DE60109498T2 - Amidinophenylalaninderivate als thrombininhibitoren - Google Patents
Amidinophenylalaninderivate als thrombininhibitoren Download PDFInfo
- Publication number
- DE60109498T2 DE60109498T2 DE60109498T DE60109498T DE60109498T2 DE 60109498 T2 DE60109498 T2 DE 60109498T2 DE 60109498 T DE60109498 T DE 60109498T DE 60109498 T DE60109498 T DE 60109498T DE 60109498 T2 DE60109498 T2 DE 60109498T2
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- Prior art keywords
- formula
- methyl
- hydrazino
- compound
- pip
- 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 - Lifetime
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- 229940122388 Thrombin inhibitor Drugs 0.000 title abstract description 9
- 239000003868 thrombin inhibitor Substances 0.000 title abstract description 9
- MVTHUEOHHHQQKY-QMMMGPOBSA-N (2s)-2-(diaminomethylideneamino)-3-phenylpropanoic acid Chemical class NC(N)=N[C@H](C(O)=O)CC1=CC=CC=C1 MVTHUEOHHHQQKY-QMMMGPOBSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 48
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 6
- 238000004519 manufacturing process Methods 0.000 claims abstract description 4
- 150000003839 salts Chemical class 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 38
- 229960004072 thrombin Drugs 0.000 claims description 25
- 108090000190 Thrombin Proteins 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- -1 {2 - [(6-methoxy-2-naphthyl) sulfonyl] -1 - [(2-methyl-1-piperidinyl) carbonyl] hydrazino} methyl Chemical group 0.000 claims description 14
- UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 claims description 13
- 230000015572 biosynthetic process Effects 0.000 claims description 10
- 210000004369 blood Anatomy 0.000 claims description 10
- 239000008280 blood Substances 0.000 claims description 10
- 102000009123 Fibrin Human genes 0.000 claims description 8
- 108010073385 Fibrin Proteins 0.000 claims description 8
- BWGVNKXGVNDBDI-UHFFFAOYSA-N Fibrin monomer Chemical compound CNC(=O)CNC(=O)CN BWGVNKXGVNDBDI-UHFFFAOYSA-N 0.000 claims description 8
- 150000001412 amines Chemical class 0.000 claims description 8
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 8
- 229950003499 fibrin Drugs 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 230000008569 process Effects 0.000 claims description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- 230000002829 reductive effect Effects 0.000 claims description 6
- HGZJJKZPPMFIBU-UHFFFAOYSA-N 3-formylbenzonitrile Chemical compound O=CC1=CC=CC(C#N)=C1 HGZJJKZPPMFIBU-UHFFFAOYSA-N 0.000 claims description 5
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 claims description 5
- ZYUZLEUJKZZXNN-UHFFFAOYSA-N C1=CC(CC(N)C(O)=O)=CC=C1OS(=O)(=O)C1=CC=C(C=CC=C2)C2=C1 Chemical group C1=CC(CC(N)C(O)=O)=CC=C1OS(=O)(=O)C1=CC=C(C=CC=C2)C2=C1 ZYUZLEUJKZZXNN-UHFFFAOYSA-N 0.000 claims description 4
- PXXJHWLDUBFPOL-UHFFFAOYSA-N benzamidine Chemical compound NC(=N)C1=CC=CC=C1 PXXJHWLDUBFPOL-UHFFFAOYSA-N 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 4
- 230000005764 inhibitory process Effects 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- NMVVJCLUYUWBSZ-UHFFFAOYSA-N aminomethylideneazanium;chloride Chemical compound Cl.NC=N NMVVJCLUYUWBSZ-UHFFFAOYSA-N 0.000 claims description 3
- NQMRYBIKMRVZLB-UHFFFAOYSA-N methylamine hydrochloride Chemical compound [Cl-].[NH3+]C NQMRYBIKMRVZLB-UHFFFAOYSA-N 0.000 claims description 3
- DBGRZURIIFFWFO-UHFFFAOYSA-N tert-butyl hydrazinecarbonyl carbonate Chemical compound CC(C)(C)OC(=O)OC(=O)NN DBGRZURIIFFWFO-UHFFFAOYSA-N 0.000 claims description 3
- 238000002560 therapeutic procedure Methods 0.000 claims description 3
- GJDCYHGXHQTSHH-UHFFFAOYSA-N 3-[[azepane-1-carbonyl-(naphthalen-2-ylsulfonylamino)amino]methyl]-n'-hydroxybenzenecarboximidamide Chemical compound ON=C(N)C1=CC=CC(CN(NS(=O)(=O)C=2C=C3C=CC=CC3=CC=2)C(=O)N2CCCCCC2)=C1 GJDCYHGXHQTSHH-UHFFFAOYSA-N 0.000 claims description 2
- UZDLVNRFMPETNI-UHFFFAOYSA-N 3-[[azepane-1-carbonyl-[(6-methoxynaphthalen-2-yl)sulfonylamino]amino]methyl]-n'-hydroxybenzenecarboximidamide Chemical compound C1=CC2=CC(OC)=CC=C2C=C1S(=O)(=O)NN(C(=O)N1CCCCCC1)CC1=CC=CC(C(N)=NO)=C1 UZDLVNRFMPETNI-UHFFFAOYSA-N 0.000 claims description 2
- 229910004373 HOAc Inorganic materials 0.000 claims description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
- 239000000654 additive Substances 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 2
