DD223148A5 - Verfahren zur herstellung von gem-diaminoal-kanderivaten - Google Patents

Verfahren zur herstellung von gem-diaminoal-kanderivaten Download PDF

Info

Publication number
DD223148A5
DD223148A5 DD84263717A DD26371784A DD223148A5 DD 223148 A5 DD223148 A5 DD 223148A5 DD 84263717 A DD84263717 A DD 84263717A DD 26371784 A DD26371784 A DD 26371784A DD 223148 A5 DD223148 A5 DD 223148A5
Authority
DD
German Democratic Republic
Prior art keywords
formula
item
product
aspartyl
hydrogen
Prior art date
Application number
DD84263717A
Other languages
German (de)
English (en)
Inventor
Michael St Verlander
William D Fuller
Murray Goodman
Original Assignee
Cumberland Packing Corp
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
Application filed by Cumberland Packing Corp filed Critical Cumberland Packing Corp
Publication of DD223148A5 publication Critical patent/DD223148A5/de

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07KPEPTIDES
    • C07K5/00Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/06Dipeptides
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/03Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by addition of hydroxy groups to unsaturated carbon-to-carbon bonds, e.g. with the aid of H2O2
    • C07C29/04Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by addition of hydroxy groups to unsaturated carbon-to-carbon bonds, e.g. with the aid of H2O2 by hydration of carbon-to-carbon double bonds
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/44Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q11/00Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C13/00Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
    • C07C13/02Monocyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
    • C07C13/08Monocyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with a five-membered ring
    • C07C13/10Monocyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with a five-membered ring with a cyclopentane ring
    • C07C13/11Monocyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with a five-membered ring with a cyclopentane ring substituted by unsaturated hydrocarbon groups
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/36Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal
    • C07C29/38Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones
    • C07C29/40Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones with compounds containing carbon-to-metal bonds
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/68Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/385Saturated compounds containing a keto group being part of a ring
    • C07C49/395Saturated compounds containing a keto group being part of a ring of a five-membered ring
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C53/00Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
    • C07C53/126Acids containing more than four carbon atoms
    • C07C53/128Acids containing more than four carbon atoms the carboxylic group being bound to a carbon atom bound to at least two other carbon atoms, e.g. neo-acids
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C53/00Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
    • C07C53/132Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen containing rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C53/00Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
    • C07C53/38Acyl halides
    • C07C53/42Acyl halides of acids containing three or more carbon atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C53/00Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
    • C07C53/38Acyl halides
    • C07C53/44Acyl halides containing rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C61/00Compounds having carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C07C61/06Saturated compounds having a carboxyl group bound to a five-membered ring
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C61/00Compounds having carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C07C61/08Saturated compounds having a carboxyl group bound to a six-membered ring
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C61/00Compounds having carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C07C61/15Saturated compounds containing halogen
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D331/00Heterocyclic compounds containing rings of less than five members, having one sulfur atom as the only ring hetero atom
    • C07D331/04Four-membered rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00Systems containing only non-condensed rings
    • C07C2601/06Systems containing only non-condensed rings with a five-membered ring
    • C07C2601/08Systems containing only non-condensed rings with a five-membered ring the ring being saturated
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00Systems containing at least three condensed rings
    • C07C2603/02Ortho- or ortho- and peri-condensed systems
    • C07C2603/04Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/06Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
    • C07C2603/10Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
    • C07C2603/12Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
    • C07C2603/18Fluorenes; Hydrogenated fluorenes

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Oral & Maxillofacial Surgery (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Biochemistry (AREA)
  • Biophysics (AREA)
  • Genetics & Genomics (AREA)
  • Medicinal Chemistry (AREA)
  • Molecular Biology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Seasonings (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Saccharide Compounds (AREA)
  • Peptides Or Proteins (AREA)
  • Cephalosporin Compounds (AREA)
  • Confectionery (AREA)
  • Medicinal Preparation (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
DD84263717A 1983-06-13 1984-06-01 Verfahren zur herstellung von gem-diaminoal-kanderivaten DD223148A5 (de)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US06/503,853 US4571345A (en) 1983-06-13 1983-06-13 1,1-Diaminoalkane derived sweeteners

Publications (1)

