CS236471B2 - Method of cephalosporines production - Google Patents
Method of cephalosporines production Download PDFInfo
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- CS236471B2 CS236471B2 CS817055A CS705581A CS236471B2 CS 236471 B2 CS236471 B2 CS 236471B2 CS 817055 A CS817055 A CS 817055A CS 705581 A CS705581 A CS 705581A CS 236471 B2 CS236471 B2 CS 236471B2
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- Czechoslovakia
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- acid
- formula
- singlet
- compound
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- 238000000034 method Methods 0.000 title claims abstract description 25
- 238000004519 manufacturing process Methods 0.000 title description 3
- 125000001271 cephalosporin group Chemical group 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 155
- 150000003839 salts Chemical class 0.000 claims abstract description 62
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 45
- 230000008569 process Effects 0.000 claims abstract description 15
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 11
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 9
- 150000002367 halogens Chemical class 0.000 claims abstract description 8
- -1 2-carboxyphenyl Chemical group 0.000 claims description 161
- 238000006243 chemical reaction Methods 0.000 claims description 65
- 239000000203 mixture Substances 0.000 claims description 63
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 37
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 36
- 229910052739 hydrogen Inorganic materials 0.000 claims description 35
- 125000000217 alkyl group Chemical group 0.000 claims description 27
- 125000001424 substituent group Chemical group 0.000 claims description 24
- 239000001257 hydrogen Substances 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 11
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 150000001782 cephems Chemical group 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 210000003041 ligament Anatomy 0.000 claims 1
- 230000002441 reversible effect Effects 0.000 claims 1
- 239000002253 acid Substances 0.000 abstract description 112
- 229910052717 sulfur Inorganic materials 0.000 abstract description 13
- 125000003545 alkoxy group Chemical group 0.000 abstract description 7
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 abstract description 6
- 241000894006 Bacteria Species 0.000 abstract description 4
- 125000004442 acylamino group Chemical group 0.000 abstract description 3
- 231100000053 low toxicity Toxicity 0.000 abstract description 3
- 239000003960 organic solvent Substances 0.000 abstract description 3
- 239000000463 material Substances 0.000 abstract description 2
- 239000003242 anti bacterial agent Substances 0.000 abstract 1
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 abstract 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 abstract 1
- 125000001550 cephem group Chemical group 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 92
- 238000002844 melting Methods 0.000 description 61
- 230000008018 melting Effects 0.000 description 61
- 239000000243 solution Substances 0.000 description 60
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 53
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 48
- 238000002329 infrared spectrum Methods 0.000 description 45
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 39
- 229910052799 carbon Inorganic materials 0.000 description 38
- 239000002904 solvent Substances 0.000 description 38
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 37
- 229910052757 nitrogen Inorganic materials 0.000 description 35
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 33
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 32
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 29
- 230000002829 reductive effect Effects 0.000 description 29
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 26
- 238000005481 NMR spectroscopy Methods 0.000 description 26
- 150000002148 esters Chemical class 0.000 description 25
- 238000001816 cooling Methods 0.000 description 24
- 239000012044 organic layer Substances 0.000 description 22
- 150000007513 acids Chemical class 0.000 description 21
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 20
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 20
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 18
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 18
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical class FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 17
- 239000013078 crystal Substances 0.000 description 17
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 17
- 238000001228 spectrum Methods 0.000 description 17
- 239000007858 starting material Substances 0.000 description 17
- 239000011541 reaction mixture Substances 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 239000000047 product Substances 0.000 description 15
- 125000006239 protecting group Chemical group 0.000 description 15
- 239000000725 suspension Substances 0.000 description 14
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 12
- 229920002472 Starch Polymers 0.000 description 12
- 125000003118 aryl group Chemical group 0.000 description 12
- 239000008107 starch Substances 0.000 description 12
- 235000019698 starch Nutrition 0.000 description 12
- 229930186147 Cephalosporin Natural products 0.000 description 11
- 229940124587 cephalosporin Drugs 0.000 description 11
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 11
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 10
- 150000001780 cephalosporins Chemical class 0.000 description 10
- 125000000623 heterocyclic group Chemical group 0.000 description 10
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 10
- 235000017557 sodium bicarbonate Nutrition 0.000 description 10
- 229910015900 BF3 Inorganic materials 0.000 description 9
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 9
- 150000001408 amides Chemical class 0.000 description 9
- 239000000460 chlorine Substances 0.000 description 9
- 235000019359 magnesium stearate Nutrition 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- 125000002252 acyl group Chemical group 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- 150000001735 carboxylic acids Chemical class 0.000 description 8
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 7
