ZA200200177B - Indole derivatives and their use for the treatment of osteoporosis amongst other applications. - Google Patents
Indole derivatives and their use for the treatment of osteoporosis amongst other applications. Download PDFInfo
- Publication number
- ZA200200177B ZA200200177B ZA200200177A ZA200200177A ZA200200177B ZA 200200177 B ZA200200177 B ZA 200200177B ZA 200200177 A ZA200200177 A ZA 200200177A ZA 200200177 A ZA200200177 A ZA 200200177A ZA 200200177 B ZA200200177 B ZA 200200177B
- Authority
- ZA
- South Africa
- Prior art keywords
- formula
- compound
- pharmaceutically acceptable
- indol
- dichloro
- Prior art date
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- 238000011282 treatment Methods 0.000 title claims description 20
- 208000001132 Osteoporosis Diseases 0.000 title claims description 6
- 229940054051 antipsychotic indole derivative Drugs 0.000 title description 2
- 150000002475 indoles Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 85
- 150000003839 salts Chemical class 0.000 claims description 40
- 239000012453 solvate Substances 0.000 claims description 33
- -1 hydroxy, methoxy, ethoxy, propoxy, benzyloxy, carboxyethoxy, hydroxyethoxy Chemical group 0.000 claims description 28
- 229910052739 hydrogen Inorganic materials 0.000 claims description 25
- 239000001257 hydrogen Substances 0.000 claims description 25
- 201000010099 disease Diseases 0.000 claims description 20
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 20
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- 210000002997 osteoclast Anatomy 0.000 claims description 11
- 125000000623 heterocyclic group Chemical group 0.000 claims description 10
- 150000002431 hydrogen Chemical class 0.000 claims description 10
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 9
- 230000000694 effects Effects 0.000 claims description 7
- 206010028980 Neoplasm Diseases 0.000 claims description 6
- 238000007112 amidation reaction Methods 0.000 claims description 6
- 238000011321 prophylaxis Methods 0.000 claims description 6
- 230000009435 amidation Effects 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 125000003386 piperidinyl group Chemical group 0.000 claims description 5
- CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 claims description 4
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- 230000002491 angiogenic effect Effects 0.000 claims description 4
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- 239000003814 drug Substances 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 229940037467 helicobacter pylori Drugs 0.000 claims description 4
- 208000037797 influenza A Diseases 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 4
- 208000003265 stomatitis Diseases 0.000 claims description 4
- 208000005925 vesicular stomatitis Diseases 0.000 claims description 4
- 241000124008 Mammalia Species 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000006239 protecting group Chemical group 0.000 claims description 2
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- 231100000397 ulcer Toxicity 0.000 claims 3
- 230000003612 virological effect Effects 0.000 claims 3
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 2
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 2
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims 2
- FQZJDLJDCHIFIS-UHFFFAOYSA-N 4-(5,6-dichloro-1h-indol-2-yl)-2,5-dimethoxy-n-(1,2,2,6,6-pentamethylpiperidin-4-yl)benzamide Chemical compound COC1=CC(C=2NC3=CC(Cl)=C(Cl)C=C3C=2)=C(OC)C=C1C(=O)NC1CC(C)(C)N(C)C(C)(C)C1 FQZJDLJDCHIFIS-UHFFFAOYSA-N 0.000 claims 1
