IL86822A - 6-alkyl-4-amino-5,6-dihydro-4h-thieno(2,3-b)thiopyran-2-sulfonamide-7,7-dioxides and antiglaucoma compositions containing them - Google Patents

6-alkyl-4-amino-5,6-dihydro-4h-thieno(2,3-b)thiopyran-2-sulfonamide-7,7-dioxides and antiglaucoma compositions containing them

Info

Publication number
IL86822A
IL86822A IL86822A IL8682288A IL86822A IL 86822 A IL86822 A IL 86822A IL 86822 A IL86822 A IL 86822A IL 8682288 A IL8682288 A IL 8682288A IL 86822 A IL86822 A IL 86822A
Authority
IL
Israel
Prior art keywords
thiopyran
dioxides
thieno
sulfonamide
dihydro
Prior art date
Application number
IL86822A
Other languages
English (en)
Other versions
IL86822A0 (en
Original Assignee
Merck & Co Inc
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
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=26747752&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=IL86822(A) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Priority claimed from US07/067,326 external-priority patent/US4797413A/en
Application filed by Merck & Co Inc filed Critical Merck & Co Inc
Publication of IL86822A0 publication Critical patent/IL86822A0/xx
Publication of IL86822A publication Critical patent/IL86822A/xx

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D495/00Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02Heterocyclic 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
    • C07D495/04Ortho-condensed systems
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00Drugs for disorders of the senses
    • A61P27/02Ophthalmic agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00Drugs for disorders of the senses
    • A61P27/02Ophthalmic agents
    • A61P27/06Antiglaucoma agents or miotics
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D307/00Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/56Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D307/64Sulfur atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D333/00Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur 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
    • C07D333/30Hetero atoms other than halogen
    • C07D333/34Sulfur atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D333/00Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/52Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
    • C07D333/54Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D333/00Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/52Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
    • C07D333/62Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes 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 carbon atoms of the hetero ring
    • 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
    • C07D495/00Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02Heterocyclic 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
    • C07D495/10Spiro-condensed systems

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Ophthalmology & Optometry (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
  • Lubricants (AREA)
  • Photosensitive Polymer And Photoresist Processing (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Peptides Or Proteins (AREA)
  • Heat Sensitive Colour Forming Recording (AREA)
  • Dental Preparations (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
IL86822A 1987-06-26 1988-06-21 6-alkyl-4-amino-5,6-dihydro-4h-thieno(2,3-b)thiopyran-2-sulfonamide-7,7-dioxides and antiglaucoma compositions containing them IL86822A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US07/067,326 US4797413A (en) 1986-05-14 1987-06-26 Thieno thiopyran sulfonamide derivatives, pharmaceutical compositions and use
US07/208,314 US4863922A (en) 1984-12-12 1988-06-15 Substituted aromatic sulfonamides as antiglaucoma agents, compositions and use

Publications (2)

Publication Number Publication Date
IL86822A0 IL86822A0 (en) 1988-11-30
IL86822A true IL86822A (en) 1992-01-15

Family

ID=26747752

Family Applications (1)

Application Number Title Priority Date Filing Date
IL86822A IL86822A (en) 1987-06-26 1988-06-21 6-alkyl-4-amino-5,6-dihydro-4h-thieno(2,3-b)thiopyran-2-sulfonamide-7,7-dioxides and antiglaucoma compositions containing them

Country Status (18)

Country Link
US (1) US4863922A (https=)
EP (1) EP0296879B1 (https=)
JP (1) JPH0631247B2 (https=)
AT (1) ATE86998T1 (https=)
AU (1) AU616664B2 (https=)
CA (2) CA1328262C (https=)
CY (1) CY1772A (https=)
DE (2) DE19575017I2 (https=)
DK (1) DK167684B1 (https=)
ES (1) ES2053738T4 (https=)
GR (1) GR3007407T3 (https=)
IE (1) IE62255B1 (https=)
IL (1) IL86822A (https=)
LU (1) LU88633I2 (https=)
NL (1) NL950006I2 (https=)
NZ (1) NZ225166A (https=)
PT (1) PT87832B (https=)
SG (1) SG24394G (https=)

