SU791245A3 - Способ получени производных 6-амино- 2,3,5,6-тетрагидроспиро пенам-2,44н (тио)пиран -3-карбоновой кислоты или их фармацевтически приемлемых солей - Google Patents
Способ получени производных 6-амино- 2,3,5,6-тетрагидроспиро пенам-2,44н (тио)пиран -3-карбоновой кислоты или их фармацевтически приемлемых солей Download PDFInfo
- Publication number
- SU791245A3 SU791245A3 SU782566099A SU2566099A SU791245A3 SU 791245 A3 SU791245 A3 SU 791245A3 SU 782566099 A SU782566099 A SU 782566099A SU 2566099 A SU2566099 A SU 2566099A SU 791245 A3 SU791245 A3 SU 791245A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- carboxylic acid
- amino
- tetrahydrospiro
- thiopyran
- penam
- Prior art date
Links
- 150000003839 salts Chemical class 0.000 title claims abstract description 7
- 238000000034 method Methods 0.000 title claims description 3
- 125000000446 sulfanediyl group Chemical group *S* 0.000 title 1
- -1 2-phenylacetyl Chemical group 0.000 claims abstract description 48
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
- 239000001257 hydrogen Substances 0.000 claims abstract description 6
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 5
- 125000004434 sulfur atom Chemical group 0.000 claims abstract description 5
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims abstract description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract 3
- 239000011593 sulfur Substances 0.000 claims abstract 3
- 150000001875 compounds Chemical class 0.000 claims description 11
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 9
- 150000002148 esters Chemical class 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 4
- 238000007327 hydrogenolysis reaction Methods 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 229910052763 palladium Inorganic materials 0.000 claims description 3
- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 claims description 3
- 239000012442 inert solvent Substances 0.000 claims description 2
- 150000001451 organic peroxides Chemical class 0.000 claims description 2
- 230000003647 oxidation Effects 0.000 claims description 2
- 238000007254 oxidation reaction Methods 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 150000001718 carbodiimides Chemical class 0.000 claims 1
- 239000003880 polar aprotic solvent Substances 0.000 claims 1
- 229930182555 Penicillin Natural products 0.000 abstract 1
- 241000534944 Thia Species 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 231100000252 nontoxic Toxicity 0.000 abstract 1
- 230000003000 nontoxic effect Effects 0.000 abstract 1
- 150000002960 penicillins Chemical class 0.000 abstract 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 150000001408 amides Chemical class 0.000 description 10
- 238000002329 infrared spectrum Methods 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- LZNNMMKMGKFYLL-UHFFFAOYSA-N 2h-pyran-3-carboxylic acid Chemical compound OC(=O)C1=CC=COC1 LZNNMMKMGKFYLL-UHFFFAOYSA-N 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 150000003952 β-lactams Chemical class 0.000 description 7
- 239000006260 foam Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- DWLHTIPCWYOEMT-UHFFFAOYSA-N 2h-thiopyran-3-carboxylic acid Chemical compound OC(=O)C1=CC=CSC1 DWLHTIPCWYOEMT-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 241000894006 Bacteria Species 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- LSBDFXRDZJMBSC-UHFFFAOYSA-N 2-phenylacetamide Chemical compound NC(=O)CC1=CC=CC=C1 LSBDFXRDZJMBSC-UHFFFAOYSA-N 0.000 description 2
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- VMZCDNSFRSVYKQ-UHFFFAOYSA-N 2-phenylacetyl chloride Chemical compound ClC(=O)CC1=CC=CC=C1 VMZCDNSFRSVYKQ-UHFFFAOYSA-N 0.000 description 1
- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 description 1
- HXEVQMXCHCDPSO-UHFFFAOYSA-N 5-methyl-3-phenyl-1,2-oxazole-4-carbonyl chloride Chemical compound ClC(=O)C1=C(C)ON=C1C1=CC=CC=C1 HXEVQMXCHCDPSO-UHFFFAOYSA-N 0.000 description 1
- 208000035473 Communicable disease Diseases 0.000 description 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
- 108090000204 Dipeptidase 1 Proteins 0.000 description 1
- 101000579647 Penaeus vannamei Penaeidin-2a Proteins 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
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- ZGUNAGUHMKGQNY-UHFFFAOYSA-N alpha-phenylglycine Chemical class OC(=O)C(N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-UHFFFAOYSA-N 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
- 102000006635 beta-lactamase Human genes 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 238000004587 chromatography analysis Methods 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
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 235000015872 dietary supplement Nutrition 0.000 description 1
- 150000004683 dihydrates Chemical class 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- BLSRNVDCHVKXSO-UHFFFAOYSA-M sodium;2-ethylbutanoate Chemical compound [Na+].CCC(CC)C([O-])=O BLSRNVDCHVKXSO-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B60—VEHICLES IN GENERAL
- B60W—CONJOINT CONTROL OF VEHICLE SUB-UNITS OF DIFFERENT TYPE OR DIFFERENT FUNCTION; CONTROL SYSTEMS SPECIALLY ADAPTED FOR HYBRID VEHICLES; ROAD VEHICLE DRIVE CONTROL SYSTEMS FOR PURPOSES NOT RELATED TO THE CONTROL OF A PARTICULAR SUB-UNIT
- B60W2510/00—Input parameters relating to a particular sub-units
- B60W2510/02—Clutches
- B60W2510/0208—Clutch engagement state, e.g. engaged or disengaged
- B60W2510/0225—Clutch actuator position
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B60—VEHICLES IN GENERAL
- B60W—CONJOINT CONTROL OF VEHICLE SUB-UNITS OF DIFFERENT TYPE OR DIFFERENT FUNCTION; CONTROL SYSTEMS SPECIALLY ADAPTED FOR HYBRID VEHICLES; ROAD VEHICLE DRIVE CONTROL SYSTEMS FOR PURPOSES NOT RELATED TO THE CONTROL OF A PARTICULAR SUB-UNIT
- B60W2510/00—Input parameters relating to a particular sub-units
- B60W2510/02—Clutches
- B60W2510/0241—Clutch slip, i.e. difference between input and output speeds
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B60—VEHICLES IN GENERAL
- B60W—CONJOINT CONTROL OF VEHICLE SUB-UNITS OF DIFFERENT TYPE OR DIFFERENT FUNCTION; CONTROL SYSTEMS SPECIALLY ADAPTED FOR HYBRID VEHICLES; ROAD VEHICLE DRIVE CONTROL SYSTEMS FOR PURPOSES NOT RELATED TO THE CONTROL OF A PARTICULAR SUB-UNIT
- B60W2510/00—Input parameters relating to a particular sub-units
- B60W2510/06—Combustion engines, Gas turbines
- B60W2510/0638—Engine speed
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B60—VEHICLES IN GENERAL
- B60W—CONJOINT CONTROL OF VEHICLE SUB-UNITS OF DIFFERENT TYPE OR DIFFERENT FUNCTION; CONTROL SYSTEMS SPECIALLY ADAPTED FOR HYBRID VEHICLES; ROAD VEHICLE DRIVE CONTROL SYSTEMS FOR PURPOSES NOT RELATED TO THE CONTROL OF A PARTICULAR SUB-UNIT
- B60W2710/00—Output or target parameters relating to a particular sub-units
- B60W2710/02—Clutches
- B60W2710/025—Clutch slip, i.e. difference between input and output speeds
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B60—VEHICLES IN GENERAL
- B60W—CONJOINT CONTROL OF VEHICLE SUB-UNITS OF DIFFERENT TYPE OR DIFFERENT FUNCTION; CONTROL SYSTEMS SPECIALLY ADAPTED FOR HYBRID VEHICLES; ROAD VEHICLE DRIVE CONTROL SYSTEMS FOR PURPOSES NOT RELATED TO THE CONTROL OF A PARTICULAR SUB-UNIT
- B60W2710/00—Output or target parameters relating to a particular sub-units
- B60W2710/02—Clutches
- B60W2710/027—Clutch torque
