DE2257624A1 - PROCESS FOR PREPARING N- (LAETHYL-2-PYRROLIDYLMETHYL) -2-METHOXY-5AETHYLSULFONYL-BENZAMIDE - Google Patents
PROCESS FOR PREPARING N- (LAETHYL-2-PYRROLIDYLMETHYL) -2-METHOXY-5AETHYLSULFONYL-BENZAMIDEInfo
- Publication number
- DE2257624A1 DE2257624A1 DE2257624A DE2257624A DE2257624A1 DE 2257624 A1 DE2257624 A1 DE 2257624A1 DE 2257624 A DE2257624 A DE 2257624A DE 2257624 A DE2257624 A DE 2257624A DE 2257624 A1 DE2257624 A1 DE 2257624A1
- Authority
- DE
- Germany
- Prior art keywords
- methoxy
- ethyl
- benzamide
- pyrrolidylmethyl
- laethyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 238000004519 manufacturing process Methods 0.000 title 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 12
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 6
- DMSZORWOGDLWGN-UHFFFAOYSA-N ctk1a3526 Chemical compound NP(N)(N)=O DMSZORWOGDLWGN-UHFFFAOYSA-N 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 3
- 239000011707 mineral Substances 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- NBFYWQQYIJTQQV-UHFFFAOYSA-N 5-ethylsulfonyl-2-methoxybenzoic acid Chemical compound CCS(=O)(=O)C1=CC=C(OC)C(C(O)=O)=C1 NBFYWQQYIJTQQV-UHFFFAOYSA-N 0.000 claims description 2
- UNRHXEPDKXPRTM-UHFFFAOYSA-N Sultopride Chemical compound CCN1CCCC1CNC(=O)C1=CC(S(=O)(=O)CC)=CC=C1OC UNRHXEPDKXPRTM-UHFFFAOYSA-N 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
- 235000005985 organic acids Nutrition 0.000 claims description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 2
- 150000007522 mineralic acids Chemical class 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 230000003474 anti-emetic effect Effects 0.000 description 1
- 239000002111 antiemetic agent Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 150000003936 benzamides Chemical class 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- -1 phosphoramide chlorohydrate Chemical compound 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000000506 psychotropic effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/22—Amides of acids of phosphorus
- C07F9/224—Phosphorus triamides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
- C07D207/09—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/572—Five-membered rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Pyridine Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Description
2257S242257S24
RENFAG S. A. COLOGNY / SchweizRENFAG S. A. COLOGNY / Switzerland
Verfahren zur Herstellung von N-(l-Aethyl-2-pyrrolidylmethyl)-2-methoxy-5-aethylsulfonyl-benzamidProcess for the preparation of N- (1-ethyl-2-pyrrolidylmethyl) -2-methoxy-5-ethylsulfonyl-benzamide
Die Erfindung betrifft ein Verfahren zur Herstellung von N-(l-Aethyl-2- -pyrrolidylmethyl)-2-methoxy-5-aethylsulfonyl-benzamid und seiner Additionssalze mit für pharmazeutische Zwecke geeigneten Mineral- oder organischen Säuren sowie seiner quaternären Ammoniumsalze durch Umsetzung dieses Benzamids mit einem aliphatischen oder aromatischen Alkyli e r ung s mittel.The invention relates to a process for the preparation of N- (l-ethyl-2- -pyrrolidylmethyl) -2-methoxy-5-aethylsulfonyl-benzamide and its Addition salts with mineral or mineral salts suitable for pharmaceutical purposes organic acids and its quaternary ammonium salts by reacting this benzamide with an aliphatic or aromatic one Alkylating agents.
Das erfindungsgemässe Verfahren ist dadurch gekennzeichnet, dass N-Aethyl-OC-aminomethyl-pyrrolidin mit Phosphoroxychlorid umgesetzt und dann das erhaltene N1, N", NIM-(N-Aethyl-OC-methylpyrrolidin)-phosphoramid kondensiert wird mit 2-Methoxy-5-aethylsulfonyl-benzoesäure.The process according to the invention is characterized in that N-ethyl-OC-aminomethyl-pyrrolidine is reacted with phosphorus oxychloride and the N 1 , N ", N IM - (N-ethyl-OC-methylpyrrolidine) phosphoramide obtained is then condensed with 2-methoxy -5-ethylsulfonylbenzoic acid.
Das auf diese Weise erhaltene Benzamid besitzt wertvolle pharmakologische Eigenschaften, insbesondere als Antiemetikum und Psychotropikum.The benzamide obtained in this way has valuable pharmacological properties Properties, especially as an anti-emetic and psychotropic.
