DE69934309T2 - Hydroxamsäurederivate als antibakterielle arzneimittel - Google Patents
Hydroxamsäurederivate als antibakterielle arzneimittel Download PDFInfo
- Publication number
- DE69934309T2 DE69934309T2 DE69934309T DE69934309T DE69934309T2 DE 69934309 T2 DE69934309 T2 DE 69934309T2 DE 69934309 T DE69934309 T DE 69934309T DE 69934309 T DE69934309 T DE 69934309T DE 69934309 T2 DE69934309 T2 DE 69934309T2
- Authority
- DE
- Germany
- Prior art keywords
- alkyl
- group
- phenyl
- cycloalkyl
- alkenyl
- 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.)
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- 239000003814 drug Substances 0.000 title claims description 6
- 230000000844 anti-bacterial effect Effects 0.000 title abstract description 15
- 239000002253 acid Substances 0.000 title description 6
- NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 title description 5
- -1 hydroxy, mercapto Chemical group 0.000 claims abstract description 112
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 36
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 32
- 239000001257 hydrogen Substances 0.000 claims abstract description 31
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 28
- 150000001875 compounds Chemical class 0.000 claims abstract description 26
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 23
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract description 21
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 21
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 16
- 125000003118 aryl group Chemical group 0.000 claims abstract description 13
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims abstract description 12
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 9
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 8
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims abstract description 7
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract description 6
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims abstract description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 5
- 125000005843 halogen group Chemical group 0.000 claims abstract description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 27
- 125000004432 carbon atom Chemical group C* 0.000 claims description 19
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 12
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical group 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 235000008206 alpha-amino acids Nutrition 0.000 claims description 9
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- 125000001424 substituent group Chemical group 0.000 claims description 9
- 150000001370 alpha-amino acid derivatives Chemical class 0.000 claims description 8
- 230000002401 inhibitory effect Effects 0.000 claims description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 7
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims description 6
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 5
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000004076 pyridyl group Chemical group 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 4
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims description 4
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 claims description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 239000011630 iodine Substances 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000006590 (C2-C6) alkenylene group Chemical group 0.000 claims description 2
- 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims description 2
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 2
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 2
- 125000002837 carbocyclic group Chemical group 0.000 claims description 2
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
- 125000002950 monocyclic group Chemical group 0.000 claims description 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 2
- 125000004344 phenylpropyl group Chemical group 0.000 claims description 2
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims 1
- 229940088710 antibiotic agent Drugs 0.000 abstract description 6
- 125000004450 alkenylene group Chemical group 0.000 abstract 1
- 125000001246 bromo group Chemical group Br* 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- 125000001153 fluoro group Chemical group F* 0.000 abstract 1
- 125000002346 iodo group Chemical group I* 0.000 abstract 1
- 108010026809 Peptide deformylase Proteins 0.000 description 20
- 102100021418 Peptide deformylase, mitochondrial Human genes 0.000 description 19
- 241000894006 Bacteria Species 0.000 description 11
- 239000003242 anti bacterial agent Substances 0.000 description 11
- 230000005764 inhibitory process Effects 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- 210000004027 cell Anatomy 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 7
