NO129682B - - Google Patents
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- Publication number
- NO129682B NO129682B NO02289/70A NO228970A NO129682B NO 129682 B NO129682 B NO 129682B NO 02289/70 A NO02289/70 A NO 02289/70A NO 228970 A NO228970 A NO 228970A NO 129682 B NO129682 B NO 129682B
- Authority
- NO
- Norway
- Prior art keywords
- pepstatin
- methanol
- pepsin
- growth
- inhibition
- Prior art date
Links
- 108010091212 pepstatin Proteins 0.000 claims description 160
- 229950000964 pepstatin Drugs 0.000 claims description 160
- FAXGPCHRFPCXOO-LXTPJMTPSA-N pepstatin A Chemical compound OC(=O)C[C@H](O)[C@H](CC(C)C)NC(=O)[C@H](C)NC(=O)C[C@H](O)[C@H](CC(C)C)NC(=O)[C@H](C(C)C)NC(=O)[C@H](C(C)C)NC(=O)CC(C)C FAXGPCHRFPCXOO-LXTPJMTPSA-N 0.000 claims description 158
- 102000057297 Pepsin A Human genes 0.000 claims description 40
- 108090000284 Pepsin A Proteins 0.000 claims description 40
- 229940111202 pepsin Drugs 0.000 claims description 40
- 238000000034 method Methods 0.000 claims description 24
- 150000002148 esters Chemical class 0.000 claims description 19
- 150000003839 salts Chemical class 0.000 claims description 16
- 241000187747 Streptomyces Species 0.000 claims description 7
- 150000001408 amides Chemical class 0.000 claims description 7
- 239000003112 inhibitor Substances 0.000 claims description 7
- 235000015097 nutrients Nutrition 0.000 claims description 6
- 241000958254 Streptomyces argenteolus Species 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 135
- 230000012010 growth Effects 0.000 description 39
- 230000005764 inhibitory process Effects 0.000 description 33
- 239000000843 powder Substances 0.000 description 32
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 30
- 239000000049 pigment Substances 0.000 description 23
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 22
- 239000000243 solution Substances 0.000 description 22
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 21
- 239000000706 filtrate Substances 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- 239000002609 medium Substances 0.000 description 17
- 238000000855 fermentation Methods 0.000 description 16
- 230000004151 fermentation Effects 0.000 description 16
- 239000012488 sample solution Substances 0.000 description 16
- 241000700159 Rattus Species 0.000 description 15
- 238000004519 manufacturing process Methods 0.000 description 15
- 150000004702 methyl esters Chemical class 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- 239000013078 crystal Substances 0.000 description 14
- 239000000284 extract Substances 0.000 description 13
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 12
- -1 Sakaguchi Chemical compound 0.000 description 12
- 239000008103 glucose Substances 0.000 description 12
- 229920001817 Agar Polymers 0.000 description 11
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 11
- 208000007107 Stomach Ulcer Diseases 0.000 description 11
- 239000008272 agar Substances 0.000 description 11
- 239000008101 lactose Substances 0.000 description 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 10
- 230000002401 inhibitory effect Effects 0.000 description 10
- 239000007788 liquid Substances 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 229920002472 Starch Polymers 0.000 description 9
- 239000003610 charcoal Substances 0.000 description 9
- 238000000746 purification Methods 0.000 description 9
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- 239000008107 starch Substances 0.000 description 9
- 235000019698 starch Nutrition 0.000 description 9
- 241000186361 Actinobacteria <class> Species 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 239000001888 Peptone Substances 0.000 description 8
- 108010080698 Peptones Proteins 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- 229940041514 candida albicans extract Drugs 0.000 description 8
- 229910052799 carbon Inorganic materials 0.000 description 8
- 235000019319 peptone Nutrition 0.000 description 8
- 239000012138 yeast extract Substances 0.000 description 8
- 239000011575 calcium Substances 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 239000011777 magnesium Substances 0.000 description 7
- 241000894007 species Species 0.000 description 7
