SU398031A1 - - Google Patents
Info
- Publication number
- SU398031A1 SU398031A1 SU1649251A SU1649251A SU398031A1 SU 398031 A1 SU398031 A1 SU 398031A1 SU 1649251 A SU1649251 A SU 1649251A SU 1649251 A SU1649251 A SU 1649251A SU 398031 A1 SU398031 A1 SU 398031A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- chloro
- trifluoromethylphenyl
- ether
- propane
- hydrochloride
- Prior art date
Links
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 48
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 30
- -1 4-Chloro-3-trifluoromethylphenyl Chemical group 0.000 description 27
- WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
- XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 14
- 239000000203 mixture Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 239000000155 melt Substances 0.000 description 8
- 238000001953 recrystallisation Methods 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- 235000019439 ethyl acetate Nutrition 0.000 description 7
- HZSSZTZLKVHTEA-UHFFFAOYSA-N 1-[4-chloro-3-(trifluoromethyl)phenyl]propan-2-amine Chemical compound CC(N)CC1=CC=C(Cl)C(C(F)(F)F)=C1 HZSSZTZLKVHTEA-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 239000001294 propane Substances 0.000 description 6
- AFVFQIVMOAPDHO-UHFFFAOYSA-N methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 5
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- FYSNRJHAOHDILO-UHFFFAOYSA-N Thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- DHMQDGOQFOQNFH-UHFFFAOYSA-N glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- OSDLLIBGSJNGJE-UHFFFAOYSA-N Chloroxylenol Chemical compound CC1=CC(O)=CC(C)=C1Cl OSDLLIBGSJNGJE-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 125000003944 tolyl group Chemical group 0.000 description 3
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 2
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 2
- 239000004471 Glycine Substances 0.000 description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 2
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N Theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 2
- 125000004442 acylamino group Chemical group 0.000 description 2
- 238000007792 addition Methods 0.000 description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine hydrate Chemical compound O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 229940098779 methanesulfonic acid Drugs 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- UMSVPCYSAUKCAZ-UHFFFAOYSA-N propane;hydrochloride Chemical compound Cl.CCC UMSVPCYSAUKCAZ-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000001187 sodium carbonate Substances 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 2
- DGRVQOKCSKDWIH-UHFFFAOYSA-N 1-chloro-2-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1Cl DGRVQOKCSKDWIH-UHFFFAOYSA-N 0.000 description 1
- OJZHQPYRNNWXJU-UHFFFAOYSA-N 2-(benzylamino)-N-[1-[4-chloro-3-(trifluoromethyl)phenyl]propan-2-yl]acetamide Chemical compound C=1C=CC=CC=1CNCC(=O)NC(C)CC1=CC=C(Cl)C(C(F)(F)F)=C1 OJZHQPYRNNWXJU-UHFFFAOYSA-N 0.000 description 1
- DQEGGVXQDFWFRE-UHFFFAOYSA-N 2-[1-[4-chloro-3-(trifluoromethyl)phenyl]propan-2-ylamino]-1-phenylethanone Chemical compound C=1C=CC=CC=1C(=O)CNC(C)CC1=CC=C(Cl)C(C(F)(F)F)=C1 DQEGGVXQDFWFRE-UHFFFAOYSA-N 0.000 description 1
- RKCUWMDOGLJXLM-UHFFFAOYSA-N 4-chloro-1-(chloromethyl)-2-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC(Cl)=CC=C1CCl RKCUWMDOGLJXLM-UHFFFAOYSA-N 0.000 description 1
- NIHMMULLFBKTOK-UHFFFAOYSA-N 4-chloro-3-(trifluoromethyl)benzaldehyde Chemical compound FC(F)(F)C1=CC(C=O)=CC=C1Cl NIHMMULLFBKTOK-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- WGQKYBSKWIADBV-UHFFFAOYSA-N Benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 1
- 101710040959 CA3 Proteins 0.000 description 1
- AENJRRVHWLLHJQ-UHFFFAOYSA-N Cl.ClC1=C(C=C(C=C1)CC(C)NCCC#N)C(F)(F)F Chemical compound Cl.ClC1=C(C=C(C=C1)CC(C)NCCC#N)C(F)(F)F AENJRRVHWLLHJQ-UHFFFAOYSA-N 0.000 description 1
- UBYRIZVDMHUORK-UHFFFAOYSA-N ClC1=C(C=C(C=C1)CC(C)=O)C(F)(F)F Chemical compound ClC1=C(C=C(C=C1)CC(C)=O)C(F)(F)F UBYRIZVDMHUORK-UHFFFAOYSA-N 0.000 description 1
