KR880007451A - 신규한 화합물 - Google Patents
신규한 화합물 Download PDFInfo
- Publication number
- KR880007451A KR880007451A KR1019870015022A KR870015022A KR880007451A KR 880007451 A KR880007451 A KR 880007451A KR 1019870015022 A KR1019870015022 A KR 1019870015022A KR 870015022 A KR870015022 A KR 870015022A KR 880007451 A KR880007451 A KR 880007451A
- Authority
- KR
- South Korea
- Prior art keywords
- carbonyl
- methyl
- ethyl
- methylamino
- amino
- 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.)
- Withdrawn
Links
- 150000001875 compounds Chemical class 0.000 title claims 17
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 32
- -1 -NR 6 R 7 Chemical compound 0.000 claims 22
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 16
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 16
- 239000001257 hydrogen Substances 0.000 claims 13
- 229910052739 hydrogen Inorganic materials 0.000 claims 13
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 10
- 125000000217 alkyl group Chemical group 0.000 claims 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 6
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 6
- 125000003545 alkoxy group Chemical group 0.000 claims 5
- XNCNNDVCAUWAIT-UHFFFAOYSA-N Methyl heptanoate Chemical compound CCCCCCC(=O)OC XNCNNDVCAUWAIT-UHFFFAOYSA-N 0.000 claims 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 4
- VPJAVANMJXMGDB-CGZBRXJRSA-N 4-[[(2s)-3-(4-methoxyphenyl)-1-(methylamino)-1-oxopropan-2-yl]carbamoyl]-6-methyl-3-sulfanylheptanoic acid Chemical compound OC(=O)CC(S)C(CC(C)C)C(=O)N[C@H](C(=O)NC)CC1=CC=C(OC)C=C1 VPJAVANMJXMGDB-CGZBRXJRSA-N 0.000 claims 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 3
- 150000002431 hydrogen Chemical class 0.000 claims 3
- DKORFFHGSOICFE-GPJFCIFZSA-N 2-[[3-acetylsulfanyl-4-[[(2s)-3-(4-methoxyphenyl)-1-(methylamino)-1-oxopropan-2-yl]carbamoyl]-6-methylheptanoyl]amino]acetic acid Chemical compound OC(=O)CNC(=O)CC(SC(C)=O)C(CC(C)C)C(=O)N[C@H](C(=O)NC)CC1=CC=C(OC)C=C1 DKORFFHGSOICFE-GPJFCIFZSA-N 0.000 claims 2
- CRNFNVKHCQAPQV-XBMUEBEBSA-N 3-acetylsulfanyl-4-[[(2s)-3-(4-methoxyphenyl)-1-(methylamino)-1-oxopropan-2-yl]carbamoyl]-6-methylheptanoic acid Chemical compound OC(=O)CC(SC(C)=O)C(CC(C)C)C(=O)N[C@H](C(=O)NC)CC1=CC=C(OC)C=C1 CRNFNVKHCQAPQV-XBMUEBEBSA-N 0.000 claims 2
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 2
- 229960000583 acetic acid Drugs 0.000 claims 2
- 235000011054 acetic acid Nutrition 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 230000011382 collagen catabolic process Effects 0.000 claims 2
- 208000018631 connective tissue disease Diseases 0.000 claims 2
- 125000004494 ethyl ester group Chemical group 0.000 claims 2
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 125000003107 substituted aryl group Chemical group 0.000 claims 2
- CVUCAISIRGBOGT-ADKAHSJRSA-N 2-[[4-[[(2s)-3-(4-methoxyphenyl)-1-(methylamino)-1-oxopropan-2-yl]carbamoyl]-6-methyl-3-sulfanylheptanoyl]amino]acetic acid Chemical compound OC(=O)CNC(=O)CC(S)C(CC(C)C)C(=O)N[C@H](C(=O)NC)CC1=CC=C(OC)C=C1 CVUCAISIRGBOGT-ADKAHSJRSA-N 0.000 claims 1
- ZLBOFWKXUNYHIM-CGZBRXJRSA-N 3-acetylsulfanyl-4-[[(2s)-1-amino-1-oxo-3-phenylpropan-2-yl]carbamoyl]-6-methylheptanoic acid Chemical compound OC(=O)CC(SC(C)=O)C(CC(C)C)C(=O)N[C@H](C(N)=O)CC1=CC=CC=C1 ZLBOFWKXUNYHIM-CGZBRXJRSA-N 0.000 claims 1
- MOCJBYMGCWJTNY-ADKAHSJRSA-N 3-acetylsulfanyl-6-methyl-4-[[(2s)-1-(methylamino)-1-oxo-3-phenylpropan-2-yl]carbamoyl]heptanoic acid Chemical compound OC(=O)CC(SC(C)=O)C(CC(C)C)C(=O)N[C@H](C(=O)NC)CC1=CC=CC=C1 MOCJBYMGCWJTNY-ADKAHSJRSA-N 0.000 claims 1
- 241000124008 Mammalia Species 0.000 claims 1
- RNFCYFVPNIXAHP-UHFFFAOYSA-N N-heptanoylglycine Chemical compound CCCCCCC(=O)NCC(O)=O RNFCYFVPNIXAHP-UHFFFAOYSA-N 0.000 claims 1
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims 1
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims 1
- 125000004104 aryloxy group Chemical group 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
