GB1492494A - Derivatives of 4-aminopiperidine - Google Patents

Derivatives of 4-aminopiperidine

Info

Publication number
GB1492494A
GB1492494A GB23226/75A GB2322675A GB1492494A GB 1492494 A GB1492494 A GB 1492494A GB 23226/75 A GB23226/75 A GB 23226/75A GB 2322675 A GB2322675 A GB 2322675A GB 1492494 A GB1492494 A GB 1492494A
Authority
GB
United Kingdom
Prior art keywords
alkyl
group
hydrogen atom
aralkyl
formula
Prior art date
Legal status (The legal status 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 status listed.)
Expired
Application number
GB23226/75A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Novartis AG
Sankyo Co Ltd
Original Assignee
Ciba Geigy AG
Sankyo Co Ltd
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 Ciba Geigy AG, Sankyo Co Ltd filed Critical Ciba Geigy AG
Priority to GB23226/75A priority Critical patent/GB1492494A/en
Priority to SE7605286*7A priority patent/SE7605286L/en
Priority to DE19762621870 priority patent/DE2621870A1/en
Priority to CH644776A priority patent/CH601401A5/xx
Priority to FR7615923A priority patent/FR2333795A1/en
Priority to BE167341A priority patent/BE842236A/en
Priority to AT389276A priority patent/ATA389276A/en
Priority to JP51061548A priority patent/JPS51143673A/en
Priority to NL7605796A priority patent/NL7605796A/en
Priority to FR7700701A priority patent/FR2357546A1/en
Priority to FR7700702A priority patent/FR2333797A1/en
Priority to US05/853,658 priority patent/US4191683A/en
Publication of GB1492494A publication Critical patent/GB1492494A/en
Priority to JP59065524A priority patent/JPS6046142B2/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
    • C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
    • C07D221/20—Spiro-condensed ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D211/56—Nitrogen atoms
    • C07D211/58—Nitrogen atoms attached in position 4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D211/72—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D211/74—Oxygen atoms
    • C07D211/76—Oxygen atoms attached in position 2 or 6
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/92—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with a hetero atom directly attached to the ring nitrogen atom
    • C07D211/94—Oxygen atom, e.g. piperidine N-oxide
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
    • C07F9/576—Six-membered rings
    • C07F9/58—Pyridine rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
    • C07F9/576—Six-membered rings
    • C07F9/59—Hydrogenated pyridine rings
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
    • C08K5/3432—Six-membered rings
    • C08K5/3435—Piperidines