0900/R4U. 12D. 2 - BIl/KW/eb0900 / R4U. 12D. 2 - BIl / KW / eb
309886/1U7309886 / 1U7
Das erfindungsgemässe Verfahren verläuft gemäss nachfolgendein R eaktions schema:The method according to the invention proceeds according to the following Reaction scheme:
O=P-Cl +O = P-Cl +
C2H5 C 2 H 5
O=PO = P
-NH-CH-NH-CH
KJKJ
2 52 5
• 3 HCl• 3 HCl
OHOH
O=PO = P
-NH-CH-NH-CH
(II)(II)
COOHCOOH
H5C2°2S H 5 C 2 ° 2 S
OCH,OCH,
CO-NH-CH-QHCO-NH-CH-QH
OCHOCH
H5C2°2S H 5 C 2 ° 2 S
(I)(I)
(ΠΙ)(ΠΙ)
309886/1147309886/1147
Die vorstehend aufgezeichneten Umsetzungen können in geeigneten Lösungsmitteln durchgeführt werden, wie Bioxaa, Pyridin oder dergleichen, wobei auf Rückflusstemperatur erhitzt wird»The reactions recorded above can be carried out in suitable solvents be carried out, such as Bioxaa, pyridine or the like, heating to reflux temperature »
Die Verwendung von Pyridin als Lösungsmittel bietet den Vorteil, dass das Chlorhydrat des Phosphoramids nicht isoliert zu werden braucht.The use of pyridine as a solvent has the advantage that the chlorohydrate of the phosphoramide need not be isolated.
Die nachfolgenden Beispiele zeigen eine praktische Anwendungsmöglichkeit des erfindungsgemässen Verfahrens.The following examples show a practical application of the method according to the invention.
BEISPIEL 1EXAMPLE 1
N-(I- Ae thyl-2-pyrr olidylraethjjj^-tnethoxy-5-aethylsulfonyl-benzainidchlorhydrat N- (I-ethyl-2-pyrrol idylrae thjjj ^ -tnethoxy-5-ethylsulfonyl-benzainide chlorohydrate
In einem Reaktionsgefäss von einem Liter Inhalt löst man 27g N-Aethyl-GS,-aminomethylpyrrolidin in 56ο ml Pyridin.27 g of N-ethyl-GS, -aminomethylpyrrolidine are dissolved in a one-liter reaction vessel in 56ο ml of pyridine.
Bei Umgebungstemperatur fügt man eine Lösung von 6, Ig Phosphoroxychlorid in 65 ml Pyridin hinzu und rührt die Reaktionsmischung während einer halben Stunde. Darauf wird 15a 6g E-Methosy-5-aethylsulfonylbenzoesäure zugesetzt, worauf die Reaktionsmischung während vier Stunden am Rückfluss gekocht wird.A solution of 6.5 lg phosphorus oxychloride in 65 ml of pyridine is added at ambient temperature and the reaction mixture is stirred for half an hour. This will be added to 15 a 6g E-Methosy-5-aethylsulfonylbenzoesäure, is cooked and the reaction mixture for four hours at reflux.
Nach erfolgter Umsetzung wird das Pyridin im Vakuum verdampft und der Rückstand in 300 ml Wasser und 40 ml Salzsäure (36%) aufgenommen, um etwaige Reste nicht umgesetzter Säure zu entfernen. Die Lösung wird mit einer Lauge alkalisch gemacht und mit Methylenchlorid extrahiert.After the reaction has taken place, the pyridine is evaporated in vacuo and the residue was taken up in 300 ml of water and 40 ml of hydrochloric acid (36%), to remove any residues of unreacted acid. The solution is made alkaline with an alkali and extracted with methylene chloride.
309886/1147309886/1147
Die organische Schicht wird getrocknet, filtriert und im Vakuum eingedampft. Man löst den Rückstand in 20 ml Aceton, und fällt das Chlorhydrat durch Zusatz von Salzsäure aus. Es wird filtriert, mit 10 ml Aethanol gewaschen und im Trockenschrank bei 50 C getrocknet. Man erhält 16g des Chlorhydrates des Be nzamids mit einem Schmelzpunkt von 188-189°C.The organic layer is dried, filtered and evaporated in vacuo. The residue is dissolved in 20 ml of acetone, and the hydrochloric acid is precipitated by adding hydrochloric acid. It is filtered with 10 ml Washed ethanol and dried at 50 ° C. in a drying cabinet. 16 g of the hydrochloride of benzamide with a melting point are obtained from 188-189 ° C.
Dieses Produkt wird zweimal aus Aethanol umkristallisiert und man erhält 10g N-(I- Aethyl-2-pyrrolidylmethyl)-2-methoxy-5-aethyl-sulfonyl benzamidchlorhydrat mit einem Schmelzpunkt von 190-192 C.This product is recrystallized twice from ethanol and 10 g of N- (I-ethyl-2-pyrrolidylmethyl) -2-methoxy-5-ethyl-sulfonyl benzamide chlorohydrate are obtained with a melting point of 190-192 C.