- 238000011282 treatment Methods 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
- 230000008020 evaporation Effects 0.000 description 6
- 238000000605 extraction Methods 0.000 description 6
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 6
- 244000061456 Solanum tuberosum Species 0.000 description 5
- 235000002595 Solanum tuberosum Nutrition 0.000 description 5
- 240000008042 Zea mays Species 0.000 description 5
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 5
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 5
- 239000002021 butanolic extract Substances 0.000 description 5
- 150000001720 carbohydrates Chemical class 0.000 description 5
- 235000014633 carbohydrates Nutrition 0.000 description 5
- 239000005018 casein Substances 0.000 description 5
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 5
- 235000021240 caseins Nutrition 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 235000005822 corn Nutrition 0.000 description 5
- 239000012153 distilled water Substances 0.000 description 5
- 238000002329 infrared spectrum Methods 0.000 description 5
- 235000013372 meat Nutrition 0.000 description 5
- 239000011877 solvent mixture Substances 0.000 description 5
- OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 description 4
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical class [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 description 4
- QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical group CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 description 4
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 description 4
- GUBGYTABKSRVRQ-PICCSMPSSA-N Maltose Natural products O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-PICCSMPSSA-N 0.000 description 4
- 239000004365 Protease Substances 0.000 description 4
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- UGZVBQBZBBMPMB-UHFFFAOYSA-N acetic acid butan-1-ol butyl acetate hydrate Chemical compound O.CC(O)=O.CCCCO.CCCCOC(C)=O UGZVBQBZBBMPMB-UHFFFAOYSA-N 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
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- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 4
- GUBGYTABKSRVRQ-QUYVBRFLSA-N beta-maltose Chemical compound OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O GUBGYTABKSRVRQ-QUYVBRFLSA-N 0.000 description 4
- 229910052791 calcium Inorganic materials 0.000 description 4
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- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 238000010898 silica gel chromatography Methods 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 3
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 3
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- 238000000921 elemental analysis Methods 0.000 description 3
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07K14/8107—Endopeptidase (E.C. 3.4.21-99) inhibitors
- C07K14/8142—Aspartate protease (E.C. 3.4.23) inhibitors, e.g. HIV protease inhibitors
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K7/02—Linear peptides containing at least one abnormal peptide link
-
- 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
- Y10S435/00—Chemistry: molecular biology and microbiology
- Y10S435/803—Physical recovery methods, e.g. chromatography, grinding
-
- 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
- Y10S435/00—Chemistry: molecular biology and microbiology
- Y10S435/8215—Microorganisms
- Y10S435/822—Microorganisms using bacteria or actinomycetales
- Y10S435/886—Streptomyces
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Molecular Biology (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Medicinal Chemistry (AREA)
- Biochemistry (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Biophysics (AREA)
- AIDS & HIV (AREA)
- Gastroenterology & Hepatology (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Enzymes And Modification Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4616669 | 1969-06-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO129682B true NO129682B (de) | 1974-05-13 |
Family
ID=12739413
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO02289/70A NO129682B (de) | 1969-06-13 | 1970-06-12 |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US3740319A (de) |
| AT (1) | AT295454B (de) |
