IL105003A - History of carboxamide of indole and esters of tricyclic tricyclic indole acids, their preparation and pharmaceutical preparations containing - Google Patents
History of carboxamide of indole and esters of tricyclic tricyclic indole acids, their preparation and pharmaceutical preparations containingInfo
- Publication number
- IL105003A IL105003A IL10500393A IL10500393A IL105003A IL 105003 A IL105003 A IL 105003A IL 10500393 A IL10500393 A IL 10500393A IL 10500393 A IL10500393 A IL 10500393A IL 105003 A IL105003 A IL 105003A
- Authority
- IL
- Israel
- Prior art keywords
- indole
- alkyl
- methyl
- hydrogen
- treated
- Prior art date
Links
Classifications
-
- 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
- C07D471/04—Ortho-condensed systems
-
- 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
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A61K31/235—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids having an aromatic ring attached to a carboxyl group
- A61K31/24—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids having an aromatic ring attached to a carboxyl group having an amino or nitro group
- A61K31/245—Amino benzoic acid types, e.g. procaine, novocaine
-
- 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
- A61K31/4353—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 ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—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 ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
-
- 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
- A61K31/4453—Non condensed piperidines, e.g. piperocaine only substituted in position 1, e.g. propipocaine, diperodon
-
- 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
- A61K31/452—Piperidinium derivatives
-
- 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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive 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
-
- 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
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
-
- 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
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Cardiology (AREA)
- Neurosurgery (AREA)
- Heart & Thoracic Surgery (AREA)
- Emergency Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Indole Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB929205428A GB9205428D0 (en) | 1992-03-12 | 1992-03-12 | Pharmaceuticals |
GB929218846A GB9218846D0 (en) | 1992-09-05 | 1992-09-05 | Pharmaceuticals |
GB929227045A GB9227045D0 (en) | 1992-12-29 | 1992-12-29 | Pharmaceuticals |
Publications (2)
Publication Number | Publication Date |
---|---|
IL105003A0 IL105003A0 (en) | 1993-07-08 |
IL105003A true IL105003A (en) | 1996-09-12 |
Family
ID=27266092
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
IL10500393A IL105003A (en) | 1992-03-12 | 1993-03-10 | History of carboxamide of indole and esters of tricyclic tricyclic indole acids, their preparation and pharmaceutical preparations containing |
Country Status (30)
Country | Link |
---|---|
EP (2) | EP0884319B1 (no) |
JP (1) | JP2831467B2 (no) |
KR (1) | KR100282730B1 (no) |
CN (2) | CN1043893C (no) |
AP (1) | AP401A (no) |
