CS202096B2 - Method of preparing analogues of somatostatine - Google Patents
Method of preparing analogues of somatostatine Download PDFInfo
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- CS202096B2 CS202096B2 CS782580A CS258078A CS202096B2 CS 202096 B2 CS202096 B2 CS 202096B2 CS 782580 A CS782580 A CS 782580A CS 258078 A CS258078 A CS 258078A CS 202096 B2 CS202096 B2 CS 202096B2
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- Czechoslovakia
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- group
- phe
- acid
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- lys
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- 238000000034 method Methods 0.000 title claims description 15
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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 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 125000002228 disulfide group Chemical group 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- 230000002183 duodenal effect Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- DNORZUSMZSZZKU-UHFFFAOYSA-N ethyl 2-[5-(4-chlorophenyl)pentyl]oxirane-2-carboxylate Chemical compound C=1C=C(Cl)C=CC=1CCCCCC1(C(=O)OCC)CO1 DNORZUSMZSZZKU-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 230000003890 fistula Effects 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- MASNOZXLGMXCHN-ZLPAWPGGSA-N glucagon Chemical compound C([C@@H](C(=O)N[C@H](C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(O)=O)C(C)C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](C)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CO)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](N)CC=1NC=NC=1)[C@@H](C)O)[C@@H](C)O)C1=CC=CC=C1 MASNOZXLGMXCHN-ZLPAWPGGSA-N 0.000 description 1
- 229960004666 glucagon Drugs 0.000 description 1
- 125000006277 halobenzyl group Chemical group 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 238000002649 immunization Methods 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 230000003914 insulin secretion Effects 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- JCCNYMKQOSZNPW-UHFFFAOYSA-N loratadine Chemical compound C1CN(C(=O)OCC)CCC1=C1C2=NC=CC=C2CCC2=CC(Cl)=CC=C21 JCCNYMKQOSZNPW-UHFFFAOYSA-N 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000004005 microsphere Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000017066 negative regulation of growth Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 description 1
- 238000010647 peptide synthesis reaction Methods 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 229920001184 polypeptide Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 210000001187 pylorus Anatomy 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- IZTQOLKUZKXIRV-YRVFCXMDSA-N sincalide Chemical compound C([C@@H](C(=O)N[C@@H](CCSC)C(=O)NCC(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC=1C=CC=CC=1)C(N)=O)NC(=O)[C@@H](N)CC(O)=O)C1=CC=C(OS(O)(=O)=O)C=C1 IZTQOLKUZKXIRV-YRVFCXMDSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 238000010532 solid phase synthesis reaction Methods 0.000 description 1
- 230000000392 somatic effect Effects 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 125000004149 thio group Chemical group *S* 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000000430 tryptophan group Chemical group [H]N([H])C(C(=O)O*)C([H])([H])C1=C([H])N([H])C2=C([H])C([H])=C([H])C([H])=C12 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 239000004474 valine Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000005303 weighing Methods 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
- 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
-
- 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
- Y10S930/28—Bound to a nonpeptide drug, nonpeptide label, nonpeptide carrier, or a nonpeptide resin
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biophysics (AREA)
- Medicinal Chemistry (AREA)
- Zoology (AREA)
- Biochemistry (AREA)
- Toxicology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Gastroenterology & Hepatology (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Endocrinology (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Steroid Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS796664A CS212246B2 (cs) | 1977-04-21 | 1979-10-02 | Způsob přípravy tetradekapeptidu |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/789,472 US4100117A (en) | 1977-04-21 | 1977-04-21 | Somatostatin analogs and intermediates thereto |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS202096B2 true CS202096B2 (en) | 1980-12-31 |