| AU (1) | AU1584970A (de) |
| BE (1) | BE751931A (de) |
| CA (1) | CA928238A (de) |
| CH (1) | CH550247A (de) |
| CS (1) | CS171685B2 (de) |
| DE (1) | DE2028403C3 (de) |
| DK (1) | DK128124B (de) |
| ES (1) | ES380545A1 (de) |
| FI (2) | FI47498C (de) |
| FR (1) | FR2052964B1 (de) |
| GB (1) | GB1314231A (de) |
| IE (1) | IE34196B1 (de) |
| IL (1) | IL34543A (de) |
| LU (1) | LU61119A1 (de) |
| NL (1) | NL166279C (de) |
| NO (1) | NO129682B (de) |
| PH (2) | PH9382A (de) |
| PL (1) | PL81272B1 (de) |
| RO (1) | RO71556B (de) |
| SE (1) | SE381673B (de) |
| YU (1) | YU35272B (de) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5022116B1 (de) * | 1970-04-28 | 1975-07-28 | ||
| JPS5434837B2 (de) * | 1972-02-08 | 1979-10-29 | ||
| DK132899C (da) * | 1972-04-07 | 1976-07-26 | Takeda Chemical Industries Ltd | Fremgangsmade til fremstilling af de proteaseinhiberende stoffer pepsinostreptiner eller salte deraf |
| US3963579A (en) * | 1973-10-17 | 1976-06-15 | Sanraku-Ocean Co., Ltd. | Microbiological process for the production of pepstatins |
| US4206283A (en) * | 1975-09-12 | 1980-06-03 | Sumitomo Chemical Company, Limited | Protease inhibitors |
| US4101650A (en) * | 1977-04-06 | 1978-07-18 | Zaidan Hojin Biseibutsu Kagaku Kenkyu Kai | Pepstatin floating minicapsules |
| US5833946A (en) * | 1995-06-06 | 1998-11-10 | Bayer Corporation | Dissemination of fungal infections: animal model and method of prophylaxis |
| GB0807621D0 (en) * | 2008-04-25 | 2008-06-04 | Ineos Healthcare Ltd | Use |
-
1970
- 1970-05-14 US US00037165A patent/US3740319A/en not_active Expired - Lifetime
- 1970-05-18 GB GB2392870A patent/GB1314231A/en not_active Expired
- 1970-05-18 IE IE644/70A patent/IE34196B1/xx unknown
- 1970-05-18 IL IL34543A patent/IL34543A/xx unknown
- 1970-06-02 PH PH11496*UA patent/PH9382A/en unknown
- 1970-06-03 AU AU15849/70A patent/AU1584970A/en not_active Expired
- 1970-06-04 AT AT500570A patent/AT295454B/de not_active IP Right Cessation
- 1970-06-05 CS CS3969*BA patent/CS171685B2/cs unknown
- 1970-06-08 ES ES380545A patent/ES380545A1/es not_active Expired
- 1970-06-08 YU YU1462/70A patent/YU35272B/xx unknown
- 1970-06-09 DE DE2028403A patent/DE2028403C3/de not_active Expired
- 1970-06-12 FI FI701670A patent/FI47498C/fi active
- 1970-06-12 FI FI01670/70A patent/FI47498B/fi active
- 1970-06-12 PL PL1970141274A patent/PL81272B1/pl unknown
- 1970-06-12 NL NL7008657.A patent/NL166279C/xx not_active IP Right Cessation
- 1970-06-12 CA CA085332A patent/CA928238A/en not_active Expired
- 1970-06-12 CH CH894270A patent/CH550247A/de not_active IP Right Cessation
- 1970-06-12 DK DK304570AA patent/DK128124B/da not_active IP Right Cessation
- 1970-06-12 SE SE7008222A patent/SE381673B/xx unknown
- 1970-06-12 NO NO02289/70A patent/NO129682B/no unknown
- 1970-06-12 FR FR7021557A patent/FR2052964B1/fr not_active Expired
- 1970-06-12 BE BE751931D patent/BE751931A/xx not_active IP Right Cessation
- 1970-06-12 LU LU61119D patent/LU61119A1/xx unknown
- 1970-06-13 RO RO76141A patent/RO71556B/ro unknown
-
1974
- 1974-07-09 PH PH16026A patent/PH10881A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NL166279B (nl) | 1981-02-16 |
| YU146270A (en) | 1980-04-30 |
| BE751931A (fr) | 1970-11-16 |
| IE34196B1 (en) | 1975-03-05 |
| FI47498B (de) | 1973-08-31 |
| AT295454B (de) | 1972-01-10 |
| IE34196L (en) | 1970-12-13 |
| FR2052964B1 (de) | 1974-10-11 |
| DE2028403C3 (de) | 1975-11-27 |
| DK128124B (da) | 1974-03-04 |
| NL166279C (nl) | 1981-07-15 |
| GB1314231A (en) | 1973-04-18 |
| CS171685B2 (de) | 1976-10-29 |
| PH9382A (en) | 1975-10-22 |
| AU1584970A (en) | 1971-12-09 |
| CA928238A (en) | 1973-06-12 |
| FI47498C (fi) | 1973-12-10 |
| ES380545A1 (es) | 1972-10-01 |
| NL7008657A (de) | 1970-12-15 |
| DE2028403A1 (de) | 1971-01-28 |
| RO71556B (ro) | 1984-07-30 |
| PH10881A (en) | 1977-09-26 |
| RO71556A (ro) | 1984-05-23 |
| LU61119A1 (de) | 1970-08-12 |
| IL34543A (en) | 1974-03-14 |
| SE381673B (sv) | 1975-12-15 |
| CH550247A (de) | 1974-06-14 |
| YU35272B (en) | 1980-10-31 |
| IL34543A0 (en) | 1970-07-19 |
| FR2052964A1 (de) | 1971-04-16 |
| DE2028403B2 (de) | 1975-04-24 |
| PL81272B1 (de) | 1975-08-30 |
| US3740319A (en) | 1973-06-19 |
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