Families Citing this family (52)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA1320487C (en) * 1987-08-03 1993-07-20 George D. Hartman Substituted thieno[2,3-.beta.]thiophene-2-sulfonamides as antiglaucoma agents
US5260453A (en) * 1988-09-23 1993-11-09 Ortho Pharmaceutical Corporation Substituted thienopyrans as antihypertensive agents
US4876271A (en) * 1988-12-20 1989-10-24 Merck & Co., Inc. Substituted thieno[3,2-b]thiophene-2-sulfonamides as topically active carbonic anhydrase inhibitors
US4929549A (en) * 1989-02-08 1990-05-29 Merck & Co., Inc. 5-carbamoylthieno[2,3-b]thiophene-2-sulfon-amides as topically active carbonic anhydrase inhibitors
US4946859A (en) * 1989-07-31 1990-08-07 Merck & Co., Inc. 4-(2-methyl-2-hydroxypropylamino)-5,6-dihydrothieno-[2,3-b]thiopyran-2-sulfonamide-7,7-dioxide
US5120757A (en) * 1989-07-31 1992-06-09 Merck & Co., Inc. Substituted aromatic sulfonamides as antiglaucoma agents
CA2028496A1 (en) * 1989-10-31 1991-05-01 Tohru Nakao Thiophene compounds and their pharmaceutical uses
IE911192A1 (en) * 1990-04-12 1991-10-23 Merck & Co Inc Substituted aromatic sulfonamides as antiglaucoma agents
JP3031498B2 (ja) * 1990-04-12 2000-04-10 メルク エンド カムパニー インコーポレーテッド 抗緑内障剤としての置換芳香族スルホンアミド類
US5045561A (en) * 1990-04-12 1991-09-03 Merck & Co., Inc. Substituted furan sulfonamides as antiglaucoma agents
US5157129A (en) * 1990-04-18 1992-10-20 Merck & Co., Inc. Enantiospecific synthesis of s-(+)-5,6-dihydro-4-(r-amino)-4h-thieno(2,3-b)thiopyran-2-sulfonamide-7,7-dioxide
US5091409A (en) * 1990-05-17 1992-02-25 Merck & Co., Inc. 4-alkylamino-6-(C3-5 -hydrocarbyl)thieno[2,3-B]thiopyran-2-sulfonamide-7,7-dioxides
US5093332A (en) * 1990-10-01 1992-03-03 Merck & Co., Inc. Substituted thieno(2,3-b)(1,4)thiazine-6-sulfonamides as antiglaucoma agents
EP0480745A3 (en) * 1990-10-12 1992-07-29 Merck & Co. Inc. Substituted dihydrothieno-thiophene-2-sulfonamides and dioxides thereof
US5216020A (en) * 1990-10-12 1993-06-01 Merck & Co., Inc. Substituted 4,5-dihydrothieno(2,3-b)thiophene-2-sulfonamides and 6,6-dioxides thereof
SG84487A1 (en) 1991-04-17 2001-11-20 Merck & Co Inc Ophthalmic compositions comprising combinations of a carbonic anhydrase inhibitor and a b-adrenergic antagonist
CZ285129B6 (cs) * 1991-04-17 1999-05-12 Merck & Co., Inc. Oftalmické přípravky, obsahující kombinace inhibitoru karboanhydrasy a beta-adrenergního antagonisty
JPH0830067B2 (ja) * 1991-10-15 1996-03-27 メルク エンド カムパニー インコーポレーテッド 三環チエノチオピラン類
US5932572A (en) * 1992-02-21 1999-08-03 Alcon Laboratories, Inc. Topical anti-glaucoma compositions
EP0625903B1 (en) * 1992-02-21 1998-08-12 Alcon Laboratories, Inc. Topical antiglaucoma compositions comprising carbonic anhydrase inhibitors and beta-blockers
KR100319837B1 (ko) * 1992-08-28 2002-04-22 커스티 마가렛 핀더 4h-티에노(2,3-6)티오피란유도체를제조하기위한효소적비대칭환원방법
JP3279671B2 (ja) * 1992-09-28 2002-04-30 鐘淵化学工業株式会社 チエノチオピラン誘導体の製造方法
TW265343B (https=) * 1993-03-22 1995-12-11 Merck & Co Inc
US6316443B1 (en) 1994-08-04 2001-11-13 Merck & Co., Inc. Ophthalmic compositions comprising combinations of a carbonic anhydrase inhibitor and a β-adrenergic antagonist
TWI238064B (en) * 1995-06-20 2005-08-21 Takeda Chemical Industries Ltd A pharmaceutical composition for prophylaxis and treatment of diabetes
FR2754712B1 (fr) 1996-10-17 1999-09-03 Merck Sharp Dohme Chibret Lab Compositions ophtalmiques
JP4000505B2 (ja) 1999-12-01 2007-10-31 第一三共株式会社 緑内障を治療するための併用剤
AU771130B2 (en) * 2000-01-18 2004-03-11 Merck & Co., Inc. Ophthalmic compositions for treating ocular hypertension
US6548535B2 (en) * 2000-01-18 2003-04-15 Merck & Co., Inc. Method for treating ocular hypertension
ES2177415B1 (es) * 2000-09-04 2004-10-16 Ragactives, S.L. Procedimiento para la obtencion de 4-alquilamino-5, 6-dihidro-4h-tieno-(2,3b)-tiopiran-2-sulfonamida-7-dioxidos, e intermedios.
US20040254230A1 (en) * 2001-12-03 2004-12-16 Ogidigben Miller J. Method for treating ocular hypertension
EP1487438A4 (en) * 2002-03-15 2007-08-15 Merck & Co Inc COMPOSITIONS AND METHODS FOR TREATING GLUCKOM AND OKULAR HYPERTENSION
WO2003103664A1 (en) * 2002-06-06 2003-12-18 Merck Frosst Canada & Co. 1,5-disubstituted imidazolidin-2-one derivatives for use as ep4 receptor agonists in the treatment of eye and bone diseases
US20050256117A1 (en) * 2002-06-14 2005-11-17 Meng Hsin Chen Ophthalmic compositions for treating ocular hypertension
WO2003105724A2 (en) * 2002-06-17 2003-12-24 Merck & Co., Inc. Novel maxi-k channel blockers, methods of use and process for making the same
JP2005532361A (ja) * 2002-06-17 2005-10-27 メルク エンド カムパニー インコーポレーテッド 高眼圧症の治療用の眼科用組成物
EP1515730A4 (en) * 2002-06-17 2005-07-20 Merck & Co Inc NEW MAXI-K CHANNEL BLOCKS, USE METHOD AND METHOD FOR THE PRODUCTION THEREOF
AU2003258433A1 (en) * 2002-08-28 2004-03-19 Merck Frosst Canada Ltd Oxazolidin-2-one and thiazolidin-2-one derivatives for use as ep4 receptor agonists in the treatment of glaucoma
US20060167081A1 (en) * 2002-10-25 2006-07-27 Xavier Billot Ep4 receptor agonists
US7414067B2 (en) * 2003-03-27 2008-08-19 Merck & Co. Inc. Ophthalmic compositions for treating ocular hypertension
WO2006068333A1 (en) 2004-12-20 2006-06-29 Sk Corporation Method for separating of optically pure thiophene compounds using simulated moving bed chromatography
MX2007007923A (es) * 2004-12-28 2007-11-14 Usv Ltd Procedimiento para preparar clorhidrato de 5,6-dihidro-4-(s)- (etilamino)-6-(s)metil-4h-tieno[2,3b]tiopiran-2-sulfonamida-7,7- dioxido.
US7109353B2 (en) * 2004-12-28 2006-09-19 Council Of Scientific And Industrial Research Process for preparing 5,6-dihydro-4-(S)-(ethylamino)-6-(S) methyl-4H-thieno[2,3b]thiopyran-2-sulphonamide-7,7-dioxide HCl
SI2010544T1 (sl) * 2006-04-21 2009-12-31 Zach System Spa Popstopek za pripravo dorzolamida
EP1918293A1 (en) * 2006-10-02 2008-05-07 Sandoz AG Process for the preparation of 6-substituted-4-oxo-thieno [2,3b]thiopyran-2-sulfonic acid
US7964613B2 (en) 2007-02-28 2011-06-21 Asahi Kasei Pharma Corporation Sulfonamide compound
US8263787B2 (en) 2007-05-07 2012-09-11 Cipla Limited Process for preparing dorzolamide
JP2011517313A (ja) 2007-12-11 2011-06-02 ビアメト ファーマシューティカルズ,インク. 金属結合部分を標的化部分と組み合わせて使用する金属酵素阻害剤
WO2010061398A1 (en) * 2008-11-27 2010-06-03 Suven Life Sciences Limited Process for preparing dorzolamide hydrochloride and its intermediate
BR112013023130B1 (pt) 2011-03-10 2020-02-18 F.I.S. - Fabbrica Italiana Sintetici S.P.A. Processo de redução assimétrica
ITMI20121165A1 (it) * 2012-07-03 2014-01-04 Zach System Spa Processo di riduzione asimmetrica
CN103497202B (zh) * 2013-10-23 2015-12-02 武汉武药科技有限公司 盐酸多佐胺中间体的合成方法

