antagonists for the treatment of inflammatory diseases |
US6683092B1 (en) | 2003-04-09 | 2004-01-27 | Allergan, Inc. | [3-(c5-14alkyl-2-oxo-1,2,3,4-tetrahydro-quinolin-6-yl)-3-oxo-propenyl]-phenyl and [3-(c5-14alkyl-2-oxo-1,2,3,4- tetrahydro-quinolin-6-yl)-3-oxo-propenyl]-heteroaryl derivatives having anti-tumor activity |
US6734193B1 (en) | 2003-06-03 | 2004-05-11 | Allergan, Inc. | (1,2,3,4-tetrahydroquinolin-8-yl)-heptatrienoic acid derivatives having serum glucose reducing activity |
US6936636B2 (en) * | 2003-06-26 | 2005-08-30 | Allergan, Inc. | 5-[phenyl-tetrahydronaphthalene-2-yl dihydronaphthalen-2-yl and heteroaryl-cyclopropyl]-pentadienoic acid derivatives having serum glucose reducing activity |
US6887896B1 (en) | 2003-10-29 | 2005-05-03 | Allergan, Inc. | 7-[(7-Alkoxy)-chrom-3-en-6-yl]-heptatrienoic acid and 7-[(3-alkoxy)-5,6-dihydronaphthalen-2-yl]-heptatrienoic acid derivatives having serum glucose reducing activity |
US7476673B2 (en) * | 2003-12-30 | 2009-01-13 | Allergan, Inc. | Disubstituted chalcone oximes as selective agonists of RARγ retinoid receptors |
UA90706C2 (ru) * | 2005-02-24 | 2010-05-25 | Милленниум Фармасьютикалз, Инк. | Антагонисты рецептора pgd2 для лечения воспалительных заболеваний |
AU2006299645B2 (en) | 2005-09-30 | 2011-02-03 | Io Therapeutics, Llc | Treatment of cancer with specific RXR agonists |
US7638533B2 (en) * | 2005-09-30 | 2009-12-29 | Janssen Pharmaceutica N.V. | Dihydro-1[1H]-quinolin-2-one derivatives as RXR agonists for the treatment of dyslipidemia, hypercholesterolemia and diabetes |
CN101316827A (zh) * | 2005-09-30 | 2008-12-03 | 詹森药业有限公司 | 作为rxr激动剂用于治疗异常脂肪血症、高胆固醇血症和糖尿病的杂环酰胺衍生物 |
EP1937640A2 (en) * | 2005-09-30 | 2008-07-02 | Janssen Pharmaceutica N.V. | 1,2,3,5-tetrahydro-cyclopental[c]quinolin-4-one derivatives as rxr agonists for the treatment of dyslipidemia, hypercholesterolemia and diabetes |
US20070185055A1 (en) * | 2006-02-06 | 2007-08-09 | Guang Liang Jiang | Method for treating cachexia with retinoid ligands |
US20090197878A1 (en) * | 2008-02-01 | 2009-08-06 | Wyeth | SUBSTITUTED BENZO[d][1,3]OXAZIN-2(4H)-ONES AND RELATED DERIVATIVES AND THEIR USES FOR MODULATING THE PROGESTERONE RECEPTOR |
CN110151745A (zh) | 2011-12-13 | 2019-08-23 | Io治疗公司 | 使用rxr激动剂的自身免疫紊乱的治疗 |
HUE053645T2 (hu) | 2013-11-18 | 2021-07-28 | Forma Therapeutics Inc | Tetrahidrokinolin kompozíciók mint BET bromodomén inhibitorok |
US9422281B2 (en) | 2013-11-18 | 2016-08-23 | Forma Therapeutics, Inc. | Benzopiperazine compositions as BET bromodomain inhibitors |
KR102651292B1 (ko) | 2015-10-31 | 2024-03-25 | 아이오 테라퓨틱스, 인크. | Rxr 아고니스트와 갑상선 호르몬의 조합을 사용한 신경계 질환의 치료 |
JP7169647B2 (ja) | 2016-03-10 | 2022-11-11 | アイオー セラピューティクス インコーポレイテッド | Rxrアゴニストおよび甲状腺ホルモンの組み合わせでの筋肉障害の治療 |
JP7169646B2 (ja) | 2016-03-10 | 2022-11-11 | アイオー セラピューティクス インコーポレイテッド | Rxrアゴニストおよび甲状腺ホルモンの組み合わせでの自己免疫疾患の治療 |
EP3684348A4 (en) | 2017-09-20 | 2021-08-18 | IO Therapeutics, Inc. | TREATMENT OF DISEASE WITH SELECTIVE RXR AGONIST ESTERS |
SG11202003733RA (en) * | 2017-11-17 | 2020-05-28 | Io Therapeutics Inc | Compounds and synthetic methods for the preparation of retinoid x receptor-specific retinoids |
US10966950B2 (en) | 2019-06-11 | 2021-04-06 | Io Therapeutics, Inc. | Use of an RXR agonist in treating HER2+ cancers |
WO2023108012A1 (en) | 2021-12-07 | 2023-06-15 | Io Therapeutics, Inc. | Use of an rxr agonist and taxanes in treating her2+ cancers |
Family Cites Families (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5264578A (en) * | 1987-03-20 | 1993-11-23 | Allergan, Inc. | Disubstituted acetylenes bearing heterobicyclic groups and heteroaromatic or phenyl groups having retinoid like activity |
DK0617614T3 (da) * | 1991-12-18 | 1998-09-28 | Salk Inst For Biological Studi | Midler til modulering af processer medieret af retinoide receptorer og forbindelser anvendlige dertil |