AT (2) | ATE266033T1 (no) |
AU (1) | AU671102B2 (no) |
CA (1) | CA2131797C (no) |
CY (1) | CY2510B1 (no) |
CZ (1) | CZ286194B6 (no) |
DE (2) | DE69325167T2 (no) |
DK (2) | DK0630376T3 (no) |
ES (2) | ES2219813T3 (no) |
FI (1) | FI107158B (no) |
GR (1) | GR3030668T3 (no) |
HK (1) | HK1012352A1 (no) |
HU (1) | HU219121B (no) |
IL (1) | IL105003A (no) |
MA (1) | MA22819A1 (no) |
MX (1) | MX9301348A (no) |
MY (1) | MY110110A (no) |
NO (1) | NO303638B1 (no) |
NZ (1) | NZ249565A (no) |
PT (1) | PT884319E (no) |
RU (1) | RU2104279C1 (no) |
SG (1) | SG50693A1 (no) |
SI (1) | SI9300114B (no) |
SK (1) | SK281423B6 (no) |
UA (1) | UA41311C2 (no) |
WO (1) | WO1993018036A1 (no) |
Families Citing this family (37)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5852014A (en) * | 1992-03-12 | 1998-12-22 | Smithkline Beecham P.L.C. | Condensed indole derivatives as 5HT4 -receptor antagonists |
GB9316195D0 (en) * | 1993-08-05 | 1993-09-22 | Smithkline Beecham Plc | Pharmaceuticals |
US5998409A (en) * | 1992-03-12 | 1999-12-07 | Smithkline Beecham Plc | Condensed indole derivatives as 5HT4 -receptor antagonists |
MX9305947A (es) * | 1992-09-29 | 1994-06-30 | Smithkline Beecham Plc | Compuestos antagonistas del receptor 5-ht4, procedimiento para su preparacion y composiciones farmaceuticas que las contienen. |
WO1994008965A1 (en) * | 1992-10-16 | 1994-04-28 | Smithkline Beecham Plc | N-alkylpiperidinyl-4-methyl carboxylic esters/amides of condensed ring systems as 5-ht4 receptor antagonists |
WO1994010174A1 (en) * | 1992-11-05 | 1994-05-11 | Smithkline Beecham Plc | Piperidine derivatives as 5-ht4 receptor antagonists |
FR2699921B1 (fr) * | 1992-12-30 | 1995-02-10 | Synthelabo | Dérivés d'acide 2-(thien-2-yl)imidazo[2,1-b]benzothiazole-3-acétique, leur préparation et leur application en thérapeutique. |
GB9303340D0 (en) * | 1993-02-19 | 1993-04-07 | Smithkline Beecham Plc | Pharmaceuticals |
GB9310582D0 (en) * | 1993-05-22 | 1993-07-07 | Smithkline Beecham Plc | Pharmaceuticals |
GB9312348D0 (en) * | 1993-06-16 | 1993-07-28 | Smithkline Beecham Plc | Pharmaceuticals |
KR100219922B1 (ko) * | 1996-05-16 | 1999-09-01 | 이서봉 | 신규한 항바이러스성 6-아릴옥시 및 6-아릴카르보닐 2,4-피리미딘디온 유도체 및 그의 제조 방법 |
US6013666A (en) * | 1996-07-02 | 2000-01-11 | Sang Sup Jew | Oxirane carboxylic acid derivative and its manufacturing method |
CZ290517B6 (cs) * | 1996-08-16 | 2002-08-14 | Smithkline Beecham Plc | Způsob přípravy N-[(1-n-butyl-4-piperidinyl)methyl]-3,4-dihydro-2H-[1,3]-oxazino [3,2-a]indol-10-karboxamidu nebo jeho soli a meziprodukt pro tento způsob |
US6100397A (en) * | 1996-08-16 | 2000-08-08 | Smithkline Beecham Plc | Process for the preparation of N-[(1-n butyl-4-piperidyl)methyl]-3,4-dihydro-2H-[1,3]oxazino[3,2-a] indole-10-carboxamide and salts and intermediates in the process |
GB9618967D0 (en) * | 1996-09-11 | 1996-10-23 | Smithkline Beecham Plc | Pharmaceuticals |
GB9725933D0 (en) * | 1997-12-05 | 1998-02-04 | Smithkline Beecham Plc | Pharmaceuticals |
US6251893B1 (en) * | 1998-06-15 | 2001-06-26 | Nps Allelix Corp. | Bicyclic piperidine and piperazine compounds having 5-HT6 receptor affinity |
US20020091271A1 (en) | 1998-07-16 | 2002-07-11 | Smithkline Beecham Plc | Process for the preparation of an indole derivative |
