GB1582378A - Method of preparing n-glycosyl derivatives of polyene macrolide and the salts thereof - Google Patents
Method of preparing n-glycosyl derivatives of polyene macrolide and the salts thereof Download PDFInfo
- Publication number
- GB1582378A GB1582378A GB15058/77A GB1505877A GB1582378A GB 1582378 A GB1582378 A GB 1582378A GB 15058/77 A GB15058/77 A GB 15058/77A GB 1505877 A GB1505877 A GB 1505877A GB 1582378 A GB1582378 A GB 1582378A
- Authority
- GB
- United Kingdom
- Prior art keywords
- temperature
- glycosyl
- salt
- water
- derivative
- 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
Links
- 239000003120 macrolide antibiotic agent Substances 0.000 title claims abstract description 27
- 150000004291 polyenes Chemical class 0.000 title claims abstract description 27
- 150000003839 salts Chemical class 0.000 title claims abstract description 17
- 238000000034 method Methods 0.000 title claims description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 39
- 239000007864 aqueous solution Substances 0.000 claims abstract description 15
- 238000002425 crystallisation Methods 0.000 claims abstract description 10
- 208000007976 Ketosis Diseases 0.000 claims abstract description 8
- 229920001542 oligosaccharide Polymers 0.000 claims abstract description 8
- 229910017053 inorganic salt Inorganic materials 0.000 claims abstract description 7
- 125000003277 amino group Chemical group 0.000 claims abstract description 5
- 239000003960 organic solvent Substances 0.000 claims abstract description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 72
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 49
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 claims description 45
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 42
- 230000003115 biocidal effect Effects 0.000 claims description 24
- 239000002244 precipitate Substances 0.000 claims description 23
- APKFDSVGJQXUKY-KKGHZKTASA-N Amphotericin-B Natural products O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1C=CC=CC=CC=CC=CC=CC=C[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 APKFDSVGJQXUKY-KKGHZKTASA-N 0.000 claims description 22
- APKFDSVGJQXUKY-INPOYWNPSA-N amphotericin B Chemical compound O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 APKFDSVGJQXUKY-INPOYWNPSA-N 0.000 claims description 22
- 229960003942 amphotericin b Drugs 0.000 claims description 22
- 239000000243 solution Substances 0.000 claims description 20
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 14
- -1 aldose monosaccharides Chemical class 0.000 claims description 14
- 239000008103 glucose Substances 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 14
- 229940041033 macrolides Drugs 0.000 claims description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 12
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 claims description 12
- 229910052921 ammonium sulfate Inorganic materials 0.000 claims description 12
- 239000001166 ammonium sulphate Substances 0.000 claims description 12
- 235000011130 ammonium sulphate Nutrition 0.000 claims description 12
- 239000007983 Tris buffer Substances 0.000 claims description 10
- 229960000988 nystatin Drugs 0.000 claims description 9
- 239000000706 filtrate Substances 0.000 claims description 6
- 239000003208 petroleum Substances 0.000 claims description 4
- 238000001953 recrystallisation Methods 0.000 claims description 4
- 150000001720 carbohydrates Chemical class 0.000 claims description 3
- 230000001376 precipitating effect Effects 0.000 claims description 3
- 239000000401 methanolic extract Substances 0.000 claims description 2
- VQOXZBDYSJBXMA-NQTDYLQESA-N nystatin A1 Chemical compound O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/CC/C=C/C=C/[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 VQOXZBDYSJBXMA-NQTDYLQESA-N 0.000 claims description 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 claims description 2
- 239000013049 sediment Substances 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims 1
- 239000002904 solvent Substances 0.000 abstract description 3
- 150000002482 oligosaccharides Chemical class 0.000 abstract description 2