DE69333894D1 (de) * | 1992-04-22 | 2005-12-01 | Ligand Pharm Inc | Verbindungen mit Retinoid x rezeptorselektivität |
DK0678087T3 (da) * | 1993-01-11 | 1999-09-27 | Ligand Pharm Inc | Forbindelser med selektiv aktivitet til retinoid-X-receptorer og metoder til modulering af processer medieret af retinoid-X |
US5455265A (en) * | 1993-02-11 | 1995-10-03 | Allergan, Inc. | Method of treatment with compounds having selective agonist-like activity on RXR retinoid receptors |
WO1996005165A1 (en) * | 1994-08-10 | 1996-02-22 | F. Hoffmann-La Roche Ag | Retinoic acid x-receptor ligands |
JP3826182B2 (ja) * | 1994-10-31 | 2006-09-27 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | モノ又はポリエンカルボン酸誘導体 |
US5616712A (en) * | 1995-05-16 | 1997-04-01 | Allergan | Acetylenes disubstituted with a phenyl or heteroaryl group and a 2-thio-1,2,3,4-tetrahdroquinolinyl, 2-alkylthio-3,4-dihydroquinolinyl or 2-alkoxy-3,4-dihydroquinolinyl group having retinoid-like biological activity |
US5675033A (en) * | 1995-06-06 | 1997-10-07 | Allergan | 2,4-pentadienoic acid derivatives having retinoid-like biological activity |
US5776699A (en) * | 1995-09-01 | 1998-07-07 | Allergan, Inc. | Method of identifying negative hormone and/or antagonist activities |
PT873295E (pt) * | 1995-10-06 | 2003-08-29 | Ligand Pharm Inc | Moduladores de rxr selectivos para dimeros para a sua utilizacao |
AU7598596A (en) * | 1995-11-01 | 1997-05-22 | Allergan, Inc. | Sulfides, sulfoxides and sulfones disubstituted with a tetrahydronaphthalenyl, chromanyl, thiochromanyl or tetrahydroquinolinyl and substituted phenyl or heteroaryl group, having retinoid-like biological activity |
US5739338A (en) * | 1996-11-05 | 1998-04-14 | Allergan | N-aryl substituted tetrahydroquinolines having retinoid agonist, retinoid antagonist or retinoid inverse agonist type biological activity |
-
1998
- 1998-10-01 US US09/164,949 patent/US6048873A/en not_active Expired - Fee Related
-
1999
- 1999-09-21 JP JP2000574514A patent/JP2002526534A/ja active Pending
- 1999-09-21 EP EP99970084A patent/EP1117648B1/en not_active Expired - Lifetime
- 1999-09-21 AU AU60547/99A patent/AU763108B2/en not_active Ceased
- 1999-09-21 ES ES99970084T patent/ES2201835T3/es not_active Expired - Lifetime
- 1999-09-21 AT AT99970084T patent/ATE246676T1/de not_active IP Right Cessation
- 1999-09-21 AT AT03016595T patent/ATE310727T1/de not_active IP Right Cessation
- 1999-09-21 EP EP03016595A patent/EP1354878B1/en not_active Expired - Lifetime
- 1999-09-21 WO PCT/US1999/021857 patent/WO2000020397A1/en active IP Right Grant
- 1999-09-21 DE DE69910231T patent/DE69910231T2/de not_active Expired - Fee Related
- 1999-09-21 CA CA002346037A patent/CA2346037A1/en not_active Abandoned
- 1999-09-21 DK DK99970084T patent/DK1117648T3/da active
- 1999-09-21 DE DE69928583T patent/DE69928583T2/de not_active Expired - Fee Related
-
2002
- 2002-01-24 HK HK02100562A patent/HK1039121A1/xx not_active IP Right Cessation
-
2004
- 2004-01-06 HK HK04100089A patent/HK1057213A1/xx not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
HK1039121A1 (en) | 2002-04-12 |
EP1354878A2 (en) | 2003-10-22 |
DK1117648T3 (da) | 2003-11-17 |
ES2201835T3 (es) | 2004-03-16 |
DE69910231T2 (de) | 2004-06-09 |
DE69928583D1 (de) | 2005-12-29 |
ATE310727T1 (de) | 2005-12-15 |
US6048873A (en) | 2000-04-11 |
EP1117648B1 (en) | 2003-08-06 |
DE69928583T2 (de) | 2006-08-10 |
EP1117648A1 (en) | 2001-07-25 |
JP2002526534A (ja) | 2002-08-20 |
AU763108B2 (en) | 2003-07-10 |
AU6054799A (en) | 2000-04-26 |
EP1354878A3 (en) | 2003-12-10 |
CA2346037A1 (en) | 2000-04-13 |
ATE246676T1 (de) | 2003-08-15 |
WO2000020397A1 (en) | 2000-04-13 |
EP1354878B1 (en) | 2005-11-23 |
DE69910231D1 (de) | 2003-09-11 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
PC | Patent ceased (i.e. patent has lapsed due to the failure to pay the renewal fee) |
Effective date: 20090921 |