Die Reinheitsbestimmung mit Perchlorsäure ergibt 99» 7 %.The purity determination with perchloric acid gives 99 »7%.
BEISPIEL 2EXAMPLE 2
In ein Reaktionsgefäss von 250 ml Inhalt bringt man die Lösung von 15, 3g N-Aethyl-Or-aminomethyl-pyrrolidin in 60 ml Toluol. Bei Umgebungstemperatur fügt man hierzu 6,1g Phosphoroxychlorid, gelöst in 40 ml Toluol.The 15.3g solution is placed in a 250 ml reaction vessel N-ethyl-or-aminomethyl-pyrrolidine in 60 ml of toluene. At ambient temperature 6.1 g of phosphorus oxychloride dissolved in 40 ml of toluene are added to this.
Nach Rühren bei Umgebungstemperatur während zwei Stunden wird der gebildete Niederschlag abfiltriert, gewaschen und getrocknet. Man erhält 20, 3g N1, N", Ntll-(N-Aethyl-OC-methylpyrrolidin)-phosphoramid-chlorhydrat mit einem Schmelzpunkt von 106-110 C.After stirring at ambient temperature for two hours, the precipitate formed is filtered off, washed and dried. 20.3 g of N 1 , N ", N tll - (N-ethyl-OC-methylpyrrolidine) phosphoramide chlorohydrate with a melting point of 106-110 ° C. are obtained.
Das auf diese Weise erhaltene Chlorhydrat wird in 350 ml "Wasser gelöstThe hydrochloride obtained in this way is dissolved in 350 ml of "water"
309886/1U7309886 / 1U7
und die Lösung mit einer Lauge alkalisch gemacht. Diese Lösung wird dann mit Chloroform extrahiert. Die organische Schicht wird über Kaliumcarbonat getrocknet und im Vakuum eingedampft. Man erhält 10, 5g N1, N", Nm-(N-Aethyl-Ct-methylpyrrolidin)-phosphoramid.and made the solution alkaline with a lye. This solution is then extracted with chloroform. The organic layer is dried over potassium carbonate and evaporated in vacuo. 10.5 g of N 1 , N ″, N m - (N-ethyl-Ct-methylpyrrolidine) phosphoramide are obtained.
Die Reinheitsbestimmung mit Perchlorsäure ergibt 98,2 %.The purity determination with perchloric acid gives 98.2%.
303888/1U7303888 / 1U7
Claims (2)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1080272A CH565149A5 (en) | 1972-07-19 | 1972-07-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2257624A1 true DE2257624A1 (en) | 1974-02-07 |
Family
ID=4367011
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2257624A Pending DE2257624A1 (en) | 1972-07-19 | 1972-11-24 | PROCESS FOR PREPARING N- (LAETHYL-2-PYRROLIDYLMETHYL) -2-METHOXY-5AETHYLSULFONYL-BENZAMIDE |
Country Status (29)
| Country | Link |
|---|---|
| JP (2) | JPS4935377A (en) |
| KR (1) | KR780000089B1 (en) |
| AR (1) | AR194145A1 (en) |
| AT (1) | AT319932B (en) |
| AU (1) | AU471164B2 (en) |
| BE (1) | BE793871A (en) |
| BG (1) | BG20347A3 (en) |
| CA (1) | CA976974A (en) |
| CH (1) | CH565149A5 (en) |
| CS (1) | CS174865B2 (en) |
| DD (1) | DD102380A5 (en) |
| DE (1) | DE2257624A1 (en) |
| EG (1) | EG11435A (en) |
| ES (1) | ES409348A1 (en) |
| FR (1) | FR2192820B1 (en) |
| GB (1) | GB1394409A (en) |
| HU (1) | HU167514B (en) |
| IE (1) | IE37363B1 (en) |
| IL (1) | IL41522A (en) |
| LU (1) | LU66787A1 (en) |
| MC (1) | MC961A1 (en) |
| NL (1) | NL7215710A (en) |
| OA (1) | OA04313A (en) |
| PH (1) | PH9390A (en) |
| PL (1) | PL82470B1 (en) |
| RO (1) | RO62350A (en) |
| YU (1) | YU36499B (en) |
| ZA (1) | ZA73537B (en) |
| ZM (1) | ZM1773A1 (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1151533B (en) * | 1982-03-29 | 1986-12-24 | Ravizza Spa | PROCEDURE FOR THE PREPARATION OF P. CHLOROFENOSSIACETIL-PIPERONILPIPERAZINA |