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1906/77A GB1567562A (en) | 1977-01-18 | 1977-01-18 | Amino-spiro(oxy(or thia) cycloalkane - penam) - carboxylicacid derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU791245A3 true SU791245A3 (ru) | 1980-12-23 |
Family
ID=9730122
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU782566099A SU791245A3 (ru) | 1977-01-18 | 1978-01-18 | Способ получени производных 6-амино- 2,3,5,6-тетрагидроспиро пенам-2,44н (тио)пиран -3-карбоновой кислоты или их фармацевтически приемлемых солей |
Country Status (26)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2052496B (en) * | 1979-06-25 | 1983-06-29 | Ucb Sa | 6 - amino - spiro - (penam - 2,4' - piperidine) - 3 - carboxylic acid derivatives |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2951839A (en) * | 1959-07-15 | 1960-09-06 | Doyle Frank Peter | Synthetic penicillins |
-
1977
- 1977-01-18 GB GB1906/77A patent/GB1567562A/en not_active Expired
-
1978
- 1978-01-12 FI FI780089A patent/FI780089A/fi not_active Application Discontinuation
- 1978-01-12 DK DK15778A patent/DK15778A/da not_active Application Discontinuation
- 1978-01-12 NO NO780111A patent/NO780111L/no unknown
- 1978-01-12 SE SE7800368A patent/SE7800368L/xx unknown
- 1978-01-12 NL NL7800395A patent/NL7800395A/xx not_active Application Discontinuation
- 1978-01-16 US US05/869,860 patent/US4139628A/en not_active Expired - Lifetime
- 1978-01-17 CA CA295,138A patent/CA1101841A/en not_active Expired
- 1978-01-17 PT PT67538A patent/PT67538B/pt unknown
- 1978-01-17 IL IL53826A patent/IL53826A/xx unknown
- 1978-01-17 DD DD78203262A patent/DD134525A5/xx unknown
- 1978-01-17 LU LU78884A patent/LU78884A1/xx unknown
- 1978-01-17 HU HU78UE85A patent/HU173787B/hu unknown
- 1978-01-17 IT IT47659/78A patent/IT1103253B/it active
- 1978-01-17 ES ES466054A patent/ES466054A1/es not_active Expired
- 1978-01-17 FR FR7801579A patent/FR2377409A1/fr active Granted
- 1978-01-17 ZA ZA00780305A patent/ZA78305B/xx unknown
- 1978-01-17 CH CH44978A patent/CH629812A5/fr not_active IP Right Cessation
- 1978-01-17 YU YU00086/78A patent/YU8678A/xx unknown
- 1978-01-17 AU AU32496/78A patent/AU512339B2/en not_active Expired
- 1978-01-17 JP JP366778A patent/JPS5390291A/ja active Pending
- 1978-01-17 DE DE19782801850 patent/DE2801850A1/de not_active Withdrawn
- 1978-01-17 BE BE1008647A patent/BE862973A/xx not_active IP Right Cessation
- 1978-01-17 AT AT32278A patent/AT355209B/de not_active IP Right Cessation
- 1978-01-18 SU SU782566099A patent/SU791245A3/ru active
- 1978-01-18 PL PL20406578A patent/PL204065A1/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR2377409A1 (fr) | 1978-08-11 |
| PT67538A (fr) | 1978-02-01 |
| ZA78305B (en) | 1978-12-27 |
| GB1567562A (en) | 1980-05-14 |
| CA1101841A (en) | 1981-05-26 |
| DD134525A5 (de) | 1979-03-07 |
| YU8678A (en) | 1983-01-21 |
| PL204065A1 (pl) | 1979-04-09 |
| US4139628A (en) | 1979-02-13 |
| AU3249678A (en) | 1979-07-26 |
| AU512339B2 (en) | 1980-10-02 |
| NO780111L (no) | 1978-07-19 |
| LU78884A1 (fr) | 1978-09-18 |
| JPS5390291A (en) | 1978-08-08 |
| CH629812A5 (fr) | 1982-05-14 |
| IL53826A0 (en) | 1978-04-30 |
| AT355209B (de) | 1980-02-25 |
| BE862973A (fr) | 1978-07-17 |
| PT67538B (fr) | 1979-06-15 |
| SE7800368L (sv) | 1978-07-19 |
| DK15778A (da) | 1978-07-19 |
| HU173787B (hu) | 1979-08-28 |
| IT1103253B (it) | 1985-10-14 |
| NL7800395A (nl) | 1978-07-20 |
| DE2801850A1 (de) | 1978-07-20 |
| IL53826A (en) | 1981-01-30 |
| ES466054A1 (es) | 1979-01-01 |
| FI780089A (fi) | 1978-07-19 |
| ATA32278A (de) | 1979-07-15 |
| FR2377409B1 (US06338842-20020115-C00008.png) | 1980-06-13 |
| IT7847659A0 (it) | 1978-01-17 |
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