FI110871B - Menetelmä polysyklisten antiparasiittisten aineiden valmistamiseksi ja menetelmässä käytettävä mikro-organismi - Google Patents
Menetelmä polysyklisten antiparasiittisten aineiden valmistamiseksi ja menetelmässä käytettävä mikro-organismi Download PDFInfo
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- FI110871B FI110871B FI961839A FI961839A FI110871B FI 110871 B FI110871 B FI 110871B FI 961839 A FI961839 A FI 961839A FI 961839 A FI961839 A FI 961839A FI 110871 B FI110871 B FI 110871B
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- 229910052708 sodium Inorganic materials 0.000 description 1
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- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
- C07D491/16—Peri-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/22—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains four or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
- C12P17/18—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms containing at least two hetero rings condensed among themselves or condensed with a common carbocyclic ring system, e.g. rifamycin
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S435/00—Chemistry: molecular biology and microbiology
- Y10S435/8215—Microorganisms
- Y10S435/911—Microorganisms using fungi
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Veterinary Medicine (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Microbiology (AREA)
- Medicinal Chemistry (AREA)
- Tropical Medicine & Parasitology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US14663893 | 1993-11-01 | ||
| US08/146,638 US5399582A (en) | 1993-11-01 | 1993-11-01 | Antiparasitic agents |
| PCT/US1994/012302 WO1995012599A1 (en) | 1993-11-01 | 1994-10-27 | Polycyclic antiparasitic agents, process and strain for their preparation and their use |
| US9412302 | 1994-10-27 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI961839L FI961839L (fi) | 1996-04-30 |
| FI961839A0 FI961839A0 (fi) | 1996-04-30 |
| FI110871B true FI110871B (fi) | 2003-04-15 |
Family
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Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI961839A FI110871B (fi) | 1993-11-01 | 1996-04-30 | Menetelmä polysyklisten antiparasiittisten aineiden valmistamiseksi ja menetelmässä käytettävä mikro-organismi |
| FI20012318A FI112503B (fi) | 1993-11-01 | 2001-11-27 | Polysyklisiä antiparasiittisia aineita ja niiden käyttö |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI20012318A FI112503B (fi) | 1993-11-01 | 2001-11-27 | Polysyklisiä antiparasiittisia aineita ja niiden käyttö |
Country Status (24)
| Country | Link |
|---|---|
| US (2) | US5399582A (cs) |
| EP (1) | EP0726902B1 (cs) |
| JP (1) | JP3557212B2 (cs) |
| KR (1) | KR100333017B1 (cs) |
| CN (2) | CN1046943C (cs) |
| AT (1) | ATE188476T1 (cs) |
| AU (1) | AU688405B2 (cs) |
| CA (1) | CA2174645C (cs) |
| CZ (1) | CZ286032B6 (cs) |
| DE (1) | DE69422526T2 (cs) |
| DK (1) | DK0726902T3 (cs) |
| ES (1) | ES2143558T3 (cs) |
| FI (2) | FI110871B (cs) |
| GR (1) | GR3032493T3 (cs) |
| HU (1) | HU221276B1 (cs) |
| NO (1) | NO315942B1 (cs) |
| NZ (1) | NZ275339A (cs) |
| PL (1) | PL178879B1 (cs) |
| PT (1) | PT726902E (cs) |
| RU (1) | RU2139874C1 (cs) |
| SI (1) | SI0726902T1 (cs) |
| SK (1) | SK281510B6 (cs) |
| WO (1) | WO1995012599A1 (cs) |
| ZA (1) | ZA948542B (cs) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US5399582A (en) * | 1993-11-01 | 1995-03-21 | Merck & Co., Inc. | Antiparasitic agents |
| US5541208A (en) * | 1994-01-24 | 1996-07-30 | Merck & Co., Inc. | Indole diterpene alkaloid compounds |
| CA2215982C (en) * | 1995-03-20 | 2001-06-12 | Merck & Co., Inc. | Nodulisporic acid derivatives |
| US6221894B1 (en) | 1995-03-20 | 2001-04-24 | Merck & Co., Inc. | Nodulisporic acid derivatives |