- 239000012429 reaction media Substances 0.000 abstract description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- 150000001323 aldoses Chemical class 0.000 abstract 1
- 150000002584 ketoses Chemical class 0.000 abstract 1
- 150000002772 monosaccharides Chemical class 0.000 abstract 1
- 239000003791 organic solvent mixture Substances 0.000 abstract 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 11
- 229960001031 glucose Drugs 0.000 description 11
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 159000000000 sodium salts Chemical class 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 241000222122 Candida albicans Species 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 4
- 229960004348 candicidin Drugs 0.000 description 4
- 229940095731 candida albicans Drugs 0.000 description 4
- 201000007336 Cryptococcosis Diseases 0.000 description 3
- 241000221204 Cryptococcus neoformans Species 0.000 description 3
- 239000003242 anti bacterial agent Substances 0.000 description 3
- 230000000843 anti-fungal effect Effects 0.000 description 3
- ZWLQACFYTXLLEJ-UHFFFAOYSA-N butan-1-ol;methanol Chemical compound OC.CCCCO ZWLQACFYTXLLEJ-UHFFFAOYSA-N 0.000 description 3
- 230000001988 toxicity Effects 0.000 description 3
- 231100000419 toxicity Toxicity 0.000 description 3
- 241000222120 Candida <Saccharomycetales> Species 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 241000233866 Fungi Species 0.000 description 2
- 244000168141 Geotrichum candidum Species 0.000 description 2
- 235000017388 Geotrichum candidum Nutrition 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 241000767994 Torula sp. Species 0.000 description 2
- 241000224527 Trichomonas vaginalis Species 0.000 description 2
- 229940088710 antibiotic agent Drugs 0.000 description 2
- 229940121375 antifungal agent Drugs 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 239000002034 butanolic fraction Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000002512 chemotherapy Methods 0.000 description 2
- 210000003743 erythrocyte Anatomy 0.000 description 2
- 150000002460 imidazoles Chemical class 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- 239000002032 methanolic fraction Substances 0.000 description 2
- 229910001414 potassium ion Inorganic materials 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 210000002966 serum Anatomy 0.000 description 2
- YKSVGLFNJPQDJE-YDMQLZBCSA-N (19E,21E,23E,25E,27E,29E,31E)-33-[(2R,3S,4R,5S,6R)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy-17-[7-(4-aminophenyl)-5-hydroxy-4-methyl-7-oxoheptan-2-yl]-1,3,5,7,37-pentahydroxy-18-methyl-9,13,15-trioxo-16,39-dioxabicyclo[33.3.1]nonatriaconta-19,21,23,25,27,29,31-heptaene-36-carboxylic acid Chemical compound CC(CC(C)C1OC(=O)CC(=O)CCCC(=O)CC(O)CC(O)CC(O)CC2(O)CC(O)C(C(CC(O[C@@H]3O[C@H](C)[C@@H](O)[C@@H](N)[C@@H]3O)\C=C\C=C\C=C\C=C\C=C\C=C\C=C\C1C)O2)C(O)=O)C(O)CC(=O)C1=CC=C(N)C=C1 YKSVGLFNJPQDJE-YDMQLZBCSA-N 0.000 description 1
- 241000228212 Aspergillus Species 0.000 description 1
- 241000222178 Candida tropicalis Species 0.000 description 1
- 206010017533 Fungal infection Diseases 0.000 description 1
- 241000159512 Geotrichum Species 0.000 description 1
- 206010018910 Haemolysis Diseases 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 208000031888 Mycoses Diseases 0.000 description 1
- 241000235645 Pichia kudriavzevii Species 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 235000014680 Saccharomyces cerevisiae Nutrition 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- SIHHLZPXQLFPMC-UHFFFAOYSA-N chloroform;methanol;hydrate Chemical compound O.OC.ClC(Cl)Cl SIHHLZPXQLFPMC-UHFFFAOYSA-N 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- MNQZXJOMYWMBOU-UHFFFAOYSA-N glyceraldehyde Chemical compound OCC(O)C=O MNQZXJOMYWMBOU-UHFFFAOYSA-N 0.000 description 1
- 125000003147 glycosyl group Chemical class 0.000 description 1
- 230000008588 hemolysis Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 150000002596 lactones Chemical group 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- FHHPUSMSKHSNKW-SMOYURAASA-M sodium deoxycholate Chemical compound [Na+].C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC([O-])=O)C)[C@@]2(C)[C@@H](O)C1 FHHPUSMSKHSNKW-SMOYURAASA-M 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 239000000003 vaginal tablet Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
