CZ333895A3 - Starting compounds for synthesis of serine-prosthetic inhibitor - Google Patents
Starting compounds for synthesis of serine-prosthetic inhibitor Download PDFInfo
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- CZ333895A3 CZ333895A3 CZ953338A CZ333895A CZ333895A3 CZ 333895 A3 CZ333895 A3 CZ 333895A3 CZ 953338 A CZ953338 A CZ 953338A CZ 333895 A CZ333895 A CZ 333895A CZ 333895 A3 CZ333895 A3 CZ 333895A3
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- 230000015572 biosynthetic process Effects 0.000 title claims abstract description 14
- 238000003786 synthesis reaction Methods 0.000 title claims abstract description 13
- 239000007858 starting material Substances 0.000 title claims description 5
- 239000003112 inhibitor Substances 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 155
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 229940122055 Serine protease inhibitor Drugs 0.000 claims description 7
- 101710102218 Serine protease inhibitor Proteins 0.000 claims description 7
- 239000003001 serine protease inhibitor Substances 0.000 claims description 7
- 229940122388 Thrombin inhibitor Drugs 0.000 claims description 6
- 239000003868 thrombin inhibitor Substances 0.000 claims description 6
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 101000712605 Theromyzon tessulatum Theromin Proteins 0.000 claims description 4
- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims description 2
- 238000011282 treatment Methods 0.000 abstract description 9
- 239000003146 anticoagulant agent Substances 0.000 abstract description 6
- 229940127219 anticoagulant drug Drugs 0.000 abstract description 6
- 238000011321 prophylaxis Methods 0.000 abstract description 6
- 108090000190 Thrombin Proteins 0.000 abstract description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract description 5
- 229960004072 thrombin Drugs 0.000 abstract description 4
- 239000008194 pharmaceutical composition Substances 0.000 abstract description 3
- 208000001435 Thromboembolism Diseases 0.000 abstract description 2
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- 125000005842 heteroatom Chemical group 0.000 abstract description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 abstract description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 description 138
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 100
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- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 52
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 50
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 50
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 49
- 238000010511 deprotection reaction Methods 0.000 description 49
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 48
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- -1 stereomers Chemical class 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
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- 238000002360 preparation method Methods 0.000 description 7
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 6
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- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 4
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- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
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- MKRTXPORKIRPDG-UHFFFAOYSA-N diphenylphosphoryl azide Chemical compound C=1C=CC=CC=1P(=O)(N=[N+]=[N-])C1=CC=CC=C1 MKRTXPORKIRPDG-UHFFFAOYSA-N 0.000 description 1
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- ARMVCJBCFMWHCA-PLNGDYQASA-N ethyl (z)-3-bromobut-2-enoate Chemical compound CCOC(=O)\C=C(\C)Br ARMVCJBCFMWHCA-PLNGDYQASA-N 0.000 description 1
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- MDFRYRPNRLLJHT-UHFFFAOYSA-N methyl carbamimidate;sulfuric acid Chemical compound COC(N)=N.OS(O)(=O)=O MDFRYRPNRLLJHT-UHFFFAOYSA-N 0.000 description 1
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- DHRLEVQXOMLTIM-UHFFFAOYSA-N phosphoric acid;trioxomolybdenum Chemical compound O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.OP(O)(O)=O DHRLEVQXOMLTIM-UHFFFAOYSA-N 0.000 description 1
