FI59249C - Foerfarande foer framstaellning av hydroxialkylxantiner - Google Patents
Foerfarande foer framstaellning av hydroxialkylxantiner Download PDFInfo
- Publication number
- FI59249C FI59249C FI751958A FI751958A FI59249C FI 59249 C FI59249 C FI 59249C FI 751958 A FI751958 A FI 751958A FI 751958 A FI751958 A FI 751958A FI 59249 C FI59249 C FI 59249C
- Authority
- FI
- Finland
- Prior art keywords
- reaction
- theory
- reaction mixture
- yield
- neutralized
- Prior art date
Links
- 238000006243 chemical reaction Methods 0.000 claims description 37
- -1 7- (6-Hydroxyheptyl) -3-n-butylxanthine 7- (6-Heptenyl) -3-n-butylxanthine Chemical compound 0.000 claims description 35
- 150000001875 compounds Chemical class 0.000 claims description 35
- 239000011541 reaction mixture Substances 0.000 claims description 34
- 238000000605 extraction Methods 0.000 claims description 32
- 230000008018 melting Effects 0.000 claims description 30
- 238000002844 melting Methods 0.000 claims description 30
- 238000004809 thin layer chromatography Methods 0.000 claims description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 5
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 3
- 238000010168 coupling process Methods 0.000 claims description 3
- 238000005859 coupling reaction Methods 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 230000008878 coupling Effects 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 50
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
- 239000000243 solution Substances 0.000 description 24
- 238000002425 crystallisation Methods 0.000 description 22
- 230000008025 crystallization Effects 0.000 description 22
- 239000000047 product Substances 0.000 description 13
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 6
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- LZRTZRBKFZHHQT-UHFFFAOYSA-N 1-hex-5-enyl-3,7-dimethylpurine-2,6-dione Chemical compound CN1C(=O)N(CCCCC=C)C(=O)C2=C1N=CN2C LZRTZRBKFZHHQT-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- ZGIBYCLLIMGXEZ-UHFFFAOYSA-N 1,3-dimethyl-7-prop-2-enylpurine-2,6-dione Chemical compound O=C1N(C)C(=O)N(C)C2=C1N(CC=C)C=N2 ZGIBYCLLIMGXEZ-UHFFFAOYSA-N 0.000 description 3
- NSMXQKNUPPXBRG-UHFFFAOYSA-N 1-(5-hydroxyhexyl)-3,7-dimethyl-3,7-dihydro-1H-purine-2,6-dione Chemical compound O=C1N(CCCCC(O)C)C(=O)N(C)C2=C1N(C)C=N2 NSMXQKNUPPXBRG-UHFFFAOYSA-N 0.000 description 3
- BTFHIKZOEZREBX-UHFFFAOYSA-N 3,7-dimethyl-1-prop-2-enylpurine-2,6-dione Chemical compound CN1C(=O)N(CC=C)C(=O)C2=C1N=CN2C BTFHIKZOEZREBX-UHFFFAOYSA-N 0.000 description 3
- UZRCRCBKXULVTM-UHFFFAOYSA-N 3-hex-5-enyl-1,7-dimethylpurine-2,6-dione Chemical compound C=CCCCCN1C(=O)N(C)C(=O)C2=C1N=CN2C UZRCRCBKXULVTM-UHFFFAOYSA-N 0.000 description 3
- PESRCCQMYJSHAV-UHFFFAOYSA-N 7-(3-hydroxybutyl)-1,3-dimethylpurine-2,6-dione Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2CCC(O)C PESRCCQMYJSHAV-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 238000010471 Markovnikov's rule Methods 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- QUNWUDVFRNGTCO-UHFFFAOYSA-N 1,7-dimethylxanthine Chemical compound N1C(=O)N(C)C(=O)C2=C1N=CN2C QUNWUDVFRNGTCO-UHFFFAOYSA-N 0.000 description 2
- LMCWCVODLNWLCV-UHFFFAOYSA-N 7-but-3-enyl-1,3-dimethylpurine-2,6-dione Chemical compound O=C1N(C)C(=O)N(C)C2=C1N(CCC=C)C=N2 LMCWCVODLNWLCV-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- IVLTXYULUWLVRP-UHFFFAOYSA-N O=C1N(C)C(=O)N(CCCCC(O)C)C2=C1N(C)C=N2 Chemical compound O=C1N(C)C(=O)N(CCCCC(O)C)C2=C1N(C)C=N2 IVLTXYULUWLVRP-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000010348 incorporation Methods 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000010791 quenching Methods 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- NHAXKHSVJBVINX-UHFFFAOYSA-N 3,7-dimethylpurine-2,6-dione;sodium Chemical compound [Na].CN1C(=O)NC(=O)C2=C1N=CN2C NHAXKHSVJBVINX-UHFFFAOYSA-N 0.000 description 1
- GEPVMDINFCTKRV-UHFFFAOYSA-N 8,8-dimethyl-3H-purine-2,6-dione Chemical class CC1(N=C2NC(NC(C2=N1)=O)=O)C GEPVMDINFCTKRV-UHFFFAOYSA-N 0.000 description 1
- SFTKJENFAOTMFI-UHFFFAOYSA-N CC(CCC=CN1C2=C(C(=O)N(C1=O)C)N(C=N2)C)O Chemical compound CC(CCC=CN1C2=C(C(=O)N(C1=O)C)N(C=N2)C)O SFTKJENFAOTMFI-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
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 101100336126 Mus musculus Gatad1 gene Proteins 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- KYHQZNGJUGFTGR-UHFFFAOYSA-N Proxyphylline Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2CC(O)C KYHQZNGJUGFTGR-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- TXHIDIHEXDFONW-UHFFFAOYSA-N benzene;propan-2-one Chemical compound CC(C)=O.C1=CC=CC=C1 TXHIDIHEXDFONW-UHFFFAOYSA-N 0.000 description 1
- AITBHTAFQQYBHP-UHFFFAOYSA-N benzene;pyridine Chemical compound C1=CC=CC=C1.C1=CC=NC=C1 AITBHTAFQQYBHP-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 238000003682 fluorination reaction Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005283 haloketone group Chemical group 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- QVGLHVDBDYLFON-UHFFFAOYSA-M sodium;1,3-dimethylpurin-7-ide-2,6-dione Chemical compound [Na+].O=C1N(C)C(=O)N(C)C2=C1[N-]C=N2 QVGLHVDBDYLFON-UHFFFAOYSA-M 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000003459 sulfonic acid esters Chemical class 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 229960004559 theobromine Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/04—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms
- C07D473/06—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3
- C07D473/10—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3 with methyl radicals in positions 3 and 7, e.g. theobromine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/04—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms
- C07D473/06—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/04—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms
- C07D473/06—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3
- C07D473/08—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3 with methyl radicals in positions 1 and 3, e.g. theophylline
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Steroid Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US48587074A | 1974-07-05 | 1974-07-05 | |
| US48586974 | 1974-07-05 | ||
| US48587074 | 1974-07-05 | ||
| US05/485,869 US4108995A (en) | 1973-07-11 | 1974-07-05 | Hydroxyhexyl-alkylxanthines and pharmaceutical compositions containing hydroxyhexyl-alkylxanthines |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI751958A7 FI751958A7 (en, 2012) | 1976-01-06 |
| FI59249B FI59249B (fi) | 1981-03-31 |
| FI59249C true FI59249C (fi) | 1981-07-10 |
Family
ID=27048497
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI751958A FI59249C (fi) | 1974-07-05 | 1975-07-04 | Foerfarande foer framstaellning av hydroxialkylxantiner |