- 229940079593 drug Drugs 0.000 claims description 2
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 2
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 230000001225 therapeutic effect Effects 0.000 claims description 2
- 241000124008 Mammalia Species 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- 238000002483 medication Methods 0.000 claims 1
- 230000001681 protective effect Effects 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 23
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 21
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
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- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
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- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 230000015271 coagulation Effects 0.000 description 6
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- 108010000499 Thromboplastin Proteins 0.000 description 5
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- 125000003564 m-cyanobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(C#N)=C1[H])C([H])([H])* 0.000 description 5
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- PGOHTUIFYSHAQG-LJSDBVFPSA-N (2S)-6-amino-2-[[(2S)-5-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-4-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-5-amino-2-[[(2S)-5-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S,3R)-2-[[(2S)-5-amino-2-[[(2S)-2-[[(2S)-2-[[(2S,3R)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-5-amino-2-[[(2S)-1-[(2S,3R)-2-[[(2S)-2-[[(2S)-2-[[(2R)-2-[[(2S)-2-[[(2S)-2-[[2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-1-[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-amino-4-methylsulfanylbutanoyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-5-carbamimidamidopentanoyl]amino]propanoyl]pyrrolidine-2-carbonyl]amino]-3-methylbutanoyl]amino]-4-methylpentanoyl]amino]-4-methylpentanoyl]amino]acetyl]amino]-3-hydroxypropanoyl]amino]-4-methylpentanoyl]amino]-3-sulfanylpropanoyl]amino]-4-methylsulfanylbutanoyl]amino]-5-carbamimidamidopentanoyl]amino]-3-hydroxybutanoyl]pyrrolidine-2-carbonyl]amino]-5-oxopentanoyl]amino]-3-hydroxypropanoyl]amino]-3-hydroxypropanoyl]amino]-3-(1H-imidazol-5-yl)propanoyl]amino]-4-methylpentanoyl]amino]-3-hydroxybutanoyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-5-carbamimidamidopentanoyl]amino]-5-oxopentanoyl]amino]-3-hydroxybutanoyl]amino]-3-hydroxypropanoyl]amino]-3-carboxypropanoyl]amino]-3-hydroxypropanoyl]amino]-5-oxopentanoyl]amino]-5-oxopentanoyl]amino]-3-phenylpropanoyl]amino]-5-carbamimidamidopentanoyl]amino]-3-methylbutanoyl]amino]-4-methylpentanoyl]amino]-4-oxobutanoyl]amino]-5-carbamimidamidopentanoyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-4-carboxybutanoyl]amino]-5-oxopentanoyl]amino]hexanoic acid Chemical compound CSCC[C@H](N)C(=O)N[C@@H](Cc1c[nH]c2ccccc12)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](C)C(=O)N1CCC[C@H]1C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(=O)NCC(=O)N[C@@H](CO)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CS)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H]([C@@H](C)O)C(=O)N1CCC[C@H]1C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CO)C(=O)N[C@@H](CO)C(=O)N[C@@H](Cc1cnc[nH]1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](Cc1c[nH]c2ccccc12)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](Cc1c[nH]c2ccccc12)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCCCN)C(O)=O PGOHTUIFYSHAQG-LJSDBVFPSA-N 0.000 description 4
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 4
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- LWMGBUNUFGDPRY-UHFFFAOYSA-N [3-[[azepane-1-carbonyl-[(6-methoxynaphthalen-2-yl)sulfonylamino]amino]methyl]benzenecarboximidoyl]azanium;chloride Chemical compound [Cl-].C1=CC2=CC(OC)=CC=C2C=C1S(=O)(=O)NN(C(=O)N1CCCCCC1)CC1=CC=CC(C([NH3+])=N)=C1 LWMGBUNUFGDPRY-UHFFFAOYSA-N 0.000 description 1
- FUHTUNPITJNEPF-UHFFFAOYSA-N [azepane-1-carbonyl-[(3-cyanophenyl)methyl]amino]azanium;chloride Chemical compound [Cl-].C1CCCCCN1C(=O)N([NH3+])CC1=CC=CC(C#N)=C1 FUHTUNPITJNEPF-UHFFFAOYSA-N 0.000 description 1
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- 238000004458 analytical method Methods 0.000 description 1
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- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 description 1
