DE69908819D1 - Glycopeptid-derivate und pharmazeutische zusammensetzungen, die sie enthalten - Google Patents

Glycopeptid-derivate und pharmazeutische zusammensetzungen, die sie enthalten

Info

Publication number
DE69908819D1
DE69908819D1 DE69908819T DE69908819T DE69908819D1 DE 69908819 D1 DE69908819 D1 DE 69908819D1 DE 69908819 T DE69908819 T DE 69908819T DE 69908819 T DE69908819 T DE 69908819T DE 69908819 D1 DE69908819 D1 DE 69908819D1
Authority
DE
Germany
Prior art keywords
pharmaceutical compositions
derivatives
glycopeptide
glycopeptide derivatives
disclosed
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 - Lifetime
Application number
DE69908819T
Other languages
English (en)
Other versions
DE69908819T2 (de
Inventor
Kevin Judice
Ross Fatheree
M Lam
Michael Leadbetter
Sheringham Linsell
Yongqi Mu
Gary Trapp
Guang Yang
Yan Zhu
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.)
Innoviva Inc
Original Assignee
Theravance Inc
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 Theravance Inc filed Critical Theravance Inc
Publication of DE69908819D1 publication Critical patent/DE69908819D1/de
Application granted granted Critical
Publication of DE69908819T2 publication Critical patent/DE69908819T2/de
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K9/00—Peptides having up to 20 amino acids, containing saccharide radicals and having a fully defined sequence; Derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K9/00—Peptides having up to 20 amino acids, containing saccharide radicals and having a fully defined sequence; Derivatives thereof
    • C07K9/006—Peptides having up to 20 amino acids, containing saccharide radicals and having a fully defined sequence; Derivatives thereof the peptide sequence being part of a ring structure
    • C07K9/008—Peptides having up to 20 amino acids, containing saccharide radicals and having a fully defined sequence; Derivatives thereof the peptide sequence being part of a ring structure directly attached to a hetero atom of the saccharide radical, e.g. actaplanin, avoparcin, ristomycin, vancomycin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
    • C07K7/04—Linear peptides containing only normal peptide links
    • C07K7/06—Linear peptides containing only normal peptide links having 5 to 11 amino acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides
DE69908819T 1998-12-23 1999-12-22 Glycopeptid-derivate und pharmazeutische zusammensetzungen, die sie enthalten Expired - Lifetime DE69908819T2 (de)

Applications Claiming Priority (9)

Application Number Priority Date Filing Date Title
US11372898P 1998-12-23 1998-12-23
US113728P 1998-12-23
US12931399P 1999-04-14 1999-04-14
US129313P 1999-04-14
US16402499P 1999-11-04 1999-11-04
US164024P 1999-11-04
US16997899P 1999-12-10 1999-12-10
US169978P 1999-12-10
PCT/US1999/030543 WO2000039156A1 (en) 1998-12-23 1999-12-22 Glycopeptide derivatives and pharmaceutical compositions containing the same

Publications (2)

Publication Number Publication Date
DE69908819D1 true DE69908819D1 (de) 2003-07-17
DE69908819T2 DE69908819T2 (de) 2004-05-06

Family

ID=27493926

Family Applications (1)

Application Number Title Priority Date Filing Date
DE69908819T Expired - Lifetime DE69908819T2 (de) 1998-12-23 1999-12-22 Glycopeptid-derivate und pharmazeutische zusammensetzungen, die sie enthalten

Country Status (23)

Country Link
US (9) US6392012B1 (de)
EP (1) EP1140993B1 (de)
JP (1) JP4362017B2 (de)
KR (1) KR100665204B1 (de)
CN (1) CN1249081C (de)
AT (1) ATE242783T1 (de)
AU (1) AU768204B2 (de)
BR (1) BRPI9914221B8 (de)
CA (1) CA2336445C (de)
CZ (1) CZ301184B6 (de)
DE (1) DE69908819T2 (de)
DK (1) DK1140993T3 (de)
ES (1) ES2201825T3 (de)
HK (1) HK1040721B (de)
HU (1) HU230190B1 (de)
IL (2) IL140093A0 (de)
NO (1) NO326066B1 (de)
NZ (1) NZ508594A (de)
PL (1) PL198311B1 (de)
PT (1) PT1140993E (de)
SI (1) SI1140993T1 (de)
WO (1) WO2000039156A1 (de)
ZA (1) ZA200007222B (de)