Country Status (14)
| Country | Link |
|---|---|
| JP (1) | JPS5250800B2 (en, 2012) |
| AR (1) | AR210330A1 (en, 2012) |
| AT (1) | AT339917B (en, 2012) |
| CA (1) | CA1062710A (en, 2012) |
| CH (2) | CH622519A5 (en, 2012) |
| DK (1) | DK140214B (en, 2012) |
| ES (1) | ES439141A1 (en, 2012) |
| FI (1) | FI59249C (en, 2012) |
| FR (1) | FR2277089A1 (en, 2012) |
| GB (1) | GB1500039A (en, 2012) |
| LU (1) | LU72897A1 (en, 2012) |
| NL (1) | NL166476C (en, 2012) |
| NO (1) | NO143224C (en, 2012) |
| SE (2) | SE420097B (en, 2012) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU197569B (en) * | 1984-01-12 | 1989-04-28 | Sandoz Ag | Process for producing 8alpha-acylaminoergoline derivatives and pharmaceuticals comprising such compounds |
| DE3525801A1 (de) * | 1985-07-19 | 1987-01-22 | Hoechst Ag | Tertiaere hydroxyalkylxanthine, verfahren zu ihrer herstellung, die sie enthaltenden arzneimittel und ihre verwendung |
| EP0570831A2 (de) * | 1992-05-20 | 1993-11-24 | Hoechst Aktiengesellschaft | Verwendung von Xanthinderivaten zur Behandlung von Nervenschädigungen nach Unterbrechung der Blutzirkulation |
-
1975
- 1975-07-02 CH CH859275A patent/CH622519A5/de not_active IP Right Cessation
- 1975-07-03 DK DK301775AA patent/DK140214B/da not_active IP Right Cessation
- 1975-07-03 LU LU72897A patent/LU72897A1/xx unknown
- 1975-07-03 JP JP50081475A patent/JPS5250800B2/ja not_active Expired
- 1975-07-04 NL NL7507976.A patent/NL166476C/xx not_active IP Right Cessation
- 1975-07-04 ES ES439141A patent/ES439141A1/es not_active Expired
- 1975-07-04 SE SE7507726A patent/SE420097B/xx not_active IP Right Cessation
- 1975-07-04 AR AR258487A patent/AR210330A1/es active
- 1975-07-04 GB GB28341/75A patent/GB1500039A/en not_active Expired
- 1975-07-04 NO NO752423A patent/NO143224C/no unknown
- 1975-07-04 AT AT517275A patent/AT339917B/de not_active IP Right Cessation
- 1975-07-04 FI FI751958A patent/FI59249C/fi not_active IP Right Cessation
- 1975-07-04 CA CA230,790A patent/CA1062710A/en not_active Expired
- 1975-07-04 FR FR7521043A patent/FR2277089A1/fr active Granted
-
1978
- 1978-07-14 SE SE7807853A patent/SE427183B/sv not_active IP Right Cessation
-
1980
- 1980-04-29 CH CH331680A patent/CH622018A5/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| SE427183B (sv) | 1983-03-14 |
| AR210330A1 (es) | 1977-07-29 |
| NL166476C (nl) | 1981-08-17 |
| ES439141A1 (es) | 1977-02-16 |
| ATA517275A (de) | 1977-03-15 |
| DK140214C (en, 2012) | 1979-12-03 |
| AT339917B (de) | 1977-11-10 |
| FR2277089B1 (en, 2012) | 1978-03-17 |
| JPS5134194A (en, 2012) | 1976-03-23 |
| DK140214B (da) | 1979-07-09 |
| GB1500039A (en) | 1978-02-08 |
| SE7507726L (sv) | 1976-01-07 |
| NO143224C (no) | 1981-01-02 |
| AU8275575A (en) | 1977-01-06 |
| NO752423L (en, 2012) | 1976-01-06 |
| NL166476B (nl) | 1981-03-16 |
| CH622018A5 (en) | 1981-03-13 |
| FI59249B (fi) | 1981-03-31 |
| NL7507976A (nl) | 1976-01-07 |
| FI751958A7 (en, 2012) | 1976-01-06 |
| CA1062710A (en) | 1979-09-18 |
| SE7807853L (sv) | 1978-07-14 |
| NO143224B (no) | 1980-09-22 |
| CH622519A5 (en) | 1981-04-15 |
| DK301775A (en, 2012) | 1976-01-06 |
| SE420097B (sv) | 1981-09-14 |
| FR2277089A1 (fr) | 1976-01-30 |
| JPS5250800B2 (en, 2012) | 1977-12-27 |
| LU72897A1 (en, 2012) | 1976-05-31 |
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