Abstract

1492494 Piperidine derivatives CIBAGEIGY AG 14 May 1976 [28 May 1975] 23226/75 Heading C2C Novel piperidine derivatives of the Formula I or acid-addition salts thereof, wherein R<SP>1</SP> is a C 2-6 alkyl group, R<SP>2</SP> is a C 1-6 alkyl group, R<SP>3</SP> is a C 1-9 alkyl, phenyl, benzyl or phenethyl group and R<SP>4</SP> is a C 1-6 alkyl group or R<SP>3</SP> and R<SP>4</SP> together complete a cyclopentyl or cyclohexyl group, one of R<SP>5</SP> and R<SP>6</SP> is a C 1-5 alkyl, C 3-4 alkenyl, C 3-4 alkynyl or C 7-8 aralkyl group and the other is a hydrogen atom or a C 1-5 alkyl, C 3-4 alkenyl, C 3-4 alkynyl or C 7-8 aralkyl group, n is 1, 2 or 3, R<SP>7</SP> is a hydrogen atom or a C 1-12 alkyl, C 5-7 cycloalkyl or C 7-8 aralkyl group, or in some instances it is one of certain acyl groups, X is a hydrogen atom or an oxyl, C 1-8 alkyl, C 3-6 alkenyl, C 2-21 alkoxyalkyl, optionally substituted C 7-8 aralkyl, 2,3-epoxypropyl or C 1-12 aliphatic acyl group or a group of the formula -CH 2 COOR<SP>8</SP>, -CH 2 -CH(R<SP>9</SP>)OR<SP>10</SP>, -COOR<SP>11</SP> or -CONHR<SP>12</SP>, R<SP>8</SP> being a C 1-8 alkyl, C 3-6 alkenyl, phenyl, C 7-8 aralkyl or cyclohexyl group, R<SP>9</SP> being a hydrogen atom or a methyl or phenyl group, R<SP>10</SP> being a hydrogen atom or one of certain organic radicals, R<SP>11</SP> being a C 1-8 alkyl, phenyl. benzyl or cyclohexyl group and R<SP>12</SP> being a C 1-12 alkyl, C 6-10 aryl, optionally substituted by chlorine or C 1-4 alkyl, C 7-8 aralkyl or cyclohexyl group and Y is a hydrogen atom or one of various organic radicals of valency n or, when n is 1, Y and R<SP>7</SP> together can complete a succinimide, maleimide or phthalimide ring, are obtained from the appropriately substituted piperidines of the Formula III below by various methods. Amino-piperidines of the Formula III wherein R<SP>7</SP> is a hydrogen atom or an alkyl or cycloalkyl group, are obtained by catalytically hydrogenating appropriate 4-oxo-piperidines in the presences of ammonia or amines of the formula R<SP>7</SP>NH 2 . The above compounds of Formula I are useful as stabilizers for polymers. 2,6 - Diethyl - 2,3,6 - trimethyl - 4 - piperidone is obtained by reacting 2,4,6-triethyl-2,6-dimethyl 1,2,5,6-tetrahydro pyrimidine with ammonium bromide and methanol.
GB23226/75A 1975-05-28 1975-05-28 Derivatives of 4-aminopiperidine Expired GB1492494A (en)

Priority Applications (13)

Application Number Priority Date Filing Date Title
GB23226/75A GB1492494A (en) 1975-05-28 1975-05-28 Derivatives of 4-aminopiperidine
SE7605286*7A SE7605286L (en) 1975-05-28 1976-05-10 NEW DERIVATIVES OF 4-AMINOPIPERIDINE
DE19762621870 DE2621870A1 (en) 1975-05-28 1976-05-17 NEW DERIVATIVES OF 4-AMINOPIPERIDINE
CH644776A CH601401A5 (en) 1975-05-28 1976-05-21
FR7615923A FR2333795A1 (en) 1975-05-28 1976-05-26 4-AMINOPIPERIDINE DERIVATIVES USED TO STABILIZE POLYMERIC MATERIALS
BE167341A BE842236A (en) 1975-05-28 1976-05-26 4-AMINOPIPERIDINE DERIVATIVES USED TO STABILIZE POLYMERIC MATERIALS
AT389276A ATA389276A (en) 1975-05-28 1976-05-26 METHOD FOR STABILIZING ORGANIC POLYMERS
JP51061548A JPS51143673A (en) 1975-05-28 1976-05-27 New derivatives of 4-aminopiperidines
NL7605796A NL7605796A (en) 1975-05-28 1976-05-28 PROCEDURE FOR STABILIZING ORGANIC POLYMERS AGAINST DEGRADATION CAUSED BY LIGHT AND 4-AMINOPIPERIDINE DERIVATIVES.
FR7700701A FR2357546A1 (en) 1975-05-28 1977-01-12 BIS (4-AMINOPIPERIDINE) DERIVATIVES USED TO STABILIZE POLYMERIC MATERIALS
FR7700702A FR2333797A1 (en) 1975-05-28 1977-01-12 TRIS (4-AMINOPIPERIDINE) DERIVATIVES USED TO STABILIZE POLYMERIC MATERIALS
US05/853,658 US4191683A (en) 1975-05-28 1977-11-21 Derivatives of 4-aminopiperidine as stabilizers for polymers
JP59065524A JPS6046142B2 (en) 1975-05-28 1984-04-02 Stabilized organic polymer composition

