FR2477537A1 - Nouvelles guanidines acylees, urees et urees substituees, leur procede de fabrication et leur application en tant que medicaments - Google Patents
Nouvelles guanidines acylees, urees et urees substituees, leur procede de fabrication et leur application en tant que medicaments Download PDFInfo
- Publication number
- FR2477537A1 FR2477537A1 FR8005190A FR8005190A FR2477537A1 FR 2477537 A1 FR2477537 A1 FR 2477537A1 FR 8005190 A FR8005190 A FR 8005190A FR 8005190 A FR8005190 A FR 8005190A FR 2477537 A1 FR2477537 A1 FR 2477537A1
- Authority
- FR
- France
- Prior art keywords
- group
- radical
- found
- ureas
- calculated
- 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.)
- Granted
Links
- 150000002357 guanidines Chemical class 0.000 title claims abstract description 6
- 239000003814 drug Substances 0.000 title claims abstract description 5
- 150000003672 ureas Chemical class 0.000 title claims description 9
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 26
- 239000002904 solvent Substances 0.000 claims abstract description 6
- 238000010438 heat treatment Methods 0.000 claims abstract description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 50
- 125000003118 aryl group Chemical group 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 125000004104 aryloxy group Chemical group 0.000 claims description 9
- 235000013877 carbamide Nutrition 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 101100295738 Gallus gallus COR3 gene Proteins 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 238000010992 reflux Methods 0.000 claims description 4
- 229940079593 drug Drugs 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000000879 imine group Chemical group 0.000 claims description 2
- 208000031225 myocardial ischemia Diseases 0.000 claims description 2
- 230000033764 rhythmic process Effects 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 206010020772 Hypertension Diseases 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 208000037849 arterial hypertension Diseases 0.000 abstract 2
- 208000019622 heart disease Diseases 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 20
- 239000000047 product Substances 0.000 description 20
- 229910001868 water Inorganic materials 0.000 description 15
- -1 2-hydroxypropyl Chemical group 0.000 description 8
- 235000010650 Hyssopus officinalis Nutrition 0.000 description 8
- 240000001812 Hyssopus officinalis Species 0.000 description 8
- 238000001802 infusion Methods 0.000 description 6
- 230000001975 sympathomimetic effect Effects 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 229960002508 pindolol Drugs 0.000 description 4
- PHUTUTUABXHXLW-UHFFFAOYSA-N pindolol Chemical compound CC(C)NCC(O)COC1=CC=CC2=NC=C[C]12 PHUTUTUABXHXLW-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- 206010062119 Sympathomimetic effect Diseases 0.000 description 3
- 230000036772 blood pressure Effects 0.000 description 3
- 230000002860 competitive effect Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 210000003462 vein Anatomy 0.000 description 3
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 2
- 241000282472 Canis lupus familiaris Species 0.000 description 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 239000000150 Sympathomimetic Substances 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 230000000747 cardiac effect Effects 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- 229960001317 isoprenaline Drugs 0.000 description 2
- CQINCUVDUJRJSB-UHFFFAOYSA-N n-[[2-[2-hydroxy-3-(2-methylphenoxy)propyl]-2-propan-2-ylhydrazinyl]methylidene]benzamide Chemical compound C=1C=CC=CC=1C(=O)N=CNN(C(C)C)CC(O)COC1=CC=CC=C1C CQINCUVDUJRJSB-UHFFFAOYSA-N 0.000 description 2
- WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 2
- DGMKFQYCZXERLX-UHFFFAOYSA-N proglumide Chemical compound CCCN(CCC)C(=O)C(CCC(O)=O)NC(=O)C1=CC=CC=C1 DGMKFQYCZXERLX-UHFFFAOYSA-N 0.000 description 2
- 239000008223 sterile water Substances 0.000 description 2
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 1
- 125000006519 CCH3 Chemical group 0.000 description 1
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 208000001953 Hypotension Diseases 0.000 description 1
- KOGVDCPMCJJZTB-UHFFFAOYSA-N INNI Chemical compound INNI KOGVDCPMCJJZTB-UHFFFAOYSA-N 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 1
- UIQMVEYFGZJHCZ-SSTWWWIQSA-N Nalorphine Chemical compound C([C@@H](N(CC1)CC=C)[C@@H]2C=C[C@@H]3O)C4=CC=C(O)C5=C4[C@@]21[C@H]3O5 UIQMVEYFGZJHCZ-SSTWWWIQSA-N 0.000 description 1
