NO133708B - - Google Patents
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- Publication number
- NO133708B NO133708B NO1615/71A NO161571A NO133708B NO 133708 B NO133708 B NO 133708B NO 1615/71 A NO1615/71 A NO 1615/71A NO 161571 A NO161571 A NO 161571A NO 133708 B NO133708 B NO 133708B
- Authority
- NO
- Norway
- Prior art keywords
- chloro
- trifluoromethylphenyl
- group
- general formula
- residues
- Prior art date
Links
- -1 hydroxyl- Chemical group 0.000 claims description 35
- 150000001875 compounds Chemical class 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 16
- 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 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 239000000460 chlorine Substances 0.000 claims description 11
- 150000002431 hydrogen Chemical class 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 8
- 150000001412 amines Chemical class 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 5
- OWIKHYCFFJSOEH-UHFFFAOYSA-N Isocyanic acid Chemical group N=C=O OWIKHYCFFJSOEH-UHFFFAOYSA-N 0.000 claims description 4
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 238000009833 condensation Methods 0.000 claims description 4
- 230000005494 condensation Effects 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 150000002576 ketones Chemical class 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 239000003638 chemical reducing agent Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 230000007062 hydrolysis Effects 0.000 claims description 3
- 238000006460 hydrolysis reaction Methods 0.000 claims description 3
- 229910052744 lithium Inorganic materials 0.000 claims description 3
- 150000003141 primary amines Chemical class 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 230000010933 acylation Effects 0.000 claims description 2
- 238000005917 acylation reaction Methods 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 230000029936 alkylation Effects 0.000 claims description 2
- 238000005804 alkylation reaction Methods 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 150000001450 anions Chemical class 0.000 claims description 2
- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 125000000524 functional group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 238000007327 hydrogenolysis reaction Methods 0.000 claims description 2
- 230000003301 hydrolyzing effect Effects 0.000 claims description 2
- 239000000543 intermediate Substances 0.000 claims description 2
- 238000002955 isolation Methods 0.000 claims description 2
- 229910052987 metal hydride Inorganic materials 0.000 claims description 2
- 150000004681 metal hydrides Chemical class 0.000 claims description 2
- 125000002560 nitrile group Chemical group 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000005544 phthalimido group Chemical group 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims 2
- 150000003254 radicals Chemical class 0.000 claims 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 51
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 48
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 45
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- 239000000203 mixture Substances 0.000 description 24
- 238000002844 melting Methods 0.000 description 15
- 230000008018 melting Effects 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 239000000155 melt Substances 0.000 description 12
- 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 11
- SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical compound CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-UHFFFAOYSA-N 0.000 description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 11