- 108010059993 Vancomycin Proteins 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 229960003165 vancomycin Drugs 0.000 description 7
- MYPYJXKWCTUITO-UHFFFAOYSA-N vancomycin Natural products O1C(C(=C2)Cl)=CC=C2C(O)C(C(NC(C2=CC(O)=CC(O)=C2C=2C(O)=CC=C3C=2)C(O)=O)=O)NC(=O)C3NC(=O)C2NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(CC(C)C)NC)C(O)C(C=C3Cl)=CC=C3OC3=CC2=CC1=C3OC1OC(CO)C(O)C(O)C1OC1CC(C)(N)C(O)C(C)O1 MYPYJXKWCTUITO-UHFFFAOYSA-N 0.000 description 7
- MYPYJXKWCTUITO-LYRMYLQWSA-O vancomycin(1+) Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=C2C=C3C=C1OC1=CC=C(C=C1Cl)[C@@H](O)[C@H](C(N[C@@H](CC(N)=O)C(=O)N[C@H]3C(=O)N[C@H]1C(=O)N[C@H](C(N[C@@H](C3=CC(O)=CC(O)=C3C=3C(O)=CC=C1C=3)C([O-])=O)=O)[C@H](O)C1=CC=C(C(=C1)Cl)O2)=O)NC(=O)[C@@H](CC(C)C)[NH2+]C)[C@H]1C[C@](C)([NH3+])[C@H](O)[C@H](C)O1 MYPYJXKWCTUITO-LYRMYLQWSA-O 0.000 description 7
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- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 6
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- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 3
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- RJQXTJLFIWVMTO-TYNCELHUSA-N Methicillin Chemical compound COC1=CC=CC(OC)=C1C(=O)N[C@@H]1C(=O)N2[C@@H](C(O)=O)C(C)(C)S[C@@H]21 RJQXTJLFIWVMTO-TYNCELHUSA-N 0.000 description 3
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 3
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- 125000003277 amino group Chemical group 0.000 description 3
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- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
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- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4453—Non condensed piperidines, e.g. piperocaine only substituted in position 1, e.g. propipocaine, diperodon
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- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
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- A61K31/167—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide having the nitrogen of a carboxamide group directly attached to the aromatic ring, e.g. lidocaine, paracetamol
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- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
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- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
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- A—HUMAN NECESSITIES
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- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4402—Non condensed pyridines; Hydrogenated derivatives thereof only substituted in position 2, e.g. pheniramine, bisacodyl
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- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
Landscapes
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- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9810464.9A GB9810464D0 (en) | 1998-05-16 | 1998-05-16 | Hydroxamic acid derivatives |
| GB9810464 | 1998-05-16 | ||
| PCT/GB1999/001541 WO1999059568A1 (en) | 1998-05-16 | 1999-05-14 | Hydroxamic acid derivatives as antibacterials |
Publications (2)
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| DE69934309D1 DE69934309D1 (de) | 2007-01-18 |
| DE69934309T2 true DE69934309T2 (de) | 2007-07-05 |
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| DE69934309T Expired - Fee Related DE69934309T2 (de) | 1998-05-16 | 1999-05-14 | Hydroxamsäurederivate als antibakterielle arzneimittel |
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| GB9810464D0 (en) * | 1998-05-16 | 1998-07-15 | British Biotech Pharm | Hydroxamic acid derivatives |
| ES2242411T3 (es) * | 1999-08-10 | 2005-11-01 | Vernalis (Oxford) Ltd | Agentes antibacterianos. |
| FR2801591B1 (fr) * | 1999-11-30 | 2002-03-01 | Aventis Pharma Sa | Derives macrocycliques de l'acide hydroxamique, leur preparation et les compositions qui les contiennent |
| AU2180201A (en) * | 1999-11-30 | 2001-06-12 | Aventis Pharma S.A. | Hydroxamic acid macrocyclic derivatives, preparation method and compositions containing same |
| EP1237862A1 (en) * | 1999-12-17 | 2002-09-11 | Versicor, Inc. | Succinate compounds, compositions and methods of use and preparation |
| GB9929979D0 (en) * | 1999-12-17 | 2000-02-09 | Darwin Discovery Ltd | Hydroxamic acid derivatives |
| WO2002028829A2 (en) * | 2000-09-25 | 2002-04-11 | Questcor Pharmaceuticals, Inc. | Peptide deformylase inhibitors |
| AU2002212541A1 (en) * | 2000-11-23 | 2002-06-03 | British Biotech Pharmaceuticals Ltd | Ydroxamic acid or n-formyl hydroxylamine derivatives as inhibitors of bakterial polypeptide deformylase for treating microbial infections |
| JP2004532826A (ja) * | 2001-03-19 | 2004-10-28 | スローン−ケッタリング インスティトゥート フォー カンサー リサーチ | （ｓ，ｒ，ｒ）−（−）−アクチノニンおよびそのアナログの不斉合成、ならびにそれらの使用 |
| US20040267015A1 (en) * | 2001-04-05 | 2004-12-30 | Ajita Bhat | Peptide deformylase inhibitors |
| GB0128943D0 (en) | 2001-12-04 | 2002-01-23 | Novo Pharmaceuticals De Ltd | Bacterial enzyme inhibitors |
