BG62287B1 - Метод и междинен продукт за пречистване на окситетрациклин - Google Patents
Метод и междинен продукт за пречистване на окситетрациклин Download PDFInfo
- Publication number
- BG62287B1 BG62287B1 BG99161A BG9916194A BG62287B1 BG 62287 B1 BG62287 B1 BG 62287B1 BG 99161 A BG99161 A BG 99161A BG 9916194 A BG9916194 A BG 9916194A BG 62287 B1 BG62287 B1 BG 62287B1
- Authority
- BG
- Bulgaria
- Prior art keywords
- oxytetracycline
- hydrochloride
- oxytetracycline hydrochloride
- acetate
- acetic acid
- Prior art date
Links
- 239000004100 Oxytetracycline Substances 0.000 title claims abstract description 39
- 229960000625 oxytetracycline Drugs 0.000 title claims abstract description 39
- 235000019366 oxytetracycline Nutrition 0.000 title claims abstract description 38
- IWVCMVBTMGNXQD-UHFFFAOYSA-N terramycin dehydrate Natural products C1=CC=C2C(O)(C)C3C(O)C4C(N(C)C)C(O)=C(C(N)=O)C(=O)C4(O)C(O)=C3C(=O)C2=C1O IWVCMVBTMGNXQD-UHFFFAOYSA-N 0.000 title claims abstract description 38
- 238000000034 method Methods 0.000 title claims abstract description 14
- IWVCMVBTMGNXQD-PXOLEDIWSA-N oxytetracycline Chemical compound C1=CC=C2[C@](O)(C)[C@H]3[C@H](O)[C@H]4[C@H](N(C)C)C(O)=C(C(N)=O)C(=O)[C@@]4(O)C(O)=C3C(=O)C2=C1O IWVCMVBTMGNXQD-PXOLEDIWSA-N 0.000 title claims abstract 5
- 239000013067 intermediate product Substances 0.000 title abstract description 3
- 238000000746 purification Methods 0.000 title description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims abstract description 51
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 31
- 229960000583 acetic acid Drugs 0.000 claims abstract description 22
- 239000012362 glacial acetic acid Substances 0.000 claims abstract description 14
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 10
- 229960004368 oxytetracycline hydrochloride Drugs 0.000 claims description 51
- MWKJTNBSKNUMFN-UHFFFAOYSA-N trifluoromethyltrimethylsilane Chemical compound C[Si](C)(C)C(F)(F)F MWKJTNBSKNUMFN-UHFFFAOYSA-N 0.000 claims description 51
- 238000003756 stirring Methods 0.000 claims description 19
- 229960003924 oxytetracycline dihydrate Drugs 0.000 claims description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- 239000002244 precipitate Substances 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 5
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 5
- WJGAPUXHSQQWQF-UHFFFAOYSA-N acetic acid;hydrochloride Chemical compound Cl.CC(O)=O WJGAPUXHSQQWQF-UHFFFAOYSA-N 0.000 abstract description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract description 3
- 150000001875 compounds Chemical class 0.000 abstract description 3
- 239000012535 impurity Substances 0.000 abstract description 3
- 238000013019 agitation Methods 0.000 abstract 1
- 238000004062 sedimentation Methods 0.000 abstract 1
- IMLJLCJZQLGHJS-JEKSYDDFSA-N (4s,4ar,5s,5ar,6s,12ar)-4-(dimethylamino)-1,5,6,10,11,12a-hexahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide;dihydrate Chemical compound O.O.C1=CC=C2[C@](O)(C)[C@H]3[C@H](O)[C@H]4[C@H](N(C)C)C(=O)C(C(N)=O)=C(O)[C@@]4(O)C(=O)C3=C(O)C2=C1O IMLJLCJZQLGHJS-JEKSYDDFSA-N 0.000 description 51
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 239000000203 mixture Substances 0.000 description 10
