IL118221A - צפאלוספורינים מותמרים, תהליך להכנתם ותכשירי רוקחות המכילים אותם - Google Patents

צפאלוספורינים מותמרים, תהליך להכנתם ותכשירי רוקחות המכילים אותם

Info

Publication number
IL118221A
IL118221A IL11822196A IL11822196A IL118221A IL 118221 A IL118221 A IL 118221A IL 11822196 A IL11822196 A IL 11822196A IL 11822196 A IL11822196 A IL 11822196A IL 118221 A IL118221 A IL 118221A
Authority
IL
Israel
Prior art keywords
denotes
lower alkyl
formula
lactam
alkyl
Prior art date
Application number
IL11822196A
Other languages
English (en)
Other versions
IL118221A0 (en
Original Assignee
Biochemie Gmbh
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
Priority claimed from AT79495A external-priority patent/AT402820B/de
Priority claimed from AT99295A external-priority patent/AT402821B/de
Priority claimed from AT69896A external-priority patent/AT403283B/de
Priority claimed from AT73396A external-priority patent/AT403284B/de
Application filed by Biochemie Gmbh filed Critical Biochemie Gmbh
Priority to IL14144296A priority Critical patent/IL141442A/en
Publication of IL118221A0 publication Critical patent/IL118221A0/xx
Priority to IL14144201A priority patent/IL141442A0/xx
Publication of IL118221A publication Critical patent/IL118221A/he

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D501/00Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D501/00Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
    • C07D501/14Compounds having a nitrogen atom directly attached in position 7
    • C07D501/16Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
    • C07D501/207-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
    • C07D501/247-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with hydrocarbon radicals, substituted by hetero atoms or hetero rings, attached in position 3
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N3/00Preservation of plants or parts thereof, e.g. inhibiting evaporation, improvement of the appearance of leaves or protection against physical influences such as UV radiation using chemical compositions; Grafting wax
    • A01N3/02Keeping cut flowers fresh chemically
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/02Saturated carboxylic acids or thio analogues thereof; Derivatives thereof
    • A01N37/04Saturated carboxylic acids or thio analogues thereof; Derivatives thereof polybasic
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/44Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
    • A01N37/46N-acyl derivatives
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N41/00Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
    • A01N41/02Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
    • A01N41/04Sulfonic acids; Derivatives thereof
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N57/00Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
    • A01N57/18Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
    • A01N57/20Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing acyclic or cycloaliphatic radicals
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/54Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
    • A61K31/542Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame ortho- or peri-condensed with heterocyclic ring systems
    • A61K31/545Compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins, cefaclor, or cephalexine
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04Antibacterial agents
    • CCHEMISTRY; METALLURGY
    • C05FERTILISERS; MANUFACTURE THEREOF
    • C05FORGANIC FERTILISERS NOT COVERED BY SUBCLASSES C05B, C05C, e.g. FERTILISERS FROM WASTE OR REFUSE
    • C05F11/00Other organic fertilisers
    • CCHEMISTRY; METALLURGY
    • C05FERTILISERS; MANUFACTURE THEREOF
    • C05FORGANIC FERTILISERS NOT COVERED BY SUBCLASSES C05B, C05C, e.g. FERTILISERS FROM WASTE OR REFUSE
    • C05F11/00Other organic fertilisers
    • C05F11/10Fertilisers containing plant vitamins or hormones
    • CCHEMISTRY; METALLURGY
    • C05FERTILISERS; MANUFACTURE THEREOF
    • C05GMIXTURES OF FERTILISERS COVERED INDIVIDUALLY BY DIFFERENT SUBCLASSES OF CLASS C05; MIXTURES OF ONE OR MORE FERTILISERS WITH MATERIALS NOT HAVING A SPECIFIC FERTILISING ACTIVITY, e.g. PESTICIDES, SOIL-CONDITIONERS, WETTING AGENTS; FERTILISERS CHARACTERISED BY THEIR FORM
    • C05G3/00Mixtures of one or more fertilisers with additives not having a specially fertilising activity
    • CCHEMISTRY; METALLURGY
    • C05FERTILISERS; MANUFACTURE THEREOF
    • C05GMIXTURES OF FERTILISERS COVERED INDIVIDUALLY BY DIFFERENT SUBCLASSES OF CLASS C05; MIXTURES OF ONE OR MORE FERTILISERS WITH MATERIALS NOT HAVING A SPECIFIC FERTILISING ACTIVITY, e.g. PESTICIDES, SOIL-CONDITIONERS, WETTING AGENTS; FERTILISERS CHARACTERISED BY THEIR FORM
    • C05G5/00Fertilisers characterised by their form
    • C05G5/20Liquid fertilisers
    • C05G5/23Solutions
    • YGENERAL 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
    • Y02TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02EREDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E50/00Technologies for the production of fuel of non-fossil origin
    • Y02E50/30Fuel from waste, e.g. synthetic alcohol or diesel
    • YGENERAL 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
    • Y02TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02WCLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO WASTEWATER TREATMENT OR WASTE MANAGEMENT
    • Y02W30/00Technologies for solid waste management
    • Y02W30/40Bio-organic fraction processing; Production of fertilisers from the organic fraction of waste or refuse