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 7
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 7
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 7
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 7
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 description 6
- HSHGZXNAXBPPDL-HZGVNTEJSA-N 7beta-aminocephalosporanic acid Chemical compound S1CC(COC(=O)C)=C(C([O-])=O)N2C(=O)[C@@H]([NH3+])[C@@H]12 HSHGZXNAXBPPDL-HZGVNTEJSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- 101150065749 Churc1 gene Proteins 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 238000005917 acylation reaction Methods 0.000 description 6
- 239000002775 capsule Substances 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 239000012043 crude product Substances 0.000 description 6
- 125000000753 cycloalkyl group Chemical group 0.000 description 6
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 5
- 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 5
- 239000002841 Lewis acid Chemical class 0.000 description 5
- 102100038239 Protein Churchill Human genes 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- 125000004423 acyloxy group Chemical group 0.000 description 5
- 125000001931 aliphatic group Chemical group 0.000 description 5
- 125000003342 alkenyl group Chemical group 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
- 239000007924 injection Substances 0.000 description 5
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- 239000000741 silica gel Substances 0.000 description 5
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- 239000011734 sodium Substances 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
- 150000003852 triazoles Chemical class 0.000 description 5
- KJUGUADJHNHALS-UHFFFAOYSA-N 1H-tetrazole Chemical compound C=1N=NNN=1 KJUGUADJHNHALS-UHFFFAOYSA-N 0.000 description 4
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 4
- ONIKNECPXCLUHT-UHFFFAOYSA-N 2-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1Cl ONIKNECPXCLUHT-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 4
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- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 4
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- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
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- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 4
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
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- 241000196833 Kocuria rhizophila DC2201 Species 0.000 description 3
- 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 3
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Classifications
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- 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
- Cephalosporin Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS827529A CS236491B2 (en) | 1980-12-13 | 1981-09-24 | Method of cephalosporines preparation |
| CS827530A CS236492B2 (en) | 1980-12-13 | 1981-09-24 | Method of cephalosporines preparation |
| CS827531A CS236493B2 (en) | 1980-09-25 | 1982-10-22 | Method of 7-amino-3-substituted methyl-delta 3-cephem-4-carboxyl acid's preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP55175263A JPS6052755B2 (ja) | 1980-12-13 | 1980-12-13 | 新規セファロスポリン類 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS236471B2 true CS236471B2 (en) | 1985-05-15 |
Family
ID=15993092
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS817055A CS236471B2 (en) | 1980-09-25 | 1981-09-24 | Method of cephalosporines production |
| CS827529A CS236491B2 (en) | 1980-12-13 | 1981-09-24 | Method of cephalosporines preparation |
| CS827530A CS236492B2 (en) | 1980-12-13 | 1981-09-24 | Method of cephalosporines preparation |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS827529A CS236491B2 (en) | 1980-12-13 | 1981-09-24 | Method of cephalosporines preparation |
| CS827530A CS236492B2 (en) | 1980-12-13 | 1981-09-24 | Method of cephalosporines preparation |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS6052755B2 (pl) |
| CS (3) | CS236471B2 (pl) |
| IL (2) | IL74413A (pl) |
| PL (2) | PL135611B1 (pl) |
| SU (4) | SU1190987A3 (pl) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS604189A (ja) * | 1983-06-20 | 1985-01-10 | Sankyo Co Ltd | β−ラクタム系化合物の製造法 |
| JPH0662635B2 (ja) * | 1984-04-26 | 1994-08-17 | 富山化学工業株式会社 | セフアロスポリン類の新規製造法 |
| JPS6137788A (ja) * | 1984-07-31 | 1986-02-22 | Taito Pfizer Kk | 新規なセフアロスポリン化合物 |
| JPS6251688A (ja) * | 1985-08-30 | 1987-03-06 | Taito Pfizer Kk | 新規なセフアロスポリン化合物 |
| JPH08831B2 (ja) * | 1985-09-20 | 1996-01-10 | 富山化学工業株式会社 | セファロスポリンの精製法 |
| EP0238060B1 (en) | 1986-03-19 | 1992-01-08 | Banyu Pharmaceutical Co., Ltd. | Cephalosporin derivatives, processes for their preparation and antibacterial agents |
| WO2019055231A1 (en) | 2017-09-14 | 2019-03-21 | Apple Inc. | FACIAL SEAL FOR VISIOCASQUE |
| KR102749812B1 (ko) * | 2023-08-29 | 2025-01-03 | 주식회사 긱스로프트 | 디스플레이부를 구비한 헤드셋 |
| CN118879153A (zh) * | 2024-07-04 | 2024-11-01 | 广东绿树环保涂料科技有限公司 | 一种地坪漆用耐磨环氧树脂的制备工艺 |
-
1980
- 1980-12-13 JP JP55175263A patent/JPS6052755B2/ja not_active Expired
-
1981
- 1981-09-20 IL IL74413A patent/IL74413A/xx not_active IP Right Cessation
- 1981-09-23 PL PL1981238230A patent/PL135611B1/pl unknown
- 1981-09-23 PL PL1981233143A patent/PL135446B1/pl unknown
- 1981-09-24 CS CS817055A patent/CS236471B2/cs unknown
- 1981-09-24 CS CS827529A patent/CS236491B2/cs unknown
- 1981-09-24 SU SU813340952A patent/SU1190987A3/ru active
- 1981-09-24 CS CS827530A patent/CS236492B2/cs unknown
-
1982
- 1982-12-09 SU SU823523100A patent/SU1274625A3/ru active
- 1982-12-09 SU SU823529508A patent/SU1249017A1/ru active
- 1982-12-09 SU SU823520351A patent/SU1418329A1/ru active
-
1985
- 1985-02-21 IL IL74413A patent/IL74413A0/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5799592A (en) | 1982-06-21 |
| SU1190987A3 (ru) | 1985-11-07 |
| SU1418329A1 (ru) | 1988-08-23 |
| SU1274625A3 (ru) | 1986-11-30 |
| IL74413A0 (en) | 1985-05-31 |
| SU1249017A1 (ru) | 1986-08-07 |
| PL233143A1 (en) | 1983-05-23 |
| IL74413A (en) | 1986-08-31 |
| CS236491B2 (en) | 1985-05-15 |
| CS236492B2 (en) | 1985-05-15 |
| PL135446B1 (en) | 1985-10-31 |
| JPS6052755B2 (ja) | 1985-11-21 |
| PL238230A1 (en) | 1983-05-23 |
| PL135611B1 (en) | 1985-11-30 |
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