| US5595991A (en) * | 1995-03-20 | 1997-01-21 | Merck & Co., Inc. | Anthelmintic use of nodulisporic acid and analogs thereof |
| US5962499A (en) * | 1995-03-20 | 1999-10-05 | Merck & Co., Inc. | Nodulisporic acid derivatives |
| US5834260A (en) * | 1996-08-30 | 1998-11-10 | Merck & Co., Inc. | Antiparasitic agents |
| JP3502103B2 (ja) * | 1996-09-19 | 2004-03-02 | メルク エンド カンパニー インコーポレーテッド | ノジュリスポリン酸誘導体 |
| WO1999018796A2 (en) * | 1997-10-09 | 1999-04-22 | Rhone-Poulenc Agro | Pesticidal combination |
| US6733767B2 (en) * | 1998-03-19 | 2004-05-11 | Merck & Co., Inc. | Liquid polymeric compositions for controlled release of bioactive substances |
| US6787342B2 (en) | 2000-02-16 | 2004-09-07 | Merial Limited | Paste formulations |
| US6586452B1 (en) | 2000-07-14 | 2003-07-01 | Merck & Co., Inc. | C1 to C4 side chain modified nodulisporic acid analogs |
| US6399786B1 (en) * | 2000-07-14 | 2002-06-04 | Merck & Co., Inc. | Nonacyclic nodulisporic acid derivatives |
| US20040077703A1 (en) * | 2002-10-02 | 2004-04-22 | Soll Mark D. | Nodulisporic acid derivative spot-on formulations for combating parasites |
| US8362086B2 (en) | 2005-08-19 | 2013-01-29 | Merial Limited | Long acting injectable formulations |
| ES2564782T3 (es) | 2006-07-05 | 2016-03-29 | Merial, Inc. | Compuestos derivados de 1-aril-5-alquil pirazol, procedimientos de fabricación y procedimientos de utilización de los mismos |
| PT3428148T (pt) | 2007-05-15 | 2020-10-13 | Aventis Agriculture | Compostos de ariloazol-2-il-cianoetilamino, método de fabrico e seu método de utilização |
| TWI556741B (zh) | 2007-08-17 | 2016-11-11 | 英特威特國際股份有限公司 | 異唑啉組成物及其作為抗寄生蟲藥上的應用 |
| AU2008340434B2 (en) | 2007-12-21 | 2014-02-06 | Boehringer Ingelheim Animal Health USA Inc. | The use of 6-halogeno-[1,2,4]-triazolo-[1,5-a]-pyrimidine compounds for combating pests in and on animals |
| EP3050874B1 (en) | 2008-11-14 | 2019-01-09 | Merial Inc. | Enantiomerially enriched aryloazol-2-yl cyanoethylamino paraciticidal compounds |
| RU2011124948A (ru) | 2008-11-19 | 2012-12-27 | Мериал Лимитед | Композиции, включающие 1-арилпиразол сам по себе или в комбинации с формамидином, для лечения паразитарных инфекций |
| JP5595412B2 (ja) | 2008-12-04 | 2014-09-24 | メリアル リミテッド | 二量体アベルメクチン及びミルベマイシン誘導体 |
| WO2011014660A1 (en) | 2009-07-30 | 2011-02-03 | Merial Limited | Insecticidal 4-amino-thieno[2,3-d]-pyrimidine compounds and methods of their use |
| MX2012006366A (es) | 2009-12-04 | 2012-06-27 | Basf Se | Compuesto de bis-organoazufre plaguicidas. |
| ME02432B (me) | 2009-12-17 | 2016-09-20 | Merial Inc | Antiparazitska jedinjenja dihidroazola i kompozicije koje ih sadrže |
| EP2512467A1 (en) | 2009-12-17 | 2012-10-24 | Merial Limited | Compositions comprising macrocyclic lactone compounds and spirodioxepinoindoles |
| WO2011095581A1 (en) | 2010-02-05 | 2011-08-11 | Intervet International B.V. | S piroindoline compounds for use as anthelminthi cs |
| UA108641C2 (uk) | 2010-04-02 | 2015-05-25 | Паразитицидна композиція, яка містить чотири активних агенти, та спосіб її застосування | |
| KR101916481B1 (ko) | 2010-09-29 | 2018-11-07 | 인터벳 인터내셔널 비.브이. | Ｎ-헤테로아릴 화합물 |
| BR112013006953A2 (pt) | 2010-09-29 | 2016-07-26 | Intervet Int Bv | composto, composições farmacêutica e anti-helmíntica, uso de um composto, kit, e, método de tratamento de uma doença |
| NZ610547A (en) | 2010-11-16 | 2015-07-31 | Merial Ltd | Novel monensin derivatives for the treatment and prevention of protozoal infections |
| MX2013014326A (es) | 2011-06-20 | 2014-01-23 | Du Pont | Compuestos heterociclicos para tratar infecciones por helmintos. |
| BR112013033568B1 (pt) | 2011-06-27 | 2020-11-24 | Merial, Inc | Compostos eter amidopiridil e composiqoes, e seu uso contra parasitas |
| US20120329832A1 (en) | 2011-06-27 | 2012-12-27 | Jean Delaveau | Novel Insect-Repellent Coumarin Derivatives, Syntheses, and Methods of Use |
