SU659083A3 - Способ получени сульфата октапептидамида-терминального октапетида холецистокининпанкреазимина - Google Patents
Способ получени сульфата октапептидамида-терминального октапетида холецистокининпанкреазиминаInfo
- Publication number
- SU659083A3 SU659083A3 SU772477001A SU2477001A SU659083A3 SU 659083 A3 SU659083 A3 SU 659083A3 SU 772477001 A SU772477001 A SU 772477001A SU 2477001 A SU2477001 A SU 2477001A SU 659083 A3 SU659083 A3 SU 659083A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- ether
- tert
- solution
- mmol
- methionyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 14
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 title claims description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 57
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 42
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 claims description 31
- 239000000203 mixture Substances 0.000 claims description 23
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- -1 amide hydrochloride Chemical class 0.000 claims description 13
- 239000000047 product Substances 0.000 claims description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 12
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical group O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 claims description 11
- 229960000583 acetic acid Drugs 0.000 claims description 8
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 claims description 8
- 238000003756 stirring Methods 0.000 claims description 8
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 6
- 239000012362 glacial acetic acid Substances 0.000 claims description 6
- 239000000741 silica gel Substances 0.000 claims description 6
- 229910002027 silica gel Inorganic materials 0.000 claims description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 5
- 125000006239 protecting group Chemical group 0.000 claims description 5
- 239000011541 reaction mixture Substances 0.000 claims description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 4
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 claims description 4
- CHKVPAROMQMJNQ-UHFFFAOYSA-M potassium bisulfate Chemical compound [K+].OS([O-])(=O)=O CHKVPAROMQMJNQ-UHFFFAOYSA-M 0.000 claims description 4
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 4
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 238000004587 chromatography analysis Methods 0.000 claims description 3
- ZNEWHQLOPFWXOF-UHFFFAOYSA-N coenzyme M Chemical compound OS(=O)(=O)CCS ZNEWHQLOPFWXOF-UHFFFAOYSA-N 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 229960004635 mesna Drugs 0.000 claims description 3
- 229910000343 potassium bisulfate Inorganic materials 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 229910021653 sulphate ion Inorganic materials 0.000 claims description 3
- 239000000725 suspension Substances 0.000 claims description 3
- 238000003786 synthesis reaction Methods 0.000 claims description 3
- 150000003512 tertiary amines Chemical class 0.000 claims description 3
- CIPFDHFTBYJKQB-UHFFFAOYSA-N 1,2,3,4,5-pentachloro-6-(2,3,4,5,6-pentachlorophenoxy)benzene Chemical compound ClC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl CIPFDHFTBYJKQB-UHFFFAOYSA-N 0.000 claims description 2
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 4
- IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachlorophenol Chemical compound OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 claims 4
- 239000002244 precipitate Substances 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
- 239000000706 filtrate Substances 0.000 claims 2
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 claims 1
- SHXWCVYOXRDMCX-UHFFFAOYSA-N 3,4-methylenedioxymethamphetamine Chemical compound CNC(C)CC1=CC=C2OCOC2=C1 SHXWCVYOXRDMCX-UHFFFAOYSA-N 0.000 claims 1
- 101800001982 Cholecystokinin Proteins 0.000 claims 1
- 102100025841 Cholecystokinin Human genes 0.000 claims 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims 1
- 241000110847 Kochia Species 0.000 claims 1
- OBSIQMZKFXFYLV-QMMMGPOBSA-N L-phenylalanine amide Chemical compound NC(=O)[C@@H](N)CC1=CC=CC=C1 OBSIQMZKFXFYLV-QMMMGPOBSA-N 0.000 claims 1
- 241001139947 Mida Species 0.000 claims 1
- 101150025129 POP1 gene Proteins 0.000 claims 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 235000005505 Ziziphus oenoplia Nutrition 0.000 claims 1
- 244000104547 Ziziphus oenoplia Species 0.000 claims 1
- CPFYYCSSFPWSNB-UHFFFAOYSA-N amino 2-aminopropanoate Chemical compound CC(N)C(=O)ON CPFYYCSSFPWSNB-UHFFFAOYSA-N 0.000 claims 1
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 claims 1
- 229940107137 cholecystokinin Drugs 0.000 claims 1
- 125000001891 dimethoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 238000006073 displacement reaction Methods 0.000 claims 1
- 238000001914 filtration Methods 0.000 claims 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 229910052700 potassium Inorganic materials 0.000 claims 1
- 239000011591 potassium Substances 0.000 claims 1
- 239000001120 potassium sulphate Substances 0.000 claims 1