- 125000000268 heptanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 150000004677 hydrates Chemical class 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 150000004702 methyl esters Chemical class 0.000 claims 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 150000002829 nitrogen Chemical group 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- RCCYSVYHULFYHE-UHFFFAOYSA-N pentanediamide Chemical compound NC(=O)CCCC(N)=O RCCYSVYHULFYHE-UHFFFAOYSA-N 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 230000010287 polarization Effects 0.000 claims 1
- IBKIIWQFBWQFNS-XBMUEBEBSA-N s-[4-carbamoyl-1-[[(2s)-3-(4-methoxyphenyl)-1-(methylamino)-1-oxopropan-2-yl]amino]-6-methyl-1-oxoheptan-3-yl] ethanethioate Chemical compound CC(C)CC(C(N)=O)C(SC(C)=O)CC(=O)N[C@H](C(=O)NC)CC1=CC=C(OC)C=C1 IBKIIWQFBWQFNS-XBMUEBEBSA-N 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 239000012453 solvate Substances 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/24—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/25—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
-
- 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
- C07D295/18—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 carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D209/20—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 substituted additionally by nitrogen atoms, e.g. tryptophane
-
- 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
- C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
- C07K5/06034—Dipeptides with the first amino acid being neutral and aliphatic the side chain containing 2 to 4 carbon atoms
- C07K5/06043—Leu-amino acid
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8630928 | 1986-12-24 | ||
| GB868630928A GB8630928D0 (en) | 1986-12-24 | 1986-12-24 | Compounds |
| GB878717924A GB8717924D0 (en) | 1987-07-29 | 1987-07-29 | Compounds |
| GB8717924 | 1987-07-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR880007451A true KR880007451A (ko) | 1988-08-27 |
Family
ID=26291743
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019870015022A Withdrawn KR880007451A (ko) | 1986-12-24 | 1987-12-23 | 신규한 화합물 |
Country Status (12)
| Country | Link |
|---|---|
| US (2) | US4937243A (enExample) |
| EP (1) | EP0273689B1 (enExample) |
| KR (1) | KR880007451A (enExample) |
| AU (1) | AU599736B2 (enExample) |
| CA (1) | CA1322073C (enExample) |
| DE (1) | DE3774858D1 (enExample) |
| DK (1) | DK681287A (enExample) |
| ES (1) | ES2038678T3 (enExample) |
| GR (1) | GR3003761T3 (enExample) |
| IE (1) | IE60751B1 (enExample) |
| NZ (1) | NZ223037A (enExample) |
| PT (1) | PT86433B (enExample) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8729804D0 (en) * | 1987-12-22 | 1988-02-03 | Beecham Group Plc | Novel compounds |
| GB8814813D0 (en) * | 1988-06-22 | 1988-07-27 | Beecham Group Plc | Novel compounds |
| WO1990005141A1 (en) * | 1988-11-10 | 1990-05-17 | Australian Commercial Research & Development Limited | Amino acid and peptide inhibitors of human leukocytic elastase and collagenase |
| GB9000846D0 (en) * | 1990-01-15 | 1990-03-14 | Beecham Group Plc | Novel compounds |
| GB9022117D0 (en) * | 1990-10-11 | 1990-11-21 | Beecham Group Plc | Novel compounds |
| US5187305A (en) * | 1990-11-26 | 1993-02-16 | Glaxo Inc. | S-nitroso-N-alkonoylpenicillamines |
| GB9107367D0 (en) * | 1991-04-08 | 1991-05-22 | Smithkline Beecham Plc | Novel compounds |
| WO1993014112A1 (en) * | 1992-01-15 | 1993-07-22 | Merck & Co., Inc. | Substituted phosphinic acid-containing peptidyl derivatives as antidegenerative agents |
| AU4267293A (en) * | 1992-05-01 | 1993-11-29 | British Biotech Pharmaceuticals Limited | Use of MMP inhibitors |
| GB9211707D0 (en) * | 1992-06-03 | 1992-07-15 | Celltech Ltd | Peptidyl derivatives |
| US5629343A (en) * | 1992-10-02 | 1997-05-13 | Merck & Co., Inc. | N-(mercaptoacyl) peptidyl derivatives as antidegenerative agents |