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Dentistry (AREA)
  • Engineering & Computer Science (AREA)
  • Wood Science & Technology (AREA)
  • Plant Pathology (AREA)
  • Zoology (AREA)
  • Agronomy & Crop Science (AREA)
  • Environmental Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Toxicology (AREA)
  • Botany (AREA)
  • Medicinal Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oncology (AREA)
  • Communicable Diseases (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Cephalosporin Compounds (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
IL11822196A 1995-05-11 1996-05-10 צפאלוספורינים מותמרים, תהליך להכנתם ותכשירי רוקחות המכילים אותם IL118221A (he)

Priority Applications (2)

Application Number Priority Date Filing Date Title
IL14144296A IL141442A (en) 1995-05-11 1996-05-10 Guanidine derivatives of cephalosporins
IL14144201A IL141442A0 (en) 1995-05-11 2001-02-15 Guanidine derivatives useful in the preparation of substituted cephalosporines

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
AT79495A AT402820B (de) 1995-05-11 1995-05-11 Organische verbindungen
AT99295A AT402821B (de) 1995-06-12 1995-06-12 Organische verbindungen
AT69896A AT403283B (de) 1996-04-17 1996-04-17 3-methylimino-3-cephemderivate
AT73396A AT403284B (de) 1996-04-23 1996-04-23 3-methylimino-3-cephemderivate

Publications (2)

Publication Number Publication Date
IL118221A0 IL118221A0 (en) 1996-09-12
IL118221A true IL118221A (he) 2004-06-01

Family

ID=27421316

Family Applications (2)

Application Number Title Priority Date Filing Date
IL13253296A IL132532A (en) 1995-05-11 1996-05-10 Intermediates for the preparation of substituted cephalosporins
IL11822196A IL118221A (he) 1995-05-11 1996-05-10 צפאלוספורינים מותמרים, תהליך להכנתם ותכשירי רוקחות המכילים אותם

Family Applications Before (1)

Application Number Title Priority Date Filing Date
IL13253296A IL132532A (en) 1995-05-11 1996-05-10 Intermediates for the preparation of substituted cephalosporins

Country Status (30)

Country Link
US (2) US6531465B1 (he)
EP (2) EP0824535B1 (he)
JP (2) JPH11506429A (he)
KR (1) KR100451336B1 (he)
CN (1) CN1142937C (he)
AR (1) AR001931A1 (he)
AT (2) ATE292637T1 (he)
AU (1) AU712814B2 (he)
BR (1) BR9608517A (he)
CA (1) CA2219656C (he)
CO (1) CO4750666A1 (he)
CY (1) CY2445B1 (he)
CZ (1) CZ352997A3 (he)
DE (2) DE69634581T2 (he)
DK (1) DK0824535T3 (he)
ES (1) ES2193246T3 (he)
HK (1) HK1008993A1 (he)
HU (1) HUP9801387A3 (he)
IL (2) IL132532A (he)
MX (1) MX9708696A (he)
NO (1) NO326126B1 (he)
NZ (1) NZ308518A (he)
PE (1) PE8398A1 (he)
PL (1) PL193133B1 (he)
PT (1) PT824535E (he)
RU (1) RU2183212C2 (he)
SK (1) SK284962B6 (he)
TW (1) TW452579B (he)
WO (1) WO1996035692A1 (he)
ZA (1) ZA963758B (he)