Publication Number Publication Date
DD223148A5 true DD223148A5 (de) 1985-06-05

Family

ID=24003790

Family Applications (1)

Application Number Title Priority Date Filing Date
DD84263717A DD223148A5 (de) 1983-06-13 1984-06-01 Verfahren zur herstellung von gem-diaminoal-kanderivaten

Country Status (21)

Country Link
US (1) US4571345A (es)
EP (2) EP0242896A3 (es)
JP (1) JPS59231050A (es)
KR (1) KR910000406B1 (es)
AT (1) ATE47385T1 (es)
AU (1) AU567944B2 (es)
CA (1) CA1221683A (es)
DD (1) DD223148A5 (es)
DE (1) DE3480200D1 (es)
DK (1) DK287284A (es)
ES (3) ES533690A0 (es)
FI (1) FI842356A (es)
GR (1) GR82143B (es)
HU (1) HU199393B (es)
IL (1) IL71447A (es)
MX (1) MX7621E (es)
NO (1) NO165491C (es)
NZ (1) NZ208075A (es)
PT (1) PT78712B (es)
SU (1) SU1494862A3 (es)
ZA (1) ZA843198B (es)

Families Citing this family (33)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4692512A (en) * 1984-07-13 1987-09-08 The Procter & Gamble Company Alpha-L-aspartyl-D-phenylglycine esters and amides useful as high intensity sweeteners
US4654219A (en) * 1984-12-27 1987-03-31 General Foods Corporation L-aminodicarboxylic-(O-cycloalkyl)-L-aminocarboxylate alkyl ester sweeteners
EP0196461A3 (en) * 1985-03-01 1987-04-22 Kyowa Hakko Kogyo Co., Ltd. Cyclopentane derivatives
US4636396A (en) * 1985-04-15 1987-01-13 General Foods Corporation Foodstuff with L-aminodicarboxylic acid gem-diamines
US4619782A (en) * 1985-04-15 1986-10-28 General Foods Corporation L-aminodicarboxylic acid gem-diamines
US4654439A (en) * 1985-05-24 1987-03-31 General Foods Corporation L-aminodicarboxylic acid amides of alkoxyalkylamines
US4666729A (en) * 1985-05-24 1987-05-19 General Foods Corporation Sweetening with L-aminodicarboxylic acid amides of alkoxyalkylamines
IL80577A0 (en) * 1985-11-27 1987-02-27 Schering Ag Process for the preparation of cyclopentanecarboxylic acid derivatives
US4692513A (en) * 1985-12-20 1987-09-08 The Procter & Gamble Company Alpha-L-aspartyl-D-heteroaromatic-substituted glycine esters and amides useful as high intensity sweeteners
DE3617605A1 (de) * 1986-05-23 1987-11-26 Schering Ag Verfahren zur herstellung von diaminoalkan-derivaten
FR2630304B1 (fr) * 1988-04-22 1990-08-31 Bernard Lyon I Universite Clau Derives n-hydrocarbones des acides aspartique et glutamique alpha-monoamides utiles comme agents edulcorants
IT1228451B (it) * 1989-02-22 1991-06-19 Sclavo S P A Siena Nuovi derivati diamminici geminali e loro impiego nelle sintesi di peptidi retro-inversi
WO1996028413A1 (en) * 1995-03-16 1996-09-19 Hoechst Celanese Corporation Synthesis of amidocarboxylic acid derivatives
BRPI0413324A (pt) 2003-08-06 2006-10-10 Senomyx Inc receptores de paladar hetero-oligoméricos t1r, linhas de células que expressam os ditos receptores, e compostos de paladar
