IL123583A - 3-substituted -8-azabicyclo [3,2,1] oct-2-ene derivatives, their preparation and pharmaceutical compositions containing them - Google Patents
3-substituted -8-azabicyclo [3,2,1] oct-2-ene derivatives, their preparation and pharmaceutical compositions containing themInfo
- Publication number
- IL123583A IL123583A IL12358396A IL12358396A IL123583A IL 123583 A IL123583 A IL 123583A IL 12358396 A IL12358396 A IL 12358396A IL 12358396 A IL12358396 A IL 12358396A IL 123583 A IL123583 A IL 123583A
- Authority
- IL
- Israel
- Prior art keywords
- substituted
- heteroaryl
- alkynyl
- cycloalkyl
- alkenyl
- Prior art date
Links
- -1 3-substituted -8-azabicyclo [3,2,1] oct-2-ene Chemical class 0.000 title abstract 2
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 5
- 125000000217 alkyl group Chemical group 0.000 abstract 5
- 125000000304 alkynyl group Chemical group 0.000 abstract 5
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 5
- 125000001072 heteroaryl group Chemical group 0.000 abstract 5
- 125000003545 alkoxy group Chemical group 0.000 abstract 4
- 125000003118 aryl group Chemical group 0.000 abstract 4
- 125000000000 cycloalkoxy group Chemical group 0.000 abstract 4
- 229910052736 halogen Inorganic materials 0.000 abstract 4
- 150000002367 halogens Chemical group 0.000 abstract 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 4
- 125000001424 substituent group Chemical group 0.000 abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 abstract 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 239000003112 inhibitor Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 125000001624 naphthyl group Chemical group 0.000 abstract 1
- 230000001561 neurotransmitter reuptake Effects 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
- C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
-
- 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
- A61K31/46—8-Azabicyclo [3.2.1] octane; Derivatives thereof, e.g. atropine, cocaine
-
- 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
- A61P25/22—Anxiolytics
-
- 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
- A61P25/24—Antidepressants
-
- 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
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
- C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
- C07D451/04—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof with hetero atoms directly attached in position 3 of the 8-azabicyclo [3.2.1] octane or in position 7 of the 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring system
- C07D451/06—Oxygen atoms
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)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Biomedical Technology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Psychiatry (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Pain & Pain Management (AREA)
- Child & Adolescent Psychology (AREA)
- Hospice & Palliative Care (AREA)
- Emergency Medicine (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DK115695 | 1995-10-13 | ||
| PCT/EP1996/004449 WO1997013770A1 (en) | 1995-10-13 | 1996-10-11 | 8-azabicyclo[3.2.1]oct-2-ene derivatives, their preparation and use |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL123583A0 IL123583A0 (en) | 1998-10-30 |
| IL123583A true IL123583A (en) | 2003-07-31 |
Family
ID=8101642
