FI64358C - Foerfarande foer framstaellning av 4-fenyl-2(1h)-kinazolinoner - Google Patents
Foerfarande foer framstaellning av 4-fenyl-2(1h)-kinazolinoner Download PDFInfo
- Publication number
- FI64358C FI64358C FI773659A FI773659A FI64358C FI 64358 C FI64358 C FI 64358C FI 773659 A FI773659 A FI 773659A FI 773659 A FI773659 A FI 773659A FI 64358 C FI64358 C FI 64358C
- Authority
- FI
- Finland
- Prior art keywords
- alkyl
- trifluoromethyl
- methyl
- phenyl
- formula
- Prior art date
Links
- 238000000034 method Methods 0.000 claims description 25
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- -1 6,7-methylenedioxy Chemical group 0.000 claims description 12
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 12
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 10
- 239000004202 carbamide Substances 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 9
- 239000005711 Benzoic acid Substances 0.000 claims description 8
- 235000010233 benzoic acid Nutrition 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 8
- GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 claims description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 239000000460 chlorine Substances 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 125000004414 alkyl thio group Chemical group 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- MAOBFOXLCJIFLV-UHFFFAOYSA-N (2-aminophenyl)-phenylmethanone Chemical compound NC1=CC=CC=C1C(=O)C1=CC=CC=C1 MAOBFOXLCJIFLV-UHFFFAOYSA-N 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 239000011737 fluorine Substances 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- LPNBBFKOUUSUDB-UHFFFAOYSA-N p-toluic acid Chemical compound CC1=CC=C(C(O)=O)C=C1 LPNBBFKOUUSUDB-UHFFFAOYSA-N 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 3
- JTIGKVIOEQASGT-UHFFFAOYSA-N proquazone Chemical compound N=1C(=O)N(C(C)C)C2=CC(C)=CC=C2C=1C1=CC=CC=C1 JTIGKVIOEQASGT-UHFFFAOYSA-N 0.000 claims description 3
- FHUBTSLLILWICW-UHFFFAOYSA-N 4-phenyl-1h-quinazolin-2-one Chemical class C12=CC=CC=C2NC(=O)N=C1C1=CC=CC=C1 FHUBTSLLILWICW-UHFFFAOYSA-N 0.000 claims description 2
- ZWOUXWWGKJBAHQ-UHFFFAOYSA-N fluproquazone Chemical compound N=1C(=O)N(C(C)C)C2=CC(C)=CC=C2C=1C1=CC=C(F)C=C1 ZWOUXWWGKJBAHQ-UHFFFAOYSA-N 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical compound CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 claims description 2
- 229920002472 Starch Polymers 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 125000006413 ring segment Chemical group 0.000 claims 1
- 235000019698 starch Nutrition 0.000 claims 1
- 239000008107 starch Substances 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000011592 zinc chloride Substances 0.000 description 6
- 235000005074 zinc chloride Nutrition 0.000 description 6