| US6090785A (en) * | 1992-10-15 | 2000-07-18 | Merck & Co., Inc. | Substituted N-carboxyalkylpeptidyl derivatives as antidegenerative agents |
| WO1994012169A1 (en) * | 1992-11-25 | 1994-06-09 | Merck & Co., Inc. | Carboxy-peptidyl derivatives as antidegenerative active agents |
| GB9323165D0 (en) * | 1993-11-10 | 1994-01-05 | Chiros Ltd | Compounds |
| US5840698A (en) * | 1994-10-27 | 1998-11-24 | Affymax Technologies N.V. | Inhibitors of collagenase-1 and stormelysin-I metalloproteases, pharmaceutical compositions comprising same and methods of their use |
| US5831004A (en) | 1994-10-27 | 1998-11-03 | Affymax Technologies N.V. | Inhibitors of metalloproteases, pharmaceutical compositions comprising same and methods of their use |
| US5789434A (en) * | 1994-11-15 | 1998-08-04 | Bayer Corporation | Derivatives of substituted 4-biarylbutyric acid as matrix metalloprotease inhibitors |
| HRP950558A2 (en) * | 1994-11-15 | 1997-12-31 | Scott M. Wilhelm | Substituted 4-biarylbutric or biarylpentanoic acids and derivatives as matrix metalloprotease inhibitors |
| WO1996035714A1 (en) * | 1995-05-10 | 1996-11-14 | Chiroscience Limited | Peptide compounds which inhibit metalloproteinase and tnf liberation and their therapeutic uses |
| CA2219973A1 (en) * | 1995-05-10 | 1996-11-14 | Chiroscience Limited | Peptidyl compounds and their therapeutic use |
| US5932579A (en) | 1996-06-18 | 1999-08-03 | Affymax Technologies N.V. | Collagenase-1 and stromelysin-1 inhibitors, pharmaceutical compositions comprising same and methods of their use |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH628247A5 (en) * | 1975-01-03 | 1982-02-26 | Ciba Geigy Ag | Aqueous, film-forming concentrates for extinguishing or preventing fire with a content of non-anionic compounds containing perfluoroalkylalkylenethio groups |
| US4263293A (en) * | 1980-05-30 | 1981-04-21 | E. R. Squibb & Sons, Inc. | Heterocyclic containing amides as inhibitors of mammalian collagenase |
| US4410543A (en) * | 1981-03-26 | 1983-10-18 | Ciba-Geigy Corporation | Carboxylated oxime-carbamates and their use in controlling pests |
| DE3467754D1 (de) * | 1983-10-03 | 1988-01-07 | Squibb & Sons Inc | Enkephalinase inhibitors |
| US4595700A (en) * | 1984-12-21 | 1986-06-17 | G. D. Searle & Co. | Thiol based collagenase inhibitors |
-
1987
- 1987-12-22 AU AU82926/87A patent/AU599736B2/en not_active Ceased
- 1987-12-22 US US07/136,913 patent/US4937243A/en not_active Expired - Fee Related
- 1987-12-22 EP EP87311321A patent/EP0273689B1/en not_active Expired - Lifetime
- 1987-12-22 DK DK681287A patent/DK681287A/da not_active Application Discontinuation
- 1987-12-22 CA CA000555081A patent/CA1322073C/en not_active Expired - Fee Related
- 1987-12-22 ES ES198787311321T patent/ES2038678T3/es not_active Expired - Lifetime
- 1987-12-22 DE DE8787311321T patent/DE3774858D1/de not_active Expired - Fee Related
- 1987-12-22 PT PT86433A patent/PT86433B/pt not_active IP Right Cessation
- 1987-12-22 NZ NZ223037A patent/NZ223037A/en unknown
- 1987-12-22 IE IE350587A patent/IE60751B1/en not_active IP Right Cessation
- 1987-12-23 KR KR1019870015022A patent/KR880007451A/ko not_active Withdrawn
-
1990
- 1990-04-30 US US07/517,391 patent/US5109000A/en not_active Expired - Fee Related
-
1992
- 1992-02-11 GR GR920400183T patent/GR3003761T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP0273689A2 (en) | 1988-07-06 |
| EP0273689A3 (en) | 1989-07-12 |
| IE873505L (en) | 1988-06-24 |
| AU8292687A (en) | 1988-09-01 |
| DK681287A (da) | 1988-06-25 |
| US5109000A (en) | 1992-04-28 |
| IE60751B1 (en) | 1994-08-10 |
| DE3774858D1 (de) | 1992-01-09 |
| EP0273689B1 (en) | 1991-11-27 |
| ES2038678T3 (es) | 1993-08-01 |
| DK681287D0 (da) | 1987-12-22 |
| NZ223037A (en) | 1991-04-26 |
| GR3003761T3 (enExample) | 1993-03-16 |
| AU599736B2 (en) | 1990-07-26 |
| PT86433A (en) | 1988-01-01 |
| CA1322073C (en) | 1993-09-07 |
| US4937243A (en) | 1990-06-26 |
| PT86433B (pt) | 1990-11-20 |
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