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4416890A (en) * 1981-07-13 1983-11-22 Merck & Co., Inc. Benzothiazolesulfonamide derivatives for the topical treatment of elevated intraocular pressure
US4386098A (en) * 1981-11-03 1983-05-31 Merck & Co., Inc. 6-Hydroxy-2-benzothiazolesulfonamide for the topical treatment of elevated intraocular pressure
US4426388A (en) * 1982-04-02 1984-01-17 Merck & Co., Inc. 5-Benzothiazolesulfonamide derivatives for the topical treatment of elevated intraocular pressure
US4499103A (en) * 1983-03-17 1985-02-12 Merck & Co., Inc. Benzothiazole-2-sulfonamide derivatives for the topical treatment of elevated intraocular pressure
EP0189690B1 (en) * 1984-12-12 1989-03-01 Merck & Co. Inc. Substituted aromatic sulfonamides, their preparation and ophthalmic compositions containing them
US4677115A (en) * 1984-12-12 1987-06-30 Merck & Co., Inc. Antiglaucoma thieno-thiopyran and thieno-thiepin sulfonamide derivatives, compositions, and method of use thereof
US4731368A (en) * 1986-12-08 1988-03-15 Merck & Co., Inc. Thienopyridine sulfonamides and their ophthalmological formulation