- VNVUDBDBNZARAF-UHFFFAOYSA-N 4-(5,6-dichloro-1h-indol-2-yl)-3-ethoxy-n-(2,2,6,6-tetramethylpiperidin-4-yl)benzamide Chemical compound C=1C=C(C=2NC3=CC(Cl)=C(Cl)C=C3C=2)C(OCC)=CC=1C(=O)NC1CC(C)(C)NC(C)(C)C1 VNVUDBDBNZARAF-UHFFFAOYSA-N 0.000 claims 1
- QACGTAHQFJDDGA-UHFFFAOYSA-N 4-(5,6-dichloro-1h-indol-2-yl)-3-ethoxy-n-pyridin-3-ylbenzamide Chemical compound C=1C=C(C=2NC3=CC(Cl)=C(Cl)C=C3C=2)C(OCC)=CC=1C(=O)NC1=CC=CN=C1 QACGTAHQFJDDGA-UHFFFAOYSA-N 0.000 claims 1
- XVWQBCXFAYCVTE-UHFFFAOYSA-N 4-(5,6-dichloro-1h-indol-2-yl)-3-hydroxy-n-(2,2,6,6-tetramethylpiperidin-4-yl)benzamide Chemical compound C1C(C)(C)NC(C)(C)CC1NC(=O)C(C=C1O)=CC=C1C1=CC2=CC(Cl)=C(Cl)C=C2N1 XVWQBCXFAYCVTE-UHFFFAOYSA-N 0.000 claims 1
- LBCZIZBNERCLNA-UHFFFAOYSA-N 4-(5,6-dichloro-1h-indol-2-yl)-3-methoxy-n-[3-[4-(3-methoxyphenyl)piperazin-1-yl]propyl]benzamide Chemical compound COC1=CC=CC(N2CCN(CCCNC(=O)C=3C=C(OC)C(C=4NC5=CC(Cl)=C(Cl)C=C5C=4)=CC=3)CC2)=C1 LBCZIZBNERCLNA-UHFFFAOYSA-N 0.000 claims 1
- RRIJSBXUALMIPL-UHFFFAOYSA-N 4-(5,6-dichloro-1h-indol-2-yl)-3-phenylmethoxy-n-(2,2,6,6-tetramethylpiperidin-4-yl)benzamide Chemical compound C1C(C)(C)NC(C)(C)CC1NC(=O)C(C=C1OCC=2C=CC=CC=2)=CC=C1C1=CC2=CC(Cl)=C(Cl)C=C2N1 RRIJSBXUALMIPL-UHFFFAOYSA-N 0.000 claims 1
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- PJJBAZMFVZAAPU-UHFFFAOYSA-N 4-(6-chloro-5-methoxy-1h-indol-2-yl)-3-ethoxy-n-(2,2,6,6-tetramethylpiperidin-4-yl)benzamide Chemical compound C=1C=C(C=2NC3=CC(Cl)=C(OC)C=C3C=2)C(OCC)=CC=1C(=O)NC1CC(C)(C)NC(C)(C)C1 PJJBAZMFVZAAPU-UHFFFAOYSA-N 0.000 claims 1
- 125000002474 dimethylaminoethoxy group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])O* 0.000 claims 1
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- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- RLISWLLILOTWGG-UHFFFAOYSA-N salamidacetic acid Chemical compound NC(=O)C1=CC=CC=C1OCC(O)=O RLISWLLILOTWGG-UHFFFAOYSA-N 0.000 claims 1
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- 125000000217 alkyl group Chemical group 0.000 description 7
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- HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 description 1
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- 239000000010 aprotic solvent Substances 0.000 description 1
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- 108010009896 bone resorption factor Proteins 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- UTBIMNXEDGNJFE-UHFFFAOYSA-N collidine Natural products CC1=CC=C(C)C(C)=N1 UTBIMNXEDGNJFE-UHFFFAOYSA-N 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
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- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
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- 229910052736 halogen Inorganic materials 0.000 description 1
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- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
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- RRNKTEDWRCQWSN-UHFFFAOYSA-N n-[3-[4-(3-chlorophenyl)piperazin-1-yl]propyl]-4-(5,6-dichloro-1h-indol-2-yl)-2-methoxybenzamide Chemical compound COC1=CC(C=2NC3=CC(Cl)=C(Cl)C=C3C=2)=CC=C1C(=O)NCCCN(CC1)CCN1C1=CC=CC(Cl)=C1 RRNKTEDWRCQWSN-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
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- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000012026 peptide coupling reagents Substances 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
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- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 description 1
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- 239000011591 potassium Substances 0.000 description 1