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB23226/75A GB1492494A (en) 1975-05-28 1975-05-28 Derivatives of 4-aminopiperidine

Publications (1)

Publication Number Publication Date
GB1492494A true GB1492494A (en) 1977-11-23

Family

ID=10192206

Family Applications (1)

Application Number Title Priority Date Filing Date
GB23226/75A Expired GB1492494A (en) 1975-05-28 1975-05-28 Derivatives of 4-aminopiperidine

Country Status (9)

Country Link
JP (2) JPS51143673A (en)
AT (1) ATA389276A (en)
BE (1) BE842236A (en)
CH (1) CH601401A5 (en)
DE (1) DE2621870A1 (en)
FR (3) FR2333795A1 (en)
GB (1) GB1492494A (en)
NL (1) NL7605796A (en)
SE (1) SE7605286L (en)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0034829A1 (en) * 1980-02-22 1981-09-02 Montedison S.p.A. Tetra-alkyl-4-amino-piperidine containing acids and corresponding salts and use thereof as stabilizers for polymers
JPS61241335A (en) * 1985-04-17 1986-10-27 Sumitomo Chem Co Ltd Stabilizer for synthetic resin
GB2179940A (en) * 1985-09-03 1987-03-18 Basf Ag Furan-3-carboxylic acid derivatives
GB2180537A (en) * 1985-09-13 1987-04-01 Sandoz Ltd 4-oxalamido-2,2,6,6-tetraalkylpiperidine compounds and compositions
FR2606407A1 (en) * 1986-11-07 1988-05-13 Sandoz Sa NOVEL TETRAALKYLPIPERIDINES, THEIR PREPARATION AND THEIR USE AS STABILIZERS OF POLYMERIC MATERIALS
FR2672889A1 (en) * 1991-02-19 1992-08-21 Sandoz Sa NOVEL TETRAALKYLPIPERIDINES, THEIR PREPARATION AND THEIR USE AS STABILIZERS OF POLYMER MATERIALS.
WO2004014999A1 (en) * 2002-08-07 2004-02-19 Ciba Specialty Chemicals Holding Inc. Beta-nucleating, light stabilizing agents for polypropylene
US6891008B2 (en) 2000-03-22 2005-05-10 Ciba Specialty Chemicals Corp. 2,2,6,6 diethyl-dimethyl-1-alkoxy-piperidine compounds and their corresponding 1-oxides