GB9819035D0 (en) * | 1998-09-01 | 1998-10-28 | Cerebrus Res Ltd | Chemical compounds VII |
BRPI9913542B8 (pt) * | 1998-09-10 | 2021-05-25 | Hoffmann La Roche | derivados de dihidrobenzodioxina carboxamida e dihidrobenzodioxina cetona como antagonistas do receptor 5-ht4 bem como composição farmacêutica, processo para a preparação dos referidos derivados e uso dos mesmos |
GB9820294D0 (en) * | 1998-09-17 | 1998-11-11 | Smithkline Beecham Plc | Pharmaceuticals |
US6545004B1 (en) | 1999-10-27 | 2003-04-08 | Cytokinetics, Inc. | Methods and compositions utilizing quinazolinones |
AU782870C (en) * | 2000-08-07 | 2007-03-15 | Glaxo Group Limited | The use of 5HT4 receptor antagonists in the prophylaxis or treatment of certain cardiovascular conditions |
AU2005203196B9 (en) * | 2000-08-07 | 2009-04-09 | Glaxo Group Limited | The use of 5HT4 receptor antagonists in the prophylaxis or treatment of certain cardiovascular conditions |
AU782863C (en) * | 2000-08-07 | 2006-08-31 | Glaxo Group Limited | The use of 5HT4 receptor antagonists in the prophylaxis or treatment of certain cardiovascular conditions |
MXPA03001210A (es) * | 2000-08-07 | 2004-08-12 | Smithkline Beecham Corp | Uso de antagonista del receptor 5-ht4 en la fabricacion de un medicamento para la profilaxis o tratamiento de fibrilacion atrial. |
AU2001276558B2 (en) * | 2000-08-08 | 2005-11-24 | Smithkline Beecham P.L.C. | Pharmaceutical composition comprising condensed indole compound |
NZ535261A (en) * | 2000-08-08 | 2004-12-24 | Smithkline Beecham P | A tablet comprising the hydrochloride salt of N-(1-nbutyl-4-piperidinyl)methyl]-3,4-[1,3]oxazino[3,2-a] indole-10-carboxamide |
NZ534333A (en) * | 2002-02-14 | 2006-05-26 | Glaxo Group Ltd | Pharmaceutical composition comprising N-[(1-n-butyl-4-piperidinyl) methyl]-3,4-dihydro-2H-[1, 3]oxazino[3, 2-a]indole-10-carboxamide or salt, and process for preparing thereof comprising dry granulation |
GB0211230D0 (en) | 2002-05-16 | 2002-06-26 | Medinnova Sf | Treatment of heart failure |
ITMI20031467A1 (it) * | 2003-07-18 | 2005-01-19 | Acraf | Farmaco attivo nel dolore neuropatico |
ITMI20031468A1 (it) | 2003-07-18 | 2005-01-19 | Acraf | Farmaco ativo nel dolore neuropatico |
US7834010B2 (en) | 2003-12-23 | 2010-11-16 | Serodus As | Modulators of peripheral 5-HT receptors |
JP4612301B2 (ja) * | 2003-12-26 | 2011-01-12 | 広栄化学工業株式会社 | 1−アルキル−4−アミノメチルピペリジンの製造法 |
EP2173724B1 (en) | 2007-06-22 | 2012-12-05 | ArQule, Inc. | Quinazolinone compounds and methods of use thereof |
GB0905641D0 (en) * | 2009-04-01 | 2009-05-13 | Serodus As | Compounds |
WO2021116487A1 (en) | 2019-12-13 | 2021-06-17 | Som Innovation Biotech, S.A. | Compounds for use in the treatment of niemann-pick c disease |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2557342A1 (de) * | 1975-12-19 | 1977-06-30 | Hoechst Ag | Basisch substituierte indolderivate und verfahren zu ihrer herstellung |
AU622330B2 (en) * | 1989-06-23 | 1992-04-02 | Takeda Chemical Industries Ltd. | Condensed heterocyclic compounds having a nitrogen atom in the bridgehead for use as fungicides |
CA2030051C (en) * | 1989-11-17 | 2001-08-07 | Haruhiko Kikuchi | Indole derivatives |