| EP2739626B1 (en) | 2011-08-04 | 2016-05-04 | Intervet International B.V. | Novel spiroindoline compounds |
| CA2848317C (en) | 2011-09-12 | 2021-01-19 | Merial Limited | Parasiticidal compositions comprising an isoxazoline active agent, methods and uses thereof. |
| WO2013044118A2 (en) | 2011-09-23 | 2013-03-28 | Merial Limited | Indirect modeling of new repellent molecules active against insects, acarids, and other arthropods |
| EP2780008B1 (en) | 2011-11-17 | 2017-07-05 | Merial, Inc. | Compositions comprising an aryl pyrazole and a substituted imidazole, methods and uses thereof |
| JP2015502936A (ja) | 2011-11-28 | 2015-01-29 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニーＥ．Ｉ．Ｄｕ Ｐｏｎｔ Ｄｅ Ｎｅｍｏｕｒｓ Ａｎｄ Ｃｏｍｐａｎｙ | スルホンアミド駆虫薬 |
| CA3082432C (en) | 2011-12-02 | 2023-01-03 | Boehringer Ingelheim Animal Health USA Inc. | Long-acting injectable moxidectin formulations and novel moxidectin crystal forms |
| SI2811998T1 (sl) | 2012-02-06 | 2019-02-28 | Merial, Inc. | Paraziticidni peroralni veterinarski sestavki, ki obsegajo sistemsko delujoče učinkovine, postopki in njihove uporabe |
| JO3626B1 (ar) | 2012-02-23 | 2020-08-27 | Merial Inc | تركيبات موضعية تحتوي على فيبرونيل و بيرميثرين و طرق استخدامها |
| AU2013241853B2 (en) | 2012-03-28 | 2017-11-09 | Intervet International B.V. | Heteroaryl compounds with A-cyclic bridging unit |
| US9260441B2 (en) | 2012-03-28 | 2016-02-16 | Intervet Inc. | Heteroaryl compounds with cyclic bridging unit |
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| ES2893777T3 (es) | 2012-11-20 | 2022-02-10 | Boehringer Ingelheim Animal Health Usa Inc | Compuestos y composiciones antihelmínticas y procedimiento de utilización de los mismos |
| WO2014099837A1 (en) | 2012-12-18 | 2014-06-26 | E. I. Du Pont De Nemours And Company | Sulfonamide anthelmintics |
| EP3063144B1 (en) | 2013-11-01 | 2021-09-08 | Boehringer Ingelheim Animal Health USA Inc. | Antiparasitic and pesticidal isoxazoline compounds |
| EP3131398B1 (en) | 2014-04-17 | 2019-10-23 | Boehringer Ingelheim Animal Health USA Inc. | Use of malononitrile compounds for protecting animals from parasites |
| CN106536518B (zh) | 2014-05-19 | 2020-05-12 | 勃林格殷格翰动物保健美国公司 | 驱蠕虫化合物 |
| EP3157912B1 (en) | 2014-06-19 | 2019-02-20 | Merial, Inc. | Parasiticidal compositions comprising indole derivatives, methods and uses thereof |
| WO2016069983A1 (en) | 2014-10-31 | 2016-05-06 | Merial, Inc. | Parasiticidal composition comprising fipronil |
| UY36570A (es) | 2015-02-26 | 2016-10-31 | Merial Inc | Formulaciones inyectables de acción prolongada que comprenden un agente activo isoxazolina, métodos y usos de las mismas |
| PL3298027T3 (pl) | 2015-05-20 | 2021-11-08 | Boehringer Ingelheim Animal Health USA Inc. | Przeciwrobacze związki depsipeptydów |
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| CN111542602B (zh) | 2017-09-29 | 2025-03-11 | 维多利亚联结有限公司 | 多节孢酸(Nodulisporic acid)的异源生物合成 |
| WO2019157241A1 (en) | 2018-02-08 | 2019-08-15 | Boehringer Ingelheim Animal Health USA Inc. | Parasiticidal compositions comprising eprinomectin and praziquantel, methods and uses thereof |
| WO2020002593A1 (en) | 2018-06-29 | 2020-01-02 | Intervet International B.V. | Compound for use against helminthic infection |
| AU2019301510B2 (en) | 2018-07-09 | 2024-06-13 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Anthelminthic heterocyclic compounds |
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| US20230110397A1 (en) | 2019-12-18 | 2023-04-13 | Intervet Inc. | Anthelmintic compounds comprising azaindoles structure |
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| PH12022553222A1 (en) | 2020-05-29 | 2024-02-12 | Boehringer Ingelheim Animal Health Usa Inc | Anthelmintic heterocyclic compounds |