Family
ID=25147748
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS782580A CS202096B2 (en) | 1977-04-21 | 1978-04-21 | Method of preparing analogues of somatostatine |
Country Status (31)
| Country | Link |
|---|---|
| US (1) | US4100117A (fr) |
| JP (1) | JPS53132588A (fr) |
| AR (1) | AR221699A1 (fr) |
| AT (1) | AT361142B (fr) |
| AU (1) | AU519275B2 (fr) |
| BE (1) | BE866117A (fr) |
| BG (1) | BG28703A3 (fr) |
| CA (2) | CA1102315A (fr) |
| CH (1) | CH634039A5 (fr) |
| CS (1) | CS202096B2 (fr) |
| DD (1) | DD135900A5 (fr) |
| DE (1) | DE2816854A1 (fr) |
| DK (1) | DK174278A (fr) |
| ES (2) | ES469005A1 (fr) |
| FI (1) | FI64576C (fr) |
| FR (1) | FR2387941A1 (fr) |
| GB (1) | GB1596328A (fr) |
| GR (1) | GR68945B (fr) |
| HU (1) | HU177435B (fr) |
| IE (1) | IE46868B1 (fr) |
| IL (1) | IL54533A (fr) |
| IT (1) | IT1094462B (fr) |
| NL (1) | NL7804218A (fr) |
| NZ (1) | NZ187009A (fr) |
| PL (2) | PL114533B1 (fr) |
| PT (1) | PT67913B (fr) |
| RO (2) | RO76054A (fr) |
| SE (1) | SE7804397L (fr) |
| SU (2) | SU730295A3 (fr) |
| YU (1) | YU91578A (fr) |
| ZA (1) | ZA782247B (fr) |
Families Citing this family (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4202802A (en) * | 1978-10-02 | 1980-05-13 | Eli Lilly And Company | Peptides related to somatostatin |
| US4199501A (en) * | 1978-11-20 | 1980-04-22 | Eli Lilly And Company | Peptides related to somatostatin |
| US4199500A (en) * | 1978-11-20 | 1980-04-22 | Eli Lilly And Company | Peptides related to somatostatin |
| US4428942A (en) | 1982-05-17 | 1984-01-31 | The Salk Institute For Biological Studies | Analogs of somatostatin |
| GB8423431D0 (en) * | 1984-09-17 | 1984-10-24 | Sandoz Ltd | Organic compounds |
| SE8702550D0 (sv) * | 1987-06-18 | 1987-06-18 | Anders Grubb | Cysteinproteashemmare |
| NO302481B1 (no) | 1990-10-16 | 1998-03-09 | Takeda Chemical Industries Ltd | Polymer for et preparat med forlenget frigjöring, samt preparat med forlenget frigjöring |
| DK0582459T3 (da) | 1992-08-07 | 1998-04-27 | Takeda Chemical Industries Ltd | Fremstilling af mikrokapsler af vandopløselige lægemidler |
| DE69508985T2 (de) * | 1994-02-21 | 1999-08-19 | Takeda Chemical Industries | Polyester Matrix für eine pharmazeutische Zusammensetzung mit verzögerter Freigabe |
| US6117455A (en) * | 1994-09-30 | 2000-09-12 | Takeda Chemical Industries, Ltd. | Sustained-release microcapsule of amorphous water-soluble pharmaceutical active agent |
| CA2192782C (fr) | 1995-12-15 | 2008-10-14 | Nobuyuki Takechi | Production de microsphere |
| CN1095681C (zh) * | 1996-06-20 | 2002-12-11 | 久光制药株式会社 | 一种用于离子电渗疗法的装置结构 |
| US7169889B1 (en) | 1999-06-19 | 2007-01-30 | Biocon Limited | Insulin prodrugs hydrolyzable in vivo to yield peglylated insulin |
| US6309633B1 (en) | 1999-06-19 | 2001-10-30 | Nobex Corporation | Amphiphilic drug-oligomer conjugates with hydroyzable lipophile components and methods for making and using the same |
| DE60136958D1 (de) | 2000-12-01 | 2009-01-22 | Takeda Pharmaceutical | Verfahren zur herstellung einer zubereitung mit einer bioaktiven substanz |
| US7060675B2 (en) | 2001-02-15 | 2006-06-13 | Nobex Corporation | Methods of treating diabetes mellitus |
| US6867183B2 (en) * | 2001-02-15 | 2005-03-15 | Nobex Corporation | Pharmaceutical compositions of insulin drug-oligomer conjugates and methods of treating diseases therewith |
| US6858580B2 (en) * | 2001-06-04 | 2005-02-22 | Nobex Corporation | Mixtures of drug-oligomer conjugates comprising polyalkylene glycol, uses thereof, and methods of making same |
| US6713452B2 (en) | 2001-06-04 | 2004-03-30 | Nobex Corporation | Mixtures of calcitonin drug-oligomer conjugates comprising polyalkylene glycol, uses thereof, and methods of making same |
| US7713932B2 (en) | 2001-06-04 | 2010-05-11 | Biocon Limited | Calcitonin drug-oligomer conjugates, and uses thereof |
| US6828297B2 (en) | 2001-06-04 | 2004-12-07 | Nobex Corporation | Mixtures of insulin drug-oligomer conjugates comprising polyalkylene glycol, uses thereof, and methods of making same |
