NO800743L - Nye peptider og fremgangsmaate til deres fremstilling - Google Patents
Nye peptider og fremgangsmaate til deres fremstillingInfo
- Publication number
- NO800743L NO800743L NO800743A NO800743A NO800743L NO 800743 L NO800743 L NO 800743L NO 800743 A NO800743 A NO 800743A NO 800743 A NO800743 A NO 800743A NO 800743 L NO800743 L NO 800743L
- Authority
- NO
- Norway
- Prior art keywords
- trp
- phe
- thr
- solution
- lys
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 32
- 238000002360 preparation method Methods 0.000 title claims description 16
- 108090000765 processed proteins & peptides Proteins 0.000 title abstract description 26
- 102000004196 processed proteins & peptides Human genes 0.000 title abstract description 11
- 150000001875 compounds Chemical class 0.000 claims abstract description 42
- 239000002253 acid Substances 0.000 claims abstract description 31
- 150000003839 salts Chemical class 0.000 claims abstract description 28
- 229960000553 somatostatin Drugs 0.000 claims abstract description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 8
- 239000000825 pharmaceutical preparation Substances 0.000 claims abstract description 7
- 125000005843 halogen group Chemical group 0.000 claims abstract description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 6
- 235000008206 alpha-amino acids Nutrition 0.000 claims abstract description 4
- 150000001370 alpha-amino acid derivatives Chemical group 0.000 claims abstract 2
- 125000006239 protecting group Chemical group 0.000 claims description 32
- 229910052799 carbon Inorganic materials 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- 150000007513 acids Chemical class 0.000 claims description 10
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000002585 base Substances 0.000 claims description 8
- 125000003277 amino group Chemical group 0.000 claims description 6
- 239000007795 chemical reaction product Substances 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- QIVBCDIJIAJPQS-SECBINFHSA-N D-tryptophane Chemical compound C1=CC=C2C(C[C@@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-SECBINFHSA-N 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 claims description 3
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- 238000002156 mixing Methods 0.000 claims description 3
- 239000012458 free base Substances 0.000 claims description 2
- 239000012876 carrier material Substances 0.000 claims 1
- NHXLMOGPVYXJNR-ATOGVRKGSA-N somatostatin Chemical compound C([C@H]1C(=O)N[C@H](C(N[C@@H](CO)C(=O)N[C@@H](CSSC[C@@H](C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CC=2C3=CC=CC=C3NC=2)C(=O)N[C@@H](CCCCN)C(=O)N[C@H](C(=O)N1)[C@@H](C)O)NC(=O)CNC(=O)[C@H](C)N)C(O)=O)=O)[C@H](O)C)C1=CC=CC=C1 NHXLMOGPVYXJNR-ATOGVRKGSA-N 0.000 abstract description 13
- 102000005157 Somatostatin Human genes 0.000 abstract description 10
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- 239000000543 intermediate Substances 0.000 abstract description 6
- 125000003941 D-tryptophan group Chemical group [H]C1=C([H])C([H])=C2C(C([C@@](N([H])[H])(C(=O)[*])[H])([H])[H])=C([H])N([H])C2=C1[H] 0.000 abstract description 4
- 230000000694 effects Effects 0.000 abstract description 4
- LEVWYRKDKASIDU-QWWZWVQMSA-N D-cystine Chemical compound OC(=O)[C@H](N)CSSC[C@@H](N)C(O)=O LEVWYRKDKASIDU-QWWZWVQMSA-N 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
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- 229960003067 cystine Drugs 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 abstract 1
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- 238000010647 peptide synthesis reaction Methods 0.000 abstract 1
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- -1 alkyl carboxylic acid Chemical class 0.000 description 60
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 39
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 8
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- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical class C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 7
- 238000004440 column chromatography Methods 0.000 description 7
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 7
- ZUSSTQCWRDLYJA-UHFFFAOYSA-N n-hydroxy-5-norbornene-2,3-dicarboximide Chemical compound C1=CC2CC1C1C2C(=O)N(O)C1=O ZUSSTQCWRDLYJA-UHFFFAOYSA-N 0.000 description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 7
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical class OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
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- CEGOLXSVJUTHNZ-UHFFFAOYSA-K aluminium tristearate Chemical compound [Al+3].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CEGOLXSVJUTHNZ-UHFFFAOYSA-K 0.000 description 6
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- 125000003275 alpha amino acid group Chemical group 0.000 description 5
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- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 5