- 150000003839 salts Chemical class 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- 239000000047 product Substances 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 6
- 150000004683 dihydrates Chemical class 0.000 description 6
- 238000001914 filtration Methods 0.000 description 5
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 5
- 230000004071 biological effect Effects 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 238000000855 fermentation Methods 0.000 description 3
- 230000004151 fermentation Effects 0.000 description 3
- 238000010561 standard procedure Methods 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- 239000004098 Tetracycline Substances 0.000 description 2
- 230000003115 biocidal effect Effects 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 239000012634 fragment Substances 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- -1 oxytetracycline hydride Chemical class 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 229960002180 tetracycline Drugs 0.000 description 2
- 238000004448 titration Methods 0.000 description 2
- CXSLZLZWQICHIJ-UHFFFAOYSA-N 2-Acetyl-2-decarboxamidooxytetracycline Natural products CN(C)C1C2C(O)C3C(=C(O)C2(O)C(=O)C(=C1O)C(=O)C)C(=O)c4c(O)cccc4C3(C)O CXSLZLZWQICHIJ-UHFFFAOYSA-N 0.000 description 1
- WDJHALXBUFZDSR-UHFFFAOYSA-N Acetoacetic acid Natural products CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- NMKSBNZBSLHAKW-UHFFFAOYSA-N Cl.ClO Chemical compound Cl.ClO NMKSBNZBSLHAKW-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 238000001159 Fisher's combined probability test Methods 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- 159000000021 acetate salts Chemical class 0.000 description 1
- IRAVYHIRJICKRS-UHFFFAOYSA-N acetic acid;hypochlorous acid Chemical compound ClO.CC(O)=O IRAVYHIRJICKRS-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 229940060038 chlorine Drugs 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 238000013375 chromatographic separation Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- WOWBFOBYOAGEEA-UHFFFAOYSA-N diafenthiuron Chemical compound CC(C)C1=C(NC(=S)NC(C)(C)C)C(C(C)C)=CC(OC=2C=CC=CC=2)=C1 WOWBFOBYOAGEEA-UHFFFAOYSA-N 0.000 description 1
- 230000003292 diminished effect Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229960001484 edetic acid Drugs 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 230000002906 microbiologic effect Effects 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000005201 scrubbing Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 235000019364 tetracycline Nutrition 0.000 description 1
- 229930101283 tetracycline Natural products 0.000 description 1
- 229960004989 tetracycline hydrochloride Drugs 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/24—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a ring other than a six-membered aromatic ring of the carbon skeleton
- C07C237/26—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a ring other than a six-membered aromatic ring of the carbon skeleton of a ring being part of a condensed ring system formed by at least four rings, e.g. tetracycline
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/40—Ortho- or ortho- and peri-condensed systems containing four condensed rings
- C07C2603/42—Ortho- or ortho- and peri-condensed systems containing four condensed rings containing only six-membered rings