| US6828305B2 (en) * | 2001-06-04 | 2004-12-07 | Nobex Corporation | Mixtures of growth hormone drug-oligomer conjugates comprising polyalkylene glycol, uses thereof, and methods of making same |
| US6835802B2 (en) * | 2001-06-04 | 2004-12-28 | Nobex Corporation | Methods of synthesizing substantially monodispersed mixtures of polymers having polyethylene glycol moieties |
| US7312192B2 (en) * | 2001-09-07 | 2007-12-25 | Biocon Limited | Insulin polypeptide-oligomer conjugates, proinsulin polypeptide-oligomer conjugates and methods of synthesizing same |
| US7196059B2 (en) | 2001-09-07 | 2007-03-27 | Biocon Limited | Pharmaceutical compositions of insulin drug-oligomer conjugates and methods of treating diseases therewith |
| US6913903B2 (en) | 2001-09-07 | 2005-07-05 | Nobex Corporation | Methods of synthesizing insulin polypeptide-oligomer conjugates, and proinsulin polypeptide-oligomer conjugates and methods of synthesizing same |
| US7166571B2 (en) * | 2001-09-07 | 2007-01-23 | Biocon Limited | Insulin polypeptide-oligomer conjugates, proinsulin polypeptide-oligomer conjugates and methods of synthesizing same |
| AU2003236521A1 (en) * | 2002-06-13 | 2003-12-31 | Nobex Corporation | Methods of reducing hypoglycemic episodes in the treatment of diabetes mellitus |
| KR101276754B1 (ko) * | 2004-07-19 | 2013-06-19 | 바이오콘 리미티드 | 인슐린―올리고머 접합체，제형 및 이들의 용도 |
| ES2664822T3 (es) | 2007-10-16 | 2018-04-23 | Biocon Limited | Una composición farmacéutica sólida administrable por vía oral y un proceso de la misma |
| JP6224586B2 (ja) | 2012-07-10 | 2017-11-01 | 武田薬品工業株式会社 | 注射用製剤 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2608336A1 (de) * | 1975-03-11 | 1976-09-30 | Sandoz Ag | Neue organische verbindungen, ihre herstellung und verwendung |
| US4372884A (en) * | 1975-08-06 | 1983-02-08 | The Salk Institute For Biological Studies | Pharmaceutically active peptides |
-
1977
- 1977-04-21 US US05/789,472 patent/US4100117A/en not_active Expired - Lifetime
-
1978
- 1978-04-17 GB GB14916/78A patent/GB1596328A/en not_active Expired
- 1978-04-18 SE SE7804397A patent/SE7804397L/xx unknown
- 1978-04-18 JP JP4621378A patent/JPS53132588A/ja active Pending
- 1978-04-18 RO RO7893835A patent/RO76054A/fr unknown
- 1978-04-18 FI FI781184A patent/FI64576C/fi not_active IP Right Cessation
- 1978-04-18 YU YU00915/78A patent/YU91578A/xx unknown
- 1978-04-18 PT PT67913A patent/PT67913B/pt unknown
- 1978-04-18 AR AR271820A patent/AR221699A1/es active
- 1978-04-18 RO RO78102194A patent/RO81079A/fr unknown
- 1978-04-18 NZ NZ187009A patent/NZ187009A/xx unknown
- 1978-04-18 DE DE19782816854 patent/DE2816854A1/de not_active Withdrawn
- 1978-04-18 IL IL54533A patent/IL54533A/xx unknown
- 1978-04-19 FR FR7811580A patent/FR2387941A1/fr active Granted
- 1978-04-19 ZA ZA00782247A patent/ZA782247B/xx unknown
- 1978-04-19 IE IE765/78A patent/IE46868B1/en unknown
- 1978-04-19 GR GR56030A patent/GR68945B/el unknown
- 1978-04-19 BE BE1008847A patent/BE866117A/fr not_active IP Right Cessation
- 1978-04-19 CA CA301,500A patent/CA1102315A/fr not_active Expired
- 1978-04-19 AU AU35253/78A patent/AU519275B2/en not_active Expired
- 1978-04-20 HU HU78EI790A patent/HU177435B/hu unknown
- 1978-04-20 IT IT22552/78A patent/IT1094462B/it active
- 1978-04-20 ES ES469005A patent/ES469005A1/es not_active Expired
- 1978-04-20 AT AT282878A patent/AT361142B/de not_active IP Right Cessation
- 1978-04-20 NL NL7804218A patent/NL7804218A/xx not_active Application Discontinuation
- 1978-04-20 DK DK174278A patent/DK174278A/da active IP Right Grant
- 1978-04-20 CH CH425778A patent/CH634039A5/de not_active IP Right Cessation
- 1978-04-20 SU SU782607708A patent/SU730295A3/ru active
- 1978-04-21 PL PL1978206280A patent/PL114533B1/pl unknown
- 1978-04-21 CS CS782580A patent/CS202096B2/cs unknown
- 1978-04-21 PL PL1978217479A patent/PL115827B1/pl unknown
- 1978-04-21 BG BG039503A patent/BG28703A3/xx unknown
- 1978-04-21 DD DD78204957A patent/DD135900A5/xx unknown
-
1979
- 1979-01-05 SU SU792705047A patent/SU904519A3/ru active
- 1979-01-16 ES ES476901A patent/ES476901A1/es not_active Expired
-
1980
- 1980-12-08 CA CA366,345A patent/CA1113928A/fr not_active Expired
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