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- VBZWSGALLODQNC-UHFFFAOYSA-N hexafluoroacetone Chemical compound FC(F)(F)C(=O)C(F)(F)F VBZWSGALLODQNC-UHFFFAOYSA-N 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 238000006698 hydrazinolysis reaction Methods 0.000 description 1
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- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
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- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 210000004153 islets of langerhan Anatomy 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- 235000010755 mineral Nutrition 0.000 description 1
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- CZFNISFYDPIDNM-UHFFFAOYSA-N n,n-dimethylformamide;oxolane Chemical compound CN(C)C=O.C1CCOC1 CZFNISFYDPIDNM-UHFFFAOYSA-N 0.000 description 1
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- NUVBSKCKDOMJSU-UHFFFAOYSA-N para-hydroxybenzoic acid ethyl ester Natural products CCOC(=O)C1=CC=C(O)C=C1 NUVBSKCKDOMJSU-UHFFFAOYSA-N 0.000 description 1
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- 125000000612 phthaloyl group Chemical group C(C=1C(C(=O)*)=CC=CC1)(=O)* 0.000 description 1
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- SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical compound CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-UHFFFAOYSA-N 0.000 description 1
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- 235000019830 sodium polyphosphate Nutrition 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000003797 solvolysis reaction Methods 0.000 description 1
- 229940035044 sorbitan monolaurate Drugs 0.000 description 1
- 239000001593 sorbitan monooleate Substances 0.000 description 1
- 235000011069 sorbitan monooleate Nutrition 0.000 description 1
- 229940035049 sorbitan monooleate Drugs 0.000 description 1
- 239000001587 sorbitan monostearate Substances 0.000 description 1
- 235000011076 sorbitan monostearate Nutrition 0.000 description 1
- 229940035048 sorbitan monostearate Drugs 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 230000002123 temporal effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 150000003752 zinc compounds Chemical class 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
- 229960001763 zinc sulfate Drugs 0.000 description 1
- 229910000368 zinc sulfate Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- C07K14/435—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
- C07K14/575—Hormones
- C07K14/655—Somatostatins
- C07K14/6555—Somatostatins at least 1 amino acid in D-form
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/02—Drugs for disorders of the endocrine system of the hypothalamic hormones, e.g. TRH, GnRH, CRH, GRH, somatostatin
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
- C07K1/06—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length using protecting groups or activating agents
- C07K1/061—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length using protecting groups or activating agents using protecting groups
- C07K1/065—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length using protecting groups or activating agents using protecting groups for hydroxy functions, not being part of carboxy functions
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S930/00—Peptide or protein sequence
- Y10S930/01—Peptide or protein sequence
- Y10S930/16—Somatostatin; related peptides
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Endocrinology (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Zoology (AREA)
- Gastroenterology & Hepatology (AREA)
- Toxicology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Analytical Chemistry (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH250679 | 1979-03-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO800743L true NO800743L (no) | 1980-09-17 |
Family
ID=4235326
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO800743A NO800743L (no) | 1979-03-16 | 1980-03-14 | Nye peptider og fremgangsmaate til deres fremstilling |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US4316890A (fr) |
| EP (1) | EP0017760B1 (fr) |
| JP (1) | JPS55124748A (fr) |
| KR (1) | KR830001872A (fr) |
| AT (1) | ATE3283T1 (fr) |
| AU (1) | AU5646280A (fr) |
| CA (1) | CA1140117A (fr) |
| DD (1) | DD151059A5 (fr) |
| DE (1) | DE3063028D1 (fr) |
| ES (1) | ES8103028A1 (fr) |
| FI (1) | FI800795A (fr) |
| GR (1) | GR67655B (fr) |
| IL (1) | IL59620A (fr) |
| NO (1) | NO800743L (fr) |
| NZ (1) | NZ193129A (fr) |
| PT (1) | PT70951A (fr) |
| ZA (1) | ZA801520B (fr) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4499079A (en) * | 1982-11-18 | 1985-02-12 | E. R. Squibb & Sons, Inc. | Carboxy and substituted carboxy alkanoyl and cycloalkanoyl peptides |
| US4612302A (en) * | 1983-11-14 | 1986-09-16 | Brigham And Women's Hospital | Clinical use of somatostatin analogues |
| US5504069A (en) * | 1993-02-11 | 1996-04-02 | Biomeasure, Inc. | Inhibition of trauma-induced tumor growth |
| AU6770794A (en) * | 1993-04-23 | 1994-11-21 | Herbert J. Evans | Polypeptides that include conformation-constraining groups which flank a protein-protein interaction site |