Families Citing this family (52)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
HU230190B1 (hu) * 1998-12-23 2015-09-28 Theravance, Inc Glikopeptidszármazékok és ezeket tartalmazó gyógyászati kompozíciók
US6699836B2 (en) 1999-04-02 2004-03-02 The Trustees Of Princeton University Vancomycin analogs
WO2000059528A1 (en) * 1999-04-02 2000-10-12 The Trustees Of Princeton University Desleucyl glycopeptide antibiotics and methods of making same
AU2001238020A1 (en) * 2000-02-04 2001-08-14 Advanced Medicine, Inc. Glycopeptide derivatives having antibiotic activity
WO2001083521A2 (en) 2000-05-02 2001-11-08 Theravance, Inc. Reductive alkylation process on glycopeptides
ATE416791T1 (de) * 2000-05-02 2008-12-15 Theravance Inc Zusammensetzung die eine zyklodextrin und ein glykopeptid-antibiotikum enthält
WO2001083520A2 (en) 2000-05-02 2001-11-08 Theravance,Inc Polyacid glycopeptide derivatives
AU2001259816A1 (en) * 2000-06-22 2002-01-02 Advanced Medecine, Inc. Polyhydroxy glycopeptide derivatives
UA75083C2 (uk) 2000-06-22 2006-03-15 Тераванс, Інк. Похідні глікопептидфосфонатів
AU2001259303A1 (en) 2000-06-22 2002-01-02 Advanced Medicine, Inc. Glycopeptide carboxy-saccharide derivatives
US6872804B2 (en) 2000-06-22 2005-03-29 Theravance, Inc. Glycopeptide disulfide and thioester derivatives
US6905669B2 (en) * 2001-04-24 2005-06-14 Supergen, Inc. Compositions and methods for reestablishing gene transcription through inhibition of DNA methylation and histone deacetylase
TWI312785B (en) 2001-08-24 2009-08-01 Theravance Inc Process for preparing vancomycin derivatives
TWI275594B (en) * 2001-08-24 2007-03-11 Theravance Inc Process for preparing vancomycin phosphonate derivatives
DE60118737T2 (de) 2001-09-19 2006-10-19 The Procter & Gamble Company, Cincinnati Farbbedruckte Mehrschichtstruktur, ein damit hergestellter absorbierender Artikel und Verfahren zu deren Herstellung
TWI335332B (en) 2001-10-12 2011-01-01 Theravance Inc Cross-linked vancomycin-cephalosporin antibiotics
US20040033986A1 (en) 2002-05-17 2004-02-19 Protopopova Marina Nikolaevna Anti tubercular drug: compositions and methods
CN101404986B (zh) 2002-05-17 2011-09-28 赛奎拉公司 用于诊断和治疗感染性疾病的组合物和制药方法
ES2384707T3 (es) 2002-05-24 2012-07-11 Theravance, Inc. Antibióticos entrecruzados de glucopéptidos y cefalosporinas
US6951963B2 (en) 2002-06-17 2005-10-04 Theravance, Inc. Process for preparing N-protected β-amino aldehyde compounds
CN101721412A (zh) * 2002-07-09 2010-06-09 法斯根有限责任公司 治疗人和动物中微生物感染的方法
US20060074014A1 (en) * 2002-11-18 2006-04-06 Vicuron Pharmaceuticals Inc. Dalbavancin compositions for treatment of bacterial infections
US20050130909A1 (en) * 2002-11-18 2005-06-16 Luigi Colombo Dalbavancin compositions for treatment of bacterial infections
WO2004113350A1 (en) * 2003-05-23 2004-12-29 Theravance, Inc. Cross-linked glycopeptide - cephalosporin antibiotics
JP4555823B2 (ja) * 2003-07-11 2010-10-06 セラヴァンス， インコーポレーテッド 架橋されたグリコペプチド−セファロスポリン抗生物質
DE102004055582A1 (de) 2004-11-18 2006-05-24 Bayer Cropscience Ag N-Heterocyclyl-phthalsäurediamide