- 229920002565 Polyethylene Glycol 400 Polymers 0.000 description 1
- 208000001871 Tachycardia Diseases 0.000 description 1
- 230000001800 adrenalinergic effect Effects 0.000 description 1
- 239000002876 beta blocker Substances 0.000 description 1
- 229940097320 beta blocking agent Drugs 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 210000000621 bronchi Anatomy 0.000 description 1
- 239000000496 cardiotonic agent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- GCFHZZWXZLABBL-UHFFFAOYSA-N ethanol;hexane Chemical compound CCO.CCCCCC GCFHZZWXZLABBL-UHFFFAOYSA-N 0.000 description 1
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000009499 grossing Methods 0.000 description 1
- 210000002837 heart atrium Anatomy 0.000 description 1
- 230000036543 hypotension Effects 0.000 description 1
- 239000003317 industrial substance Substances 0.000 description 1
- 230000009249 intrinsic sympathomimetic activity Effects 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- DBFAKALHTSOYSG-UHFFFAOYSA-N n-cyanobenzamide Chemical compound N#CNC(=O)C1=CC=CC=C1 DBFAKALHTSOYSG-UHFFFAOYSA-N 0.000 description 1
- 239000013588 oral product Substances 0.000 description 1
- 229940023486 oral product Drugs 0.000 description 1
- 229960001412 pentobarbital Drugs 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
- WSDQIHATCCOMLH-UHFFFAOYSA-N phenyl n-(3,5-dichlorophenyl)carbamate Chemical compound ClC1=CC(Cl)=CC(NC(=O)OC=2C=CC=CC=2)=C1 WSDQIHATCCOMLH-UHFFFAOYSA-N 0.000 description 1
- GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 description 1
- AQHHHDLHHXJYJD-UHFFFAOYSA-N propranolol Chemical class C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 AQHHHDLHHXJYJD-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 230000001502 supplementing effect Effects 0.000 description 1
- 230000002889 sympathetic effect Effects 0.000 description 1
- 229940064707 sympathomimetics Drugs 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000006794 tachycardia Effects 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 210000002465 tibial artery Anatomy 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 238000002627 tracheal intubation Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/04—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms
- C07C275/06—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms of an acyclic and saturated carbon skeleton
- C07C275/10—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms of an acyclic and saturated carbon skeleton being further substituted by singly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C279/20—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups containing any of the groups, X being a hetero atom, Y being any atom, e.g. acylguanidines
- C07C279/22—Y being a hydrogen or a carbon atom, e.g. benzoylguanidines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C279/20—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups containing any of the groups, X being a hetero atom, Y being any atom, e.g. acylguanidines
- C07C279/24—Y being a hetero atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8005190A FR2477537A1 (fr) | 1980-03-07 | 1980-03-07 | Nouvelles guanidines acylees, urees et urees substituees, leur procede de fabrication et leur application en tant que medicaments |
| PT72601A PT72601B (fr) | 1980-03-07 | 1981-03-02 | Nouvelles guanidines acylees urees et urees substituees leur procede de fabrication et leurs applications en tant que medi- caments |
| US06/240,512 US4376783A (en) | 1980-03-07 | 1981-03-04 | Acylated guanidines and medicaments containing them |
| JP3239081A JPS56164159A (en) | 1980-03-07 | 1981-03-05 | Novel acylated guanidine, urea and substituted urea, their manufacture and medicine containing them |
| ES500114A ES500114A0 (es) | 1980-03-07 | 1981-03-05 | Procedimiento de preparacion de nuevas guanidinas aciladas, ureas y ureas sustituidas |
| EP81400354A EP0035945B1 (fr) | 1980-03-07 | 1981-03-06 | Nouvelles guanidines acylées, urées et urées substituées, leur procédé de fabrication et leur application en tant que médicaments |
| DE8181400354T DE3161682D1 (en) | 1980-03-07 | 1981-03-06 | Acyl guanidines, ureas and substituted ureas, their preparation and their use as medicaments |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8005190A FR2477537A1 (fr) | 1980-03-07 | 1980-03-07 | Nouvelles guanidines acylees, urees et urees substituees, leur procede de fabrication et leur application en tant que medicaments |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2477537A1 true FR2477537A1 (fr) | 1981-09-11 |
