UA74651C2 - Indole derivatives, a pharmaceutical composition based thereon and use thereof - Google Patents
Indole derivatives, a pharmaceutical composition based thereon and use thereof Download PDFInfo
- Publication number
- UA74651C2 UA74651C2 UA20031211983A UA20031211983A UA74651C2 UA 74651 C2 UA74651 C2 UA 74651C2 UA 20031211983 A UA20031211983 A UA 20031211983A UA 20031211983 A UA20031211983 A UA 20031211983A UA 74651 C2 UA74651 C2 UA 74651C2
- Authority
- UA
- Ukraine
- Prior art keywords
- indol
- piperazin
- alkyl
- disorder
- compound
- Prior art date
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- 239000008194 pharmaceutical composition Substances 0.000 title claims description 4
- 150000002475 indoles Chemical class 0.000 title description 4
- 229940054051 antipsychotic indole derivative Drugs 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 77
- 208000028017 Psychotic disease Diseases 0.000 claims abstract description 9
- 208000019906 panic disease Diseases 0.000 claims abstract description 9
- 208000012902 Nervous system disease Diseases 0.000 claims abstract description 8
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims abstract description 8
- 208000019022 Mood disease Diseases 0.000 claims abstract description 7
- 208000025966 Neurological disease Diseases 0.000 claims abstract description 7
- 206010041250 Social phobia Diseases 0.000 claims abstract description 7
- 208000019454 Feeding and Eating disease Diseases 0.000 claims abstract description 6
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims description 66
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 26
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 239000001257 hydrogen Substances 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 22
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 20
- 239000002253 acid Substances 0.000 claims description 16
- 229960003638 dopamine Drugs 0.000 claims description 14
- 150000002431 hydrogen Chemical class 0.000 claims description 13
- 230000005764 inhibitory process Effects 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 201000010099 disease Diseases 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 9
- 208000035475 disorder Diseases 0.000 claims description 9
- GZPHSAQLYPIAIN-UHFFFAOYSA-N 3-pyridinecarbonitrile Chemical compound N#CC1=CC=CN=C1 GZPHSAQLYPIAIN-UHFFFAOYSA-N 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 208000011688 Generalised anxiety disease Diseases 0.000 claims description 7
- 125000002252 acyl group Chemical group 0.000 claims description 7
- 208000029364 generalized anxiety disease Diseases 0.000 claims description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
- 125000006598 aminocarbonylamino group Chemical group 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
- 230000008485 antagonism Effects 0.000 claims description 4
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 229940126601 medicinal product Drugs 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 4
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-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
- 125000004442 acylamino group Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
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- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- 230000013275 serotonin uptake Effects 0.000 claims description 3
- XTFIVUDBNACUBN-UHFFFAOYSA-N 1,3,5-trinitro-1,3,5-triazinane Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)C1 XTFIVUDBNACUBN-UHFFFAOYSA-N 0.000 claims description 2
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- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 2
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- VQGHOUODWALEFC-UHFFFAOYSA-N alpha-Phenylpyridine Natural products C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 claims 1
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 claims 1
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- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims 1
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- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- WZHJKEUHNJHDLS-QTGUNEKASA-N metergoline Chemical compound C([C@H]1CN([C@H]2[C@@H](C=3C=CC=C4N(C)C=C(C=34)C2)C1)C)NC(=O)OCC1=CC=CC=C1 WZHJKEUHNJHDLS-QTGUNEKASA-N 0.000 description 1
- 229960004650 metergoline Drugs 0.000 description 1
- 206010027599 migraine Diseases 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 210000001577 neostriatum Anatomy 0.000 description 1
- 230000000926 neurological effect Effects 0.000 description 1
- 230000009871 nonspecific binding Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
- 239000004031 partial agonist Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000002285 radioactive effect Effects 0.000 description 1
- 229940044551 receptor antagonist Drugs 0.000 description 1
- 239000002464 receptor antagonist Substances 0.000 description 1
- 238000006268 reductive amination reaction Methods 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000000862 serotonergic effect Effects 0.000 description 1
