PT98473A - Processo de preparacao de piperazinas 1,4-dissubstituidas e de composicoes farmaceuticas - Google Patents
Processo de preparacao de piperazinas 1,4-dissubstituidas e de composicoes farmaceuticasInfo
- Publication number
- PT98473A PT98473A PT98473A PT9847391A PT98473A PT 98473 A PT98473 A PT 98473A PT 98473 A PT98473 A PT 98473A PT 9847391 A PT9847391 A PT 9847391A PT 98473 A PT98473 A PT 98473A
- Authority
- PT
- Portugal
- Prior art keywords
- substituted
- alkyl
- cyano
- alkenyl
- alkoxy
- Prior art date
Links
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- 238000002360 preparation method Methods 0.000 title 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 abstract 2
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 2
- -1 disubstituted piperazine compound Chemical class 0.000 abstract 2
- 125000001424 substituent group Chemical group 0.000 abstract 2
- 125000000229 (C1-C4)alkoxy group Chemical class 0.000 abstract 1
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 abstract 1
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical class C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000001891 dimethoxy group Chemical class [H]C([H])([H])O* 0.000 abstract 1
- 230000006744 dopaminergic deficit Effects 0.000 abstract 1
- 125000002541 furyl group Chemical class 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical class C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 abstract 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical class C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 abstract 1
- 125000005646 oximino group Chemical group 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- CMPQUABWPXYYSH-UHFFFAOYSA-N phenyl phosphate Chemical class OP(O)(=O)OC1=CC=CC=C1 CMPQUABWPXYYSH-UHFFFAOYSA-N 0.000 abstract 1
- 208000020016 psychiatric disease Diseases 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 238000006467 substitution reaction Methods 0.000 abstract 1
- 150000003512 tertiary amines Chemical class 0.000 abstract 1
- 125000001544 thienyl group Chemical class 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/10—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- 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
- A61P25/24—Antidepressants
-
- 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
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/08—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
-
- 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
- C07D295/04—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
-
- 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
- C07D295/04—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- 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
- C07D295/04—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/14—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D295/145—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/15—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/22—Radicals substituted by doubly bound hetero atoms, or by two hetero atoms other than halogen singly bound to the same carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
- C07F9/6509—Six-membered rings
- C07F9/650952—Six-membered rings having the nitrogen atoms in the positions 1 and 4
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Physical Water Treatments (AREA)
- Water Treatment By Sorption (AREA)
- Removal Of Specific Substances (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DK178590A DK178590D0 (da) | 1990-07-26 | 1990-07-26 | 1,4-disubstituerede piperaziner |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PT98473A true PT98473A (pt) | 1992-05-29 |
| PT98473B PT98473B (pt) | 1999-04-30 |
Family
ID=8108040
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PT98473A PT98473B (pt) | 1990-07-26 | 1991-07-26 | Processo de preparacao de piperazinas 1,4-dissubstituidas e de composicoes farmaceuticas |
Country Status (16)
| Country | Link |
|---|---|
| EP (1) | EP0541617B1 (pt) |
| JP (1) | JPH05509311A (pt) |
| AT (1) | ATE154018T1 (pt) |
| AU (1) | AU665172B2 (pt) |
| CA (1) | CA2087855A1 (pt) |
| DE (1) | DE69126433T2 (pt) |
| DK (2) | DK178590D0 (pt) |
| ES (1) | ES2103820T3 (pt) |
| FI (1) | FI930296A (pt) |
| GR (1) | GR3024502T3 (pt) |
| IE (1) | IE912492A1 (pt) |
| IL (1) | IL98696A (pt) |
| NZ (1) | NZ239115A (pt) |
| PT (1) | PT98473B (pt) |
| WO (1) | WO1992001679A1 (pt) |
| ZA (1) | ZA915403B (pt) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9200293D0 (en) * | 1992-01-08 | 1992-02-26 | Wyeth John & Brother Ltd | Piperazine derivatives |
| US6048859A (en) * | 1992-06-29 | 2000-04-11 | Merck & Co., Inc. | Morpholine and thiomorpholine tachykinin receptor antagonists |
| US5637699A (en) * | 1992-06-29 | 1997-06-10 | Merck & Co., Inc. | Process for preparing morpholine tachykinin receptor antagonists |