| WO1991017144A1 (en) * | 1990-05-02 | 1991-11-14 | Yoshitomi Pharmaceutical Industries, Ltd. | Amide compound, pharmaceutical use thereof and novel 1-substituted pyrrolidinemethyl-amines |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4940459B1 (en) * | 1970-12-21 | 1974-11-02 |
-
0
- BE BE793871D patent/BE793871A/en not_active IP Right Cessation
-
1972
- 1972-07-19 CH CH1080272A patent/CH565149A5/xx not_active IP Right Cessation
- 1972-11-20 NL NL7215710A patent/NL7215710A/xx unknown
- 1972-11-22 AR AR245248A patent/AR194145A1/en active
- 1972-11-24 PL PL1972159072A patent/PL82470B1/pl unknown
- 1972-11-24 HU HURE521A patent/HU167514B/hu unknown
- 1972-11-24 DE DE2257624A patent/DE2257624A1/en active Pending
- 1972-11-30 BG BG22005A patent/BG20347A3/xx unknown
- 1972-12-01 RO RO73014A patent/RO62350A/ro unknown
- 1972-12-05 YU YU03015/72A patent/YU36499B/en unknown
- 1972-12-06 ES ES409348A patent/ES409348A1/en not_active Expired
- 1972-12-06 CS CS8355A patent/CS174865B2/cs unknown
- 1972-12-06 AT AT1038972A patent/AT319932B/en not_active IP Right Cessation
- 1972-12-11 FR FR7244002A patent/FR2192820B1/fr not_active Expired
- 1972-12-15 MC MC1024A patent/MC961A1/en unknown
- 1972-12-28 DD DD167945A patent/DD102380A5/xx unknown
-
1973
- 1973-01-03 LU LU66787A patent/LU66787A1/xx unknown
- 1973-01-12 OA OA54805A patent/OA04313A/en unknown
- 1973-01-18 CA CA161,588A patent/CA976974A/en not_active Expired
- 1973-01-24 ZA ZA730537A patent/ZA73537B/en unknown
- 1973-01-26 AU AU51514/73A patent/AU471164B2/en not_active Expired
- 1973-02-06 JP JP48014354A patent/JPS4935377A/ja active Pending
- 1973-02-12 ZM ZM17/73A patent/ZM1773A1/en unknown
- 1973-02-13 IL IL41522A patent/IL41522A/en unknown
- 1973-02-14 KR KR7300264A patent/KR780000089B1/en active
- 1973-02-21 GB GB846873A patent/GB1394409A/en not_active Expired
- 1973-03-02 IE IE339/73A patent/IE37363B1/en unknown
- 1973-04-03 JP JP3749673A patent/JPS5532704B2/ja not_active Expired
- 1973-04-23 PH PH14537*UA patent/PH9390A/en unknown
- 1973-07-15 EG EG277/73A patent/EG11435A/en active
Also Published As
| Publication number | Publication date |
|---|---|
| BG20347A3 (en) | 1975-11-05 |
| HU167514B (en) | 1975-10-28 |
| AU471164B2 (en) | 1976-04-08 |
| DD102380A5 (en) | 1973-12-12 |
| GB1394409A (en) | 1975-05-14 |
| AT319932B (en) | 1975-01-10 |
| IL41522A (en) | 1977-11-30 |
| AU5151473A (en) | 1974-08-01 |
| IE37363L (en) | 1974-01-19 |
| JPS4943966A (en) | 1974-04-25 |
| YU301572A (en) | 1982-02-25 |
| AR194145A1 (en) | 1973-06-22 |
| EG11435A (en) | 1977-03-31 |
| NL7215710A (en) | 1974-01-22 |
| CS174865B2 (en) | 1977-04-29 |
| RO62350A (en) | 1977-08-15 |
| PH9390A (en) | 1975-10-22 |
| IL41522A0 (en) | 1973-04-30 |
| CA976974A (en) | 1975-10-28 |
| PL82470B1 (en) | 1975-10-31 |
| OA04313A (en) | 1980-01-15 |
| MC961A1 (en) | 1973-12-07 |
| FR2192820A1 (en) | 1974-02-15 |
| FR2192820B1 (en) | 1976-07-02 |
| IE37363B1 (en) | 1977-07-06 |
| KR780000089B1 (en) | 1978-04-08 |
| LU66787A1 (en) | 1973-03-19 |
| ZA73537B (en) | 1973-10-31 |
| ES409348A1 (en) | 1975-11-16 |
| CH565149A5 (en) | 1975-08-15 |
| BE793871A (en) | 1973-05-02 |
| YU36499B (en) | 1984-02-29 |
| JPS4935377A (en) | 1974-04-01 |
| JPS5532704B2 (en) | 1980-08-26 |
| ZM1773A1 (en) | 1973-10-22 |
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