Families Citing this family (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20020115852A1 (en) * 1997-04-01 2002-08-22 Gerd Ascher Antibacterial substituted 7-acylamino-3-(methylhydrazono) methyl-cephalosporins and intermediates
EP0973780B1 (en) * 1997-04-01 2003-07-02 Biochemie Gesellschaft M.B.H. Antibacterial substituted 7-acylamino -3-(methylhydrazono) methyl-cephalosporins and intermediates
AT405180B (de) * 1997-04-01 1999-06-25 Biochemie Gmbh Neue derivate von substituierten 3-cephem-4-carbonsäurederivaten und verfahren zu deren herstellung
AT406772B (de) * 1998-03-23 2000-08-25 Biochemie Gmbh Antibakterielle 7-acylamino-3-iminomethyl- cephalosporine und verfahren zu deren herstellung
JP4803935B2 (ja) 1999-10-08 2011-10-26 アフィニアム・ファーマシューティカルズ・インコーポレイテッド Fabi阻害剤
KR100739830B1 (ko) * 2001-03-23 2007-07-13 주식회사 하원제약 세파로스포린 유도체의 제조방법
ATE420640T1 (de) * 2001-04-06 2009-01-15 Affinium Pharm Inc Fab-i-inhibitoren
PE20040657A1 (es) * 2002-07-15 2004-11-08 Sandoz Ag Cefalosporinas
US7790709B2 (en) * 2002-12-06 2010-09-07 Affinium Pharmaceuticals, Inc. Heterocyclic compounds, methods of making them and their use in therapy
CA2519429C (en) * 2003-03-17 2013-08-06 Affinium Pharmaceuticals, Inc. Pharmaceutical compositions comprising inhibitors of fab i and further antibiotics
DK1828167T3 (da) 2004-06-04 2014-10-20 Debiopharm Int Sa Acrylamidderivater som antibiotiske midler
US20090156578A1 (en) * 2005-12-05 2009-06-18 PAULS Henry 3-Heterocyclylacrylamide Compounds as Fab I Inhibitors and Antibacterial Agents
CA2658506C (en) 2006-07-20 2016-01-26 Affinium Pharmaceuticals, Inc. Acrylamide derivatives as fab 1 inhibitors
US8263613B2 (en) * 2007-02-16 2012-09-11 Affinium Pharmaceuticals, Inc. Salts, prodrugs and polymorphs of fab I inhibitors
NZ702695A (en) 2012-06-19 2015-10-30 Debiopharm Int Sa Prodrug derivatives of (e)-n-methyl-n-((3-methylbenzofuran-2-yl)methyl)-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylamide
PT3419628T (pt) 2016-02-26 2021-01-05 Debiopharm Int Sa Medicamento para o tratamento de infeções do pé diabético
US20220332728A1 (en) * 2019-09-06 2022-10-20 Nabriva Therapeutics GmbH Siderophore cephalosporin conjugates and uses thereof
CN110590814A (zh) * 2019-09-29 2019-12-20 天津力生制药股份有限公司 一种生产头孢唑林钠产生的二聚体杂质的合成方法