KR20070092719A (ko) 2004-11-29 2007-09-13 고쿠리츠 다이가쿠 호우징 나고야 다이가쿠 글리코펩타이드 항생 물질 모노머 유도체
US8304597B2 (en) 2004-12-15 2012-11-06 The Procter And Gamble Company Method of using an absorbent article having a functional enhancement indicator
US20070185015A1 (en) * 2005-02-28 2007-08-09 Chiron Corporation and North China Pharmaceutical Corporation Semi-synthetic desmethyl-vancomycin-based glycopeptides with antibiotic activity
US7632918B2 (en) * 2005-02-28 2009-12-15 Novartis Vaccines And Diagnostics, Inc. Semi-synthetic glycopeptides with antibiotic activity
US7368422B2 (en) * 2005-02-28 2008-05-06 Novartis Vaccines And Diagnostics Inc. Semi-synthetic rearranged vancomycin/desmethyl-vancomycin-based glycopeptides with antibiotic activity
CA2623198C (en) 2005-09-22 2014-08-05 Medivas, Llc Bis-(a-amino)-diol-diester-containing poly(ester amide) and poly(ester urethane) compositions and methods of use
EP1933881B1 (de) 2005-09-22 2019-03-13 Medivas, LLC Feste polymer-abgabezusammensetzungen und anwendungsverfahren dafür
WO2007084507A2 (en) * 2006-01-13 2007-07-26 The Scripps Research Institute [ψ[CH2NH]PG4] GLYCOPEPTIDE ANTIBIOTIC ANALOGS
TW200808818A (en) * 2006-05-26 2008-02-16 Shionogi & Co Glycopeptide antibiotic derivatives
JP2011507959A (ja) * 2007-12-26 2011-03-10 レアド トヘラペウトイクス，インコーポレーテッド 抗菌薬としての新規半合成糖ペプチド
TW200930397A (en) 2007-12-26 2009-07-16 Shionogi & Co Glycosylated glycopeptide antibiotic derivatives
WO2009123713A1 (en) 2008-04-01 2009-10-08 Cornell University Organo-soluble chitosan salts and chitosan-derived biomaterials prepared thereof
GB2465863A (en) * 2008-12-05 2010-06-09 Lead Therapeutics Inc Semi-synthetic heptapeptidic glycopeptides for the treatment of bacterial infections
CN101928330B (zh) * 2009-06-26 2013-10-16 上海来益生物药物研究开发中心有限责任公司 一种新的化合物及其应用
CA2868343A1 (en) * 2011-03-24 2012-09-27 Seachaid Pharmaceuticals, Inc. Vancomycin derivatives
US20160303184A1 (en) * 2013-09-23 2016-10-20 Jawaharlal Nehru Centre for Advanced Scientific Research (JNCASR) Vancomycin-sugar conjugates and uses thereof
WO2016103284A1 (en) * 2014-12-25 2016-06-30 Jawaharlal Nehru Centre for Advanced Scientific Research (JNCASR) Glycopeptides and uses thereof
CA3011208A1 (en) * 2016-01-15 2017-07-20 Universitat Hamburg Methods for the production of rhamnosylated flavonoids
US10689407B2 (en) * 2016-01-28 2020-06-23 Envista Photo-cleavable primer compositions and methods of use
CN107325159A (zh) * 2016-04-29 2017-11-07 中国科学院上海药物研究所 一类万古霉素衍生物、其制备方法、药物组合物和用途
JP7165146B2 (ja) 2017-05-22 2022-11-02 インスメッド インコーポレイテッド グリコペプチド誘導体化合物およびそれらの使用
CN107987131B (zh) * 2017-11-16 2021-03-09 上海来益生物药物研究开发中心有限责任公司 一组具有抗耐药性细菌活性的化合物、其制备方法和应用
CN108409837B (zh) 2018-03-06 2021-09-24 上海来益生物药物研究开发中心有限责任公司 一组具有抗耐药性细菌活性的糖肽类化合物、其制备方法和应用
NL2023883B1 (en) * 2019-09-24 2021-04-26 Univ Leiden Antibiotic compounds
CN111620931B (zh) * 2020-06-12 2021-12-17 苏州博源医疗科技有限公司 万古霉素衍生物及其制备方法和应用
CN114213284B (zh) * 2022-01-04 2023-08-01 丽珠集团福州福兴医药有限公司 (9h-芴-9-基)-癸基(2-氧代乙基)氨基甲酸甲酯及其合成方法