- AVRPFRMDMNDIDH-UHFFFAOYSA-N 1h-quinazolin-2-one Chemical class C1=CC=CC2=NC(O)=NC=C21 AVRPFRMDMNDIDH-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 210000003298 dental enamel Anatomy 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000007363 ring formation reaction Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- 210000002700 urine Anatomy 0.000 description 2
- 239000002351 wastewater Substances 0.000 description 2
- QVHATTMFVNBSBM-UHFFFAOYSA-N 1-ethyl-4-phenyl-6-(trifluoromethyl)quinazolin-2-one Chemical compound N=1C(=O)N(CC)C2=CC=C(C(F)(F)F)C=C2C=1C1=CC=CC=C1 QVHATTMFVNBSBM-UHFFFAOYSA-N 0.000 description 1
- HHTYFUMRSWVPQZ-UHFFFAOYSA-N 1-ethyl-6-nitro-4-phenylquinazolin-2-one Chemical compound N=1C(=O)N(CC)C2=CC=C([N+]([O-])=O)C=C2C=1C1=CC=CC=C1 HHTYFUMRSWVPQZ-UHFFFAOYSA-N 0.000 description 1
- GGQFTYRITULEJT-UHFFFAOYSA-N 1-methyl-4-[3-(trifluoromethyl)phenyl]quinazolin-2-one Chemical compound CN1C(N=C(C2=CC=CC=C12)C1=CC(=CC=C1)C(F)(F)F)=O GGQFTYRITULEJT-UHFFFAOYSA-N 0.000 description 1
- NDLOZXIIOJGQIS-UHFFFAOYSA-N 1-methyl-4-phenylquinazolin-2-one Chemical compound N=1C(=O)N(C)C2=CC=CC=C2C=1C1=CC=CC=C1 NDLOZXIIOJGQIS-UHFFFAOYSA-N 0.000 description 1
- SWDKFBABKQQWOZ-UHFFFAOYSA-N 4-(2,6-dimethoxyphenyl)-1-methylquinazolin-2-one Chemical compound CN1C(N=C(C2=CC=CC=C12)C1=C(C=CC=C1OC)OC)=O SWDKFBABKQQWOZ-UHFFFAOYSA-N 0.000 description 1
- IIVLSWIESCBUCD-UHFFFAOYSA-N 4-(4-methoxyphenyl)-1-methylquinazolin-2-one Chemical compound CN1C(N=C(C2=CC=CC=C12)C1=CC=C(C=C1)OC)=O IIVLSWIESCBUCD-UHFFFAOYSA-N 0.000 description 1
- UUONGVUQZPZQNV-UHFFFAOYSA-N 4-(4-methylphenyl)-1-propan-2-ylquinazolin-2-one Chemical compound C(C)(C)N1C(N=C(C2=CC=CC=C12)C1=CC=C(C=C1)C)=O UUONGVUQZPZQNV-UHFFFAOYSA-N 0.000 description 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
- RMGSSEYHRPEZDS-UHFFFAOYSA-N 5-methyl-4-phenyl-1-propan-2-ylquinazolin-2-one Chemical compound N=1C(=O)N(C(C)C)C2=CC=CC(C)=C2C=1C1=CC=CC=C1 RMGSSEYHRPEZDS-UHFFFAOYSA-N 0.000 description 1
- FDWQSSAKIXWXHL-UHFFFAOYSA-N 6,7-dimethoxy-1-methyl-4-phenylquinazolin-2-one Chemical compound COC=1C=C2C(=NC(N(C2=CC1OC)C)=O)C1=CC=CC=C1 FDWQSSAKIXWXHL-UHFFFAOYSA-N 0.000 description 1
- XWNIPACDYFLORY-UHFFFAOYSA-N 6,7-dimethyl-4-phenyl-1-prop-2-ynylquinazolin-2-one Chemical compound CC=1C=C2C(=NC(N(C2=CC1C)CC#C)=O)C1=CC=CC=C1 XWNIPACDYFLORY-UHFFFAOYSA-N 0.000 description 1
- AYIPUPLLAZJWMR-UHFFFAOYSA-N 6-bromo-4-phenyl-1-propan-2-ylquinazolin-2-one Chemical compound BrC=1C=C2C(=NC(N(C2=CC1)C(C)C)=O)C1=CC=CC=C1 AYIPUPLLAZJWMR-UHFFFAOYSA-N 0.000 description 1
- QGHJRJCNYBJPFL-UHFFFAOYSA-N 6-methoxy-4-phenyl-1-propan-2-ylquinazolin-2-one Chemical compound C12=CC(OC)=CC=C2N(C(C)C)C(=O)N=C1C1=CC=CC=C1 QGHJRJCNYBJPFL-UHFFFAOYSA-N 0.000 description 1
- RNAKLMONFNUKCL-UHFFFAOYSA-N 6-methylsulfanyl-4-phenyl-1-propan-2-ylquinazolin-2-one Chemical compound C(C)(C)N1C(N=C(C2=CC(=CC=C12)SC)C1=CC=CC=C1)=O RNAKLMONFNUKCL-UHFFFAOYSA-N 0.000 description 1
- DEJRAAVYHUQSQS-UHFFFAOYSA-N 7-ethyl-4-phenyl-1-propan-2-ylquinazolin-2-one Chemical compound C(C)C1=CC=C2C(=NC(N(C2=C1)C(C)C)=O)C1=CC=CC=C1 DEJRAAVYHUQSQS-UHFFFAOYSA-N 0.000 description 1