- 239000000952 serotonin receptor agonist Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 229950001675 spiperone Drugs 0.000 description 1
- 238000011064 split stream procedure Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- VOVUARRWDCVURC-UHFFFAOYSA-N thiirane Chemical compound C1CS1 VOVUARRWDCVURC-UHFFFAOYSA-N 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/14—Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Psychiatry (AREA)
- Anesthesiology (AREA)
- Pain & Pain Management (AREA)
- Nutrition Science (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DKPA200101037 | 2001-06-29 | ||
| PCT/DK2002/000436 WO2003002552A1 (en) | 2001-06-29 | 2002-06-27 | Novel indole derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UA74651C2 true UA74651C2 (en) | 2006-01-16 |
Family
ID=8160599
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UA20031211983A UA74651C2 (en) | 2001-06-29 | 2002-06-27 | Indole derivatives, a pharmaceutical composition based thereon and use thereof |
Country Status (28)
| Country | Link |
|---|---|
| US (1) | US7342015B2 (xx) |
| EP (1) | EP1399434B1 (xx) |
| JP (1) | JP2004535448A (xx) |
| KR (1) | KR20040019027A (xx) |
| CN (1) | CN100338058C (xx) |
| AR (1) | AR034658A1 (xx) |
| AT (1) | ATE304007T1 (xx) |
| AU (1) | AU2002344950B2 (xx) |
| BG (1) | BG108538A (xx) |
| BR (1) | BR0210407A (xx) |
| CA (1) | CA2451229C (xx) |
| CZ (1) | CZ2004155A3 (xx) |
| DE (1) | DE60206043T2 (xx) |
| DK (1) | DK1399434T3 (xx) |
| EA (1) | EA006104B1 (xx) |
| ES (1) | ES2247347T3 (xx) |
| HK (1) | HK1069579A1 (xx) |
| HU (1) | HUP0400834A2 (xx) |
| IL (1) | IL158830A0 (xx) |
| IS (1) | IS2431B (xx) |
| MX (1) | MXPA03011766A (xx) |
| NO (1) | NO326513B1 (xx) |
| NZ (1) | NZ529461A (xx) |
| PL (1) | PL366520A1 (xx) |
| SK (1) | SK642004A3 (xx) |
| UA (1) | UA74651C2 (xx) |
| WO (1) | WO2003002552A1 (xx) |
| ZA (1) | ZA200308848B (xx) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SI1399438T1 (sl) * | 2001-06-29 | 2006-04-30 | Lundbeck & Co As H | Novi heteroarilni derivati, njihova priprava in uporaba |
| ATE443707T1 (de) | 2004-11-26 | 2009-10-15 | Janssen Pharmaceutica Nv | Isoxazolin-indol-derivate mit verbesserter antipsychotischer und anxiolytischer aktivität |
| AR055203A1 (es) * | 2005-08-31 | 2007-08-08 | Otsuka Pharma Co Ltd | Derivados de benzotiofeno con propiedades antipsicoticas |
| JP4785881B2 (ja) * | 2007-02-27 | 2011-10-05 | 大塚製薬株式会社 | 医薬 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0900792B1 (en) | 1997-09-02 | 2003-10-29 | Duphar International Research B.V | Piperazine and piperidine derivatives as 5-HT1A and dopamine D2-receptor (ant)agonists |
| CA2330452A1 (en) * | 1998-04-29 | 1999-11-04 | American Home Products Corporation | Antipsychotic indolyl derivatives |
| AR027134A1 (es) * | 1999-12-30 | 2003-03-12 | Lundbeck & Co As H | Derivados de indol. |
| SI1399438T1 (sl) * | 2001-06-29 | 2006-04-30 | Lundbeck & Co As H | Novi heteroarilni derivati, njihova priprava in uporaba |
-
2002
- 2002-06-27 DK DK02742850T patent/DK1399434T3/da active
- 2002-06-27 NZ NZ529461A patent/NZ529461A/en unknown
- 2002-06-27 CZ CZ2004155A patent/CZ2004155A3/cs unknown
- 2002-06-27 DE DE60206043T patent/DE60206043T2/de not_active Expired - Fee Related
- 2002-06-27 JP JP2003508933A patent/JP2004535448A/ja active Pending
- 2002-06-27 HU HU0400834A patent/HUP0400834A2/hu unknown
- 2002-06-27 KR KR10-2003-7017127A patent/KR20040019027A/ko not_active Application Discontinuation
- 2002-06-27 PL PL02366520A patent/PL366520A1/xx not_active Application Discontinuation
- 2002-06-27 WO PCT/DK2002/000436 patent/WO2003002552A1/en active IP Right Grant
- 2002-06-27 EA EA200400104A patent/EA006104B1/ru not_active IP Right Cessation
- 2002-06-27 SK SK64-2004A patent/SK642004A3/sk unknown
- 2002-06-27 CN CNB028131878A patent/CN100338058C/zh not_active Expired - Fee Related
- 2002-06-27 IL IL15883002A patent/IL158830A0/xx unknown
- 2002-06-27 CA CA002451229A patent/CA2451229C/en not_active Expired - Fee Related
- 2002-06-27 US US10/482,762 patent/US7342015B2/en not_active Expired - Fee Related
- 2002-06-27 BR BR0210407-5A patent/BR0210407A/pt not_active IP Right Cessation
- 2002-06-27 ES ES02742850T patent/ES2247347T3/es not_active Expired - Lifetime
- 2002-06-27 AU AU2002344950A patent/AU2002344950B2/en not_active Ceased
- 2002-06-27 AT AT02742850T patent/ATE304007T1/de not_active IP Right Cessation
- 2002-06-27 UA UA20031211983A patent/UA74651C2/uk unknown
- 2002-06-27 EP EP02742850A patent/EP1399434B1/en not_active Expired - Lifetime
- 2002-06-27 MX MXPA03011766A patent/MXPA03011766A/es active IP Right Grant
- 2002-06-28 AR ARP020102449A patent/AR034658A1/es unknown
-
2003
- 2003-11-10 IS IS7022A patent/IS2431B/is unknown
- 2003-11-13 ZA ZA200308848A patent/ZA200308848B/en unknown
- 2003-12-18 NO NO20035672A patent/NO326513B1/no unknown
-
2004
- 2004-01-21 BG BG108538A patent/BG108538A/bg unknown
-
2005
- 2005-03-11 HK HK05102171A patent/HK1069579A1/xx not_active IP Right Cessation
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