EE200100521A - Short-chain peptide-dye conjugates as contrast agents for optical diagnostics - Google Patents
Short-chain peptide-dye conjugates as contrast agents for optical diagnosticsInfo
- Publication number
- EE200100521A EE200100521A EEP200100521A EEP200100521A EE200100521A EE 200100521 A EE200100521 A EE 200100521A EE P200100521 A EEP200100521 A EE P200100521A EE P200100521 A EEP200100521 A EE P200100521A EE 200100521 A EE200100521 A EE 200100521A
- Authority
- EE
- Estonia
- Prior art keywords
- dye
- polymethine
- group
- polymethine dye
- groups
- Prior art date
Links
- 239000002872 contrast media Substances 0.000 title 1
- 230000003287 optical effect Effects 0.000 title 1
- 239000000975 dye Substances 0.000 abstract 9
- -1 polyoxyethylene group Polymers 0.000 abstract 5
- 108010003205 Vasoactive Intestinal Peptide Proteins 0.000 abstract 3
- 102400000015 Vasoactive intestinal peptide Human genes 0.000 abstract 3
- VBUWHHLIZKOSMS-RIWXPGAOSA-N invicorp Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CO)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(N)=O)C(O)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCCCN)NC(=O)[C@@H](NC(=O)[C@H](C)NC(=O)[C@H](CCSC)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)[C@H](C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](N)CC=1NC=NC=1)C(C)C)[C@@H](C)O)[C@@H](C)O)C(C)C)C1=CC=C(O)C=C1 VBUWHHLIZKOSMS-RIWXPGAOSA-N 0.000 abstract 3
- 102400001103 Neurotensin Human genes 0.000 abstract 2
- 101800001814 Neurotensin Proteins 0.000 abstract 2
- 102000005157 Somatostatin Human genes 0.000 abstract 2
- 108010056088 Somatostatin Proteins 0.000 abstract 2
- 238000010521 absorption reaction Methods 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000003277 amino group Chemical group 0.000 abstract 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 2
- 230000005284 excitation Effects 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- NHXLMOGPVYXJNR-ATOGVRKGSA-N somatostatin Chemical compound C([C@H]1C(=O)N[C@H](C(N[C@@H](CO)C(=O)N[C@@H](CSSC[C@@H](C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CC=2C3=CC=CC=C3NC=2)C(=O)N[C@@H](CCCCN)C(=O)N[C@H](C(=O)N1)[C@@H](C)O)NC(=O)CNC(=O)[C@H](C)N)C(O)=O)=O)[C@H](O)C)C1=CC=CC=C1 NHXLMOGPVYXJNR-ATOGVRKGSA-N 0.000 abstract 2
- 229960000553 somatostatin Drugs 0.000 abstract 2
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 abstract 1
- 239000004472 Lysine Substances 0.000 abstract 1
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 abstract 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 abstract 1
- 150000001413 amino acids Chemical group 0.000 abstract 1
- 210000000621 bronchi Anatomy 0.000 abstract 1
- 235000018417 cysteine Nutrition 0.000 abstract 1
- 125000000151 cysteine group Chemical class N[C@@H](CS)C(=O)* 0.000 abstract 1
- 238000002405 diagnostic procedure Methods 0.000 abstract 1
- 238000011846 endoscopic investigation Methods 0.000 abstract 1
- 210000003238 esophagus Anatomy 0.000 abstract 1
- 239000012634 fragment Substances 0.000 abstract 1
- 210000001035 gastrointestinal tract Anatomy 0.000 abstract 1
- 125000003588 lysine group Chemical group [H]N([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(N([H])[H])C(*)=O 0.000 abstract 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 abstract 1
- PCJGZPGTCUMMOT-ISULXFBGSA-N neurotensin Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC(C)C)C(O)=O)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CCCCN)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CC(C)C)NC(=O)[C@H]1NC(=O)CC1)C1=CC=C(O)C=C1 PCJGZPGTCUMMOT-ISULXFBGSA-N 0.000 abstract 1
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 238000011895 specific detection Methods 0.000 abstract 1
- 238000005507 spraying Methods 0.000 abstract 1
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 abstract 1
- 210000003932 urinary bladder Anatomy 0.000 abstract 1
- 238000005406 washing Methods 0.000 abstract 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K49/00—Preparations for testing in vivo
- A61K49/001—Preparation for luminescence or biological staining
- A61K49/0013—Luminescence
- A61K49/0017—Fluorescence in vivo
- A61K49/005—Fluorescence in vivo characterised by the carrier molecule carrying the fluorescent agent