US8524303B2 (en) * 2005-11-23 2013-09-03 The Coca-Cola Company High-potency sweetener composition with phytosterol and compositions sweetened therewith
US8940351B2 (en) * 2005-11-23 2015-01-27 The Coca-Cola Company Baked goods comprising high-potency sweetener
US8512789B2 (en) * 2005-11-23 2013-08-20 The Coca-Cola Company High-potency sweetener composition with dietary fiber and compositions sweetened therewith
US8435588B2 (en) * 2005-11-23 2013-05-07 The Coca-Cola Company High-potency sweetener composition with an anti-inflammatory agent and compositions sweetened therewith
US8377491B2 (en) * 2005-11-23 2013-02-19 The Coca-Cola Company High-potency sweetener composition with vitamin and compositions sweetened therewith
US8945652B2 (en) * 2005-11-23 2015-02-03 The Coca-Cola Company High-potency sweetener for weight management and compositions sweetened therewith
US20070116833A1 (en) * 2005-11-23 2007-05-24 The Coca-Cola Company High-Potency Sweetener Composition with Calcium and Compositions Sweetened Therewith
DK2526783T3 (en) * 2005-11-23 2017-02-06 Coca Cola Co Natural high-potency sweetener compositions with improved time profile and / or flavor profile
US20070116839A1 (en) * 2005-11-23 2007-05-24 The Coca-Cola Company High-Potency Sweetener Composition With C-Reactive Protein Reducing Substance and Compositions Sweetened Therewith
US20070116829A1 (en) * 2005-11-23 2007-05-24 The Coca-Cola Company Pharmaceutical Composition with High-Potency Sweetener
US8435587B2 (en) * 2005-11-23 2013-05-07 The Coca-Cola Company High-potency sweetener composition with long-chain primary aliphatic saturated alcohol and compositions sweetened therewith
US20070116800A1 (en) * 2005-11-23 2007-05-24 The Coca-Cola Company Chewing Gum with High-Potency Sweetener
US9101160B2 (en) * 2005-11-23 2015-08-11 The Coca-Cola Company Condiments with high-potency sweetener
US8940350B2 (en) * 2005-11-23 2015-01-27 The Coca-Cola Company Cereal compositions comprising high-potency sweeteners
US8367138B2 (en) * 2005-11-23 2013-02-05 The Coca-Cola Company Dairy composition with high-potency sweetener
US8524304B2 (en) * 2005-11-23 2013-09-03 The Coca-Cola Company High-potency sweetener composition with probiotics/prebiotics and compositions sweetened therewith
WO2007124152A2 (en) 2006-04-21 2007-11-01 Senomyx, Inc. Comestible compositions comprising high potency savory flavorants, and processes for producing them
US8017168B2 (en) * 2006-11-02 2011-09-13 The Coca-Cola Company High-potency sweetener composition with rubisco protein, rubiscolin, rubiscolin derivatives, ace inhibitory peptides, and combinations thereof, and compositions sweetened therewith
US7632792B2 (en) * 2007-11-16 2009-12-15 International Flavors & Fragrances Inc. Methyl cyclohexane carboxylates and their use in perfume compositions