| FR2477537B1 FR2477537B1 (OSRAM) | 1983-04-01 |
Family
ID=9239448
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8005190A Granted FR2477537A1 (fr) | 1980-03-07 | 1980-03-07 | Nouvelles guanidines acylees, urees et urees substituees, leur procede de fabrication et leur application en tant que medicaments |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4376783A (OSRAM) |
| EP (1) | EP0035945B1 (OSRAM) |
| JP (1) | JPS56164159A (OSRAM) |
| DE (1) | DE3161682D1 (OSRAM) |
| ES (1) | ES500114A0 (OSRAM) |
| FR (1) | FR2477537A1 (OSRAM) |
| PT (1) | PT72601B (OSRAM) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4849527A (en) * | 1982-09-13 | 1989-07-18 | Bristol-Myers Company | Process for resolution of optical isomers |
| US5387266A (en) * | 1993-06-11 | 1995-02-07 | Ethyl Corporation | Mannich base derivatives, and the production and uses thereof |
| CA2159759A1 (en) * | 1994-10-14 | 1996-04-15 | Katherine S. Takaki | Melatonergic agents |
| US7071211B2 (en) * | 2002-09-27 | 2006-07-04 | Bausch & Lomb Inc. | Small organic molecules that increase the activity of gelatinase a in ocular cells |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1049285A (en) * | 1962-05-14 | 1966-11-23 | Smith Kline French Lab | Guanidine and dihydroimidazole derivatives |
| FR1488231A (fr) * | 1964-12-17 | 1967-07-13 | Ciba Geigy | Nouveaux dérivés de l'urée, ainsi que leur procédé de préparation et les compositions les contenant |
| FR5402M (OSRAM) * | 1965-08-19 | 1967-09-25 | ||
| US3437691A (en) * | 1967-06-02 | 1969-04-08 | Dow Chemical Co | (beta-hydroxy-omega-phenoxyalkyl) guanidine compounds |
| FR2150621A2 (en) * | 1971-09-01 | 1973-04-13 | Orsymonde | Amino-derivs of phloroglucinol - with antiarrhythmic activity |
| FR2210407A1 (OSRAM) * | 1972-12-15 | 1974-07-12 | Ici Ltd | |
| FR2401135A1 (fr) * | 1977-05-17 | 1979-03-23 | Allen & Hanburys Ltd | Nouveaux derives d'aminoalkyl-benzenes et procedes pour leur preparation |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3542873A (en) * | 1967-06-02 | 1970-11-24 | Dow Chemical Co | (2-hydroxy-3-(polychlorophenoxy)propyl)amine compounds |
| SE354851B (OSRAM) * | 1970-02-18 | 1973-03-26 | Haessle Ab |
-
1980
- 1980-03-07 FR FR8005190A patent/FR2477537A1/fr active Granted
-
1981
- 1981-03-02 PT PT72601A patent/PT72601B/pt unknown
- 1981-03-04 US US06/240,512 patent/US4376783A/en not_active Expired - Fee Related
- 1981-03-05 JP JP3239081A patent/JPS56164159A/ja active Pending
- 1981-03-05 ES ES500114A patent/ES500114A0/es active Granted
- 1981-03-06 DE DE8181400354T patent/DE3161682D1/de not_active Expired
- 1981-03-06 EP EP81400354A patent/EP0035945B1/fr not_active Expired
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1049285A (en) * | 1962-05-14 | 1966-11-23 | Smith Kline French Lab | Guanidine and dihydroimidazole derivatives |
| FR1488231A (fr) * | 1964-12-17 | 1967-07-13 | Ciba Geigy | Nouveaux dérivés de l'urée, ainsi que leur procédé de préparation et les compositions les contenant |
| FR5402M (OSRAM) * | 1965-08-19 | 1967-09-25 | ||
| US3437691A (en) * | 1967-06-02 | 1969-04-08 | Dow Chemical Co | (beta-hydroxy-omega-phenoxyalkyl) guanidine compounds |
| FR2150621A2 (en) * | 1971-09-01 | 1973-04-13 | Orsymonde | Amino-derivs of phloroglucinol - with antiarrhythmic activity |
| FR2210407A1 (OSRAM) * | 1972-12-15 | 1974-07-12 | Ici Ltd | |
| FR2401135A1 (fr) * | 1977-05-17 | 1979-03-23 | Allen & Hanburys Ltd | Nouveaux derives d'aminoalkyl-benzenes et procedes pour leur preparation |
Non-Patent Citations (2)
| Title |
|---|
| JOURNAL OF POLYMER SCIENCE, vol. 7, part A-1, no. 11, novembre 1969, Interscience publishers (US), Y. IWAKURA et al.: 'Polythiazolines', pages 3075 - 3078 * |
| METHODEN DER ORGANISCHEN CHEMIE (HOUBEN-WEYL), 4e édition, vol VIII, GEORG THIEME VERLAG, STUTTGART (DE), pages 157 -159 et 180 - 183 * |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2477537B1 (OSRAM) | 1983-04-01 |
| EP0035945A3 (en) | 1981-12-02 |
| ES8201544A1 (es) | 1981-12-16 |
| DE3161682D1 (en) | 1984-01-26 |
| PT72601B (fr) | 1982-03-26 |
| PT72601A (fr) | 1981-04-01 |
| EP0035945B1 (fr) | 1983-12-21 |
| JPS56164159A (en) | 1981-12-17 |
| US4376783A (en) | 1983-03-15 |
| ES500114A0 (es) | 1981-12-16 |
| EP0035945A2 (fr) | 1981-09-16 |
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