- A61K49/0056—Peptides, proteins, polyamino acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K49/00—Preparations for testing in vivo
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K49/00—Preparations for testing in vivo
- A61K49/001—Preparation for luminescence or biological staining
- A61K49/0013—Luminescence
- A61K49/0017—Fluorescence in vivo
- A61K49/0019—Fluorescence in vivo characterised by the fluorescent group, e.g. oligomeric, polymeric or dendritic molecules
- A61K49/0021—Fluorescence in vivo characterised by the fluorescent group, e.g. oligomeric, polymeric or dendritic molecules the fluorescent group being a small organic molecule
- A61K49/0032—Methine dyes, e.g. cyanine dyes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
- C07K1/107—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length by chemical modification of precursor peptides
- C07K1/1072—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length by chemical modification of precursor peptides by covalent attachment of residues or functional groups
- C07K1/1077—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length by chemical modification of precursor peptides by covalent attachment of residues or functional groups by covalent attachment of residues other than amino acids or peptide residues, e.g. sugars, polyols, fatty acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- C07K14/435—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
- C07K14/575—Hormones
- C07K14/57563—Vasoactive intestinal peptide [VIP]; Related peptides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- C07K14/435—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
- C07K14/575—Hormones
- C07K14/655—Somatostatins
-
- 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
- C07K7/08—Linear peptides containing only normal peptide links having 12 to 20 amino acids
- C07K7/083—Neurotensin
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
- C09B23/02—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups
Abstract
Conjugates (I) of vasoactive intestinal peptide (VIP), somatostatin or neurotensin peptides and polymethine dyes are new. Peptide-dye conjugates of formula (I) are new. X = a sequence of 5-30 alpha -, beta - or gamma -amino acids (D or L) corresponding to the amino acid sequence of VIP, somatostatin or neurotensin or a fragment, derivative or analog thereof, optionally cyclized by a disulfide bridge between two cysteines or by an amide bridge between the N and C termini; A<1> = H, acetyl, 1-10C alkyl (optionally substituted by 1-3 COOH groups and/or 1-6 OH groups), a polyoxyethylene group comprising 2-30 CH2CH2O units, or a polymethine dye having at least one absorption maximum in the 380-1200 nm range; and A<2> = OH, NH2 or a polymethine dye having at least one absorption maximum in the 380-1200 nm range; provided that at least one of A<1> and A<2> is a polymethine dye, that when A<1> is a polymethine dye, it is bonded to the N-terminal amino group and that when A<2> is a polymethine dye, it is bonded to a lysine amino group or serine hydroxy group at any position within X. Independent claims are also included for the following: (1) a diagnostic method comprising administering (I) to a patient, either intravenously or to the bronchi by inhalation or to the gastrointestinal tract, esophagus or bladder by spraying and then washing out excess (I), and then performing an endoscopic investigation by local excitation of fluorescence at an excitation wavelength of 350-1200 nm and site-specific detection of the fluorescence emitted by the dye; and (2) cyanine dyes of formula (II). p = 1-3; n = 1-4 or 10; R<1>, R<2> = 4-sulfobutyl, 3-sulfopropyl, 2-sulfoethyl, 3-methyl-3-sulfopropyl, methyl, ethyl or propyl; R<3> = H, COOE<1>, CONE<1>E<2>, NHCOE<1>, NHCONHE<1>, NE<1>E<2>, OE<1>, OSO3E<1>, SO3E<1> or SO2NHE<1>; and E<1>, E<2> = H, CH3, ethyl, or 3-6C alkyl optionally interrupted by 1-2 O atoms and/or a CO group and/or optionally substituted by 1-5 OH groups.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19917713A DE19917713A1 (en) | 1999-04-09 | 1999-04-09 | Short-chain peptide-dye conjugates as contrast agents for optical diagnostics |