- 238000001953 recrystallisation Methods 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 238000010992 reflux Methods 0.000 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
- PXUPYSJLILBVTG-UHFFFAOYSA-N 2-[1-[4-chloro-3-(trifluoromethyl)phenyl]propan-2-ylamino]ethanol Chemical compound OCCNC(C)CC1=CC=C(Cl)C(C(F)(F)F)=C1 PXUPYSJLILBVTG-UHFFFAOYSA-N 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000012362 glacial acetic acid Substances 0.000 description 4
- 235000011121 sodium hydroxide Nutrition 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 3
- 239000004471 Glycine Substances 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 235000019253 formic acid Nutrition 0.000 description 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 239000001294 propane Substances 0.000 description 3
- 230000000638 stimulation Effects 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- ZPXGOEITMQMUJX-UHFFFAOYSA-N 1-[2-chloro-5-(trifluoromethyl)phenyl]propan-2-one Chemical compound CC(=O)CC1=CC(C(F)(F)F)=CC=C1Cl ZPXGOEITMQMUJX-UHFFFAOYSA-N 0.000 description 2
- UNDNVRLJUOXXJZ-UHFFFAOYSA-N 1-[4-chloro-3-(trifluoromethyl)phenyl]-N-ethylpropan-2-amine Chemical compound FC(C=1C=C(C=CC1Cl)CC(C)NCC)(F)F UNDNVRLJUOXXJZ-UHFFFAOYSA-N 0.000 description 2
- NREUBTUYADXMHQ-UHFFFAOYSA-N 1-chloro-4-(chloromethyl)-2-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC(CCl)=CC=C1Cl NREUBTUYADXMHQ-UHFFFAOYSA-N 0.000 description 2
- ZWWTZRKPCRFXMJ-UHFFFAOYSA-N 2-[1-[4-chloro-3-(trifluoromethyl)phenyl]propan-2-ylamino]-1-phenylethanone;hydrochloride Chemical compound Cl.C=1C=CC=CC=1C(=O)CNC(C)CC1=CC=C(Cl)C(C(F)(F)F)=C1 ZWWTZRKPCRFXMJ-UHFFFAOYSA-N 0.000 description 2
- DOAYDKOKRCGVOP-UHFFFAOYSA-N 2-chloro-n-[1-[4-chloro-3-(trifluoromethyl)phenyl]propan-2-yl]acetamide Chemical compound ClCC(=O)NC(C)CC1=CC=C(Cl)C(C(F)(F)F)=C1 DOAYDKOKRCGVOP-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IEDYCRZGGDPBHA-UHFFFAOYSA-N Cl.ClC1=C(C=C(C=C1)CC(C)NCCCO)C(F)(F)F Chemical compound Cl.ClC1=C(C=C(C=C1)CC(C)NCCCO)C(F)(F)F IEDYCRZGGDPBHA-UHFFFAOYSA-N 0.000 description 2
- YVBMGWOVQHCXKE-UHFFFAOYSA-N ClC1=C(C=C(C=C1)CC(C)NCC(C1=CC=CC=C1)O)C(F)(F)F Chemical compound ClC1=C(C=C(C=C1)CC(C)NCC(C1=CC=CC=C1)O)C(F)(F)F YVBMGWOVQHCXKE-UHFFFAOYSA-N 0.000 description 2
- KGZDOICPBZMXPF-UHFFFAOYSA-N ClC1=C(C=C(C=C1)CC(C)NCC1=CC=CC=C1)C(F)(F)F Chemical compound ClC1=C(C=C(C=C1)CC(C)NCC1=CC=CC=C1)C(F)(F)F KGZDOICPBZMXPF-UHFFFAOYSA-N 0.000 description 2
- RBSSCYUESPVWCD-UHFFFAOYSA-N ClC1=C(C=C(C=C1)CC(C)OS(=O)(=O)C)C(F)(F)F Chemical compound ClC1=C(C=C(C=C1)CC(C)OS(=O)(=O)C)C(F)(F)F RBSSCYUESPVWCD-UHFFFAOYSA-N 0.000 description 2
- ZKUDOVBLPTTXMD-UHFFFAOYSA-N ClC1=CC=C(C=C1CC(C)NC)C(F)(F)F Chemical compound ClC1=CC=C(C=C1CC(C)NC)C(F)(F)F ZKUDOVBLPTTXMD-UHFFFAOYSA-N 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 150000003948 formamides Chemical class 0.000 description 2
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 229940098779 methanesulfonic acid Drugs 0.000 description 2
- MCSAJNNLRCFZED-UHFFFAOYSA-N nitroethane Chemical compound CC[N+]([O-])=O MCSAJNNLRCFZED-UHFFFAOYSA-N 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- ULSIYEODSMZIPX-UHFFFAOYSA-N phenylethanolamine Chemical compound NCC(O)C1=CC=CC=C1 ULSIYEODSMZIPX-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000006722 reduction reaction Methods 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- 150000003333 secondary alcohols Chemical class 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 238000007920 subcutaneous administration Methods 0.000 description 2
- 229960000278 theophylline Drugs 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- VCGJIIDFWDVVQE-UHFFFAOYSA-N (1,1-dichloro-2,2,2-trifluoroethyl)benzene Chemical compound FC(F)(F)C(Cl)(Cl)C1=CC=CC=C1 VCGJIIDFWDVVQE-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