- LWCXCZLHLFWSSJ-UHFFFAOYSA-N ClC1=C(C=C(C=C1)CC(C)NCCC#N)C(F)(F)F Chemical compound ClC1=C(C=C(C=C1)CC(C)NCCC#N)C(F)(F)F LWCXCZLHLFWSSJ-UHFFFAOYSA-N 0.000 description 1
- LBNGIORMZYUOLS-UHFFFAOYSA-N ClC1=C(C=C(CCN(C)CC#N)C=C1)C(F)(F)F Chemical compound ClC1=C(C=C(CCN(C)CC#N)C=C1)C(F)(F)F LBNGIORMZYUOLS-UHFFFAOYSA-N 0.000 description 1
- VKYKSIONXSXAKP-UHFFFAOYSA-N Hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 1
- 229960004011 Methenamine Drugs 0.000 description 1
- 241001024304 Mino Species 0.000 description 1
- XCVNDBIXFPGMIW-UHFFFAOYSA-N N-ethylpropan-1-amine Chemical compound CCCNCC XCVNDBIXFPGMIW-UHFFFAOYSA-N 0.000 description 1
- MCZPBVIMEOAMRR-UHFFFAOYSA-N N-ethylpropan-1-amine;hydrochloride Chemical compound Cl.CCCNCC MCZPBVIMEOAMRR-UHFFFAOYSA-N 0.000 description 1
- MCSAJNNLRCFZED-UHFFFAOYSA-N Nitroethane Chemical compound CC[N+]([O-])=O MCSAJNNLRCFZED-UHFFFAOYSA-N 0.000 description 1
- XKJCHHZQLQNZHY-UHFFFAOYSA-N Phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N Potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- 229910019023 PtO Inorganic materials 0.000 description 1
- 229960000278 Theophylline Drugs 0.000 description 1
- XBMQSWGBBPMRDW-UHFFFAOYSA-N [Cl].CC(C)=O Chemical compound [Cl].CC(C)=O XBMQSWGBBPMRDW-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 230000001476 alcoholic Effects 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000005377 alkyl thioxy group Chemical group 0.000 description 1
- 125000005466 alkylenyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- XKXHCNPAFAXVRZ-UHFFFAOYSA-N benzylazanium;chloride Chemical compound [Cl-].[NH3+]CC1=CC=CC=C1 XKXHCNPAFAXVRZ-UHFFFAOYSA-N 0.000 description 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
- CROBTXVXNQNKKO-UHFFFAOYSA-N borohydride Chemical compound [BH4-] CROBTXVXNQNKKO-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000000875 corresponding Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N ethanolamine Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- LBAQSKZHMLAFHH-UHFFFAOYSA-N ethoxyethane;hydron;chloride Chemical compound Cl.CCOCC LBAQSKZHMLAFHH-UHFFFAOYSA-N 0.000 description 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
- FFLYUXVZEPLMCL-UHFFFAOYSA-N ethylchloranuidyl formate Chemical compound CC[Cl-]OC=O FFLYUXVZEPLMCL-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 235000010299 hexamethylene tetramine Nutrition 0.000 description 1
- 239000004312 hexamethylene tetramine Substances 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N iso-propanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000002825 nitriles Chemical group 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N oxane Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 239000001184 potassium carbonate Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000003638 reducing agent Substances 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- YOQDYZUWIQVZSF-UHFFFAOYSA-N sodium borohydride Substances [BH4-].[Na+] YOQDYZUWIQVZSF-UHFFFAOYSA-N 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 229940079827 sodium hydrogen sulfite Drugs 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- ODGROJYWQXFQOZ-UHFFFAOYSA-N sodium;boron(1-) Chemical compound [B-].[Na+] ODGROJYWQXFQOZ-UHFFFAOYSA-N 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2021620A DE2021620C3 (de) | 1970-05-02 | 1970-05-02 | Neue Phenylaminoalkane und Verfahren zu deren Herstellung |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SU398031A1 true SU398031A1 (no) | |
| SU398031A3 SU398031A3 (no) | 1973-09-17 |
Family
ID=5770113
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1649251A SU398031A3 (no) | 1970-05-02 | 1971-04-28 |
Country Status (22)
| Country | Link |
|---|---|
| JP (4) | JPS5750773B1 (no) |
| AT (6) | AT317175B (no) |
| BE (1) | BE766654A (no) |
| BG (5) | BG19131A3 (no) |
| CH (4) | CH570968A5 (no) |
| CS (3) | CS175428B2 (no) |
| DE (1) | DE2021620C3 (no) |
| ES (4) | ES390778A1 (no) |
| FI (1) | FI53571C (no) |
| FR (1) | FR2092123B1 (no) |
| GB (1) | GB1354451A (no) |
| HU (1) | HU162545B (no) |
| IE (1) | IE35608B1 (no) |
| IL (1) | IL36743A (no) |
| NL (1) | NL169462C (no) |
| NO (1) | NO133708C (no) |
| PL (3) | PL91964B1 (no) |
| RO (5) | RO62296A (no) |
| SE (1) | SE374355B (no) |
| SU (1) | SU398031A3 (no) |
| YU (6) | YU35571B (no) |
| ZA (1) | ZA712788B (no) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2239012A1 (de) * | 1972-08-08 | 1974-02-21 | Knoll Ag | Basisch substituierte theophyllinabkoemmlinge |
| JPS6016016U (ja) * | 1983-07-12 | 1985-02-02 | 本田技研工業株式会社 | 位置決め用クリツプ |
| NZ210420A (en) * | 1983-12-06 | 1988-04-29 | Merrell Dow Pharma | D-amino acid oxidase substrates and pharmaceutical compositions |
| JPS6314015U (no) * | 1986-07-11 | 1988-01-29 | ||
| JPS63136497A (ja) * | 1986-11-28 | 1988-06-08 | Hitachi Medical Corp | Ｘ線装置 |
| JPH0378128U (no) * | 1989-11-30 | 1991-08-07 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2029385A1 (no) * | 1969-01-27 | 1970-10-23 | Science Union & Cie |
-
1970
- 1970-05-02 DE DE2021620A patent/DE2021620C3/de not_active Expired
-
1971
- 1971-04-28 SU SU1649251A patent/SU398031A3/ru active
- 1971-04-28 RO RO7100070107A patent/RO62296A/ro unknown
- 1971-04-28 RO RO70106A patent/RO57681A/ro unknown
- 1971-04-28 RO RO66747A patent/RO57814A/ro unknown
- 1971-04-28 RO RO7100070105A patent/RO62418A/ro unknown
- 1971-04-28 RO RO70104A patent/RO57821A/ro unknown
- 1971-04-29 CS CS2325A patent/CS175428B2/cs unknown
- 1971-04-29 CH CH29775A patent/CH570968A5/xx not_active IP Right Cessation
- 1971-04-29 CS CS3115A patent/CS170545B2/cs unknown
- 1971-04-29 NL NLAANVRAGE7105946,A patent/NL169462C/xx not_active IP Right Cessation
- 1971-04-29 CH CH29875A patent/CH579022A5/xx not_active IP Right Cessation
- 1971-04-29 YU YU1080/71A patent/YU35571B/xx unknown
- 1971-04-29 CH CH29975A patent/CH579023A5/xx not_active IP Right Cessation
- 1971-04-29 CS CS722324A patent/CS194665B2/cs unknown
- 1971-04-29 CH CH632271A patent/CH561169A5/xx not_active IP Right Cessation
- 1971-04-30 BG BG19047A patent/BG19131A3/xx unknown
- 1971-04-30 NO NO1615/71A patent/NO133708C/no unknown
- 1971-04-30 AT AT518573A patent/AT317175B/de not_active IP Right Cessation
- 1971-04-30 BG BG17446A patent/BG18601A3/xx unknown
- 1971-04-30 BG BG19045A patent/BG19589A3/xx unknown
- 1971-04-30 HU HUBO1290A patent/HU162545B/hu unknown
- 1971-04-30 PL PL1971177491A patent/PL91964B1/pl unknown
- 1971-04-30 ZA ZA712788A patent/ZA712788B/xx unknown
- 1971-04-30 PL PL1971177492A patent/PL90714B1/pl unknown
- 1971-04-30 ES ES390778A patent/ES390778A1/es not_active Expired
- 1971-04-30 AT AT518673A patent/AT317176B/de not_active IP Right Cessation
- 1971-04-30 PL PL1971147865A patent/PL85189B1/pl unknown
- 1971-04-30 IL IL36743A patent/IL36743A/xx unknown
- 1971-04-30 FI FI1212/71A patent/FI53571C/fi active
- 1971-04-30 AT AT518473A patent/AT317174B/de active
- 1971-04-30 AT AT375071A patent/AT317171B/de active
- 1971-04-30 IE IE545/71A patent/IE35608B1/xx unknown
- 1971-04-30 FR FR7115627A patent/FR2092123B1/fr not_active Expired
- 1971-04-30 AT AT518273A patent/AT317172B/de not_active IP Right Cessation
- 1971-04-30 BG BG22776A patent/BG21017A3/xx unknown
- 1971-04-30 BG BG19046A patent/BG21016A3/xx unknown
- 1971-04-30 AT AT518373A patent/AT317173B/de not_active IP Right Cessation
- 1971-04-30 SE SE7105652A patent/SE374355B/xx unknown
- 1971-04-30 GB GB1244371A patent/GB1354451A/en not_active Expired
- 1971-05-01 JP JP46029370A patent/JPS5750773B1/ja active Pending
- 1971-05-03 BE BE766654A patent/BE766654A/xx not_active IP Right Cessation
-
1972
- 1972-05-12 ES ES402638A patent/ES402638A1/es not_active Expired
- 1972-05-12 ES ES402637A patent/ES402637A1/es not_active Expired
- 1972-05-12 ES ES402636A patent/ES402636A1/es not_active Expired
-
1978
- 1978-10-26 YU YU2499/78A patent/YU36286B/xx unknown
- 1978-10-26 YU YU02500/78A patent/YU36482B/xx unknown
- 1978-10-26 YU YU2498/78A patent/YU36285B/xx unknown
-
1980
- 1980-06-16 YU YU1590/80A patent/YU37114B/xx unknown
- 1980-09-17 JP JP55129028A patent/JPS589090B2/ja not_active Expired
- 1980-09-17 JP JP12902780A patent/JPS5655350A/ja active Granted
- 1980-09-17 JP JP12902980A patent/JPS5655352A/ja active Granted
-
1981
- 1981-02-20 YU YU00433/81A patent/YU43381A/xx unknown
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