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL12358396A IL123583A (en) | 1995-10-13 | 1996-10-11 | 3-substituted -8-azabicyclo [3,2,1] oct-2-ene derivatives, their preparation and pharmaceutical compositions containing them |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US6100275A (cs) |
| EP (1) | EP0859777B1 (cs) |
| JP (1) | JP3462505B2 (cs) |
| KR (1) | KR100274829B1 (cs) |
| CN (1) | CN1083840C (cs) |
| AT (1) | ATE362931T1 (cs) |
| AU (1) | AU709327B2 (cs) |
| BR (1) | BR9610960A (cs) |
| CA (1) | CA2233541C (cs) |
| CZ (1) | CZ285093B6 (cs) |
| DE (1) | DE69637097T2 (cs) |
| DK (1) | DK0859777T3 (cs) |
| EE (1) | EE03446B1 (cs) |
| HU (1) | HUP9802433A3 (cs) |
| IL (1) | IL123583A (cs) |
| IS (1) | IS4681A (cs) |
| NO (1) | NO980919L (cs) |
| NZ (1) | NZ320216A (cs) |
| PL (1) | PL185357B1 (cs) |
| RU (1) | RU2157372C2 (cs) |
| SK (1) | SK283425B6 (cs) |
| TR (1) | TR199800628T2 (cs) |
| UA (1) | UA63894C2 (cs) |
| WO (1) | WO1997013770A1 (cs) |
Families Citing this family (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9510459D0 (en) | 1995-05-24 | 1995-07-19 | Zeneca Ltd | Bicyclic amines |
| KR20000010972A (ko) * | 1996-05-13 | 2000-02-25 | 사라 엔 람베쓰 | 살충제용 이환식 아민 |
| GB9623944D0 (en) * | 1996-11-15 | 1997-01-08 | Zeneca Ltd | Bicyclic amine derivatives |
| GB9624114D0 (en) * | 1996-11-20 | 1997-01-08 | Zeneca Ltd | Pesticidal bicyclic amine derivatives |
| AU719147B2 (en) | 1996-11-26 | 2000-05-04 | Zeneca Limited | 8-azabicyclo{3.2.1}octane-, 8-azabicyclo{3.2.1}oct-6-ene-, 9-azabicyclo{3.3.1} nonane-, 9-aza-3-oxabicyclo{3.3.1}nonane- and 9-aza-3-thiabicyclo{3.3.1}nonane derivatives, their preparation and their use as insecticides |
| GB9624611D0 (en) * | 1996-11-26 | 1997-01-15 | Zeneca Ltd | Bicyclic amine compounds |
| GB9706222D0 (en) * | 1997-03-26 | 1997-05-14 | Zeneca Ltd | Bicyclic amine derivatives |
| AU745964B2 (en) | 1997-05-30 | 2002-04-11 | Neurosearch A/S | 8-Azabicyclo(3,2,1)oct-2-ene and octane derivatives as cholinergic ligands at nicotinic ACh receptors |
| GB9726033D0 (en) | 1997-12-09 | 1998-02-04 | Zeneca Ltd | Chemical process |
| TWI221842B (en) * | 1997-12-11 | 2004-10-11 | Syngenta Ltd | Process for the preparation of 8-azabicyclo(3.2.1)octane derivatives |
| JP2002501921A (ja) * | 1998-01-28 | 2002-01-22 | ニューロサーチ、アクティーゼルスカブ | 標識された形での８−アザビシクロ［３．２．１］オクト−２−エン誘導体及び標識された及び標識されていない形での８−アザビシクロ［３．２．１］オクト−２−エン誘導体の使用方法 |
| US6403605B1 (en) * | 1998-05-29 | 2002-06-11 | Queen's University At Kingston | Methods for the normalization of sexual response and amelioration of long term genital tissue degradation |
| JP2002518331A (ja) * | 1998-06-19 | 2002-06-25 | イーライ・リリー・アンド・カンパニー | セロトニン再取り込みの阻害 |
| EP1382605A3 (en) * | 1998-11-27 | 2004-09-15 | Neurosearch A/S | 8-azabicyclo(3.2.1)oct-2-ene derivatives and their use as nAChR ligands |
| RU2211216C2 (ru) * | 1998-12-22 | 2003-08-27 | Мерк Патент Гмбх | Производные амидов и мочевины в качестве ингибиторов вторичного поглощения 5-ht и лигандов 5-ht1b/1d |
| AU2278700A (en) | 1999-01-28 | 2000-08-18 | Neurosearch A/S | Novel azabicyclo derivatives and their use |
| CA2365032A1 (en) * | 1999-03-01 | 2000-09-08 | Pfizer Limited | 1,2,3,4-tetrahydro-1-naphthalenamine compounds useful in therapy |
| US7718705B1 (en) | 1999-09-03 | 2010-05-18 | Eli Lilly And Company | Methods of using rapid-onset selective serotonin reuptake inhibitors for treating sexual dysfunction |