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- DGRVQOKCSKDWIH-UHFFFAOYSA-N 1-chloro-2-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1Cl DGRVQOKCSKDWIH-UHFFFAOYSA-N 0.000 description 1
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-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
- VPUGDWFTOZMWPD-UHFFFAOYSA-N 2-(benzylamino)-n-[1-[4-chloro-3-(trifluoromethyl)phenyl]propan-2-yl]acetamide;hydrochloride Chemical compound Cl.C=1C=CC=CC=1CNCC(=O)NC(C)CC1=CC=C(Cl)C(C(F)(F)F)=C1 VPUGDWFTOZMWPD-UHFFFAOYSA-N 0.000 description 1
- XNIOWJUQPMKCIJ-UHFFFAOYSA-N 2-(benzylamino)ethanol Chemical compound OCCNCC1=CC=CC=C1 XNIOWJUQPMKCIJ-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
- NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical class C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-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
- PZASAAIJIFDWSB-CKPDSHCKSA-N 8-[(1S)-1-[8-(trifluoromethyl)-7-[4-(trifluoromethyl)cyclohexyl]oxynaphthalen-2-yl]ethyl]-8-azabicyclo[3.2.1]octane-3-carboxylic acid Chemical compound FC(F)(F)C=1C2=CC([C@@H](N3C4CCC3CC(C4)C(O)=O)C)=CC=C2C=CC=1OC1CCC(C(F)(F)F)CC1 PZASAAIJIFDWSB-CKPDSHCKSA-N 0.000 description 1
- YIUIVFFUEVPRIU-UHFFFAOYSA-N 8-chlorotheophylline Chemical compound O=C1N(C)C(=O)N(C)C2=NC(Cl)=N[C]21 YIUIVFFUEVPRIU-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- HZTPWAXUEGKVCB-UHFFFAOYSA-N C(=O)N(C(CC1=CC(=CC=C1Cl)C(F)(F)F)C)C Chemical compound C(=O)N(C(CC1=CC(=CC=C1Cl)C(F)(F)F)C)C HZTPWAXUEGKVCB-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 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
- MLCYACHKZNLPIF-UHFFFAOYSA-N Cl.ClC1=CC=C(C=C1CC(C)N)C(F)(F)F Chemical compound Cl.ClC1=CC=C(C=C1CC(C)N)C(F)(F)F MLCYACHKZNLPIF-UHFFFAOYSA-N 0.000 description 1
- UDILIOSVLJDZLA-UHFFFAOYSA-N ClC1=C(C=C(C=C1)CC(C)(O)C)C(F)(F)F Chemical compound ClC1=C(C=C(C=C1)CC(C)(O)C)C(F)(F)F UDILIOSVLJDZLA-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
- CFWJDCWEUBYYAD-UHFFFAOYSA-N ClC1=C(C=C(C=C1)CC(C)[N+](=O)[O-])C(F)(F)F Chemical compound ClC1=C(C=C(C=C1)CC(C)[N+](=O)[O-])C(F)(F)F CFWJDCWEUBYYAD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 238000003747 Grignard reaction Methods 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
- 241000699670 Mus sp. Species 0.000 description 1
- XIMNNJBJXXEBTH-UHFFFAOYSA-N N-(3-chloropropyl)-1-[4-chloro-3-(trifluoromethyl)phenyl]propan-2-amine Chemical compound ClC1=C(C=C(C=C1)CC(C)NCCCCl)C(F)(F)F XIMNNJBJXXEBTH-UHFFFAOYSA-N 0.000 description 1
- UROWRWSTTHBPCG-UHFFFAOYSA-N N-(3-chloropropyl)-1-[4-chloro-3-(trifluoromethyl)phenyl]propan-2-amine hydrochloride Chemical compound Cl.CC(CC1=CC(=C(Cl)C=C1)C(F)(F)F)NCCCCl UROWRWSTTHBPCG-UHFFFAOYSA-N 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001344 alkene derivatives Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- 150000003935 benzaldehydes Chemical class 0.000 description 1
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzenecarboxaldehyde Natural products O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 1
- XKXHCNPAFAXVRZ-UHFFFAOYSA-N benzylazanium;chloride Chemical compound [Cl-].[NH3+]CC1=CC=CC=C1 XKXHCNPAFAXVRZ-UHFFFAOYSA-N 0.000 description 1
- HRQGCQVOJVTVLU-UHFFFAOYSA-N bis(chloromethyl) ether Chemical compound ClCOCCl HRQGCQVOJVTVLU-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 1
- BULLHNJGPPOUOX-UHFFFAOYSA-N chloroacetone Chemical compound CC(=O)CCl BULLHNJGPPOUOX-UHFFFAOYSA-N 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- UPQZOUHVTJNGFK-UHFFFAOYSA-N diethyl 2-methylpropanedioate Chemical compound CCOC(=O)C(C)C(=O)OCC UPQZOUHVTJNGFK-UHFFFAOYSA-N 0.000 description 1