- 102000004196 processed proteins & peptides Human genes 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 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 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 239000000243 solution Substances 0.000 description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- VUEOQWDVOXEFDJ-UHFFFAOYSA-N 2-pyridin-2-ylacetic acid;hydrate Chemical compound O.OC(=O)CC1=CC=CC=N1 VUEOQWDVOXEFDJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethyl mercaptane Natural products CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 2
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 description 1
- GOXAGHLMRPVRAF-UHFFFAOYSA-O [N-]=[N+]=[N-].N=C=[NH2+] Chemical compound [N-]=[N+]=[N-].N=C=[NH2+] GOXAGHLMRPVRAF-UHFFFAOYSA-O 0.000 description 1
- 150000001413 amino acids Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 210000000232 gallbladder Anatomy 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 238000005065 mining Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- FJUWHFVPFSHPFK-UHFFFAOYSA-N phosphoric acid 1-sulfanylethanol Chemical compound CC(O)S.OP(O)(O)=O FJUWHFVPFSHPFK-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 210000004514 sphincter of oddi Anatomy 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 229960004799 tryptophan Drugs 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
- C07K14/595—Gastrins; Cholecystokinins [CCK]
-
- 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
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Gastroenterology & Hepatology (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biophysics (AREA)
- Zoology (AREA)
- Biochemistry (AREA)
- Toxicology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Endocrinology (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU76RI589A HU174500B (hu) | 1976-05-05 | 1976-05-05 | Sposob poluchenija slozhnogo oktapeptidamid-sul'fatnogo ehfira kholecistokhinin-pankreozimina |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU659083A3 true SU659083A3 (ru) | 1979-04-25 |
Family
ID=11000996
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU772477001A SU659083A3 (ru) | 1976-05-05 | 1977-05-04 | Способ получени сульфата октапептидамида-терминального октапетида холецистокининпанкреазимина |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US4102878A (enExample) |
| JP (1) | JPS52156864A (enExample) |
| AT (1) | AT356826B (enExample) |
| BE (1) | BE854272A (enExample) |
| BG (1) | BG29869A3 (enExample) |
| CH (1) | CH628323A5 (enExample) |
| CS (1) | CS203148B2 (enExample) |
| DD (1) | DD129782A5 (enExample) |
| DK (1) | DK148235C (enExample) |
| FR (1) | FR2350335A1 (enExample) |
| HU (1) | HU174500B (enExample) |
| MX (1) | MX4867E (enExample) |
| NL (1) | NL7704904A (enExample) |
| RO (1) | RO74444A (enExample) |
| SE (1) | SE441680B (enExample) |
| SU (1) | SU659083A3 (enExample) |
| YU (1) | YU39995B (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5822474B2 (ja) * | 1980-06-10 | 1983-05-09 | 天野製薬株式会社 | コレシストキニン・パンクレオザイミンｃ端ペプチドアミドスルフエ−トエステルの製造法 |
| US4444682A (en) * | 1982-11-04 | 1984-04-24 | The Salk Institute For Biological Studies | Method of sulfation |
| US4769445A (en) * | 1985-03-04 | 1988-09-06 | Pennwalt Corporation | Process for the solid phase synthesis of peptides which contain sulfated tyrosine |
| CA2583589C (en) * | 2004-10-29 | 2012-04-24 | Sandoz Ag | Processes for preparing glatiramer |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3892726A (en) * | 1969-05-27 | 1975-07-01 | Squibb & Sons Inc | Tyrosine-O-sulfate containing peptides |
-
1976
- 1976-05-05 HU HU76RI589A patent/HU174500B/hu not_active IP Right Cessation
-
1977
- 1977-04-15 CH CH469377A patent/CH628323A5/de not_active IP Right Cessation
- 1977-04-28 US US05/792,043 patent/US4102878A/en not_active Expired - Lifetime
- 1977-04-28 YU YU1102/77A patent/YU39995B/xx unknown
- 1977-05-02 MX MX775694U patent/MX4867E/es unknown
- 1977-05-03 BG BG036189A patent/BG29869A3/xx unknown
- 1977-05-03 AT AT312477A patent/AT356826B/de not_active IP Right Cessation
- 1977-05-03 SE SE7705142A patent/SE441680B/xx not_active IP Right Cessation
- 1977-05-04 FR FR7713572A patent/FR2350335A1/fr active Granted
- 1977-05-04 SU SU772477001A patent/SU659083A3/ru active
- 1977-05-04 RO RO7790221A patent/RO74444A/ro unknown
- 1977-05-04 NL NL7704904A patent/NL7704904A/xx not_active Application Discontinuation
- 1977-05-04 DK DK196577A patent/DK148235C/da not_active IP Right Cessation
- 1977-05-04 CS CS772946A patent/CS203148B2/cs unknown
- 1977-05-04 BE BE177282A patent/BE854272A/xx not_active IP Right Cessation
- 1977-05-04 JP JP5171077A patent/JPS52156864A/ja active Granted
- 1977-05-05 DD DD7700198776A patent/DD129782A5/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SE7705142L (sv) | 1977-11-06 |
| DK196577A (da) | 1977-11-06 |
| DD129782A5 (de) | 1978-02-08 |
| BE854272A (fr) | 1977-09-01 |
| DK148235C (da) | 1985-10-21 |
| CH628323A5 (de) | 1982-02-26 |
| SE441680B (sv) | 1985-10-28 |
| CS203148B2 (en) | 1981-02-27 |
| US4102878A (en) | 1978-07-25 |
| JPS5333588B2 (enExample) | 1978-09-14 |
| HU174500B (hu) | 1980-01-28 |
| YU110277A (en) | 1982-06-30 |
| RO74444A (ro) | 1981-11-04 |
| FR2350335B1 (enExample) | 1983-10-14 |
| DK148235B (da) | 1985-05-13 |
| ATA312477A (de) | 1979-10-15 |
| FR2350335A1 (fr) | 1977-12-02 |
| NL7704904A (nl) | 1977-11-08 |
| MX4867E (es) | 1982-11-15 |
| YU39995B (en) | 1985-06-30 |
| JPS52156864A (en) | 1977-12-27 |
| BG29869A3 (en) | 1981-02-16 |
| AT356826B (de) | 1980-05-27 |
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