Also Published As

Publication number Publication date
DE3879292D1 (de) 1993-04-22
EP0296879A1 (en) 1988-12-28
AU1838788A (en) 1989-01-05
CA1328262C (en) 1994-04-05
DK348588A (da) 1989-02-24
ATE86998T1 (de) 1993-04-15
SG24394G (en) 1994-06-10
IL86822A0 (en) 1988-11-30
CY1772A (en) 1995-10-20
JPH01100174A (ja) 1989-04-18
NZ225166A (en) 1991-05-28
PT87832B (pt) 1992-10-30
ES2053738T4 (es) 2011-12-29
AU616664B2 (en) 1991-11-07
ES2053738T3 (es) 1994-08-01
DK167684B1 (da) 1993-12-06
PT87832A (pt) 1989-05-31
IE62255B1 (en) 1995-01-11
LU88633I2 (fr) 1995-09-01
DE3879292T2 (de) 1993-09-09
NL950006I1 (nl) 1995-06-16
GR3007407T3 (https=) 1993-07-30
NL950006I2 (nl) 1997-02-03
DK348588D0 (da) 1988-06-24
US4863922A (en) 1989-09-05
EP0296879B1 (en) 1993-03-17
CA1329211C (en) 1994-05-03
JPH0631247B2 (ja) 1994-04-27
DE19575017I2 (de) 2008-11-20
IE881933L (en) 1988-12-26

Similar Documents

Publication Publication Date Title
IL86822A (en) 6-alkyl-4-amino-5,6-dihydro-4h-thieno(2,3-b)thiopyran-2-sulfonamide-7,7-dioxides and antiglaucoma compositions containing them
DE3568431D1 (en) Substituted aromatic sulfonamides, their preparation and ophthalmic compositions containing them
EP0308021A3 (en) Subsituted thieno (2,3-b)pyrole-5-sulfonamides as antiglaucoma agents
EP0527801A4 (en) Thiophene sulfonamides useful as carbonic anydrase inhibitors
DE3852110D1 (de) Gerät zum Insufflieren von Gas in eine Körperhöhle.
GR3019058T3 (en) 3-Arylcarbonyl-1-aminoalkyl-1H-indole containing antiglaucoma compositions
IL89898A0 (en) Set or game for the composition of figures,shapes and patterns
JPS6450886A (en) Substituted thieno(2,3-b)thiophene-2-sulfonamides as antiglaucoma
IL97828A0 (en) Substituted aromatic sulfonamides and pharmaceutical compositions containing them
IE830331L (en) Thiophene derivatives
FR2483234B2 (https=)
IL86752A (en) Thiophene derivatives and their preparation and their use as intermediates in the preparation of n-(2,4-dimethylthien-3-yl) -n-(1-methoxyprop-2-yl) - chloroacetamide
IE892586L (en) Use of zofenopril for the treatment of rheumatoid arthritis
EP0309028A3 (en) Substituted thieno(2,3-b)furan-2-sulfonamides as antiglaucoma agents
ZA894504B (en) Use of 5,11-dihydro-6h-pyrido(2,3-b)(1,4)benzodiazepin-6-ones substituted in the 11-position
PH15806A (en) 4-phenyl-4,5,6,7-tetrahydro-thieno(2,3-c)pyridines and salts thereof
ZA892632B (en) Set or game for the composition of figures,shapes and patterns

Legal Events

Date Code Title Description
KB Patent renewed
KB Patent renewed
EXP Patent expired