- 239000012256 powdered iron Substances 0.000 description 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
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- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- AWUCVROLDVIAJX-GSVOUGTGSA-N sn-glycerol 3-phosphate Chemical compound OC[C@@H](O)COP(O)(O)=O AWUCVROLDVIAJX-GSVOUGTGSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
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- 230000000707 stereoselective effect Effects 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
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- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 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
- 125000004001 thioalkyl group Chemical group 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 231100000402 unacceptable toxicity Toxicity 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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-
- 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
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
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- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
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- Immunology (AREA)
- Pulmonology (AREA)
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- Tropical Medicine & Parasitology (AREA)
- Hospice & Palliative Care (AREA)
- AIDS & HIV (AREA)
- Ophthalmology & Optometry (AREA)
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Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9914371.1A GB9914371D0 (en) | 1999-06-18 | 1999-06-18 | Novel compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200200177B true ZA200200177B (en) | 2003-09-23 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200200177A ZA200200177B (en) | 1999-06-18 | 2002-01-09 | Indole derivatives and their use for the treatment of osteoporosis amongst other applications. |
Country Status (30)
| Country | Link |
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| US (2) | US6787550B1 (es) |
| EP (1) | EP1212317B1 (es) |
| JP (1) | JP2003503490A (es) |
| KR (1) | KR100701109B1 (es) |
| CN (1) | CN1179960C (es) |
| AR (1) | AR024390A1 (es) |
| AT (1) | ATE276245T1 (es) |
| AU (1) | AU768726B2 (es) |
| BR (1) | BR0011708A (es) |
| CA (1) | CA2376657A1 (es) |
| CO (1) | CO5200757A1 (es) |
| CZ (1) | CZ301697B6 (es) |
| DE (1) | DE60013859T2 (es) |
| DK (1) | DK1212317T3 (es) |
| ES (1) | ES2226870T3 (es) |
| GB (1) | GB9914371D0 (es) |
| GC (1) | GC0000341A (es) |
| HK (2) | HK1048468B (es) |
| HU (1) | HUP0202049A3 (es) |
| IL (2) | IL147012A0 (es) |
| MX (1) | MXPA01013277A (es) |
| MY (1) | MY129425A (es) |
| NO (1) | NO322313B1 (es) |
| NZ (1) | NZ516131A (es) |
| PL (1) | PL352964A1 (es) |
| PT (1) | PT1212317E (es) |
| TR (1) | TR200103683T2 (es) |
| TW (1) | TWI248440B (es) |
| WO (1) | WO2001002388A1 (es) |
| ZA (1) | ZA200200177B (es) |
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| BRPI0407506A (pt) | 2003-02-13 | 2006-02-14 | Wellstat Therapeutics Corp | compostos para o tratamento de distúrbios metabólicos, seu uso e composição farmacêutica compreendendo os mesmos |
| AU2004259703A1 (en) * | 2003-07-15 | 2005-02-03 | Smithkline Beecham Corporation | Novel compounds |
| ITMI20040875A1 (it) * | 2004-04-30 | 2004-07-30 | Ist Naz Stud Cura Dei Tumori | Derivati indolici utili per il trattamento della resistenza agli agenti antitumorali |
| RS50981B (sr) | 2004-09-17 | 2010-10-31 | Idenix Pharmaceuticals Inc. | Fosfoindoli kao hiv inhibitori |
| CA2582674A1 (en) * | 2004-10-04 | 2006-04-20 | Myriad Genetics, Inc. | Compounds for alzheimer's disease |