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- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
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- ODDRZJCTRIAHJN-UHFFFAOYSA-M potassium;carbonic acid;acetate Chemical compound [K+].CC([O-])=O.OC(O)=O ODDRZJCTRIAHJN-UHFFFAOYSA-M 0.000 description 1
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- 238000004809 thin layer chromatography Methods 0.000 description 1
- HNKJADCVZUBCPG-UHFFFAOYSA-N thioanisole Chemical compound CSC1=CC=CC=C1 HNKJADCVZUBCPG-UHFFFAOYSA-N 0.000 description 1
- 229960000103 thrombolytic agent Drugs 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
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- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
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- 238000010626 work up procedure Methods 0.000 description 1
- ORQXBVXKBGUSBA-QMMMGPOBSA-N β-cyclohexyl-alanine Chemical compound OC(=O)[C@@H](N)CC1CCCCC1 ORQXBVXKBGUSBA-QMMMGPOBSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06139—Dipeptides with the first amino acid being heterocyclic
-
- 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
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
- C07C237/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
- C07C237/06—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C279/04—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to acyclic carbon atoms of a carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C279/04—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to acyclic carbon atoms of a carbon skeleton
- C07C279/12—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to acyclic carbon atoms of a carbon skeleton being further substituted by nitrogen atoms not being part of nitro or nitroso groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/02—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link
- C07K5/022—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing the structure -X-C(=O)-(C)n-N-C-C(=O)-Y-; X and Y being heteroatoms; n being 1 or 2
- C07K5/0222—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing the structure -X-C(=O)-(C)n-N-C-C(=O)-Y-; X and Y being heteroatoms; n being 1 or 2 with the first amino acid being heterocyclic, e.g. Pro, Trp
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06008—Dipeptides with the first amino acid being neutral
- C07K5/06078—Dipeptides with the first amino acid being neutral and aromatic or cycloaliphatic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06191—Dipeptides containing heteroatoms different from O, S, or N
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE9103612A SE9103612D0 (sv) | 1991-12-04 | 1991-12-04 | New peptide derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CZ333895A3 true CZ333895A3 (en) | 1996-04-17 |
Family
ID=20384531
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CZ953338A CZ333895A3 (en) | 1991-12-04 | 1992-12-01 | Starting compounds for synthesis of serine-prosthetic inhibitor |
| CZ941296A CZ129694A3 (en) | 1991-12-04 | 1992-12-01 | Novel peptide derivatives |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CZ941296A CZ129694A3 (en) | 1991-12-04 | 1992-12-01 | Novel peptide derivatives |
Country Status (27)
| Country | Link |
|---|---|
| US (4) | US5614499A (enExample) |
| EP (1) | EP0618926B1 (enExample) |
| JP (1) | JP3306826B2 (enExample) |
| CN (1) | CN1076199A (enExample) |
| AP (1) | AP353A (enExample) |
| AT (1) | ATE190066T1 (enExample) |
| AU (2) | AU670052B2 (enExample) |
| CA (1) | CA2125175C (enExample) |
| CZ (2) | CZ333895A3 (enExample) |
| DE (1) | DE69230727T2 (enExample) |
| EE (1) | EE9400455A (enExample) |
| FI (1) | FI115770B (enExample) |
| HU (1) | HUT70431A (enExample) |
| IL (1) | IL103910A0 (enExample) |
| IS (1) | IS3954A (enExample) |
| MA (1) | MA22729A1 (enExample) |
| MX (1) | MX9206938A (enExample) |
| NO (1) | NO311361B1 (enExample) |
| NZ (2) | NZ246106A (enExample) |
| SE (1) | SE9103612D0 (enExample) |
| SI (1) | SI9200363A (enExample) |
