EP0057227A1 - Imino-alkyle et amino-nitrile cyano-guanidines - Google Patents
Imino-alkyle et amino-nitrile cyano-guanidinesInfo
- Publication number
- EP0057227A1 EP0057227A1 EP19810902295 EP81902295A EP0057227A1 EP 0057227 A1 EP0057227 A1 EP 0057227A1 EP 19810902295 EP19810902295 EP 19810902295 EP 81902295 A EP81902295 A EP 81902295A EP 0057227 A1 EP0057227 A1 EP 0057227A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- imino
- methyl
- cyano
- ethyl
- acid
- 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.)
- Withdrawn
Links
- -1 amino-nitrile cyano-guanidines Chemical class 0.000 title claims abstract description 30
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical class NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims abstract 9
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 26
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 22
- 239000002904 solvent Substances 0.000 claims description 14
- 230000009102 absorption Effects 0.000 claims description 9
- 238000010521 absorption reaction Methods 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 229960004198 guanidine Drugs 0.000 claims description 7
- 239000012299 nitrogen atmosphere Substances 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- ZRALSGWEFCBTJO-UHFFFAOYSA-N guanidine group Chemical group NC(=N)N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 5
- 229960000789 guanidine hydrochloride Drugs 0.000 claims description 3
- HPXWWLGOFMSKHV-UHFFFAOYSA-N [4-(chloromethyl)-1,3-thiazol-2-yl]-(diaminomethylidene)azanium;chloride Chemical compound Cl.NC(N)=NC1=NC(CCl)=CS1 HPXWWLGOFMSKHV-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims 16
- 230000009466 transformation Effects 0.000 claims 9
- 150000007522 mineralic acids Chemical class 0.000 claims 5
- 150000007524 organic acids Chemical class 0.000 claims 5
- 239000007806 chemical reaction intermediate Substances 0.000 claims 4
- 150000004703 alkoxides Chemical class 0.000 claims 3
- 239000000543 intermediate Substances 0.000 claims 3
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims 2
- UNTOHFRPVXPVBY-UHFFFAOYSA-N 1-cyano-3-imino-2-[2-[(3-methoxypyridin-2-yl)methylsulfanyl]ethyl]-1-methylguanidine Chemical compound COC1=CC=CN=C1CSCCN=C(N=N)N(C)C#N UNTOHFRPVXPVBY-UHFFFAOYSA-N 0.000 claims 1
- OJONBBMOOIYLHY-UHFFFAOYSA-N 2-[2-[(3-ethoxypyridin-2-yl)methylsulfanyl]ethyl]guanidine Chemical compound CCOC1=CC=CN=C1CSCCN=C(N)N OJONBBMOOIYLHY-UHFFFAOYSA-N 0.000 claims 1
- CUQUECGDXSSUBI-UHFFFAOYSA-N 5-(chloromethyl)-N,N,4-trimethylfuran-2-amine Chemical compound CN(C1=CC(=C(O1)CCl)C)C CUQUECGDXSSUBI-UHFFFAOYSA-N 0.000 claims 1
- VEGBSHFSQMSXJT-UHFFFAOYSA-N Cl.C(C)OC=1C(NC=CC1)(C)Cl Chemical compound Cl.C(C)OC=1C(NC=CC1)(C)Cl VEGBSHFSQMSXJT-UHFFFAOYSA-N 0.000 claims 1
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims 1
- 125000000129 anionic group Chemical group 0.000 claims 1
- 150000001768 cations Chemical class 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims 1
- QYRFJLLXPINATB-UHFFFAOYSA-N hydron;2,4,5,6-tetrafluorobenzene-1,3-diamine;dichloride Chemical compound Cl.Cl.NC1=C(F)C(N)=C(F)C(F)=C1F QYRFJLLXPINATB-UHFFFAOYSA-N 0.000 claims 1
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridine hydrochloride Substances [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 125000005219 aminonitrile group Chemical group 0.000 abstract description 2
- 230000002194 synthesizing effect Effects 0.000 abstract 1
- 239000003921 oil Substances 0.000 description 11
- 235000019198 oils Nutrition 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 150000002357 guanidines Chemical class 0.000 description 5
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 4
- 230000002496 gastric effect Effects 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 125000004103 aminoalkyl group Chemical group 0.000 description 3
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 229960001340 histamine Drugs 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 150000002825 nitriles Chemical group 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 230000028327 secretion Effects 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- CDWCUWRTIQPRPU-UHFFFAOYSA-N 1-imino-2-(2-sulfanylethyl)guanidine Chemical compound SCCNC(=N)N=N CDWCUWRTIQPRPU-UHFFFAOYSA-N 0.000 description 1
- QDGRANVCLYGLDL-UHFFFAOYSA-N 2-(2-sulfanylethyl)guanidine;hydrochloride Chemical compound [Cl-].NC([NH3+])=NCCS QDGRANVCLYGLDL-UHFFFAOYSA-N 0.000 description 1
- BVKOVRNDBVJWGM-UHFFFAOYSA-N 2-(chloromethyl)-3-methoxypyridine;hydrochloride Chemical compound Cl.COC1=CC=CN=C1CCl BVKOVRNDBVJWGM-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 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 1
- 208000007107 Stomach Ulcer Diseases 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000002280 anti-androgenic effect Effects 0.000 description 1
- 230000001263 anti-prolactin effect Effects 0.000 description 1
- 230000001262 anti-secretory effect Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 208000000718 duodenal ulcer Diseases 0.000 description 1
- 201000005917 gastric ulcer Diseases 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 210000001711 oxyntic cell Anatomy 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/65—One oxygen atom attached in position 3 or 5
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/38—Nitrogen atoms
- C07D277/44—Acylated amino or imino radicals
- C07D277/48—Acylated amino or imino radicals by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof, e.g. carbonylguanidines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/10—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/14—Radicals substituted by nitrogen atoms not forming part of a nitro radical
Definitions
- the imino-alkyl and amino-nitrile cyano-guanidines claimed in application no. 1 404 / 79-7 and in the present application are not in equilibrium with the corresponding stable imino-nitrile and amino-alkyl cyano-guanidines.
