IL35823A - Process for the preparation of 16beta-methyl-9alpha-fluoro-11beta,17alpha,21-trihydroxy-1,4-pregnadiene-3,20-dione and its 21-acylates - Google Patents
Process for the preparation of 16beta-methyl-9alpha-fluoro-11beta,17alpha,21-trihydroxy-1,4-pregnadiene-3,20-dione and its 21-acylatesInfo
- Publication number
- IL35823A IL35823A IL35823A IL3582370A IL35823A IL 35823 A IL35823 A IL 35823A IL 35823 A IL35823 A IL 35823A IL 3582370 A IL3582370 A IL 3582370A IL 35823 A IL35823 A IL 35823A
- Authority
- IL
- Israel
- Prior art keywords
- acid
- compound
- new process
- process according
- yielding
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 24
- 238000002360 preparation method Methods 0.000 title claims description 8
- 229960002537 betamethasone Drugs 0.000 claims abstract description 16
- UREBDLICKHMUKA-DVTGEIKXSA-N betamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-DVTGEIKXSA-N 0.000 claims abstract description 16
- 150000001875 compounds Chemical class 0.000 claims description 20
- 239000002253 acid Substances 0.000 claims description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 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 claims description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- 229910052708 sodium Inorganic materials 0.000 claims description 6
- 239000011734 sodium Substances 0.000 claims description 6
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 4
- 229910052700 potassium Inorganic materials 0.000 claims description 4
- 239000011591 potassium Substances 0.000 claims description 4
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical group [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 3
- 239000011575 calcium Substances 0.000 claims description 3
- 229910052791 calcium Inorganic materials 0.000 claims description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
- 239000011630 iodine Substances 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 claims description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- 159000000000 sodium salts Chemical class 0.000 claims description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims 2
- 150000007529 inorganic bases Chemical class 0.000 claims 2
- 150000007530 organic bases Chemical class 0.000 claims 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 1
- QARLTYSAFQGMMB-UHFFFAOYSA-N 2-ethylbutanenitrile Chemical compound CCC(CC)C#N QARLTYSAFQGMMB-UHFFFAOYSA-N 0.000 claims 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 claims 1
- 150000001340 alkali metals Chemical class 0.000 claims 1
- 150000001447 alkali salts Chemical class 0.000 claims 1
- 230000007775 late Effects 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 claims 1
- 235000015497 potassium bicarbonate Nutrition 0.000 claims 1
- 239000011736 potassium bicarbonate Substances 0.000 claims 1
- 230000035484 reaction time Effects 0.000 claims 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims 1
- 235000017557 sodium bicarbonate Nutrition 0.000 claims 1
- 239000001384 succinic acid Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- GWYFCOCPABKNJV-UHFFFAOYSA-M 3-Methylbutanoic acid Natural products CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-M hexadecanoate Chemical compound CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 abstract 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 abstract 1
- 229940074404 sodium succinate Drugs 0.000 abstract 1
- ZDQYSKICYIVCPN-UHFFFAOYSA-L sodium succinate (anhydrous) Chemical compound [Na+].[Na+].[O-]C(=O)CCC([O-])=O ZDQYSKICYIVCPN-UHFFFAOYSA-L 0.000 abstract 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-M succinate(1-) Chemical compound OC(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-M 0.000 abstract 1
- 229940070710 valerate Drugs 0.000 abstract 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 abstract 1
- 239000000047 product Substances 0.000 description 20
- 239000000243 solution Substances 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 230000033444 hydroxylation Effects 0.000 description 6
- 238000005805 hydroxylation reaction Methods 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 206010011878 Deafness Diseases 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 238000003682 fluorination reaction Methods 0.000 description 4
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 4
- 150000003431 steroids Chemical class 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- 206010047139 Vasoconstriction Diseases 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 239000003246 corticosteroid Substances 0.000 description 1
- 229960001334 corticosteroids Drugs 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 230000002906 microbiologic effect Effects 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 230000025033 vasoconstriction Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J5/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond
- C07J5/0046—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond substituted in position 17 alfa
- C07J5/0061—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond substituted in position 17 alfa substituted in position 16