| SK (1) | SK63194A3 (enExample) |
| TN (1) | TNSN92109A1 (enExample) |
| TW (1) | TW223078B (enExample) |
| WO (1) | WO1993011152A1 (enExample) |
| YU (1) | YU104592A (enExample) |
| ZA (1) | ZA929099B (enExample) |
Families Citing this family (73)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5583146A (en) * | 1992-12-02 | 1996-12-10 | Bristol-Myers Squibb Company | Heterocyclic thrombin inhibitors |
| US6534536B1 (en) | 1994-03-16 | 2003-03-18 | Bristol-Myers Squibb Company | Alkylsulfonamido heterocyclic thrombin inhibitors |
| US6984627B1 (en) | 1993-06-03 | 2006-01-10 | Astrazeneca Ab | Peptide derivatives |
| SE9900043D0 (sv) * | 1999-01-11 | 1999-01-11 | Astra Ab | New use |
| SE9301916D0 (sv) * | 1993-06-03 | 1993-06-03 | Ab Astra | New peptides derivatives |
| EP0648780A1 (en) * | 1993-08-26 | 1995-04-19 | Bristol-Myers Squibb Company | Heterocyclic thrombin inhibitors |
| GB9318637D0 (en) * | 1993-09-08 | 1993-10-27 | Ferring Res Ltd | Enzyme inhibitors |
| US5705487A (en) * | 1994-03-04 | 1998-01-06 | Eli Lilly And Company | Antithrombotic agents |
| ZA951618B (en) * | 1994-03-04 | 1996-08-27 | Lilly Co Eli | Antithrombotic agents |
| US5439888A (en) * | 1994-03-04 | 1995-08-08 | Eli Lilly And Company | Antithrombotic agents |
| US5885967A (en) * | 1994-03-04 | 1999-03-23 | Eli Lilly And Company | Antithrombotic agents |
| US5484772A (en) * | 1994-03-04 | 1996-01-16 | Eli Lilly And Company | Antithrombotic agents |
| US5488037A (en) * | 1994-03-04 | 1996-01-30 | Eli Lilly And Company | Antithrombotic agents |
| US5707966A (en) * | 1994-03-04 | 1998-01-13 | Eli Lilly And Company | Antithrombotic agents |
| US5726159A (en) * | 1994-03-04 | 1998-03-10 | Eli Lilly And Company | Antithrombotic agents |
| IL112795A (en) * | 1994-03-04 | 2001-01-28 | Astrazeneca Ab | Peptide derivatives as antithrombic agents their preparation and pharmaceutical compositions containing them |
| US5602101A (en) * | 1994-03-04 | 1997-02-11 | Eli Lilly And Company | Antithrombotic agents |
| US5691356A (en) * | 1994-03-21 | 1997-11-25 | Bristol-Myers Squibb Company | Disubstituted heterocyclic thrombin inhibitors |
| US5681844A (en) * | 1994-04-18 | 1997-10-28 | Corvas International, Inc. | Methionine sulfone and s-substituted cysteine sulfone derivatives as enzyme inhibitors |
| US5561146A (en) * | 1994-06-10 | 1996-10-01 | Bristol-Myers Squibb Company | Modified guanidino and amidino thrombin inhibitors |
| DE4421052A1 (de) | 1994-06-17 | 1995-12-21 | Basf Ag | Neue Thrombininhibitoren, ihre Herstellung und Verwendung |
| DE4436772A1 (de) * | 1994-10-14 | 1996-04-18 | Boehringer Mannheim Gmbh | Neues Dipeptid-Derivat, Verfahren zu seiner Herstellung sowie diese Verbindung enthaltende Arzneimittel |
| SE504185C2 (sv) * | 1994-11-08 | 1996-12-02 | Astra Ab | Lagringsstabil vattenlösning för infusion av trombininhibitorer |
| SE9404196D0 (sv) * | 1994-12-02 | 1994-12-02 | Astra Ab | New antithrombotic formulation |
| DE4443390A1 (de) * | 1994-12-06 | 1996-06-13 | Basf Ag | Neue dipeptidische p-Amidinobenzylamide mit N-terminalen Sulfonyl- bzw. Aminosulfonylresten |
| KR100388185B1 (ko) * | 1995-02-17 | 2003-11-28 | 애보트 게엠베하 운트 콤파니 카게 | 트롬빈 억제제로서의 신규 디펩티드 아미딘 |
| US5710130A (en) * | 1995-02-27 | 1998-01-20 | Eli Lilly And Company | Antithrombotic agents |
| US5914319A (en) * | 1995-02-27 | 1999-06-22 | Eli Lilly And Company | Antithrombotic agents |
| DE19512484A1 (de) | 1995-04-04 | 1996-10-17 | Bayer Ag | Kohlenhydratmodifizierte Cytostatika |
| SA96170106A (ar) | 1995-07-06 | 2005-12-03 | أسترا أكتيبولاج | مشتقات حامض أميني جديدة |
| AR005245A1 (es) | 1995-12-21 | 1999-04-28 | Astrazeneca Ab | Prodrogas de inhibidores de trombina, una formulación farmaceutica que las comprende, el uso de dichas prodrogas para la manufactura de un medicamento y un procedimiento para su preparacion |
| SE9600216D0 (sv) * | 1996-01-18 | 1996-01-18 | Hans Arne Hansson | Styrning av läkningsprocesser |
| CA2200163A1 (en) * | 1996-03-22 | 1997-09-22 | Michael Robert Wiley | Antithrombotic diamides |
| US5811402A (en) * | 1996-03-22 | 1998-09-22 | Eli Lilly And Company | Antithrombotic diamides |