| PCT/EP2000/002697 WO2000061194A2 (en) | 1999-04-09 | 2000-03-28 | Short-chain peptide dye conjugates used as contrast agents for optical diagnostics |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| EE200100521A true EE200100521A (en) | 2002-12-16 |
Family
ID=7905136
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EEP200100521A EE200100521A (en) | 1999-04-09 | 2000-03-28 | Short-chain peptide-dye conjugates as contrast agents for optical diagnostics |
Country Status (28)
| Country | Link |
|---|---|
| EP (2) | EP1176987B1 (en) |
| JP (1) | JP2002541219A (en) |
| KR (1) | KR20020000555A (en) |
| CN (1) | CN1351505A (en) |
| AT (2) | ATE421341T1 (en) |
| AU (1) | AU769392B2 (en) |
| BG (1) | BG105988A (en) |
| BR (1) | BR0009658A (en) |
| CA (1) | CA2368490A1 (en) |
| CZ (1) | CZ20013562A3 (en) |
| DE (3) | DE19917713A1 (en) |
| DK (1) | DK1176987T3 (en) |
| EE (1) | EE200100521A (en) |
| ES (2) | ES2321586T3 (en) |
| HK (1) | HK1046867A1 (en) |
| HR (1) | HRP20010833A2 (en) |
| HU (1) | HUP0202990A3 (en) |
| IL (1) | IL145596A0 (en) |
| MX (1) | MXPA01010174A (en) |
| NO (1) | NO20014911L (en) |
| NZ (2) | NZ514533A (en) |
| PL (1) | PL351766A1 (en) |
| PT (1) | PT1176987E (en) |
| RU (1) | RU2001129707A (en) |
| SK (1) | SK14152001A3 (en) |
| WO (1) | WO2000061194A2 (en) |
| YU (1) | YU70501A (en) |
| ZA (1) | ZA200109238B (en) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2428552A1 (en) | 2000-11-28 | 2002-06-06 | Mondobiotech Sa | Compounds with the biological activity of vasoactive intestinal peptide for the treatment of pulmonary and arteriolar hypertension |
| KR100406460B1 (en) * | 2001-09-29 | 2003-11-19 | 한국과학기술연구원 | Coupled Styrylcyanine Dyes and Their Synthesis |
| IL148921A0 (en) | 2002-03-26 | 2002-09-12 | Peptor Ltd | Photo active backbone cyclized somatostatin analogs for optical imaging and photodynamic therapy |
| JP4599948B2 (en) * | 2003-09-18 | 2010-12-15 | チッソ株式会社 | α-Fluoroacrylate compound, composition and polymer thereof |
| GB0328060D0 (en) * | 2003-12-04 | 2004-01-07 | Sod Conseils Rech Applic | Botulinum toxin treatment |
| NO20035683D0 (en) * | 2003-12-18 | 2003-12-18 | Amersham Health As | Optical imaging of prostate cancer |
| NO20035682D0 (en) * | 2003-12-18 | 2003-12-18 | Amersham Health As | Optical imaging of oesophageal cancer and Barrett's oesophagus |
| NO20035681D0 (en) * | 2003-12-18 | 2003-12-18 | Amersham Health As | Optical imaging of lung cancer |
| EP1679082A1 (en) * | 2005-01-07 | 2006-07-12 | Schering AG | Use of cyanine dyes for the diagnosis of proliferative diseases |
| PT1836239E (en) | 2005-01-13 | 2009-02-02 | Cinv Ag | Composite materials containing carbon nanoparticles |
| KR100716840B1 (en) * | 2005-08-29 | 2007-05-09 | 삼성전기주식회사 | Auto opening and closing device for a note book |
| GB0615211D0 (en) * | 2006-07-31 | 2006-09-06 | Ge Healthcare Uk Ltd | Asymmetric flouro-substituted polymethine dyes |
| GB0718957D0 (en) * | 2007-09-28 | 2007-11-07 | Ge Healthcare Ltd | Optical imaging agents |
| CN104939806B (en) | 2008-05-20 | 2021-12-10 | 大学健康网络 | Apparatus and method for fluorescence-based imaging and monitoring |
| CZ304948B6 (en) * | 2013-01-02 | 2015-02-04 | Vysoká škola chemicko-technologická v Praze | Use of polymethine salts as sensors for tumor markers |
| ES2894912T3 (en) | 2014-07-24 | 2022-02-16 | Univ Health Network | Collection and analysis of data for diagnostic purposes |
| JP2020066637A (en) * | 2017-02-27 | 2020-04-30 | 富士フイルム株式会社 | Dyeing agent for pathological diagnosis, cell nucleus dyeing method, manufacturing method of pathological specimen, and dye |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5627027A (en) * | 1986-04-18 | 1997-05-06 | Carnegie Mellon University | Cyanine dyes as labeling reagents for detection of biological and other materials by luminescence methods |
| JPS6488537A (en) * | 1987-09-30 | 1989-04-03 | Fuji Photo Film Co Ltd | Silver halide photographic sensitive material |
| JPS6491134A (en) * | 1987-10-02 | 1989-04-10 | Fuji Photo Film Co Ltd | Silver halide photographic sensitive material |
| MY106120A (en) * | 1988-12-05 | 1995-03-31 | Novartis Ag | Peptide derivatives. |
| US5382654A (en) * | 1992-02-05 | 1995-01-17 | Mallinckrodt Medical, Inc. | Radiolabelled peptide compounds |