| JP4190862B2 (ja) * | 2001-12-18 | 2008-12-03 | シャープ株式会社 | 表示装置およびその駆動方法 |
| GB0208579D0 (en) * | 2002-04-13 | 2002-05-22 | British Biotech Pharm | Antibacterial agents |
| DE10320453A1 (de) * | 2003-05-08 | 2004-11-25 | Morphochem AG Aktiengesellschaft für kombinatorische Chemie | Neue Bioisostere von Actinonin |
| ES2582555T3 (es) * | 2007-11-29 | 2016-09-13 | Inolex Investment Corporation | Conservantes para composiciones cosméticas, de tocador y farmacéuticas |
| DE102011088962A1 (de) * | 2011-12-19 | 2013-06-20 | Beiersdorf Ag | Wirkstoffkombinationen aus einer oder mehreren Carbonsäuren, insbesondereHydroxycarbonsäuren, und einer oder mehreren physiologisch unbedenklichen Hydroxamsäure sowie kosmetische oder dermatologische Zubereitungen, solcheWirkstoffkombinationen enthaltend |
| US10829440B2 (en) | 2015-06-12 | 2020-11-10 | Brown University | Antibacterial compounds and methods of making and using same |
| CN111787800B (zh) * | 2017-06-29 | 2022-11-25 | 金伯利-克拉克环球有限公司 | 包含二异羟肟酸的抗微生物组合物及用其抑制微生物生长的方法 |
| CN108672095A (zh) * | 2018-05-04 | 2018-10-19 | 广东省资源综合利用研究所 | γ-羟基烷基羟肟酸及其制备方法与应用 |
| US11555010B2 (en) | 2019-07-25 | 2023-01-17 | Brown University | Diamide antimicrobial agents |
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| GB1028921A (en) | 1962-01-23 | 1966-05-11 | Ranjeet Bhagwan Singh | New antibiotic |
| US4303662A (en) * | 1980-11-24 | 1981-12-01 | E. R. Squibb & Sons, Inc. | Carboxyacyl, mercapto and acylmercapto derivatives of heterobicyclo compounds |
| JPH0670019B2 (ja) | 1989-07-21 | 1994-09-07 | 明治製菓株式会社 | 新抗生物質ｓｆ２１９７ｃ物質およびその製造法 |
| GB8919251D0 (en) * | 1989-08-24 | 1989-10-04 | British Bio Technology | Compounds |
| JPH03157372A (ja) | 1989-11-13 | 1991-07-05 | Yamanouchi Pharmaceut Co Ltd | Ｙｌ―０１８６９ｐ物質及びその製造法 |
| WO1992022523A2 (en) | 1991-06-14 | 1992-12-23 | Research Corporation Technologies, Inc. | Peptide derivatives of collagenase inhibitor |
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| US6281245B1 (en) * | 1996-10-28 | 2001-08-28 | Versicor, Inc. | Methods for solid-phase synthesis of hydroxylamine compounds and derivatives, and combinatorial libraries thereof |
| AU5187698A (en) | 1996-12-06 | 1998-06-29 | Cancerforskningsfondet Af 1989 | Inhibition of invasive remodelling |
| ZA9711121B (en) * | 1996-12-13 | 1998-06-23 | Handelman Joseph H | Reduction of hair growth. |
| PL194240B1 (pl) * | 1998-02-07 | 2007-05-31 | British Biotech Pharm | Zastosowanie pochodnych N-formylohydroksyloaminy i amidowa pochodna N-formylohydroksyloaminy |
| GB9810464D0 (en) * | 1998-05-16 | 1998-07-15 | British Biotech Pharm | Hydroxamic acid derivatives |
-
1998
- 1998-05-16 GB GBGB9810464.9A patent/GB9810464D0/en not_active Ceased
-
1999
- 1999-05-14 AT AT99922317T patent/ATE347356T1/de not_active IP Right Cessation
- 1999-05-14 EP EP99922317A patent/EP1079819B1/en not_active Expired - Lifetime
- 1999-05-14 DE DE69934309T patent/DE69934309T2/de not_active Expired - Fee Related
- 1999-05-14 JP JP2000549233A patent/JP2002515427A/ja not_active Withdrawn
- 1999-05-14 IL IL13905999A patent/IL139059A0/xx not_active IP Right Cessation
- 1999-05-14 BR BR9910488-1A patent/BR9910488A/pt not_active Application Discontinuation
- 1999-05-14 DK DK99922317T patent/DK1079819T3/da active
- 1999-05-14 PT PT99922317T patent/PT1079819E/pt unknown
- 1999-05-14 EP EP06009622A patent/EP1754477A3/en not_active Withdrawn
- 1999-05-14 AU AU39421/99A patent/AU754063B2/en not_active Ceased
- 1999-05-14 NZ NZ507560A patent/NZ507560A/xx unknown
- 1999-05-14 GB GB0024789A patent/GB2353708A/en not_active Withdrawn
- 1999-05-14 KR KR1020007012819A patent/KR100634089B1/ko not_active Expired - Fee Related
- 1999-05-14 CN CN99806057A patent/CN1300210A/zh active Pending
- 1999-05-14 ES ES99922317T patent/ES2278444T3/es not_active Expired - Lifetime
- 1999-05-14 CA CA002332713A patent/CA2332713C/en not_active Expired - Fee Related
- 1999-05-14 HU HU0102290A patent/HUP0102290A3/hu unknown
- 1999-05-14 US US09/700,424 patent/US6441042B1/en not_active Expired - Fee Related
- 1999-05-14 TR TR2000/03376T patent/TR200003376T2/xx unknown
- 1999-05-14 PL PL99344438A patent/PL344438A1/xx unknown
- 1999-05-14 WO PCT/GB1999/001541 patent/WO1999059568A1/en not_active Ceased
-
2000
- 2000-10-16 IL IL139059A patent/IL139059A/en unknown
- 2000-10-30 ZA ZA200006131A patent/ZA200006131B/en unknown
- 2000-11-15 NO NO20005782A patent/NO20005782L/no not_active Application Discontinuation
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2002
- 2002-06-26 US US10/179,227 patent/US6992190B2/en not_active Expired - Fee Related
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2005
- 2005-08-22 US US11/207,813 patent/US7323563B2/en not_active Expired - Fee Related
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2007
- 2007-03-01 CY CY20071100285T patent/CY1106452T1/el unknown
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