Family Cites Families (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2333263A1 (de) * 1972-07-07 1974-01-24 Ciba Geigy Ag 7 beta-amino-3-oximinomethyl-cephem-4carbonsaeureverbindungen und verfahren zu ihrer herstellung
JPS5417030B2 (he) 1972-12-06 1979-06-27
DE2262500A1 (de) * 1972-12-20 1973-07-05 Lilly Co Eli 3-oxyiminomethylcephalosporinverbindungen
US4053469A (en) 1973-02-28 1977-10-11 Shionogi & Co., Ltd. Intermediates for the preparation of 7-acylamino-3-oxyiminomethyl-3-cephem-4-carboxylic acids
JPS49109391A (he) * 1973-02-28 1974-10-17
JPS49124091A (he) * 1973-03-30 1974-11-27
JPS5013389A (he) * 1973-06-08 1975-02-12
JPS5093989A (he) 1973-10-25 1975-07-26
JPS5076085A (he) * 1973-10-31 1975-06-21
JPS5083391A (he) * 1973-11-28 1975-07-05
JPS5715597B2 (he) * 1973-12-20 1982-03-31
JPS50131982A (he) * 1974-04-05 1975-10-18
US4101658A (en) 1975-06-04 1978-07-18 Shionogi & Co., Ltd. Antibacterial hydrazono cephalosporins
JPS5283865A (en) * 1976-01-01 1977-07-13 Takeda Chem Ind Ltd Cephalosporin derivatives
JPS5470294A (en) * 1977-11-09 1979-06-05 Takeda Chem Ind Ltd Cephalosporin derivative and its preparation
US4258181A (en) * 1978-09-05 1981-03-24 American Cyanamid Company Substituted 9,10-anthracenebishydrazones
JPS56118085A (en) * 1980-02-25 1981-09-16 Takeda Chem Ind Ltd 2-methylcephalosporin derivative and its preparation
US20020115852A1 (en) * 1997-04-01 2002-08-22 Gerd Ascher Antibacterial substituted 7-acylamino-3-(methylhydrazono) methyl-cephalosporins and intermediates

Also Published As

Publication number Publication date
ATE292637T1 (de) 2005-04-15
NO975151D0 (no) 1997-11-10
CA2219656C (en) 2008-08-19
NO975151L (no) 1997-11-10
DE69634581T2 (de) 2006-02-09
AU712814B2 (en) 1999-11-18
CO4750666A1 (es) 1999-03-31
IL118221A0 (en) 1996-09-12
DE69626389D1 (de) 2003-04-03
MX9708696A (es) 1998-08-30
ATE233268T1 (de) 2003-03-15
AU5818496A (en) 1996-11-29
WO1996035692A1 (en) 1996-11-14
HUP9801387A3 (en) 2000-12-28
EP1221446A1 (en) 2002-07-10
CN1186494A (zh) 1998-07-01
CZ352997A3 (cs) 1998-02-18
EP0824535B1 (en) 2003-02-26
US20030191105A1 (en) 2003-10-09
CA2219656A1 (en) 1996-11-14
BR9608517A (pt) 1999-06-08
KR100451336B1 (ko) 2005-01-17
DE69634581D1 (de) 2005-05-12
JPH11506429A (ja) 1999-06-08
PT824535E (pt) 2003-07-31
EP1221446B1 (en) 2005-04-06
NO326126B1 (no) 2008-09-29
SK150397A3 (en) 1998-03-04
PL193133B1 (pl) 2007-01-31
PE8398A1 (es) 1998-03-13
ZA963758B (en) 1997-11-10
PL323233A1 (en) 1998-03-16
DE69626389T2 (de) 2003-10-09
NZ308518A (en) 2000-01-28
KR19990014669A (ko) 1999-02-25
RU2183212C2 (ru) 2002-06-10
ES2193246T3 (es) 2003-11-01
TW452579B (en) 2001-09-01
CN1142937C (zh) 2004-03-24
JP2007023046A (ja) 2007-02-01
DK0824535T3 (da) 2003-06-02
AR001931A1 (es) 1997-12-10
HUP9801387A2 (hu) 1999-01-28
US6531465B1 (en) 2003-03-11
US7317101B2 (en) 2008-01-08
EP0824535A1 (en) 1998-02-25
CY2445B1 (en) 2004-11-12
HK1008993A1 (en) 1999-05-21
SK284962B6 (sk) 2006-03-02
IL132532A (en) 2003-06-24

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MM9K Patent not in force due to non-payment of renewal fees