| US5719147A (en) * | 1992-06-29 | 1998-02-17 | Merck & Co., Inc. | Morpholine and thiomorpholine tachykinin receptor antagonists |
| US5387595A (en) * | 1992-08-26 | 1995-02-07 | Merck & Co., Inc. | Alicyclic compounds as tachykinin receptor antagonists |
| US5344830A (en) * | 1992-12-10 | 1994-09-06 | Merck & Co., Inc. | N,N-diacylpiperazine tachykinin antagonists |
| US5348955A (en) * | 1993-06-22 | 1994-09-20 | Merck & Co., Inc. | N,N-diacylpiperazines |
| TW385308B (en) * | 1994-03-04 | 2000-03-21 | Merck & Co Inc | Prodrugs of morpholine tachykinin receptor antagonists |
| US6103465A (en) * | 1995-02-14 | 2000-08-15 | The Perkin-Elmer Corporation | Methods and reagents for typing HLA class I genes |
| FR2815031A1 (fr) * | 2000-10-11 | 2002-04-12 | Gilles Fillion | Compositions et methodes pour la regulation du systeme nerveux |
| NL2000351C2 (nl) | 2005-12-22 | 2007-09-11 | Pfizer Prod Inc | Estrogeen-modulatoren. |
| NZ601967A (en) | 2010-03-12 | 2015-03-27 | Omeros Corp | Pde10 inhibitors and related compositions and methods |
| NZ630810A (en) | 2014-04-28 | 2016-03-31 | Omeros Corp | Processes and intermediates for the preparation of a pde10 inhibitor |
| NZ716462A (en) | 2014-04-28 | 2017-11-24 | Omeros Corp | Optically active pde10 inhibitor |
| EP3285760A4 (en) | 2015-04-24 | 2018-09-26 | Omeros Corporation | Pde10 inhibitors and related compositions and methods |
| JP2018535969A (ja) | 2015-11-04 | 2018-12-06 | オメロス コーポレーション | Ｐｄｅ１０阻害剤の固体状態形態 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2988551A (en) * | 1954-07-30 | 1961-06-13 | Union Chimique Belge Sa | Piperazine derivatives |
| US3558631A (en) * | 1966-01-06 | 1971-01-26 | Smith Kline French Lab | Benzhydryloxycyclopropyl heterocyclic amines |
| FR2276824A1 (fr) * | 1974-07-04 | 1976-01-30 | Melon Jean Marie | Derives de la piperazine 1,4-disubstituee, leur procede de preparation et leurs applications therapeutiques |
| FR2310763A1 (fr) * | 1975-05-13 | 1976-12-10 | Buzas Andre | Derives 1,4-disubstitues de la piperazine, leur procede de preparation et leurs applications |
| CH634313A5 (en) * | 1978-01-01 | 1983-01-31 | Gist Brocades Nv | Piperazine derivatives |
| HU196194B (en) * | 1986-04-28 | 1988-10-28 | Richter Gedeon Vegyeszet | Process for producing new 1-4 disubstituted piperazines and pharmaceuticals comprising the compounds |
| FR2601366B1 (fr) * | 1986-07-10 | 1988-11-25 | Andre Buzas | Derives de la benzhydryloxyethyl-piperazine, procedes d'obtention et de compositions pharmaceutiques les contenant. |
| DE3726068A1 (de) * | 1987-08-06 | 1989-02-16 | Hoechst Ag | Diarylalkoxyalkyl-substituierte alkylamine, verfahren zu ihrer herstellung, ihre verwendung sowie sie enthaltende arzneimittel |
| US4973591A (en) * | 1988-10-21 | 1990-11-27 | Syntex Pharmaceuticals, Ltd. | Parenteral formulations of 1-diphenylmethyl-4-((2-(4-methylphenyl)-5-methyl-1H-imidazol-4-yl)methyl)piperazine |
-
1990
- 1990-07-26 DK DK178590A patent/DK178590D0/da not_active Application Discontinuation
-
1991
- 1991-07-01 IL IL9869691A patent/IL98696A/en active IP Right Grant
- 1991-07-11 ZA ZA915403A patent/ZA915403B/xx unknown
- 1991-07-15 EP EP91913695A patent/EP0541617B1/en not_active Expired - Lifetime
- 1991-07-15 ES ES91913695T patent/ES2103820T3/es not_active Expired - Lifetime
- 1991-07-15 AT AT91913695T patent/ATE154018T1/de not_active IP Right Cessation
- 1991-07-15 WO PCT/DK1991/000205 patent/WO1992001679A1/en active IP Right Grant
- 1991-07-15 CA CA002087855A patent/CA2087855A1/en not_active Abandoned
- 1991-07-15 DE DE69126433T patent/DE69126433T2/de not_active Expired - Fee Related
- 1991-07-15 AU AU83005/91A patent/AU665172B2/en not_active Ceased
- 1991-07-15 DK DK91913695.2T patent/DK0541617T3/da active
- 1991-07-15 JP JP3512984A patent/JPH05509311A/ja active Pending
- 1991-07-17 IE IE249291A patent/IE912492A1/en unknown
- 1991-07-24 NZ NZ239115A patent/NZ239115A/xx unknown
- 1991-07-26 PT PT98473A patent/PT98473B/pt not_active IP Right Cessation
-
1993
- 1993-01-25 FI FI930296A patent/FI930296A/fi unknown
-
1997
- 1997-08-21 GR GR970402141T patent/GR3024502T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE69126433T2 (de) | 1997-12-04 |
| JPH05509311A (ja) | 1993-12-22 |
| AU8300591A (en) | 1992-02-18 |
| ZA915403B (en) | 1992-04-29 |
| FI930296A0 (fi) | 1993-01-25 |
| EP0541617B1 (en) | 1997-06-04 |
| FI930296A (fi) | 1993-01-25 |
| NZ239115A (en) | 1993-07-27 |
| IL98696A (en) | 1995-11-27 |
| WO1992001679A1 (en) | 1992-02-06 |
| IL98696A0 (en) | 1992-07-15 |
| IE912492A1 (en) | 1992-01-29 |
| DK178590D0 (da) | 1990-07-26 |
| PT98473B (pt) | 1999-04-30 |
| GR3024502T3 (en) | 1997-11-28 |
| AU665172B2 (en) | 1995-12-21 |
| ATE154018T1 (de) | 1997-06-15 |
| DK0541617T3 (da) | 1997-11-03 |
| ES2103820T3 (es) | 1997-10-01 |
| DE69126433D1 (de) | 1997-07-10 |
| EP0541617A1 (en) | 1993-05-19 |
| CA2087855A1 (en) | 1992-01-27 |
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