Families Citing this family (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2642446A1 (en) * 1976-09-21 1978-03-30 Bayer Ag METHYLOL DERIVATIVES OF 2,2,6,6-TETRAALKYLPIPERIDINE, THEIR PRODUCTION AND USE
US4144224A (en) * 1976-11-26 1979-03-13 Ciba-Geigy Corporation Phosphonate stabilizers
IT1088576B (en) * 1977-11-29 1985-06-10 Montedison Spa POLYMER STABILIZERS AND POLYMER COMPOSITIONS WITH THEM STABILIZED
IT1088581B (en) * 1977-12-02 1985-06-10 Montedison Spa POLYMER STABILIZERS AND POLYMER COMPOSITIONS WITH THEM STABILIZED
DE2920918A1 (en) * 1979-05-23 1980-11-27 Hoechst Ag COPOLYMERS SUBSTITUTED PIPERIDINE, THEIR PRODUCTION AND USE
DE3066156D1 (en) * 1979-06-21 1984-02-23 Ciba Geigy Ag Polyalkylpiperidyl ureas, their application as stabilizers and polymers thus stabilized
DE3003843A1 (en) * 1980-02-02 1981-08-13 Chemische Werke Hüls AG, 4370 Marl METHOD FOR PRODUCING 4-AMINO-2,2,6,6-TETRAMETHYL PIPERIDINE
US4348524A (en) * 1980-03-28 1982-09-07 Ciba-Geigy Corporation Amide derivatives of polyalkylpiperidines
US4326063A (en) * 1980-07-24 1982-04-20 The B. F. Goodrich Company High molecular weight piperidine derivatives as UV stabilizers
US4316837A (en) * 1980-09-10 1982-02-23 Carstab Corporation Polyalkylated 4-aminopiperidine derivatives as stabilizers for synthetic polymers
DE3111209A1 (en) * 1981-03-21 1982-09-30 Hoechst Ag, 6000 Frankfurt HIGH MOLECULAR PIPERIDING GROUP-CONTAINING ESTERS AND URETHANES, METHOD FOR THE PRODUCTION THEREOF, THEIR USE AS STABILIZERS FOR POLYMERS AND POLYMERS CONTAINING THESE COMPOUNDS
US4520171A (en) * 1982-05-05 1985-05-28 Hercules Incorporated Polymeric hindered amines
US4661594A (en) * 1984-02-29 1987-04-28 Ciba-Geigy Corporation Certain [(2,2,6,6-tetramethyl-4-piperidyl)amino]-1,3,2-dioxaphosphorinanes useful as stabilizers for protecting resins
US4605743A (en) * 1985-04-16 1986-08-12 Uniroyal Chemical Company, Inc. Process for the production of 2,2,6,6-tetraalkyl-4-piperidylamines
EP0253010B1 (en) * 1986-07-16 1992-12-02 The B.F. GOODRICH Company N-(substituted cyclic alkyleneimine)-alpha-(3,5-di-alkyl-4-hydroxy-phenyl)-alpha, alpha-dialkyl acetamides
JPH01121265A (en) * 1987-11-06 1989-05-12 Sankyo Co Ltd Production of aminopiperidine derivative
DE3738736A1 (en) * 1987-11-14 1989-05-24 Basf Ag 4-FORMYLAMINOPIPERIDE DERIVATIVES AND THE USE THEREOF AS STABILIZERS
DE58907159D1 (en) * 1988-06-14 1994-04-14 Ciba Geigy Process for the photochemical stabilization of undyed and dyed polypropylene fibers.
DE19704460A1 (en) * 1997-02-06 1998-08-13 Huels Chemische Werke Ag Continuous process for the production of 4-aminopiperidines
SG82601A1 (en) * 1998-03-09 2001-08-21 Ciba Sc Holding Ag 1-alkoxy-polyalkyl-piperidine derivatives and their use as polymerization regulators
WO2010023115A1 (en) * 2008-08-28 2010-03-04 Basf Se Stabilisers for inanimate organic materials

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0034829A1 (en) * 1980-02-22 1981-09-02 Montedison S.p.A. Tetra-alkyl-4-amino-piperidine containing acids and corresponding salts and use thereof as stabilizers for polymers
JPS61241335A (en) * 1985-04-17 1986-10-27 Sumitomo Chem Co Ltd Stabilizer for synthetic resin
GB2179940A (en) * 1985-09-03 1987-03-18 Basf Ag Furan-3-carboxylic acid derivatives
GB2179940B (en) * 1985-09-03 1989-08-31 Basf Ag Furan-3-carboxylic acid derivatives
GB2180537A (en) * 1985-09-13 1987-04-01 Sandoz Ltd 4-oxalamido-2,2,6,6-tetraalkylpiperidine compounds and compositions
GB2180537B (en) * 1985-09-13 1990-01-10 Sandoz Ltd Tetralkylpiperidine derivatives useful as stabilizers for polymeric materials
FR2606407A1 (en) * 1986-11-07 1988-05-13 Sandoz Sa NOVEL TETRAALKYLPIPERIDINES, THEIR PREPARATION AND THEIR USE AS STABILIZERS OF POLYMERIC MATERIALS
FR2672889A1 (en) * 1991-02-19 1992-08-21 Sandoz Sa NOVEL TETRAALKYLPIPERIDINES, THEIR PREPARATION AND THEIR USE AS STABILIZERS OF POLYMER MATERIALS.
US5306823A (en) * 1991-02-19 1994-04-26 Sandoz Ltd. 2,2,6,6-tetraalkylpiperidine compounds useful as light stabilizers
US6891008B2 (en) 2000-03-22 2005-05-10 Ciba Specialty Chemicals Corp. 2,2,6,6 diethyl-dimethyl-1-alkoxy-piperidine compounds and their corresponding 1-oxides
WO2004014999A1 (en) * 2002-08-07 2004-02-19 Ciba Specialty Chemicals Holding Inc. Beta-nucleating, light stabilizing agents for polypropylene