- our invention which makes it possible to obtain irreversibly, by a new reaction of organic chemistry and for the first time described in Swiss application No.
- cyano-guanidines iminoalkyl and amino -nitrile basic by their guanidine function from cyano-guanidine imino-nitrile and amino-neutral alkyl function-Spar their guanidine function, we have prepared the following four new guanidines:
- guanidines have a structure allowing a higher gastric anti-secretory activity (volume of secretion and gastric acidity) higher than the same activity of the cyano-guanidines imino-nitrile and amino-alkyl already known. In addition, their toxicity (anti-androgenic effect and prolactin effect) is significantly reduced.
- R 1 -N ⁇ -NHCN NHCH 3 ,
- Said compounds of the invention and their therapeutically suitable salts can be used for the treatment of gastric and duodenal ulcer.
- excipients suitable for their pharmaceutical applications are, for example. lactose, sucrose, talc, gelatin, gum arabic, olive oil.
- Example 3 N-methyl-N'-cyano-N '' - imino- [2 - ((5-dimethylamino-methyl-2-furanyl) -methylthio) -ethyl] -guanidine.dichlorhydrate. It is brought to reflux 21 ⁇ 2 h. a solution in ethanol containing 32.5 ml of HCl, 1 N, of 4.3 g of N-methyl-N'-iraino-cyano- N'- '2- ((5-dimethylamino-raethyl-2 -furanyl) -methylthto) -ethyl -guanidine. The solvent is evaporated off under reduced pressure; the residue, as oil, is dissolved in raethanol and the solvent is again evaporated; the residual oil is subjected to the vacuum 0.05 T, 3 hours,
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Furan Compounds (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH604980 | 1980-08-11 | ||
| CH6049/80 | 1980-08-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| EP0057227A1 true EP0057227A1 (fr) | 1982-08-11 |
Family
ID=4303404
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP19810902295 Withdrawn EP0057227A1 (fr) | 1980-08-11 | 1981-08-10 | Imino-alkyle et amino-nitrile cyano-guanidines |
Country Status (3)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2022034121A1 (en) | 2020-08-11 | 2022-02-17 | Université De Strasbourg | H2 blockers targeting liver macrophages for the prevention and treatment of liver disease and cancer |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NO781300L (no) * | 1977-04-20 | 1978-10-23 | Ici Ltd | Fremgangsmaate for fremstilling av fysiologisk aktive guanidinderivater |
| DE2966646D1 (en) * | 1978-10-16 | 1984-03-15 | Ici Plc | Antisecretory branched-chain heterocyclic guanidine derivatives, processes for their manufacture, intermediates, and pharmaceutical compositions containing said derivatives |
| GR71929B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1979-11-13 | 1983-08-19 | Ici Ltd |
-
1981
- 1981-08-10 EP EP19810902295 patent/EP0057227A1/fr not_active Withdrawn
- 1981-08-10 WO PCT/CH1981/000090 patent/WO1982000462A1/en not_active Application Discontinuation
- 1981-08-10 JP JP56502640A patent/JPS57501379A/ja active Pending
Non-Patent Citations (1)
| Title |
|---|
| See references of WO8200462A1 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2022034121A1 (en) | 2020-08-11 | 2022-02-17 | Université De Strasbourg | H2 blockers targeting liver macrophages for the prevention and treatment of liver disease and cancer |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS57501379A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1982-08-05 |
| WO1982000462A1 (en) | 1982-02-18 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
Free format text: ORIGINAL CODE: 0009012 |
|
| AK | Designated contracting states |
Designated state(s): AT DE FR GB NL SE |
|
| 17P | Request for examination filed |
Effective date: 19821018 |
|
| STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN |
|
| 18D | Application deemed to be withdrawn |
Effective date: 19840301 |
|
| RIN1 | Information on inventor provided before grant (corrected) |
Inventor name: BAUDET, PIERRE |