IL118427A - N-acyl-2 aryl cycloalkylmethylamine derivatives as melatonergics and pharmaceutical compositions comprising them - Google Patents
N-acyl-2 aryl cycloalkylmethylamine derivatives as melatonergics and pharmaceutical compositions comprising themInfo
- Publication number
- IL118427A IL118427A IL11842796A IL11842796A IL118427A IL 118427 A IL118427 A IL 118427A IL 11842796 A IL11842796 A IL 11842796A IL 11842796 A IL11842796 A IL 11842796A IL 118427 A IL118427 A IL 118427A
- Authority
- IL
- Israel
- Prior art keywords
- melatonergics
- acyl
- aryl
- pharmaceutical compositions
- cycloalkylmethylamine derivatives
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/30—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/02—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C211/03—Monoamines
-
- 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
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/12—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups
- C07C233/13—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
- C07C233/17—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/18—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/57—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C233/60—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of rings other than six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C235/08—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atom of at least one of the carboxamide groups bound to an acyclic carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/58—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton
- C07C255/60—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton at least one of the singly-bound nitrogen atoms being acylated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/04—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms
- C07C275/20—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms of an unsaturated carbon skeleton
- C07C275/24—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/26—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of rings other than six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/60—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton with the carbon atom of at least one of the carboxyl groups bound to nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/04—Systems containing only non-condensed rings with a four-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Endocrinology (AREA)
- Diabetes (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Pyrrole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US48663395A | 1995-06-07 | 1995-06-07 | |
US08/487,306 US5596019A (en) | 1995-06-07 | 1995-06-07 | N-acyl-cycloalkylamine derivatives as melatonergics |
Publications (2)
Publication Number | Publication Date |
---|---|
IL118427A0 IL118427A0 (en) | 1996-09-12 |
IL118427A true IL118427A (en) | 2000-10-31 |
Family
ID=27048750
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
IL11842796A IL118427A (en) | 1995-06-07 | 1996-05-27 | N-acyl-2 aryl cycloalkylmethylamine derivatives as melatonergics and pharmaceutical compositions comprising them |
Country Status (23)
Country | Link |
---|---|
EP (1) | EP0747346B1 (de) |
JP (1) | JPH08333314A (de) |
KR (1) | KR100385360B1 (de) |
CN (1) | CN1068583C (de) |
AR (1) | AR003139A1 (de) |
AT (1) | ATE189807T1 (de) |
AU (1) | AU697028B2 (de) |
CA (1) | CA2176854A1 (de) |
CY (1) | CY2221B1 (de) |
CZ (1) | CZ291380B6 (de) |
DE (1) | DE69606665T2 (de) |
DK (1) | DK0747346T3 (de) |
ES (1) | ES2144666T3 (de) |
GR (1) | GR3033414T3 (de) |
HK (1) | HK1014704A1 (de) |
HU (1) | HUP9601565A3 (de) |
IL (1) | IL118427A (de) |
NO (1) | NO311211B1 (de) |
NZ (1) | NZ286640A (de) |
PL (1) | PL314671A1 (de) |
PT (1) | PT747346E (de) |
RU (1) | RU2162076C2 (de) |
TW (1) | TW350836B (de) |
Families Citing this family (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BR9713690B1 (pt) * | 1996-12-10 | 2009-08-11 | agentes melatoninérgicos benzodioxola, benzofurano, diidrobenzofurano e benzodioxano. | |
US6028112A (en) * | 1997-05-23 | 2000-02-22 | Bristol-Myers Squibb Company | Spirocyclopropyl fluorenes as melatonergic agents |
EP1082115A4 (de) * | 1998-06-05 | 2002-10-24 | Bristol Myers Squibb Co | Heterocyclische cis cyclopropanderivate als melatoninergische mittel |
AU4290099A (en) * | 1998-06-29 | 2000-01-17 | Mitsubishi-Tokyo Pharmaceuticals, Inc. | Process for the preparation of optically active trans-cyclohexylamine compounds |
FR2784375B1 (fr) * | 1998-10-12 | 2000-11-24 | Adir | Nouveaux derives cycliques a chaine cycloalkylenique, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
CA2347092A1 (en) | 1998-10-14 | 2000-04-20 | Ortho-Mcneil Pharmaceutical, Inc. | 1,2-disubstituted cyclopropanes |
US6900232B2 (en) | 2000-06-15 | 2005-05-31 | Pharmacia Corporation | Cycloalkyl alkanoic acids as integrin receptor antagonists |