- C07H17/08—Hetero rings containing eight or more ring members, e.g. erythromycins
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- Communicable Diseases (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL1976188979A PL100966B1 (pl) | 1976-04-22 | 1976-04-22 | Sposob otrzymywania n-glikozylowych pochodnych makrolidow polienowych oraz ich soli,zwlaszcza soli n-metyloglukaminowej |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1582378A true GB1582378A (en) | 1981-01-07 |
Family
ID=19976536
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB15058/77A Expired GB1582378A (en) | 1976-04-22 | 1977-04-12 | Method of preparing n-glycosyl derivatives of polyene macrolide and the salts thereof |
Country Status (21)
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PL122086B1 (en) * | 1979-04-09 | 1982-06-30 | Politechnika Gdanska | Process for preparing amides of antibiotics from the group of polyene macrolides and their derivativesvykh makrolidov i ikh proizvodnykh |
| GB2122892B (en) * | 1982-07-02 | 1986-01-29 | Squibb & Sons Inc | Nystantin pastille formulation |
| WO2013132014A1 (en) | 2012-03-09 | 2013-09-12 | Blirt S.A. | Semisynthetic derivatives of nystatin a1 |
| KR20150027217A (ko) * | 2012-06-15 | 2015-03-11 | 블러트 에스.에이. | 항진균성 항생 암포테리신 b의 n-치환된 제2 세대 유도체, 및 이의 제조 및 응용 방법 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FI60877C (fi) * | 1971-08-13 | 1982-04-13 | Politechnika Gdanska | Foerfarande foer framstaellning av terapeutiskt aktiva i vatten laett dispergerbara polyenmakrolidantibiot-n-glykosylderivat |
| DE2417993C2 (de) * | 1974-04-11 | 1982-07-01 | Leningradskij naučno-issledovatel'skij institut antibiotikov, Leningrad | Polyenmacrolidantibiotica-Komplexe, Verfahren zu deren Herstellung und diese Verbindungen enthaltende Arzneimittel |
-
1976
- 1976-04-22 PL PL1976188979A patent/PL100966B1/pl unknown
-
1977
- 1977-04-06 CH CH433677A patent/CH631995A5/de not_active IP Right Cessation
- 1977-04-12 YU YU00966/77A patent/YU96677A/xx unknown
- 1977-04-12 GB GB15058/77A patent/GB1582378A/en not_active Expired
- 1977-04-12 IN IN557/CAL/1977A patent/IN144113B/en unknown
- 1977-04-19 AU AU24418/77A patent/AU513015B2/en not_active Expired
- 1977-04-20 RO RO7790105A patent/RO71938A/ro unknown
- 1977-04-20 FR FR7711907A patent/FR2361418A1/fr active Granted
- 1977-04-20 DD DD7700198505A patent/DD129331A5/xx unknown
- 1977-04-21 CS CS772666A patent/CS193092B2/cs unknown
- 1977-04-21 SE SE7704604A patent/SE7704604L/xx not_active Application Discontinuation
- 1977-04-21 CA CA276,646A patent/CA1072088A/en not_active Expired
- 1977-04-21 DE DE2717811A patent/DE2717811C2/de not_active Expired
- 1977-04-21 IT IT22707/77A patent/IT1080375B/it active
- 1977-04-22 JP JP4671377A patent/JPS52131594A/ja active Granted
- 1977-04-22 BE BE176963A patent/BE853893A/xx unknown
- 1977-04-22 NL NL7704395A patent/NL7704395A/xx not_active Application Discontinuation
- 1977-04-22 ES ES458093A patent/ES458093A1/es not_active Expired
- 1977-04-22 HU HU77PO646A patent/HU177885B/hu unknown
- 1977-04-22 DK DK178077A patent/DK178077A/da unknown
- 1977-05-27 BR BR7702505A patent/BR7702505A/pt unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL100966B1 (pl) | 1978-11-30 |
| CS193092B2 (en) | 1979-09-17 |
| SE7704604L (sv) | 1977-10-23 |
| JPS5721278B2 (enrdf_load_stackoverflow) | 1982-05-06 |
| IN144113B (enrdf_load_stackoverflow) | 1978-03-25 |
| BR7702505A (pt) | 1978-03-21 |
| IT1080375B (it) | 1985-05-16 |
| BE853893A (fr) | 1977-08-16 |
| FR2361418A1 (fr) | 1978-03-10 |
| DE2717811C2 (de) | 1983-10-20 |
| JPS52131594A (en) | 1977-11-04 |
| DD129331A5 (de) | 1978-01-11 |
| CH631995A5 (en) | 1982-09-15 |
| DE2717811A1 (de) | 1977-10-27 |
| DK178077A (da) | 1977-10-23 |
| HU177885B (en) | 1982-01-28 |
| CA1072088A (en) | 1980-02-19 |
| ES458093A1 (es) | 1978-03-16 |
| FR2361418B1 (enrdf_load_stackoverflow) | 1980-04-18 |
| AU513015B2 (en) | 1980-11-06 |
| NL7704395A (nl) | 1977-10-25 |
| RO71938A (ro) | 1981-11-04 |
| AU2441877A (en) | 1978-10-26 |
| YU96677A (en) | 1982-06-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |