DE1695841C3 - 1 -(2,2,2 -TrifluoräthyD-7-chIor-13-dihydro-5-phenyl-2H-1,4-benzodiazepin-2-one, Verfahren zu ihrer Herstellung und sie enthaltende pharmazeutische Zubereitungen - Google Patents
1 -(2,2,2 -TrifluoräthyD-7-chIor-13-dihydro-5-phenyl-2H-1,4-benzodiazepin-2-one, Verfahren zu ihrer Herstellung und sie enthaltende pharmazeutische ZubereitungenInfo
- Publication number
- DE1695841C3 DE1695841C3 DE1967SC040084 DESC040084A DE1695841C3 DE 1695841 C3 DE1695841 C3 DE 1695841C3 DE 1967SC040084 DE1967SC040084 DE 1967SC040084 DE SC040084 A DESC040084 A DE SC040084A DE 1695841 C3 DE1695841 C3 DE 1695841C3
- Authority
- DE
- Germany
- Prior art keywords
- benzodiazepin
- dihydro
- phenyl
- chloro
- ones
- 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.)
- Expired
Links
- 238000000034 method Methods 0.000 title description 7
- 238000002360 preparation method Methods 0.000 title description 4
- 239000000825 pharmaceutical preparation Substances 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 description 32
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 241001465754 Metazoa Species 0.000 description 13
- 239000000243 solution Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- AAOVKJBEBIDNHE-UHFFFAOYSA-N diazepam Chemical compound N=1CC(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 AAOVKJBEBIDNHE-UHFFFAOYSA-N 0.000 description 6
- 229960003529 diazepam Drugs 0.000 description 6
- 229910052731 fluorine Chemical group 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 206010010904 Convulsion Diseases 0.000 description 5
- 230000036461 convulsion Effects 0.000 description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 208000019901 Anxiety disease Diseases 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- 208000012902 Nervous system disease Diseases 0.000 description 3
- CWRVKFFCRWGWCS-UHFFFAOYSA-N Pentrazole Chemical compound C1CCCCC2=NN=NN21 CWRVKFFCRWGWCS-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000007059 acute toxicity Effects 0.000 description 3
- 231100000403 acute toxicity Toxicity 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 230000000049 anti-anxiety effect Effects 0.000 description 3
- 230000036506 anxiety Effects 0.000 description 3
- 150000001557 benzodiazepines Chemical class 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229960005152 pentetrazol Drugs 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 229940049706 benzodiazepine Drugs 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 230000001914 calming effect Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 230000008602 contraction Effects 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000012259 ether extract Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 150000002485 inorganic esters Chemical class 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 230000000926 neurological effect Effects 0.000 description 2
- 150000002895 organic esters Chemical group 0.000 description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- MAOBFOXLCJIFLV-UHFFFAOYSA-N (2-aminophenyl)-phenylmethanone Chemical class NC1=CC=CC=C1C(=O)C1=CC=CC=C1 MAOBFOXLCJIFLV-UHFFFAOYSA-N 0.000 description 1
- TXTWXQXDMWILOF-UHFFFAOYSA-N (2-ethoxy-2-oxoethyl)azanium;chloride Chemical compound [Cl-].CCOC(=O)C[NH3+] TXTWXQXDMWILOF-UHFFFAOYSA-N 0.000 description 1
- RKOUFQLNMRAACI-UHFFFAOYSA-N 1,1,1-trifluoro-2-iodoethane Chemical compound FC(F)(F)CI RKOUFQLNMRAACI-UHFFFAOYSA-N 0.000 description 1
- RGGLEJFUEMKQSH-UHFFFAOYSA-N 1,4-benzodiazepin-2-one Chemical compound O=C1C=NC=C2C=CC=CC2=N1 RGGLEJFUEMKQSH-UHFFFAOYSA-N 0.000 description 1
- ABRHGSTXPVUNBK-UHFFFAOYSA-N 2,2,2-trifluoroethyl benzenesulfonate Chemical compound FC(F)(F)COS(=O)(=O)C1=CC=CC=C1 ABRHGSTXPVUNBK-UHFFFAOYSA-N 0.000 description 1
- ICECLJDLAVVEOW-UHFFFAOYSA-N 2,2,2-trifluoroethyl methanesulfonate Chemical compound CS(=O)(=O)OCC(F)(F)F ICECLJDLAVVEOW-UHFFFAOYSA-N 0.000 description 1
- GOIWZZQXWJVDOG-UHFFFAOYSA-N 2,2,2-trifluoroethyl trichloromethanesulfonate Chemical compound FC(F)(F)COS(=O)(=O)C(Cl)(Cl)Cl GOIWZZQXWJVDOG-UHFFFAOYSA-N 0.000 description 1
- TZNJHEHAYZJBHR-UHFFFAOYSA-N 2-bromo-1,1,1-trifluoroethane Chemical compound FC(F)(F)CBr TZNJHEHAYZJBHR-UHFFFAOYSA-N 0.000 description 1
- IVUAAOBNUNMJQC-UHFFFAOYSA-N 5-phenyl-1,3-dihydro-1,4-benzodiazepin-2-one Chemical class C12=CC=CC=C2NC(=O)CN=C1C1=CC=CC=C1 IVUAAOBNUNMJQC-UHFFFAOYSA-N 0.000 description 1
- 206010003591 Ataxia Diseases 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 206010053398 Clonic convulsion Diseases 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 206010043994 Tonic convulsion Diseases 0.000 description 1
- RHQDFWAXVIIEBN-UHFFFAOYSA-N Trifluoroethanol Chemical compound OCC(F)(F)F RHQDFWAXVIIEBN-UHFFFAOYSA-N 0.000 description 1
- QPKPRNRVRFRJLL-UHFFFAOYSA-N [3-amino-5-chloro-2-(2,2,2-trifluoroethyl)phenyl]-phenylmethanone Chemical compound NC1=CC(Cl)=CC(C(=O)C=2C=CC=CC=2)=C1CC(F)(F)F QPKPRNRVRFRJLL-UHFFFAOYSA-N 0.000 description 1
- MKBQTVZIYPYTSC-UHFFFAOYSA-N [5-chloro-2-(2,2,2-trifluoroethylamino)phenyl]-phenylmethanone Chemical compound FC(F)(F)CNC1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1 MKBQTVZIYPYTSC-UHFFFAOYSA-N 0.000 description 1
- YKSNHLNTLVRITE-UHFFFAOYSA-N [Br].CC(Br)=O Chemical compound [Br].CC(Br)=O YKSNHLNTLVRITE-UHFFFAOYSA-N 0.000 description 1
- 230000036626 alertness Effects 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 230000008485 antagonism Effects 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000001977 ataxic effect Effects 0.000 description 1
- 230000002567 autonomic effect Effects 0.000 description 1
- 230000006399 behavior Effects 0.000 description 1
- 230000003542 behavioural effect Effects 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- 230000002566 clonic effect Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 231100000225 lethality Toxicity 0.000 description 1
- WZTIKNRSYKDRQF-UHFFFAOYSA-N n-(2-benzoyl-4-chlorophenyl)-4-methylbenzenesulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1 WZTIKNRSYKDRQF-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000006684 polyhaloalkyl group Polymers 0.000 description 1
- -1 potassium carbonate Chemical class 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 210000001747 pupil Anatomy 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000012191 relaxation of muscle Effects 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 230000008925 spontaneous activity Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- 230000001256 tonic effect Effects 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/22—Di-epoxy compounds
- C08G59/24—Di-epoxy compounds carbocyclic
- C08G59/245—Di-epoxy compounds carbocyclic aromatic
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US52065866A | 1966-01-14 | 1966-01-14 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1695841A1 DE1695841A1 (de) | 1972-02-03 |
| DE1695841B2 DE1695841B2 (de) | 1980-01-31 |
| DE1695841C3 true DE1695841C3 (de) | 1980-10-02 |
Family
ID=24073541
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1967SC040084 Expired DE1695841C3 (de) | 1966-01-14 | 1967-01-13 | 1 -(2,2,2 -TrifluoräthyD-7-chIor-13-dihydro-5-phenyl-2H-1,4-benzodiazepin-2-one, Verfahren zu ihrer Herstellung und sie enthaltende pharmazeutische Zubereitungen |
| DE19671793682 Pending DE1793682A1 (de) | 1966-01-14 | 1967-01-13 | Neue Anilinderivate |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19671793682 Pending DE1793682A1 (de) | 1966-01-14 | 1967-01-13 | Neue Anilinderivate |
Country Status (15)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4410328B2 (ja) * | 1998-12-14 | 2010-02-03 | 久光製薬株式会社 | オキソクアゼパムの製造方法 |
-
1967
- 1967-01-11 IL IL2724567A patent/IL27245A/en unknown
- 1967-01-11 CH CH54167A patent/CH549585A/de not_active IP Right Cessation
- 1967-01-13 GB GB4699369A patent/GB1179125A/en not_active Expired
- 1967-01-13 NL NL6700585A patent/NL144605B/xx not_active IP Right Cessation
- 1967-01-13 BE BE692621D patent/BE692621A/xx not_active IP Right Cessation
- 1967-01-13 SE SE55167A patent/SE349806B/xx unknown
- 1967-01-13 ES ES335613A patent/ES335613A1/es not_active Expired
- 1967-01-13 DE DE1967SC040084 patent/DE1695841C3/de not_active Expired
- 1967-01-13 FR FR91019A patent/FR6110M/fr not_active Expired
- 1967-01-13 CA CA980,377A patent/CA967153A/en not_active Expired
- 1967-01-13 NO NO16637667A patent/NO120939B/no unknown
- 1967-01-13 DE DE19671793682 patent/DE1793682A1/de active Pending
- 1967-01-13 FI FI9067A patent/FI47190C/fi active
- 1967-01-13 GB GB189867A patent/GB1179124A/en not_active Expired
- 1967-01-13 DK DK21767A patent/DK124406B/da not_active IP Right Cessation
- 1967-11-16 ES ES347270A patent/ES347270A1/es not_active Expired
- 1967-11-16 ES ES347269A patent/ES347269A1/es not_active Expired
- 1967-11-16 ES ES347271A patent/ES347271A1/es not_active Expired
-
1969
- 1969-05-21 JP JP3907469A patent/JPS4811719B1/ja active Pending
-
1970
- 1970-07-17 JP JP6220970A patent/JPS5224036B1/ja active Pending
-
1973
- 1973-01-18 CY CY66973A patent/CY669A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES347270A1 (es) | 1969-01-16 |
| NL6700585A (enrdf_load_stackoverflow) | 1967-07-17 |
| CA967153A (en) | 1975-05-06 |
| DE1695841B2 (de) | 1980-01-31 |
| CY669A (en) | 1973-01-18 |
| FI47190B (enrdf_load_stackoverflow) | 1973-07-02 |
| DE1695841A1 (de) | 1972-02-03 |
| DE1793682A1 (de) | 1972-11-09 |
| NL144605B (nl) | 1975-01-15 |
| ES347269A1 (es) | 1969-01-16 |
| JPS4811719B1 (enrdf_load_stackoverflow) | 1973-04-14 |
| ES347271A1 (es) | 1969-01-16 |
| FI47190C (fi) | 1973-10-10 |
| IL27245A (en) | 1972-08-30 |
| CH549585A (en) | 1974-05-31 |
| SE349806B (enrdf_load_stackoverflow) | 1972-10-09 |
| GB1179124A (en) | 1970-01-28 |
| GB1179125A (en) | 1970-01-28 |
| JPS5224036B1 (enrdf_load_stackoverflow) | 1977-06-28 |
| NO120939B (enrdf_load_stackoverflow) | 1970-12-28 |
| DK124406B (da) | 1972-10-16 |
| BE692621A (enrdf_load_stackoverflow) | 1967-07-13 |
| ES335613A1 (es) | 1968-03-16 |
| FR6110M (enrdf_load_stackoverflow) | 1968-06-17 |
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