- ZCAZGTAWHVZVPE-UHFFFAOYSA-N 7-methylsulfanyl-4-phenyl-1-propan-2-ylquinazolin-2-one Chemical compound C(C)(C)N1C(N=C(C2=CC=C(C=C12)SC)C1=CC=CC=C1)=O ZCAZGTAWHVZVPE-UHFFFAOYSA-N 0.000 description 1
- HJICZLOIHNWNNY-UHFFFAOYSA-N 8-(4-fluorophenyl)-5-propan-2-yl-[1,3]dioxolo[4,5-g]quinazolin-6-one Chemical compound N=1C(=O)N(C(C)C)C2=CC=3OCOC=3C=C2C=1C1=CC=C(F)C=C1 HJICZLOIHNWNNY-UHFFFAOYSA-N 0.000 description 1
- FITUMOSFDCKONA-UHFFFAOYSA-N 8-phenyl-5-propan-2-yl-[1,3]dioxolo[4,5-g]quinazolin-6-one Chemical compound N=1C(=O)N(C(C)C)C2=CC=3OCOC=3C=C2C=1C1=CC=CC=C1 FITUMOSFDCKONA-UHFFFAOYSA-N 0.000 description 1
- CYFAXPONFMBLHG-UHFFFAOYSA-N C(C)(C)N1C(N=C(C2=CC(=CC=C12)OC)C1=C(C=CC=C1Cl)Cl)=O Chemical compound C(C)(C)N1C(N=C(C2=CC(=CC=C12)OC)C1=C(C=CC=C1Cl)Cl)=O CYFAXPONFMBLHG-UHFFFAOYSA-N 0.000 description 1
- IUXDSNZRXWCZMO-UHFFFAOYSA-N CN1C(N=C(C2=CC=CC=C12)C1=C(C(=CC=C1)C)C)=O Chemical compound CN1C(N=C(C2=CC=CC=C12)C1=C(C(=CC=C1)C)C)=O IUXDSNZRXWCZMO-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- MSEWZOYGLXDVPJ-UHFFFAOYSA-N ClC=1C=C2C(=NC(N(C2=CC1)C(C)C)=O)C1=C(C=CC=C1)Cl Chemical compound ClC=1C=C2C(=NC(N(C2=CC1)C(C)C)=O)C1=C(C=CC=C1)Cl MSEWZOYGLXDVPJ-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 159000000032 aromatic acids Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 125000001207 fluorophenyl group Chemical group 0.000 description 1
- 125000005059 halophenyl group Chemical group 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000004065 wastewater treatment Methods 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/78—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 2
- C07D239/80—Oxygen atoms
- C07D239/82—Oxygen atoms with an aryl radical attached in position 4
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1561976A CH625512A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1976-12-13 | 1976-12-13 | |
| CH1561976 | 1976-12-13 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI773659A7 FI773659A7 (fi) | 1978-06-14 |
| FI64358B FI64358B (fi) | 1983-07-29 |
| FI64358C true FI64358C (fi) | 1983-11-10 |
Family
ID=4410585
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI773659A FI64358C (fi) | 1976-12-13 | 1977-12-02 | Foerfarande foer framstaellning av 4-fenyl-2(1h)-kinazolinoner |
Country Status (31)
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4617392A (en) * | 1983-09-29 | 1986-10-14 | Ortho Pharmaceutical Corporation | 4-alkyl-5,6-methylenedioxy-2-1[H]-quinazolinones useful as cardiotonic agents |
| AR038658A1 (es) * | 2001-06-15 | 2005-01-26 | Novartis Ag | Derivados de 4-aril-2(1h) quinazolinona y 4-aril-quinazolina 2-sustituidas, un proceso para su preparacion, composiciones farmaceuticas y el uso de dichos derivados para la preparacion de un medicamento |