| US5849261A (en) * | 1991-02-08 | 1998-12-15 | Diatide, Inc. | Radiolabeled vasoactive intestinal peptides for diagnosis and therapy |
| JP3137349B2 (en) * | 1991-03-27 | 2001-02-19 | 生化学工業株式会社 | Peptide derivative |
| EP0591820A1 (en) * | 1992-10-05 | 1994-04-13 | E.I. Du Pont De Nemours And Company | Near-infrared absorbing dyes prepared from Stenhouse salts |
| JPH06202260A (en) * | 1993-01-07 | 1994-07-22 | Konica Corp | Silver halide photographic sensitive material and its processing method |
| DE4445065A1 (en) * | 1994-12-07 | 1996-06-13 | Diagnostikforschung Inst | Methods for in-vivo diagnostics using NIR radiation |
| US5824772A (en) * | 1995-04-04 | 1998-10-20 | Advanced Bioconcept, Inc. | Fluorescent somatostatin |
| WO1997040104A1 (en) * | 1996-04-19 | 1997-10-30 | Amersham Pharmacia Biotech Uk Limited | Squarate dyes and their use in fluorescent sequencing method |
| DE19649971A1 (en) * | 1996-11-19 | 1998-05-28 | Diagnostikforschung Inst | Optical diagnostics for the diagnosis of neurodegenerative diseases using near-infrared radiation (NIR radiation) |
| DE19717904A1 (en) * | 1997-04-23 | 1998-10-29 | Diagnostikforschung Inst | Acid-labile and enzymatically cleavable dye constructs for diagnostics with near infrared light and for therapy |
| GB9712524D0 (en) * | 1997-06-16 | 1997-08-20 | Nycomed Imaging As | Method |
| DE19817517A1 (en) * | 1998-04-09 | 1999-10-14 | Diagnostikforschung Inst | New benzylguanidine derivatives useful for diagnosis or therapy, especially of neuroblastoma |
| US6284223B1 (en) * | 1998-10-15 | 2001-09-04 | Fluoroprobe, Inc. | Method for viewing tumor tissue located within a body cavity |
-
1999
- 1999-04-09 DE DE19917713A patent/DE19917713A1/en not_active Ceased
-
2000
- 2000-03-28 ES ES02090268T patent/ES2321586T3/en not_active Expired - Lifetime
- 2000-03-28 MX MXPA01010174A patent/MXPA01010174A/en unknown
- 2000-03-28 HU HU0202990A patent/HUP0202990A3/en unknown
- 2000-03-28 CZ CZ20013562A patent/CZ20013562A3/en unknown
- 2000-03-28 NZ NZ514533A patent/NZ514533A/en unknown
- 2000-03-28 CA CA002368490A patent/CA2368490A1/en not_active Abandoned
- 2000-03-28 JP JP2000610526A patent/JP2002541219A/en active Pending
- 2000-03-28 SK SK1415-2001A patent/SK14152001A3/en unknown
- 2000-03-28 ES ES00922560T patent/ES2215641T3/en not_active Expired - Lifetime
- 2000-03-28 WO PCT/EP2000/002697 patent/WO2000061194A2/en not_active Application Discontinuation
- 2000-03-28 NZ NZ522136A patent/NZ522136A/en unknown
- 2000-03-28 PL PL00351766A patent/PL351766A1/en not_active Application Discontinuation
- 2000-03-28 BR BR0009658-0A patent/BR0009658A/en not_active IP Right Cessation
- 2000-03-28 PT PT00922560T patent/PT1176987E/en unknown
- 2000-03-28 DK DK00922560T patent/DK1176987T3/en active
- 2000-03-28 IL IL14559600A patent/IL145596A0/en unknown
- 2000-03-28 RU RU2001129707/04A patent/RU2001129707A/en not_active Application Discontinuation
- 2000-03-28 DE DE50015530T patent/DE50015530D1/en not_active Expired - Fee Related
- 2000-03-28 EP EP00922560A patent/EP1176987B1/en not_active Expired - Lifetime
- 2000-03-28 KR KR1020017012861A patent/KR20020000555A/en not_active Application Discontinuation
- 2000-03-28 EP EP02090268A patent/EP1281405B1/en not_active Expired - Lifetime
- 2000-03-28 AT AT02090268T patent/ATE421341T1/en not_active IP Right Cessation
- 2000-03-28 CN CN00806087A patent/CN1351505A/en active Pending
- 2000-03-28 YU YU70501A patent/YU70501A/en unknown
- 2000-03-28 DE DE50005261T patent/DE50005261D1/en not_active Expired - Fee Related
- 2000-03-28 AT AT00922560T patent/ATE259246T1/en not_active IP Right Cessation
- 2000-03-28 AU AU42911/00A patent/AU769392B2/en not_active Ceased
- 2000-03-28 EE EEP200100521A patent/EE200100521A/en unknown
-
2001
- 2001-10-08 BG BG105988A patent/BG105988A/en unknown
- 2001-10-09 NO NO20014911A patent/NO20014911L/en not_active Application Discontinuation
- 2001-11-08 ZA ZA200109238A patent/ZA200109238B/en unknown
- 2001-11-09 HR HR20010833A patent/HRP20010833A2/en not_active Application Discontinuation
-
2002
- 2002-11-26 HK HK02108542.4A patent/HK1046867A1/en unknown
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