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3492131A (en) * 1966-04-18 1970-01-27 Searle & Co Peptide sweetening agents
US4338346A (en) * 1978-12-21 1982-07-06 The Procter & Gamble Company Non-nutritive sweetener
US4411925A (en) * 1980-01-21 1983-10-25 Pfizer Inc. Branched amides of L-aspartyl-d-amino acid dipeptides
US4399163A (en) * 1980-11-05 1983-08-16 Pfizer Inc. Branched amides of L-aspartyl-D-amino acid dipeptides
US4423029A (en) * 1981-06-25 1983-12-27 The Procter & Gamble Company (S)-3-Amino-4-[(S,S)-1-(1-hydroxyethyl)alkyl amino]-4-oxo-butyric acid compounds suitable as non-nutritive sweetners

Also Published As

Publication number Publication date
GR82143B (es) 1984-12-13
AU567944B2 (en) 1987-12-10
ES8602596A1 (es) 1985-12-01
NZ208075A (en) 1988-06-30
IL71447A (en) 1988-01-31
AU2905884A (en) 1984-12-20
EP0128654A2 (en) 1984-12-19
DK287284D0 (da) 1984-06-12
IL71447A0 (en) 1984-07-31
ES533690A0 (es) 1985-12-01
HU199393B (en) 1990-02-28
MX7621E (es) 1990-03-27
PT78712B (en) 1986-07-15
ES552814A0 (es) 1987-04-16
FI842356A0 (fi) 1984-06-11
EP0242896A2 (en) 1987-10-28
US4571345A (en) 1986-02-18
ES8701714A1 (es) 1986-12-01
PT78712A (pt) 1985-01-01
NO165491B (no) 1990-11-12
HUT34430A (en) 1985-03-28
NO165491C (no) 1991-02-20
SU1494862A3 (ru) 1989-07-15
KR910000406B1 (ko) 1991-01-25
CA1221683A (en) 1987-05-12
EP0128654B1 (en) 1989-10-18
EP0242896A3 (en) 1988-11-30
NO842338L (no) 1984-12-14
DK287284A (da) 1984-12-14
FI842356A (fi) 1984-12-14
KR850002833A (ko) 1985-05-20
ES545627A0 (es) 1986-12-01
ES8704879A1 (es) 1987-04-16
EP0128654A3 (en) 1985-05-29
ATE47385T1 (de) 1989-11-15
ZA843198B (en) 1984-11-28
DE3480200D1 (de) 1989-11-23
JPS59231050A (ja) 1984-12-25

Similar Documents

Publication Publication Date Title
DD223148A5 (de) Verfahren zur herstellung von gem-diaminoal-kanderivaten
DE69303032T2 (de) Als süsstoffe brauchbare verbindungen und hir herstellungsverfahren
EP1219182B1 (de) Salze von L-Aminosäuren mit verbessertem Geschmack und ihre Herstellung
DE602004012214T2 (de) Aminosäurederivate und Süssungsmittel
CH661931A5 (de) N-substituierte amidoaminosaeuren, deren ester und amide.
CH643532A5 (de) Verfahren zur herstellung eines dipeptidesters.
EP0168112A2 (en) Alpha-L-aspartyl-D-phenylglycine esters and amides useful as high intensity sweeteners
DE2125065A1 (de) Verfahren zu der Herstellung von Asparagylaminosäure-Estern
DE2335010A1 (de) L-asparagyl-aminomalonsaeurealkylfenchyldiester, ihre herstellung und verwendung
DE69911061T2 (de) N-3, 3-dimethylbutyl-l-asparaginsäure und ihre ester, verfahren zur herstellung dieser und das verfahren um daraus n-[n-(3,3-dimethylbutyl)-l-alpha-aspartyl)-l-phenylalanin-1-methylester herzustellen
DE69938352T2 (de) N-alkylaspartyldipeptidester-derivate und süssstoffe
CH630892A5 (en) Process for preparing bestatin compounds.
US4692512A (en) Alpha-L-aspartyl-D-phenylglycine esters and amides useful as high intensity sweeteners
DE69830307T2 (de) Verfahren zur herstellung pharmakologisch verträglicher salze von n-(1(s)-ethoxycarbonyl-3-phenylpropyl)-l-alanyl aminosäuren
US4692513A (en) Alpha-L-aspartyl-D-heteroaromatic-substituted glycine esters and amides useful as high intensity sweeteners
DE69504651T2 (de) N-[n-(3,3-dimethylbutyl)-l-alpha-aspartyl]-l-hexahydrophenylalanine 1-methylester, als süssstoff verwendbar und deren herstellung
DE69203142T2 (de) Von l-Glutaminsäure abgeleitete Süssungsmittel, Verfahren zu ihrer Herstellung.
DE3419921C2 (es)
DE2560238C2 (de) Verfahren zur Herstellung von Desacyl-pepsidin
DE68901946T2 (de) Suessungsmittel, die sich von l-asparuginsaeure und l-glutaminsaeure-n-kohlenwasserstoffen ableiten.
DE69813801T2 (de) Verfahren zur herstellung von aspartamsalzen aus n-geschütztem aspartam
DE69010079T2 (de) Trifluoroketopeptidderivate, benutzbar als Hemmer von menschlicher Elastase aus Leukozyten.
DE3879349T2 (de) N-(l-aspartyl)aminoalkohol-derivate und diese enthaltende suessmittel.
AT394854B (de) Verfahren zur herstellung von n-l-alpha-aspartyl-l-phenylalanin(nieder)alkylestern
DE68928249T2 (de) Verfahren zur Trennung von Methylester von alpha-L-aspartyl-L-phenylalaninen

Legal Events

Date Code Title Description
ENJ Ceased due to non-payment of renewal fee