Family Cites Families (39)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4497802A (en) 1983-10-21 1985-02-05 Eli Lilly And Company N-Acyl glycopeptide derivatives
US4914187A (en) 1984-11-13 1990-04-03 Gruppo Lepetit S.P.A Ester derivatives of antibiotic L 17046
GB8428619D0 (en) 1984-11-13 1984-12-19 Lepetit Spa Derivatives of antibiotic l 17046
US4698327A (en) 1985-04-25 1987-10-06 Eli Lilly And Company Novel glycopeptide derivatives
US4643987A (en) 1985-08-14 1987-02-17 Eli Lilly And Company Modified glycopeptides
US4639433A (en) 1985-08-14 1987-01-27 Eli Lilly And Company Glycopeptide derivatives
GB8704847D0 (en) 1987-03-02 1987-04-08 Lepetit Spa Substituted alkylamides of teicoplanin compounds
FR2632185B1 (fr) * 1988-06-01 1992-05-22 Rhone Poulenc Chimie Silice pour compositions dentifrices compatible notamment avec le zinc
GB8817397D0 (en) 1988-07-21 1988-08-24 Lepetit Spa N15-alkyl & n15 n15-di-alkyl derivatives of teicoplanin antibiotics carrying functional groups on alkyl side chain
US5534420A (en) 1988-07-28 1996-07-09 Eli Lilly And Company Biotransformation of glycopeptide antibiotics
ATE134646T1 (de) * 1988-12-27 1996-03-15 Lepetit Spa C63-amidderivate von 34-de(acetylglucosaminyl)-34-deoxy-teicoplanine
IE64155B1 (en) 1989-03-29 1995-07-12 Lepetit Spa New substituted alkylamide derivatives of teicoplanin
IL96603A (en) 1989-12-13 1998-02-08 Lilly Co Eli Antibacterial glycopeptide derivativesProcess for their preparation and pharmaceutical preparations containing the same
AU647122B2 (en) 1990-05-28 1994-03-17 Gruppo Lepetit S.P.A. C63-amide derivatives of 34-de(acetylglucosaminyl)-34-deoxy- teicoplanin and their use as medicaments against bacteria resistant to glycopeptide antibiotics
WO1992017456A1 (en) 1991-03-26 1992-10-15 Fujisawa Pharmaceutical Co., Ltd. Amino acid derivative and salt thereof
ES2075709T3 (es) * 1991-07-29 1995-10-01 Lepetit Spa Derivados amidicos del antibiotico a 40926.
US5750509A (en) 1991-07-29 1998-05-12 Gruppo Lepetit S.P.A. Amide derivatives of antibiotic A 40926
US5840684A (en) 1994-01-28 1998-11-24 Eli Lilly And Company Glycopeptide antibiotic derivatives
PE40996A1 (es) 1994-01-28 1996-10-14 Lilly Co Eli Derivado de antibiotico de glucopeptido