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- DDBREPKUVSBGFI-UHFFFAOYSA-N phenobarbital Chemical compound C=1C=CC=CC=1C1(CC)C(=O)NC(=O)NC1=O DDBREPKUVSBGFI-UHFFFAOYSA-N 0.000 description 1
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- DKACXUFSLUYRFU-UHFFFAOYSA-N tert-butyl n-aminocarbamate Chemical compound CC(C)(C)OC(=O)NN DKACXUFSLUYRFU-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/20—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof
- C07D295/215—Radicals derived from nitrogen analogues of carbonic acid
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/48—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups having nitrogen atoms of sulfonamide groups further bound to another hetero atom
- C07C311/49—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups having nitrogen atoms of sulfonamide groups further bound to another hetero atom to nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Saccharide Compounds (AREA)
- Investigating Or Analysing Biological Materials (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SI200000326A SI20743A (sl) | 2000-12-22 | 2000-12-22 | Novi trombinski inhibitorji |
| SI200000326 | 2000-12-22 | ||
| PCT/IB2001/002600 WO2002051824A1 (en) | 2000-12-22 | 2001-12-20 | Amidinophenylalanine derivatives as thrombin inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE60109498D1 DE60109498D1 (en) | 2005-04-21 |
| DE60109498T2 true DE60109498T2 (de) | 2006-04-13 |
Family
ID=20432799
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60109498T Expired - Lifetime DE60109498T2 (de) | 2000-12-22 | 2001-12-20 | Amidinophenylalaninderivate als thrombininhibitoren |
Country Status (10)
| Country | Link |
|---|---|
| US (2) | US7285547B2 (enExample) |
| EP (1) | EP1355894B1 (enExample) |
| JP (1) | JP4390453B2 (enExample) |
| AT (1) | ATE291016T1 (enExample) |
| DE (1) | DE60109498T2 (enExample) |
| DK (1) | DK1355894T3 (enExample) |
| ES (1) | ES2240345T3 (enExample) |
| PT (1) | PT1355894E (enExample) |
| SI (1) | SI20743A (enExample) |
| WO (1) | WO2002051824A1 (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0507577D0 (en) | 2005-04-14 | 2005-05-18 | Novartis Ag | Organic compounds |
| GB0523539D0 (en) * | 2005-11-18 | 2005-12-28 | Lek Tovarna Farmacevtskih | New use of organic compounds |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9322976D0 (en) * | 1993-11-08 | 1994-01-05 | Pfizer Ltd | Therapeutic agents |
-
2000
- 2000-12-22 SI SI200000326A patent/SI20743A/sl not_active IP Right Cessation
-
2001
- 2001-12-20 AT AT01272199T patent/ATE291016T1/de active
- 2001-12-20 ES ES01272199T patent/ES2240345T3/es not_active Expired - Lifetime
- 2001-12-20 DE DE60109498T patent/DE60109498T2/de not_active Expired - Lifetime
- 2001-12-20 WO PCT/IB2001/002600 patent/WO2002051824A1/en not_active Ceased
- 2001-12-20 US US10/433,358 patent/US7285547B2/en not_active Expired - Fee Related
- 2001-12-20 JP JP2002552919A patent/JP4390453B2/ja not_active Expired - Fee Related
- 2001-12-20 PT PT01272199T patent/PT1355894E/pt unknown
- 2001-12-20 DK DK01272199T patent/DK1355894T3/da active
- 2001-12-20 EP EP01272199A patent/EP1355894B1/en not_active Expired - Lifetime
-
2007
- 2007-09-12 US US11/854,532 patent/US20080004256A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| WO2002051824A1 (en) | 2002-07-04 |
| PT1355894E (pt) | 2005-08-31 |
| US20080004256A1 (en) | 2008-01-03 |
| DK1355894T3 (da) | 2005-07-11 |
| ES2240345T3 (es) | 2005-10-16 |
| EP1355894B1 (en) | 2005-03-16 |
| EP1355894A1 (en) | 2003-10-29 |
| JP4390453B2 (ja) | 2009-12-24 |
| DE60109498D1 (en) | 2005-04-21 |
| ATE291016T1 (de) | 2005-04-15 |
| JP2004516317A (ja) | 2004-06-03 |
| US7285547B2 (en) | 2007-10-23 |
| SI20743A (sl) | 2002-06-30 |
| US20040048851A1 (en) | 2004-03-11 |
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Legal Events
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| 8364 | No opposition during term of opposition | ||
| 8328 | Change in the person/name/address of the agent |
Representative=s name: KROHER, STROBEL RECHTS- UND PATENTANWAELTE, 80336 |
|
| 8327 | Change in the person/name/address of the patent owner |
Owner name: LEK PHARMACEUTICALS D.D., LJUBLJANA, SI Owner name: UNIVERZA V LJUBLJANI, FAKULTETA ZA FARMACIJO, , SI |
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| 8328 | Change in the person/name/address of the agent |
Representative=s name: TBK-PATENT, 80336 MUENCHEN |