| US6835733B2 (en) | 1999-12-20 | 2004-12-28 | Eli Lilly And Company | Tropane linked benzofuran derivatives |
| JP2003534344A (ja) | 2000-05-25 | 2003-11-18 | ターガセプト，インコーポレイテッド | ニコチン性コリン受容体リガンドとしてのヘテロアリールジアザビシクロアルカン |
| US6667314B2 (en) | 2000-05-26 | 2003-12-23 | Pfizer, Inc. | Tropane derivatives useful in therapy |
| US6579878B1 (en) | 2000-07-07 | 2003-06-17 | Targacept, Inc. | Pharmaceutical compositions and methods for use |
| US6624167B1 (en) | 2000-08-04 | 2003-09-23 | Targacept, Inc. | Pharmaceutical compositions and methods for use |
| EP1358177B1 (en) * | 2000-10-13 | 2006-08-02 | NeuroSearch A/S | Treatment of affective disorders by the combined action of a nicotinic receptor agonist and a monoaminergic substance |
| US7160899B2 (en) | 2001-04-09 | 2007-01-09 | Neurosearch A/S | Adenosine A2A receptor antangonists combined with neurotrophic activity compounds in the treatment of Parkinson's disease |
| AR035898A1 (es) | 2001-05-25 | 2004-07-21 | Wyeth Corp | Aril-8-azabiciclo[3.2.1]octanos, un proceso para su preparacion, una formulacion y el uso de dichos compuestos para la manufactura de un medicamento para el tratamiento de la depresion |
| RU2203044C1 (ru) * | 2001-12-27 | 2003-04-27 | Закрытое акционерное общество "Брынцалов-А" | Антидепрессант амитриптилин-ферейн |
| AU2003222738B2 (en) * | 2002-05-07 | 2009-09-17 | Neurosearch A/S | Novel azacyclic ethynyl derivatives |
| RU2344136C2 (ru) * | 2003-06-24 | 2009-01-20 | НьюроСёрч А/С | Новые производные 8-аза-бицикло[3.2.1]октана и их применение в качестве ингибиторов обратного захвата моноаминовых нейротрансмиттеров |
| AU2005288914B2 (en) * | 2004-09-30 | 2011-05-19 | Neurosearch A/S | Novel chromen-2-one derivatives and their use as monoamine neurotransmitter re-uptake inhibitors |
| WO2006108789A1 (en) * | 2005-04-08 | 2006-10-19 | Neurosearch A/S | Novel enantiomers and their use as monoamine neurotransmitter re-uptake inhibitors |
| TW200744590A (en) * | 2005-09-01 | 2007-12-16 | Neurosearch As | Novel compounds |
| RU2315047C1 (ru) * | 2006-09-04 | 2008-01-20 | Институт нефтехимии и катализа РАН | Способ получения 8-этил-6,7-фуллеро[60]-3-окса-8-азабицикло[3.2.1]октана |
| KR100812499B1 (ko) * | 2006-10-16 | 2008-03-11 | 이도훈 | 항경련제 |
| TWI415850B (zh) * | 2007-07-20 | 2013-11-21 | Theravance Inc | 製備ｍｕ類鴉片受體拮抗劑之中間物的方法 |
| JP2011513354A (ja) * | 2008-03-05 | 2011-04-28 | ノイロサーチ アクティーゼルスカブ | 新規な４−ベンズヒドリル−テトラヒドロ−ピリジン誘導体及びモノアミン神経伝達物質再取り込み阻害薬としてのその使用 |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB247886A (en) * | 1925-11-02 | 1926-02-25 | Thomas Stewart Hamilton | Improvements in attachments for leaf springs |
| US3133073A (en) * | 1959-12-10 | 1964-05-12 | Sterling Drug Inc | 3-aryl-1, 5-iminocycloalkanes and preparation thereof |
| US3657257A (en) * | 1970-08-31 | 1972-04-18 | Robins Co Inc A H | 3-aryl-8-carbamoyl nortropanes |
| US4180669A (en) * | 1976-12-13 | 1979-12-25 | Abbott Laboratories | 2-(N-phenethyl-4-piperidino)-5-pentyl resorcinol |
| US4132710A (en) * | 1976-12-20 | 1979-01-02 | Ayerst, Mckenna And Harrison, Ltd. | [2]Benzopyrano[3,4-c]pyridines and process therefor |
| JPS55115872A (en) * | 1979-02-22 | 1980-09-06 | Wellcome Found | Imidazole derivative and medical composition |