| US6258550B1 (en) | 1993-04-23 | 2001-07-10 | Virginia Commonwealth University | Polypeptides that include conformation-constraining groups which flank a protein-protein interaction site |
| US5928896A (en) * | 1993-04-23 | 1999-07-27 | Virginia Commonwealth University | Polypeptides that include conformation-constraining groups which flank a protein--protein interaction site |
| US5965698A (en) * | 1993-04-23 | 1999-10-12 | Virginia Commonwealth University | Polypeptides that include conformation-constraining groups which flank a protein--protein interaction site |
| US5952465A (en) * | 1993-04-23 | 1999-09-14 | Virginia Commonwealth University | Polypeptides that include conformation-constraining groups which flank a protein-protein interaction site |
| US6084066A (en) * | 1993-10-29 | 2000-07-04 | Virginia Commonwealth University | Polypetides that include conformation-constraining groups which flank a protein-protein interaction site |
| US5597894A (en) * | 1995-06-05 | 1997-01-28 | The Louisiana State University Medical Center Foundation | Multi-tyrosinated somatostatin analogs |
| DK0981363T3 (da) | 1997-05-13 | 2003-12-01 | Sod Conseils Rech Applic | Somatostatinagonister til reduktion af legemsvægt |
| DE69822810T2 (de) * | 1997-05-13 | 2005-02-03 | Société de Conseils de Recherches et d'Applications Scientifiques S.A.S. | Somatostatin und somatostatin agoniste zur behandlung der insulinsunempfindlichkeit und syndrome x |
| US6004928A (en) * | 1997-05-13 | 1999-12-21 | Biomeasure, Incorporated | Method of treating hyperlipidemia |
| US7026289B2 (en) * | 1997-05-13 | 2006-04-11 | Societe De Conseils De Recherches Et D'applications Scientifiques, Sas | Method and compositions for treating hyperlipidemia and other conditions |
| US5968903A (en) * | 1998-05-07 | 1999-10-19 | Biomeasure, Incorporated | Inhibition of H. pylori proliferation |
| DK1401863T3 (da) | 2001-06-08 | 2009-05-25 | Ipsen Pharma | Kimære somatostatin-dopamin-analoge |
| EP2662087A1 (fr) | 2003-04-22 | 2013-11-13 | Ipsen Pharma | Vecteurs de somatostatine |
| CN107446053A (zh) | 2008-06-12 | 2017-12-08 | 益普生生物创新有限公司 | 癌症的抑制 |
| KR101642363B1 (ko) | 2008-06-12 | 2016-07-25 | 입센 바이오이노베이션 리미티드 | 신경내분비계 질환의 억제 |
| GB0820970D0 (en) | 2008-11-17 | 2008-12-24 | Syntaxin Ltd | Suppression of cancer |
| AU2014280847B2 (en) | 2013-06-13 | 2019-07-04 | Antisense Therapeutics Ltd | Combination therapy |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4020157A (en) * | 1975-07-08 | 1977-04-26 | Ayerst Mckenna And Harrison Ltd. | Shortened analogs of somatostatin |
| US4372884A (en) * | 1975-08-06 | 1983-02-08 | The Salk Institute For Biological Studies | Pharmaceutically active peptides |
| NL7607987A (nl) * | 1975-08-08 | 1977-02-10 | Merck & Co Inc | Werkwijze voor het bereiden van peptiden. |
| US4122077A (en) * | 1976-12-17 | 1978-10-24 | American Home Products Corporation | Somatostatin analogs |
| US4098782A (en) * | 1977-03-14 | 1978-07-04 | American Home Products Corporation | (His5)-somatostatin and analogues thereof |
| US4115554A (en) * | 1977-08-29 | 1978-09-19 | Merck & Co., Inc. | Somatostatin analogs |
| GB2019411B (en) * | 1978-04-24 | 1982-06-16 | American Home Prod | Peptides related to somatostatin |
-
1980
- 1980-03-10 US US06/129,066 patent/US4316890A/en not_active Expired - Lifetime
- 1980-03-13 DD DD80219646A patent/DD151059A5/de unknown
- 1980-03-13 EP EP80101310A patent/EP0017760B1/fr not_active Expired
- 1980-03-13 DE DE8080101310T patent/DE3063028D1/de not_active Expired
- 1980-03-13 AT AT80101310T patent/ATE3283T1/de not_active IP Right Cessation
- 1980-03-14 JP JP3170980A patent/JPS55124748A/ja active Pending
- 1980-03-14 PT PT70951A patent/PT70951A/pt unknown
- 1980-03-14 NZ NZ193129A patent/NZ193129A/xx unknown
- 1980-03-14 FI FI800795A patent/FI800795A/fi not_active Application Discontinuation
- 1980-03-14 NO NO800743A patent/NO800743L/no unknown
- 1980-03-14 AU AU56462/80A patent/AU5646280A/en not_active Abandoned
- 1980-03-14 CA CA000347728A patent/CA1140117A/fr not_active Expired
- 1980-03-14 GR GR61450A patent/GR67655B/el unknown
- 1980-03-14 ZA ZA00801520A patent/ZA801520B/xx unknown
- 1980-03-14 IL IL59620A patent/IL59620A/xx unknown
- 1980-03-14 ES ES489565A patent/ES8103028A1/es not_active Expired
- 1980-03-15 KR KR1019800001097A patent/KR830001872A/ko unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IL59620A (en) | 1983-07-31 |
| US4316890A (en) | 1982-02-23 |
| PT70951A (en) | 1980-04-01 |
| AU5646280A (en) | 1980-09-18 |
| FI800795A (fi) | 1980-09-17 |
| GR67655B (fr) | 1981-09-02 |
| EP0017760B1 (fr) | 1983-05-11 |
| DE3063028D1 (en) | 1983-06-16 |
| NZ193129A (en) | 1982-06-29 |
| ES489565A0 (es) | 1981-02-16 |
| ZA801520B (en) | 1981-03-25 |
| KR830001872A (ko) | 1983-05-19 |
| CA1140117A (fr) | 1983-01-25 |
| EP0017760A1 (fr) | 1980-10-29 |
| JPS55124748A (en) | 1980-09-26 |
| ES8103028A1 (es) | 1981-02-16 |
| DD151059A5 (de) | 1981-09-30 |
| ATE3283T1 (de) | 1983-05-15 |
| IL59620A0 (en) | 1980-06-30 |
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