IT1282586B1 (it) 1996-02-08 1998-03-31 Chemical And Biolog Ind Composizioni farmaceutiche per il trattamento biologico delle infezioni dovute a ceppi di enterococcus faecium resistenti agli
CA2249323A1 (en) 1996-03-21 1997-09-25 Transcell Technologies, Inc. Solid phase lipoglycopeptide library, compositions and methods
AU2441697A (en) 1996-04-12 1997-11-07 Eli Lilly And Company Covalently-linked glycopeptide dimers
WO1997038706A1 (en) 1996-04-12 1997-10-23 Eli Lilly And Company Glycopeptide compounds
US6218505B1 (en) 1996-04-23 2001-04-17 Biosearch Italia S.P.A. Chemical process for preparing amide derivatives of antibiotic A 40926
US5919756A (en) * 1996-06-28 1999-07-06 Eli Lilly And Company Amides
US5939382A (en) 1996-11-21 1999-08-17 Eli Lilly And Company Reducing agent for reductive alkylation of glycopeptide antibiotics
US5952466A (en) 1997-11-12 1999-09-14 Eli Lilly And Company Reductive alkylation of glycopeptide antibiotics
US5916873A (en) 1997-04-17 1999-06-29 Eli Lilly And Company Teicoplanin derivatives
US5977063A (en) 1997-05-20 1999-11-02 Eli Lilly And Company Alkylated hexapeptides
US5952310A (en) 1997-05-20 1999-09-14 Eli Lilly And Company Glycopeptide hexapeptides
US5919771A (en) 1997-05-20 1999-07-06 Eli Lilly And Company Urea and thiourea derivatives of glycopeptides
US6518242B1 (en) * 1998-02-20 2003-02-11 Theravance, Inc. Derivatives of glycopeptide antibacterial agents
EP1060189A1 (de) 1998-02-20 2000-12-20 Advanced Medicine, Inc. Glycopeptid-derivate als antibakterielle mittel
WO1999056760A1 (en) 1998-05-01 1999-11-11 Eli Lilly And Company N1-modified glycopeptides
WO2000004044A1 (en) 1998-07-14 2000-01-27 Princeton University Glycopeptide antibiotics, combinatorial libraries of glycopeptide antibiotics and methods of producing same
HU230190B1 (hu) 1998-12-23 2015-09-28 Theravance, Inc Glikopeptidszármazékok és ezeket tartalmazó gyógyászati kompozíciók
UA75083C2 (uk) * 2000-06-22 2006-03-15 Тераванс, Інк. Похідні глікопептидфосфонатів
ES2384707T3 (es) * 2002-05-24 2012-07-11 Theravance, Inc. Antibióticos entrecruzados de glucopéptidos y cefalosporinas
JP4555823B2 (ja) * 2003-07-11 2010-10-06 セラヴァンス， インコーポレーテッド 架橋されたグリコペプチド−セファロスポリン抗生物質