- C07C2603/44—Naphthacenes; Hydrogenated naphthacenes
- C07C2603/46—1,4,4a,5,5a,6,11,12a- Octahydronaphthacenes, e.g. tetracyclines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Compounds Of Unknown Constitution (AREA)
- Pyrane Compounds (AREA)
- Cleaning By Liquid Or Steam (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Cephalosporin Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CZ942420A CZ282048B6 (cs) | 1992-04-06 | 1992-04-06 | Způsob přípravy čistého oxytetracyklinu a meziprodukt pro tuto přípravu |
| PCT/EP1992/000778 WO1993020042A1 (en) | 1992-04-06 | 1992-04-06 | Process and intermediate for the purification of oxytetracycline |
| CA002133198A CA2133198A1 (en) | 1992-04-06 | 1992-04-06 | Process and intermediate for the purification of oxytetracycline |
| US08/138,221 US5387703A (en) | 1992-04-06 | 1993-10-20 | Process and intermediate for the purification of oxytetracycline |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| BG99161A BG99161A (bg) | 1996-02-28 |
| BG62287B1 true BG62287B1 (bg) | 1999-07-30 |
Family
ID=27427177
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BG99161A BG62287B1 (bg) | 1992-04-06 | 1994-11-04 | Метод и междинен продукт за пречистване на окситетрациклин |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US5387703A (cs) |
| EP (1) | EP0634995B1 (cs) |
| JP (1) | JPH07508495A (cs) |
| KR (1) | KR100206414B1 (cs) |
| AT (1) | ATE139992T1 (cs) |
| BG (1) | BG62287B1 (cs) |
| CA (1) | CA2133198A1 (cs) |
| CZ (1) | CZ282048B6 (cs) |
| DE (1) | DE69212002T2 (cs) |
| DK (1) | DK0634995T3 (cs) |
| ES (1) | ES2092679T3 (cs) |
| GR (1) | GR3021268T3 (cs) |
| HR (1) | HRP930618B1 (cs) |
| PL (1) | PL167897B1 (cs) |
| RO (1) | RO111677B1 (cs) |
| RU (1) | RU2132841C1 (cs) |
| SK (1) | SK279571B6 (cs) |
| WO (1) | WO1993020042A1 (cs) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20020077276A1 (en) * | 1999-04-27 | 2002-06-20 | Fredeking Terry M. | Compositions and methods for treating hemorrhagic virus infections and other disorders |
| CN1094484C (zh) * | 1999-09-09 | 2002-11-20 | 石家庄市华曙联合制药厂 | 土霉素纯化方法 |
| CN101823980B (zh) * | 2010-04-29 | 2013-09-18 | 赤峰制药股份有限公司 | 大颗粒盐酸土霉素的制备方法 |
| CN112851540A (zh) * | 2021-02-22 | 2021-05-28 | 扬州联博药业有限公司 | 高品质土霉素的制备方法 |
| CN115594605B (zh) * | 2022-11-29 | 2023-03-10 | 山东国邦药业有限公司 | 一种强力霉素中间体的制备方法 |
| CN118878436B (zh) * | 2024-09-27 | 2024-12-24 | 内蒙古圣雪大成制药有限公司 | 一种降低土霉素杂质c含量的制备方法 |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2649480A (en) * | 1950-04-03 | 1953-08-18 | Chas Pflzer & Co Inc | Recovery of oxytetracycline |
| US2658078A (en) * | 1950-09-19 | 1953-11-03 | Pfizer & Co C | Solvent extraction of oxytetracycline |
| US2763682A (en) * | 1954-03-03 | 1956-09-18 | American Cyanamid Co | Purification of chlortetracycline |
| GB834579A (en) * | 1955-09-19 | 1960-05-11 | Pfizer & Co C | Hydrohalide salts of oxytetracycline |
| US2897234A (en) * | 1956-04-18 | 1959-07-28 | Bristol Lab Inc | Antibiotic purification |
| US2873276A (en) * | 1956-05-18 | 1959-02-10 | Pfizer & Co C | Antibiotic purification and complex compounds |
| US2929837A (en) * | 1957-01-30 | 1960-03-22 | American Cyanamid Co | Method of purifying tetracycline |
| US2915555A (en) * | 1958-07-17 | 1959-12-01 | Pfizer & Co C | Preparation of crystalline oxytetracycline salts |