US7541055B2 (en) * | 2004-09-10 | 2009-06-02 | International Flavors & Fragrances Inc. | Saturated and unsaturated N-alkamides exhibiting taste and flavor enhancement effect in flavor compositions |
WO2007025144A1 (en) * | 2005-08-24 | 2007-03-01 | University Of Illinois - Chicago | 5-ht2c receptor agonists as anorectic agents |
TWI402261B (zh) | 2006-06-19 | 2013-07-21 | Takeda Pharmaceutical | 三環化合物及其醫藥組成物 |
US8835472B2 (en) * | 2010-09-02 | 2014-09-16 | Boehringer Ingelheim International Gmbh | Compounds, pharmaceutical compositions and uses thereof |
EP2855424B1 (de) * | 2012-05-18 | 2017-10-11 | Vanda Pharmaceuticals Inc. | Metabolite von (1r-trans-)n-[[2-(2,3-dihydro-4-benzofuranyl-)cyclopropyl-]methyl-]propanamid |
CN102863341B (zh) * | 2012-10-22 | 2014-05-07 | 南通大学 | 一种(1r,2s)-2-芳基环丙胺衍生物的化学合成方法 |
WO2016123164A1 (en) * | 2015-01-29 | 2016-08-04 | The Board Of Trustees Of The University Of Illinois | Cyclopropylmethanamines as selective 5-ht(2c) receptor agonists |
CN105949153B (zh) * | 2016-05-10 | 2018-03-02 | 浙江工业大学 | 一种他司美琼的合成方法 |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR1415997A (fr) * | 1963-11-05 | 1965-10-29 | Whitefin Holding Sa | Dérivés de phénylcyclopropane et procédés de préparation |
US5071875A (en) * | 1989-09-25 | 1991-12-10 | Northwestern University | Substituted 2-amidotetralins as melatonin agonists and antagonists |
JP3007138B2 (ja) * | 1990-11-27 | 2000-02-07 | ファイザー製薬株式会社 | 新規なヒドロキサム酸とn―ヒドロキシ尿素誘導体およびそれらの組成物 |
FR2680366B1 (fr) * | 1991-08-13 | 1995-01-20 | Adir | Nouveaux derives d'arylethylamines, leurs procedes de preparation et les compositions pharmaceutiques qui les contiennent. |
AU2807192A (en) * | 1991-10-02 | 1993-05-03 | Smithkline Beecham Corporation | Cyclopentane and cyclopentene derivatives with antiallergic antiinflammatory and tumor necrosis factor inhibiting activity |
US5541228A (en) * | 1994-10-14 | 1996-07-30 | Bristol-Myers Squibb Co. | Melatonergic agents |
-
1996
- 1996-05-17 CA CA002176854A patent/CA2176854A1/en not_active Abandoned
- 1996-05-22 NZ NZ286640A patent/NZ286640A/en unknown
- 1996-05-23 TW TW085106143A patent/TW350836B/zh active
- 1996-05-27 IL IL11842796A patent/IL118427A/xx not_active IP Right Cessation
- 1996-05-31 DE DE69606665T patent/DE69606665T2/de not_active Expired - Fee Related
- 1996-05-31 EP EP96108764A patent/EP0747346B1/de not_active Expired - Lifetime
- 1996-05-31 PT PT96108764T patent/PT747346E/pt unknown
- 1996-05-31 AT AT96108764T patent/ATE189807T1/de not_active IP Right Cessation
- 1996-05-31 ES ES96108764T patent/ES2144666T3/es not_active Expired - Lifetime
- 1996-05-31 DK DK96108764T patent/DK0747346T3/da active
- 1996-06-05 CZ CZ19961631A patent/CZ291380B6/cs not_active IP Right Cessation
- 1996-06-06 RU RU96111003/04A patent/RU2162076C2/ru not_active IP Right Cessation
- 1996-06-06 JP JP8144018A patent/JPH08333314A/ja active Pending
- 1996-06-06 AU AU54759/96A patent/AU697028B2/en not_active Ceased
- 1996-06-06 NO NO19962364A patent/NO311211B1/no not_active IP Right Cessation
- 1996-06-06 HU HU9601565A patent/HUP9601565A3/hu unknown
- 1996-06-07 PL PL96314671A patent/PL314671A1/xx unknown
- 1996-06-07 CN CN96108134A patent/CN1068583C/zh not_active Expired - Fee Related
- 1996-06-07 KR KR1019960020713A patent/KR100385360B1/ko not_active IP Right Cessation
- 1996-06-07 AR ARP960103052A patent/AR003139A1/es not_active Application Discontinuation
-
1998
- 1998-12-28 HK HK98116041A patent/HK1014704A1/xx not_active IP Right Cessation
-
2000
- 2000-05-15 GR GR20000401104T patent/GR3033414T3/el not_active IP Right Cessation
-
2001
- 2001-05-04 CY CY0100007A patent/CY2221B1/xx unknown
Also Published As
Publication number | Publication date |
---|---|
DE69606665D1 (de) | 2000-03-23 |
TW350836B (en) | 1999-01-21 |
IL118427A0 (en) | 1996-09-12 |
PL314671A1 (en) | 1996-12-09 |
ATE189807T1 (de) | 2000-03-15 |
CZ163196A3 (en) | 1997-06-11 |
GR3033414T3 (en) | 2000-09-29 |
HUP9601565A2 (en) | 1997-05-28 |
CZ291380B6 (cs) | 2003-02-12 |
HK1014704A1 (en) | 1999-09-30 |
NZ286640A (en) | 1998-06-26 |
HU9601565D0 (en) | 1996-08-28 |
JPH08333314A (ja) | 1996-12-17 |
CY2221B1 (en) | 2003-04-18 |
NO962364L (no) | 1996-12-09 |
KR100385360B1 (ko) | 2003-08-25 |
DE69606665T2 (de) | 2000-09-21 |
PT747346E (pt) | 2000-06-30 |
NO311211B1 (no) | 2001-10-29 |
AR003139A1 (es) | 1998-07-08 |
ES2144666T3 (es) | 2000-06-16 |
NO962364D0 (no) | 1996-06-06 |
DK0747346T3 (da) | 2000-06-05 |
EP0747346B1 (de) | 2000-02-16 |
AU5475996A (en) | 1996-12-19 |
RU2162076C2 (ru) | 2001-01-20 |
CN1143628A (zh) | 1997-02-26 |
EP0747346A2 (de) | 1996-12-11 |
HUP9601565A3 (en) | 1998-03-02 |
CA2176854A1 (en) | 1996-12-08 |
AU697028B2 (en) | 1998-09-24 |
KR970001306A (ko) | 1997-01-24 |
EP0747346A3 (de) | 1997-11-05 |
CN1068583C (zh) | 2001-07-18 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
FF | Patent granted | ||
KB | Patent renewed | ||
KB | Patent renewed | ||
MM9K | Patent not in force due to non-payment of renewal fees |