Also Published As

Publication number Publication date
SE7605286L (en) 1976-11-29
FR2333795A1 (en) 1977-07-01
BE842236A (en) 1976-11-26
DE2621870A1 (en) 1976-12-16
FR2357546A1 (en) 1978-02-03
JPS51143673A (en) 1976-12-10
NL7605796A (en) 1976-11-30
FR2333797A1 (en) 1977-07-01
CH601401A5 (en) 1978-07-14
FR2357546B1 (en) 1981-10-09
FR2333797B1 (en) 1980-10-03
JPS6241223B2 (en) 1987-09-02
ATA389276A (en) 1977-05-15
JPS6046142B2 (en) 1985-10-14
JPS59182826A (en) 1984-10-17
FR2333795B1 (en) 1978-08-25

Similar Documents

Publication Publication Date Title
GB1492494A (en) Derivatives of 4-aminopiperidine
CO4520230A1 (en) DERIVATIVES OF [3- (4-PHENYLPIPERACIN-1-IL) PROPYLAMINE, UNCLE AND OXYL] -PIRIDINE, PYRIMIDINE AND BENZENE AS ALPHA ANTAGONISTS 1- ADRENOCEPTORS
FI942252A (en) Piperazine
DE69020287T2 (en) Pleuromutiline.
ATE219766T1 (en) N-ACYLATED 4-AMINOPIPERIDINE DERIVATIVES AS ACTIVE COMPONENTS OF PERIPHERAL VASODILATION AGENTS
TW200503704A (en) N-(substituted arylmethyl)-4-(disubstituted methyl)piperidines and piperazines
EA199801006A1 (en) BICYCLIC AMINES AS INSECTICIDES
DE69323712T2 (en) INDOL DERIVATIVES FOR TREATING MIGRAINE
DE68911773T2 (en) Benzimidazole derivatives with pharmacological activity.
GB1325775A (en) Phosphorus-containing piperidine derivatives and their use as stabilisers for polymerica material
GB1496844A (en) Stabilization of polymers
ES8800285A1 (en) A process for preparing thermically stable olefinic polymers.
DE3067006D1 (en) Insecticides and piperidine derivative
KR950702978A (en) Amide derivatives
AU3648093A (en) Pyrrolidine derivatives useful as 5-HT3-antagonists
GB1469226A (en) Process for the preparation of 2-2-thienyl-ethylamine and derivatives thereof
JPS51125389A (en) A process for preparing heterocyclic compovnds
KR840005732A (en) N-substituted nicotinamide 1-oxide and any preparation method thereof
DE68914211T2 (en) Process for the preparation of intermediates in the synthesis of diltiazem.
GB862513A (en) Pyrrolidine compounds and methods for producing the same
DE69819315D1 (en) METHOD FOR PRODUCING PIPERIDINE CARBONIC ACID AMIDES
ATE55388T1 (en) HETEROCYCLIC AMINE COMPOUNDS.
GB1256095A (en) N-substituted 3-cyano-6-hydroxypyrid-2-ones
ATE98635T1 (en) STERICALLY HINDERED AMINO COMPOUNDS AND PROCESSES FOR THEIR PREPARATION.
ES448761A1 (en) Novel aminobenzoic acid derivatives, process for preparing the same and pharmaceutical composition containing the same

Legal Events

Date Code Title Description
PS Patent sealed
PCNP Patent ceased through non-payment of renewal fee