US5189041A (en) * | 1990-11-16 | 1993-02-23 | Syntex (U.S.A.) Inc. | Tricyclic 5-ht3 receptor antagonists |
GB9103862D0 (en) * | 1991-02-25 | 1991-04-10 | Glaxo Group Ltd | Chemical compounds |
US5206382A (en) * | 1991-06-27 | 1993-04-27 | Fidia Georgetown Institute For The Neurosciences | Indole derivatives, pharmaceutical compositions and methods of treating neurological and psychiatric disorders |
-
1993
- 1993-03-10 PT PT98114130T patent/PT884319E/pt unknown
- 1993-03-10 NZ NZ249565A patent/NZ249565A/en not_active IP Right Cessation
- 1993-03-10 SI SI9300114A patent/SI9300114B/sl active Search and Examination
- 1993-03-10 EP EP98114130A patent/EP0884319B1/en not_active Expired - Lifetime
- 1993-03-10 ES ES98114130T patent/ES2219813T3/es not_active Expired - Lifetime
- 1993-03-10 IL IL10500393A patent/IL105003A/en not_active IP Right Cessation
- 1993-03-10 MY MYPI93000436A patent/MY110110A/en unknown
- 1993-03-10 MA MA23113A patent/MA22819A1/fr unknown
- 1993-03-10 WO PCT/GB1993/000506 patent/WO1993018036A1/en active IP Right Grant
- 1993-03-10 CA CA2131797A patent/CA2131797C/en not_active Expired - Fee Related
- 1993-03-10 AT AT98114130T patent/ATE266033T1/de active
- 1993-03-10 DK DK93905561T patent/DK0630376T3/da active
- 1993-03-10 SK SK1078-94A patent/SK281423B6/sk not_active IP Right Cessation
- 1993-03-10 EP EP93905561A patent/EP0630376B1/en not_active Expired - Lifetime
- 1993-03-10 DK DK98114130T patent/DK0884319T3/da active
- 1993-03-10 CZ CZ19942210A patent/CZ286194B6/cs not_active IP Right Cessation
- 1993-03-10 HU HU9402601A patent/HU219121B/hu unknown
- 1993-03-10 DE DE69325167T patent/DE69325167T2/de not_active Expired - Lifetime
- 1993-03-10 UA UA94095780A patent/UA41311C2/uk unknown
- 1993-03-10 AT AT93905561T patent/ATE180785T1/de active
- 1993-03-10 SG SG1996008846A patent/SG50693A1/en unknown
- 1993-03-10 AU AU36448/93A patent/AU671102B2/en not_active Expired
- 1993-03-10 DE DE69333504T patent/DE69333504T2/de not_active Expired - Lifetime
- 1993-03-10 KR KR1019940703167A patent/KR100282730B1/ko not_active IP Right Cessation
- 1993-03-10 RU RU94040864A patent/RU2104279C1/ru not_active IP Right Cessation
- 1993-03-10 ES ES93905561T patent/ES2132223T3/es not_active Expired - Lifetime
- 1993-03-10 JP JP5515490A patent/JP2831467B2/ja not_active Expired - Lifetime
- 1993-03-10 AP APAP/P/1993/000494A patent/AP401A/en active
- 1993-03-11 CN CN93102648A patent/CN1043893C/zh not_active Expired - Fee Related
- 1993-03-11 MX MX9301348A patent/MX9301348A/es not_active IP Right Cessation
- 1993-05-22 CN CN93107234A patent/CN1085083A/zh active Pending
-
1994
- 1994-09-09 NO NO943348A patent/NO303638B1/no not_active IP Right Cessation
- 1994-09-12 FI FI944204A patent/FI107158B/fi not_active IP Right Cessation
-
1998
- 1998-12-15 HK HK98113467A patent/HK1012352A1/xx not_active IP Right Cessation
-
1999
- 1999-06-30 GR GR990401755T patent/GR3030668T3/el unknown
-
2005
- 2005-04-12 CY CY0500021A patent/CY2510B1/xx unknown
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
FF | Patent granted | ||
KB | Patent renewed | ||
KB | Patent renewed | ||
KB | Patent renewed | ||
KB | Patent renewed | ||
MM9K | Patent not in force due to non-payment of renewal fees |