| US5418240A (en) * | 1990-08-21 | 1995-05-23 | Novo Nordisk A/S | Heterocyclic compounds and their preparation and use |
| DK198590D0 (da) * | 1990-08-21 | 1990-08-21 | Novo Nordisk As | Heterocykliske forbindelser, deres fremstilling og anvendelse |
| GB9019973D0 (en) * | 1990-09-12 | 1990-10-24 | Wyeth John & Brother Ltd | Azabicyclic derivatives |
| FI111367B (fi) * | 1991-02-04 | 2003-07-15 | Aventis Pharma Inc | Menetelmä terapeuttisesti käyttökelpoisten N-(aryylioksialkyyli)heteroaryyli-8-atsabisyklo[3.2.1]oktaanijohdannaisten valmistamiseksi ja menetelmässä käytetyt välituotteet |
| NZ243065A (en) * | 1991-06-13 | 1995-07-26 | Lundbeck & Co As H | Piperidine derivatives and pharmaceutical compositions |
| DE4200145A1 (de) * | 1992-01-07 | 1993-07-08 | Kali Chemie Pharma Gmbh | 7,10-epoxy-oxacyclododecan-derivate, verfahren und zwischenprodukte zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| DK154192D0 (da) * | 1992-12-23 | 1992-12-23 | Neurosearch As | Heterocycliske forbindelser |
| AU672052B2 (en) * | 1992-12-23 | 1996-09-19 | Neurosearch A/S | Antidepressant and antiparkinsonian compounds |
| CA2163095A1 (en) * | 1993-05-18 | 1994-11-24 | Huw M. L. Davies | Treatment process with biologically active tropane derivatives |
| CZ284379B6 (cs) * | 1994-04-19 | 1998-11-11 | Neurosearch A/S | Tropanové deriváty, způsob jejich přípravy a jejich použití |
| US5731317A (en) * | 1995-03-10 | 1998-03-24 | Merck & Co., Inc. | Bridged piperidines promote release of growth hormone |
-
1996
- 1996-10-11 AT AT96934662T patent/ATE362931T1/de active
- 1996-10-11 CA CA002233541A patent/CA2233541C/en not_active Expired - Fee Related
- 1996-10-11 AU AU72917/96A patent/AU709327B2/en not_active Ceased
- 1996-10-11 RU RU98105169/04A patent/RU2157372C2/ru not_active IP Right Cessation
- 1996-10-11 TR TR1998/00628T patent/TR199800628T2/xx unknown
- 1996-10-11 PL PL96326195A patent/PL185357B1/pl not_active IP Right Cessation
- 1996-10-11 DE DE69637097T patent/DE69637097T2/de not_active Expired - Lifetime
- 1996-10-11 JP JP51472697A patent/JP3462505B2/ja not_active Expired - Fee Related
- 1996-10-11 IL IL12358396A patent/IL123583A/xx not_active IP Right Cessation
- 1996-10-11 BR BR9610960A patent/BR9610960A/pt not_active Application Discontinuation
- 1996-10-11 EE EE9800062A patent/EE03446B1/xx not_active IP Right Cessation
- 1996-10-11 KR KR1019980702103A patent/KR100274829B1/ko not_active Expired - Fee Related
- 1996-10-11 HU HU9802433A patent/HUP9802433A3/hu unknown
- 1996-10-11 EP EP96934662A patent/EP0859777B1/en not_active Expired - Lifetime
- 1996-10-11 CN CN96197566A patent/CN1083840C/zh not_active Expired - Fee Related
- 1996-10-11 CZ CZ98758A patent/CZ285093B6/cs not_active IP Right Cessation
- 1996-10-11 US US09/043,294 patent/US6100275A/en not_active Expired - Fee Related
- 1996-10-11 WO PCT/EP1996/004449 patent/WO1997013770A1/en active IP Right Grant
- 1996-10-11 NZ NZ320216A patent/NZ320216A/xx not_active IP Right Cessation
- 1996-10-11 SK SK287-98A patent/SK283425B6/sk unknown
- 1996-10-11 DK DK96934662T patent/DK0859777T3/da active
- 1996-11-10 UA UA98031543A patent/UA63894C2/uk unknown
-
1998
- 1998-03-03 NO NO19980919A patent/NO980919L/no not_active Application Discontinuation
- 1998-03-04 IS IS4681A patent/IS4681A/is unknown
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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 |