| US2886595A (en) * | 1958-09-30 | 1959-05-12 | Bristol Lab Inc | Tetracycline recovery |
| US2992274A (en) * | 1959-05-04 | 1961-07-11 | American Cyanamid Co | Process of preparing purified chlortetracycline hydrochloride |
| US3037973A (en) * | 1960-06-16 | 1962-06-05 | Pfizer & Co C | Tetracycline recovery process |
| CH472495A (de) * | 1963-04-16 | 1969-05-15 | Spofa Vereinigte Pharma Werke | Verfahren zur Gewinnung von pharmazeutisch reinem Tetracyklin |
| US3454639A (en) * | 1966-03-04 | 1969-07-08 | Pfizer & Co C | Tetracycline recovery |
| US3397231A (en) * | 1967-04-12 | 1968-08-13 | Pfizer & Co C | Refining of alpha-6-deoxy-5-oxytetracycline |
| PL113855B1 (en) * | 1978-02-17 | 1981-01-31 | Inst Chemii Przemyslowej | Method of isolation of tetracyclines |
| HU192799B (en) * | 1983-05-02 | 1987-07-28 | Biogal Gyogyszergyar | Process for producing rolling cristalline cristalline oxytetracycline-hydrochloride |
| DE3318194C2 (de) * | 1983-05-19 | 1987-01-22 | Fried. Krupp Gmbh, 4300 Essen | Verfahren zur Isolierung und Reinigung von Antibiotika |
-
1992
- 1992-04-06 EP EP92908194A patent/EP0634995B1/en not_active Expired - Lifetime
- 1992-04-06 CZ CZ942420A patent/CZ282048B6/cs not_active IP Right Cessation
- 1992-04-06 RO RO94-01604A patent/RO111677B1/ro unknown
- 1992-04-06 JP JP4507636A patent/JPH07508495A/ja active Pending
- 1992-04-06 DE DE69212002T patent/DE69212002T2/de not_active Expired - Fee Related
- 1992-04-06 PL PL92305301A patent/PL167897B1/pl unknown
- 1992-04-06 ES ES92908194T patent/ES2092679T3/es not_active Expired - Lifetime
- 1992-04-06 RU RU94045967A patent/RU2132841C1/ru active
- 1992-04-06 AT AT92908194T patent/ATE139992T1/de not_active IP Right Cessation
- 1992-04-06 CA CA002133198A patent/CA2133198A1/en not_active Abandoned
- 1992-04-06 SK SK1212-94A patent/SK279571B6/sk unknown
- 1992-04-06 WO PCT/EP1992/000778 patent/WO1993020042A1/en active IP Right Grant
- 1992-04-06 DK DK92908194.1T patent/DK0634995T3/da active
-
1993
- 1993-03-31 HR HRPCT/EP92/00778A patent/HRP930618B1/xx not_active IP Right Cessation
- 1993-10-20 US US08/138,221 patent/US5387703A/en not_active Expired - Fee Related
-
1994
- 1994-10-04 KR KR1019940703482A patent/KR100206414B1/ko not_active Expired - Fee Related
- 1994-11-04 BG BG99161A patent/BG62287B1/bg unknown
-
1996
- 1996-10-04 GR GR960402620T patent/GR3021268T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CZ242094A3 (en) | 1995-01-18 |
| KR100206414B1 (en) | 1999-07-01 |
| EP0634995B1 (en) | 1996-07-03 |
| JPH07508495A (ja) | 1995-09-21 |
| ATE139992T1 (de) | 1996-07-15 |
| SK279571B6 (sk) | 1999-01-11 |
| ES2092679T3 (es) | 1996-12-01 |
| SK121294A3 (en) | 1995-05-10 |
| US5387703A (en) | 1995-02-07 |
| HRP930618A2 (en) | 1994-10-31 |
| WO1993020042A1 (en) | 1993-10-14 |
| EP0634995A1 (en) | 1995-01-25 |
| DE69212002T2 (de) | 1997-01-23 |
| RU2132841C1 (ru) | 1999-07-10 |
| CA2133198A1 (en) | 1993-10-14 |
| PL167897B1 (pl) | 1995-12-30 |
| RO111677B1 (ro) | 1996-12-30 |
| HRP930618B1 (en) | 1999-12-31 |
| DK0634995T3 (da) | 1996-11-11 |
| GR3021268T3 (en) | 1997-01-31 |
| BG99161A (bg) | 1996-02-28 |
| RU94045967A (ru) | 1996-08-10 |
| CZ282048B6 (cs) | 1997-04-16 |
| DE69212002D1 (de) | 1996-08-08 |
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