- C07J5/0069—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond substituted in position 17 alfa substituted in position 16 by a saturated or unsaturated hydrocarbon group
- C07J5/0076—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond substituted in position 17 alfa substituted in position 16 by a saturated or unsaturated hydrocarbon group by an alkyl group
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
- Table Devices Or Equipment (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PT5292369 | 1969-12-13 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL35823A0 IL35823A0 (en) | 1971-02-25 |
| IL35823A true IL35823A (en) | 1977-08-31 |
Family
ID=20081704
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL35823A IL35823A (en) | 1969-12-13 | 1970-12-10 | Process for the preparation of 16beta-methyl-9alpha-fluoro-11beta,17alpha,21-trihydroxy-1,4-pregnadiene-3,20-dione and its 21-acylates |
| IL49763A IL49763A (en) | 1969-12-13 | 1970-12-10 | 16beta-methyl-9,11-epoxy-17alpha-hydroxy-1,4-pregnadiene-3,20-dione and its preparation |
| IL49763A IL49763A0 (en) | 1969-12-13 | 1976-06-10 | Novel 9,11-epoxy-pregnadienes and their preparation |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL49763A IL49763A (en) | 1969-12-13 | 1970-12-10 | 16beta-methyl-9,11-epoxy-17alpha-hydroxy-1,4-pregnadiene-3,20-dione and its preparation |
| IL49763A IL49763A0 (en) | 1969-12-13 | 1976-06-10 | Novel 9,11-epoxy-pregnadienes and their preparation |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US3792046A (cs) |
| JP (3) | JPS508080B1 (cs) |
| AT (1) | AT304774B (cs) |
| BE (1) | BE760236A (cs) |
| CA (1) | CA932321A (cs) |
| CH (1) | CH551395A (cs) |
| DE (1) | DE2059050A1 (cs) |
| DK (1) | DK130991B (cs) |
| ES (1) | ES386385A1 (cs) |
| FR (1) | FR2081356B1 (cs) |
| GB (1) | GB1328998A (cs) |
| IL (3) | IL35823A (cs) |
| NL (1) | NL166694C (cs) |
| NO (1) | NO136049C (cs) |
| ZA (1) | ZA708393B (cs) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS58212359A (ja) * | 1982-05-25 | 1983-12-10 | マグネツト・モ−トル・ゲゼルシヤフト・フユア・マグネツトモ−トリツシエ・テクニ−ク・ミツト・ベシユレンクテル・ハフツンク | 回転電気機械 |
| JPS6261175U (cs) * | 1985-10-02 | 1987-04-16 | ||
| JPS62135570U (cs) * | 1986-02-19 | 1987-08-26 | ||
| CA2448039A1 (en) * | 2001-06-18 | 2002-12-27 | Pharmacia & Upjohn Company | Process to prepare 11.beta., 17.alpha.,21-trihydroxy-6.alpha.-methylpregna-1,4-diene-3,20-dione 21-acetate |
| US20040006240A1 (en) * | 2001-06-18 | 2004-01-08 | Pearlman Bruce Allen | Process to prepare 11beta,17alpha ,21-trihydroxy-6alpha-methylpregna-1,4-diene-3,20-dione 21-acetate |
| CN101555268B (zh) * | 2009-05-21 | 2011-11-30 | 广西万德药业股份有限公司 | 一种糖皮质激素类9，11环氧物中间体制备方法 |
| CN102304163A (zh) * | 2011-07-11 | 2012-01-04 | 浙江仙居仙乐药业有限公司 | 一种倍他米松上氟合成方法 |
| CN104945464B (zh) * | 2015-04-17 | 2016-10-26 | 浙江仙居仙乐药业有限公司 | 一种倍他米松环氧水解物的合成方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1274397A (fr) * | 1958-12-16 | 1961-10-27 | Chimiotherapie Lab Franc | Procédé de préparation de dérivés 9alpha-fluoro 16alpha-méthyl delta1, 4-pregnadiènes |
| FR1243528A (fr) * | 1959-08-05 | 1960-10-14 | Chimiotherapie Lab Franc | Procédé d'acétoxylation de stéroïdes en 21 par l'intermédiaire de dérivés diiodés |
-
1970
- 1970-12-01 GB GB5696170A patent/GB1328998A/en not_active Expired
- 1970-12-01 DE DE19702059050 patent/DE2059050A1/de not_active Ceased
- 1970-12-02 DK DK613670AA patent/DK130991B/da unknown
- 1970-12-08 CA CA100128A patent/CA932321A/en not_active Expired
- 1970-12-08 NL NL7017904.A patent/NL166694C/xx not_active IP Right Cessation
- 1970-12-10 CH CH1828270A patent/CH551395A/xx not_active IP Right Cessation
- 1970-12-10 IL IL35823A patent/IL35823A/en unknown
- 1970-12-10 IL IL49763A patent/IL49763A/en unknown
- 1970-12-11 FR FR7044641A patent/FR2081356B1/fr not_active Expired
- 1970-12-11 ZA ZA708393A patent/ZA708393B/xx unknown
- 1970-12-11 NO NO4780/70A patent/NO136049C/no unknown
- 1970-12-11 BE BE760236A patent/BE760236A/xx unknown
- 1970-12-11 AT AT1119470A patent/AT304774B/de active
- 1970-12-11 JP JP45109617A patent/JPS508080B1/ja active Pending
- 1970-12-12 ES ES386385A patent/ES386385A1/es not_active Expired
-
1972
- 1972-08-07 US US00278394A patent/US3792046A/en not_active Expired - Lifetime
-
1976
- 1976-06-10 IL IL49763A patent/IL49763A0/xx unknown
-
1978
- 1978-11-08 JP JP13683778A patent/JPS5721279B1/ja active Pending
- 1978-11-08 JP JP13683678A patent/JPS5721280B1/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5721279B1 (cs) | 1982-05-06 |
| JPS508080B1 (cs) | 1975-04-01 |
| US3792046A (en) | 1974-02-12 |
| NL7017904A (cs) | 1971-06-15 |
| DK130991C (cs) | 1975-12-08 |
| FR2081356B1 (cs) | 1976-09-17 |
| NO136049B (cs) | 1977-04-04 |
| NL166694C (nl) | 1981-09-15 |
| ES386385A1 (es) | 1973-03-16 |
| IL49763A (en) | 1977-08-31 |
| AT304774B (de) | 1973-01-25 |
| NL166694B (nl) | 1981-04-15 |
| CH551395A (de) | 1974-07-15 |
| DE2059050A1 (de) | 1972-04-06 |
| IL49763A0 (en) | 1976-08-31 |
| DK130991B (da) | 1975-05-12 |
| BE760236A (fr) | 1971-05-17 |
| GB1328998A (en) | 1973-09-05 |
| IL35823A0 (en) | 1971-02-25 |
| JPS5721280B1 (cs) | 1982-05-06 |
| ZA708393B (en) | 1972-07-26 |
| FR2081356A1 (cs) | 1971-12-03 |
| CA932321A (en) | 1973-08-21 |
| NO136049C (no) | 1977-07-13 |
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