| CA3203279A1 (en) | 2020-12-11 | 2022-06-16 | Intervet International B.V. | Anthelmintic compounds comprising a thienopyridine structure |
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| JP2025507585A (ja) | 2022-02-17 | 2025-03-21 | ベーリンガー インゲルハイム フェトメディカ ゲーエムベーハー | 流体製品メーラーを提供する方法及びシステム |
| WO2025027117A1 (en) | 2023-08-02 | 2025-02-06 | Intervet International B.V. | Carboxamide-4-quinoline compounds with anthelmintic activity |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE434277B (sv) * | 1976-04-19 | 1984-07-16 | Merck & Co Inc | Sett att framstella nya antihelmintiskt verkande foreningar genom odling av streptomyces avermitilis |
| US4199569A (en) * | 1977-10-03 | 1980-04-22 | Merck & Co., Inc. | Selective hydrogenation products of C-076 compounds and derivatives thereof |
| US4378353A (en) * | 1981-02-17 | 1983-03-29 | Merck & Co., Inc. | Novel C-076 compounds |
| DE3611168C2 (de) * | 1985-04-02 | 1994-01-20 | Asahi Chemical Ind | Hydroxybenzoesäurephenylester, deren Herstellung und deren Verwendung als physiologisch wirksame Substanzen |
| US4873247A (en) * | 1987-11-27 | 1989-10-10 | Goegelman Robert T | Derivatives of paraherquamide isolated from a fermentation broth active as antiparasitic agents |
| JP2805564B2 (ja) * | 1992-08-13 | 1998-09-30 | 明治製菓株式会社 | 新規物質ｐｆ１１０１ｂ物質及びその製造法 |
| US5399582A (en) * | 1993-11-01 | 1995-03-21 | Merck & Co., Inc. | Antiparasitic agents |
-
1993
- 1993-11-01 US US08/146,638 patent/US5399582A/en not_active Expired - Lifetime
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1994
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- 1994-10-27 CA CA002174645A patent/CA2174645C/en not_active Expired - Lifetime
- 1994-10-27 CN CN94194524A patent/CN1046943C/zh not_active Expired - Lifetime
- 1994-10-27 NZ NZ275339A patent/NZ275339A/en not_active IP Right Cessation
- 1994-10-27 DK DK94932063T patent/DK0726902T3/da active
- 1994-10-27 JP JP51328695A patent/JP3557212B2/ja not_active Expired - Lifetime
- 1994-10-27 EP EP94932063A patent/EP0726902B1/en not_active Expired - Lifetime
- 1994-10-27 SK SK539-96A patent/SK281510B6/sk not_active IP Right Cessation
- 1994-10-27 PL PL94314190A patent/PL178879B1/pl unknown
- 1994-10-27 AU AU80929/94A patent/AU688405B2/en not_active Expired
- 1994-10-27 AT AT94932063T patent/ATE188476T1/de active
- 1994-10-27 RU RU96112175A patent/RU2139874C1/ru active
- 1994-10-27 WO PCT/US1994/012302 patent/WO1995012599A1/en active IP Right Grant
- 1994-10-27 ES ES94932063T patent/ES2143558T3/es not_active Expired - Lifetime
- 1994-10-27 KR KR1019960702262A patent/KR100333017B1/ko not_active Expired - Lifetime
- 1994-10-27 CZ CZ961249A patent/CZ286032B6/cs not_active IP Right Cessation
- 1994-10-27 DE DE69422526T patent/DE69422526T2/de not_active Expired - Lifetime
- 1994-10-27 HU HU9601138A patent/HU221276B1/hu unknown
- 1994-10-31 ZA ZA948542A patent/ZA948542B/xx unknown
- 1994-12-20 US US08/359,666 patent/US5614546A/en not_active Expired - Lifetime
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1996
- 1996-04-30 NO NO19961748A patent/NO315942B1/no not_active IP Right Cessation
- 1996-04-30 FI FI961839A patent/FI110871B/fi not_active IP Right Cessation
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1999
- 1999-04-24 CN CN99106438A patent/CN1082543C/zh not_active Expired - Lifetime
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2000
- 2000-01-27 GR GR20000400187T patent/GR3032493T3/el unknown
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2001
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Owner name: MERCK SHARP & DOHME CORP. Free format text: MERCK SHARP & DOHME CORP. |
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| PC | Transfer of assignment of patent |
Owner name: MERCK SHARP & DOHME CORP. |
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| MA | Patent expired |