| SE9602263D0 (sv) | 1996-06-07 | 1996-06-07 | Astra Ab | New amino acid derivatives |
| US6200967B1 (en) | 1996-06-25 | 2001-03-13 | Eli Lilly And Company | Anticoagulant agents |
| JP2000514788A (ja) * | 1996-06-25 | 2000-11-07 | イーライ・リリー・アンド・カンパニー | 抗凝固剤 |
| SE9602646D0 (sv) | 1996-07-04 | 1996-07-04 | Astra Ab | Pharmaceutically-useful compounds |
| SE9603724D0 (sv) * | 1996-10-11 | 1996-10-11 | Astra Ab | New pharmaceutical parenteral formulation of a thrombin inhibitor |
| US5877156A (en) * | 1997-04-24 | 1999-03-02 | Akzo Nobel, N.V. | Thrombin inhibitors |
| AR013084A1 (es) | 1997-06-19 | 2000-12-13 | Astrazeneca Ab | Derivados de amidino utiles como inhibidores de la trombina, composicion farmaceutica, utilizacion de dichos compuestos para la preparacion demedicamentos y proceso para la preparacion de los compuestos mencionados |
| SE9704543D0 (sv) | 1997-12-05 | 1997-12-05 | Astra Ab | New compounds |
| CN1289341A (zh) | 1998-01-26 | 2001-03-28 | Basf公司 | 凝血酶抑制剂 |
| WO1999055355A1 (en) * | 1998-04-24 | 1999-11-04 | 3-Dimensional Pharmaceuticals, Inc. | Amino acid amidinohydrazones, alkoxyguanidines and aminoguanidines as protease inhibitors |
| SE9802938D0 (sv) * | 1998-09-01 | 1998-09-01 | Astra Ab | Improved stability for injection solutions |
| SE9802973D0 (sv) | 1998-09-03 | 1998-09-03 | Astra Ab | Immediate release tablet |
| SE9804313D0 (sv) | 1998-12-14 | 1998-12-14 | Astra Ab | New compounds |
| DK1150996T3 (da) | 1999-01-13 | 2008-02-11 | Astrazeneca Ab | Nye amidinobenzylaminderivater og deres anvendelse som thrombin-inhibitorer |
| KR20000060566A (ko) * | 1999-03-17 | 2000-10-16 | 이경하 | 치환된 방향족 아미딘 유도체 및 이를 함유하는 의약조성물 |
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1991
- 1991-12-04 SE SE9103612A patent/SE9103612D0/xx unknown
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1992
- 1992-11-24 TW TW081109412A patent/TW223078B/zh active
- 1992-11-24 ZA ZA929099A patent/ZA929099B/xx unknown
- 1992-11-27 IL IL103910A patent/IL103910A0/xx unknown
- 1992-12-01 EP EP92924993A patent/EP0618926B1/en not_active Expired - Lifetime
- 1992-12-01 DE DE69230727T patent/DE69230727T2/de not_active Expired - Lifetime
- 1992-12-01 CZ CZ953338A patent/CZ333895A3/cs unknown
- 1992-12-01 JP JP51005393A patent/JP3306826B2/ja not_active Expired - Fee Related
- 1992-12-01 AT AT92924993T patent/ATE190066T1/de not_active IP Right Cessation
- 1992-12-01 NZ NZ246106A patent/NZ246106A/en not_active IP Right Cessation
- 1992-12-01 CA CA002125175A patent/CA2125175C/en not_active Expired - Fee Related
- 1992-12-01 AU AU31209/93A patent/AU670052B2/en not_active Ceased
- 1992-12-01 NZ NZ280762A patent/NZ280762A/en not_active IP Right Cessation
- 1992-12-01 SK SK631-94A patent/SK63194A3/sk unknown
- 1992-12-01 HU HU9401474A patent/HUT70431A/hu unknown
- 1992-12-01 CZ CZ941296A patent/CZ129694A3/cs unknown
- 1992-12-01 WO PCT/SE1992/000832 patent/WO1993011152A1/en not_active Ceased
- 1992-12-02 US US07/984,884 patent/US5614499A/en not_active Expired - Lifetime
- 1992-12-02 MX MX9206938A patent/MX9206938A/es unknown
- 1992-12-02 MA MA23019A patent/MA22729A1/fr unknown
- 1992-12-03 IS IS3954A patent/IS3954A/is unknown
- 1992-12-03 TN TNTNSN92109A patent/TNSN92109A1/fr unknown
- 1992-12-04 AP APAP/P/1992/000457A patent/AP353A/en active
- 1992-12-04 SI SI19929200363A patent/SI9200363A/sl unknown
- 1992-12-04 CN CN92115304A patent/CN1076199A/zh active Pending
- 1992-12-04 YU YU104592A patent/YU104592A/sh unknown
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1994
- 1994-06-03 FI FI942645A patent/FI115770B/fi not_active IP Right Cessation
- 1994-06-03 NO NO19942066A patent/NO311361B1/no not_active IP Right Cessation
- 1994-11-23 EE EE9400455A patent/EE9400455A/xx unknown
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1995
- 1995-06-07 US US08/480,818 patent/US5955433A/en not_active Expired - Fee Related
- 1995-06-07 US US08/481,810 patent/US5736521A/en not_active Expired - Lifetime
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1996
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