| US7833805B2 (en) * | 2004-10-21 | 2010-11-16 | University Of Cincinnati | Selectively permeable membranes on porous substrates |
| EP1911744B1 (en) | 2005-07-20 | 2013-09-04 | Masanori Somei | Tryptophan derivative and use thereof |
| ITRM20050390A1 (it) | 2005-07-22 | 2007-01-23 | Giuliani Spa | Composti e loro sali specifici per i recettori ppar ed i recettori per l'egf e loro uso in campo medico. |
| ITRM20050389A1 (it) | 2005-07-22 | 2007-01-23 | Giuliani Spa | Composti e loro sali specifici per i recettori ppar ed i recettori per l'egf e loro uso in campo medico. |
| AU2006279537A1 (en) * | 2005-08-15 | 2007-02-22 | Irm Llc | Compounds and compositions as TPO mimetics |
| EP1779848A1 (en) * | 2005-10-28 | 2007-05-02 | Nikem Research S.R.L. | V-ATPase inhibitors for the treatment of inflammatory and autoimmune diseases |
| EP1779849A1 (en) * | 2005-10-28 | 2007-05-02 | Nikem Research S.R.L. | V-ATPase inhibitors for the treatment of septic shock |
| JP2009524686A (ja) | 2006-01-25 | 2009-07-02 | ウェルスタット セラピューティクス コーポレイション | 代謝障害を処置するための化合物 |
| JP2009531280A (ja) | 2006-01-25 | 2009-09-03 | ウェルスタット セラピューティクス コーポレイション | 代謝障害を処置するための化合物 |
| NZ570334A (en) | 2006-02-02 | 2011-07-29 | Wellstat Therapeutics Corp | Compounds for the treatment of metabolic disorders |
| EP2043744A2 (en) * | 2006-07-13 | 2009-04-08 | SmithKline Beecham Corporation | Chemical compounds |
| US7960428B2 (en) | 2006-09-29 | 2011-06-14 | Idenix Pharmaceuticals, Inc. | Enantiomerically pure phosphoindoles as HIV inhibitors |
| UA107562C2 (uk) | 2008-12-05 | 2015-01-26 | Спосіб лікування псоріазу | |
| EP3744398A1 (en) | 2009-02-16 | 2020-12-02 | Nogra Pharma Limited | Alkylamido compounds and uses thereof |
| WO2010144611A2 (en) * | 2009-06-10 | 2010-12-16 | 3-V Biosciences, Inc. | Antivirals that target transporters, carriers, and ion channels |
| PL2614052T3 (pl) | 2010-09-08 | 2015-06-30 | Bristol Myers Squibb Co | Nowe analogi piperazyny jako środki przeciw wirusowi grypy o szerokim spektrum |
| WO2012045451A1 (en) | 2010-10-05 | 2012-04-12 | Ludwig-Maximilians-Universitaet Muenchen | Novel therapeutic treatment of progranulin-dependent diseases |
| US20120142627A1 (en) * | 2010-12-06 | 2012-06-07 | Emory University | Monophosphate prodrugs of dapd and analogs thereof |
| EA030762B1 (ru) | 2012-02-09 | 2018-09-28 | Ногра Фарма Лимитед | Способы лечения фиброза |
| EA201491894A1 (ru) | 2012-04-18 | 2015-02-27 | Ногра Фарма Лимитед | Способы лечения непереносимости лактозы |
| EA202192207A1 (ru) | 2019-02-08 | 2021-10-27 | Ногра Фарма Лимитед | Способ получения 3-(4'-аминофенил)-2-метоксипропионовой кислоты и ее аналогов и промежуточных соединений |
| CN113024432A (zh) * | 2019-12-24 | 2021-06-25 | 上海科胜药物研发有限公司 | 一种氨磺必利药典杂质的制备方法 |
Family Cites Families (4)
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|---|---|---|---|---|
| RU2124511C1 (ru) * | 1993-05-14 | 1999-01-10 | Фармасьютикал Ко., Лтд | Производные пиперазина |
| JPH10512251A (ja) * | 1995-01-10 | 1998-11-24 | スミスクライン・ビーチャム・ソシエタ・ペル・アチオニ | 骨粗鬆症の治療に有用なインドール誘導体 |
| JP2000514074A (ja) | 1996-07-09 | 2000-10-24 | スミスクライン・ビーチャム・ソシエタ・ペル・アチオニ | 骨粗鬆症の治療のためのインドール誘導体 |
| CN1208333C (zh) * | 1997-12-24 | 2005-06-29 | Nikem研究有限公司 | 主要用于治疗骨质疏松的吲哚衍生物 |
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1999
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- 2000-06-16 CZ CZ20014496A patent/CZ301697B6/cs not_active IP Right Cessation
- 2000-06-16 TR TR2001/03683T patent/TR200103683T2/xx unknown
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- 2000-06-16 WO PCT/EP2000/005672 patent/WO2001002388A1/en active IP Right Grant
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