| GB0230015D0 (en) * | 2002-12-23 | 2003-01-29 | Novartis Ag | Organic compounds |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3642897A (en) * | 1968-12-26 | 1972-02-15 | Sandoz Ag | Preparation of 2-alkylaminobenzophenones |
| US3547921A (en) * | 1968-12-26 | 1970-12-15 | Sandoz Ag | Preparation of 1-substituted-4-aryl-3,4-dihydro-2(1h)-quinazolinones |
| US3551427A (en) * | 1969-05-09 | 1970-12-29 | Sandoz Ag | 4-thienyl-2-(1h)-quinazolones |
| DK135044B (da) * | 1971-05-06 | 1977-02-28 | Sandoz Ag | Analogifremgangsmåde til fremstilling af 4-phenyl- eller 4-(2'-thienyl)-6,7-methylendioxy-2(1H)-quinazolinoner eller -2(1H)-quinazolinthioner. |
| BE790804A (fr) * | 1971-11-18 | 1973-04-30 | Sandoz Sa | Procede de preparation de derives de la quinazoline |
| CH580083A5 (en) * | 1973-04-03 | 1976-09-30 | Sumitomo Chemical Co | 4-Aryl-2-(1H)-quinazolinones prepn - by hydrolysis or thermolysis of 2-(acylureido)-benzophenones |
-
1976
- 1976-12-13 CH CH1561976A patent/CH625512A5/de not_active IP Right Cessation
-
1977
- 1977-12-02 FI FI773659A patent/FI64358C/fi not_active IP Right Cessation
- 1977-12-03 DE DE19772753970 patent/DE2753970A1/de not_active Withdrawn
- 1977-12-05 SE SE7713742A patent/SE442996B/sv not_active IP Right Cessation
- 1977-12-05 DK DK540877A patent/DK143025C/da not_active IP Right Cessation
- 1977-12-05 NO NO774147A patent/NO147484C/no unknown
- 1977-12-06 FR FR7736661A patent/FR2373534A1/fr active Granted
- 1977-12-08 GB GB51144/77A patent/GB1592687A/en not_active Expired
- 1977-12-09 CA CA292,750A patent/CA1091229A/en not_active Expired
- 1977-12-09 NL NL7713651A patent/NL7713651A/xx not_active Application Discontinuation
- 1977-12-10 GR GR54959A patent/GR71667B/el unknown
- 1977-12-12 AT AT0884677A patent/AT371450B/de not_active IP Right Cessation
- 1977-12-12 HU HU77SA3080A patent/HU176875B/hu not_active IP Right Cessation
- 1977-12-12 AR AR270333A patent/AR220526A1/es active
- 1977-12-12 ES ES464966A patent/ES464966A1/es not_active Expired
- 1977-12-12 SU SU772552353A patent/SU793391A3/ru active
- 1977-12-12 DD DD7700202556A patent/DD133327A5/xx unknown
- 1977-12-12 IL IL53588A patent/IL53588A/xx unknown
- 1977-12-12 IE IE2518/77A patent/IE46492B1/en unknown
- 1977-12-12 PT PT67388A patent/PT67388B/pt unknown
- 1977-12-12 JP JP14823077A patent/JPS5377077A/ja active Granted
- 1977-12-12 PH PH20542A patent/PH15458A/en unknown
- 1977-12-12 OA OA56337A patent/OA05821A/xx unknown
- 1977-12-12 CS CS778309A patent/CS196409B2/cs unknown
- 1977-12-12 NZ NZ185933A patent/NZ185933A/xx unknown
- 1977-12-12 BE BE183388A patent/BE861775A/xx not_active IP Right Cessation
- 1977-12-12 AU AU31438/77A patent/AU517193B2/en not_active Expired
- 1977-12-13 IT IT52191/77A patent/IT1090572B/it active
- 1977-12-13 YU YU2945/77A patent/YU40687B/xx unknown
- 1977-12-13 ZA ZA00777425A patent/ZA777425B/xx unknown
-
1979
- 1979-02-01 US US06/008,328 patent/US4236006A/en not_active Expired - Lifetime
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