Also Published As

Publication number Publication date
US20060241024A1 (en) 2006-10-26
HUP0400887A3 (en) 2012-09-28
CZ200122A3 (en) 2001-06-13
CN1315961A (zh) 2001-10-03
IL140093A (en) 2006-06-11
BR9914221A (pt) 2001-06-26
NZ508594A (en) 2003-05-30
US8030445B2 (en) 2011-10-04
BR9914221B1 (pt) 2013-12-31
NO326066B1 (no) 2008-09-08
US20080103292A1 (en) 2008-05-01
BRPI9914221B8 (pt) 2021-05-25
WO2000039156A1 (en) 2000-07-06
HU230190B1 (hu) 2015-09-28
ES2201825T3 (es) 2004-03-16
CA2336445C (en) 2011-07-19
DK1140993T3 (da) 2003-10-06
EP1140993B1 (de) 2003-06-11
US7101964B2 (en) 2006-09-05
ZA200007222B (en) 2002-03-06
US6444786B1 (en) 2002-09-03
NO20006323L (no) 2001-02-12
NO20006323D0 (no) 2000-12-12
AU3127300A (en) 2000-07-31
US7351791B2 (en) 2008-04-01
EP1140993A1 (de) 2001-10-10
US6949681B2 (en) 2005-09-27
KR100665204B1 (ko) 2007-01-04
CA2336445A1 (en) 2000-07-06
AU768204B2 (en) 2003-12-04
IL140093A0 (en) 2002-02-10
ATE242783T1 (de) 2003-06-15
DE69908819T2 (de) 2004-05-06
US20030060598A1 (en) 2003-03-27
CN1249081C (zh) 2006-04-05
JP4362017B2 (ja) 2009-11-11
HK1040721B (zh) 2003-10-17
US20090215982A1 (en) 2009-08-27
US20050239690A1 (en) 2005-10-27
SI1140993T1 (en) 2003-12-31
JP2002533472A (ja) 2002-10-08
US6455669B1 (en) 2002-09-24
PL198311B1 (pl) 2008-06-30
KR20010085857A (ko) 2001-09-07
PT1140993E (pt) 2003-10-31
US6392012B1 (en) 2002-05-21
HUP0400887A2 (hu) 2004-08-30
US7723470B2 (en) 2010-05-25
PL348451A1 (en) 2002-05-20
HK1040721A1 (en) 2002-06-21
CZ301184B6 (cs) 2009-12-02
US20040204346A1 (en) 2004-10-14
US6962970B2 (en) 2005-11-08

Similar Documents

Publication Publication Date Title
DE69908819D1 (de) Glycopeptid-derivate und pharmazeutische zusammensetzungen, die sie enthalten
DE60019693D1 (de) Pharmazeutische zusammensetzungen, die wirkstoffabsorptionsfördernde verbindungen enthalten
EA200300050A1 (ru) Гликопептидфосфонатные производные
ATE296826T1 (de) Pyrazolo(1,5)pyridinderivate
AR066982A2 (es) Compuestos heteroaromaticos sustituidos como inhibidoress tirosin quinasa, composiciones farmaceuticas que los contiene y su uso en la preparacion de medicamentos
BR1100987A (pt) Composto, composição farmacêutica da matéria, e, composição veterinária
IS6658A (is) Ný efnasambönd
PT956858E (pt) Composicoes farmaceuticas contendo lactobacilos para o tratamento de infeccoes vaginais
PT960107E (pt) Compostos de paclitaxel 6-tio-substituidos
ES2191048T3 (es) Derivados de oxazolidinona y compuestos farmaceuticos que los contienen.
ES2243579T3 (es) Derivados de pirazolopirideno.
IL151201A0 (en) Alkylated imidazopyridine derivatives and pharmaceutical compositions containing the same
SE9804212D0 (sv) Compounds
IL140070A0 (en) Benzamide derivatives and pharmaceutical compositions containing the same
AR020563A1 (es) Compuestos (poli)tia-alquinoicos y sus derivados, composiciones que los incluyen y su utilizacion
ES2116612T3 (es) Nuevas bis-naftalimidas para el tratamiento del cancer.
CA2218663A1 (en) Benzisoxazole and indazole derivatives as antipsychotic agents
DE69936052D1 (de) N1 modifizierte glycopeptide
AU2002248531A1 (en) Pyrazolopyriadine derivatives
ES2192789T3 (es) Derivados de hidrazono-benzazuleno, composiciones farmaceuticas y compuestos intermedios.
MY123217A (en) Glycopeptide derivatives and pharmaceutical compositions containing the same
TR200103169T2 (tr) 1,5-Benzodiazepin türevleri
TH57990B (th) อนุพันธ์ของไกลโคเพปไทด์และองค์ประกอบทางเภสัชกรรมซึ่งมีสารชนิดเดียวกัน
ECSP993299A (es) Derivados glicopeptidicos y composiciones farmaceuticas que los contienen
SE9803277D0 (sv) Novel compounds

Legal Events

Date Code Title Description
8364 No opposition during term of opposition