- NTNZTEQNFHNYBC-UHFFFAOYSA-N ethyl 2-aminoacetate Chemical compound CCOC(=O)CN NTNZTEQNFHNYBC-UHFFFAOYSA-N 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 235000010299 hexamethylene tetramine Nutrition 0.000 description 1
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- 230000004899 motility Effects 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- LIGACIXOYTUXAW-UHFFFAOYSA-N phenacyl bromide Chemical compound BrCC(=O)C1=CC=CC=C1 LIGACIXOYTUXAW-UHFFFAOYSA-N 0.000 description 1
- 235000011007 phosphoric acid Nutrition 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
- QJIJQNUQORKBKY-UHFFFAOYSA-N piperidin-1-ium;benzoate Chemical compound C1CCNCC1.OC(=O)C1=CC=CC=C1 QJIJQNUQORKBKY-UHFFFAOYSA-N 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 239000004289 sodium hydrogen sulphite Substances 0.000 description 1
- NVIFVTYDZMXWGX-UHFFFAOYSA-N sodium metaborate Chemical compound [Na+].[O-]B=O NVIFVTYDZMXWGX-UHFFFAOYSA-N 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 150000003509 tertiary alcohols Chemical class 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
- C07C17/32—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by introduction of halogenated alkyl groups into ring compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/07—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by halogen atoms
- C07C205/08—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by halogen atoms having nitro groups bound to acyclic carbon atoms
- C07C205/09—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by halogen atoms having nitro groups bound to acyclic carbon atoms of an unsaturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
- C07C45/562—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with nitrogen as the only hetero atom
- C07C45/565—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with nitrogen as the only hetero atom by reaction with hexamethylene-tetramine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
- C07C47/55—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/52—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen
- C07C57/58—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/64—Acyl halides
- C07C57/76—Acyl halides containing halogen outside the carbonyl halide groups
-
- 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)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Child & Adolescent Psychology (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Psychiatry (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
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 |
|---|---|
| NO133708B true NO133708B (enrdf_load_html_response) | 1976-03-08 |
| NO133708C NO133708C (enrdf_load_html_response) | 1976-06-16 |
Family
ID=5770113
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO1615/71A NO133708C (enrdf_load_html_response) | 1970-05-02 | 1971-04-30 |
Country Status (22)
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2239012A1 (de) * | 1972-08-08 | 1974-02-21 | Knoll Ag | Basisch substituierte theophyllinabkoemmlinge |
| NZ210420A (en) * | 1983-12-06 | 1988-04-29 | Merrell Dow Pharma | D-amino acid oxidase substrates and pharmaceutical compositions |
| JPS6314015U (enrdf_load_html_response) * | 1986-07-11 | 1988-01-29 | ||
| JPS63136497A (ja) * | 1986-11-28 | 1988-06-08 | Hitachi Medical Corp | Ｘ線装置 |
| JPH0378128U (enrdf_load_html_response) * | 1989-11-30 | 1991-08-07 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2029385A1 (enrdf_load_html_response) * | 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 RO RO7100070107A patent/RO62296A/ro unknown
- 1971-04-28 RO RO66747A patent/RO57814A/ro unknown
- 1971-04-28 SU SU1820124A patent/SU439963A3/ru active
- 1971-04-28 RO RO70104A patent/RO57821A/ro unknown
- 1971-04-28 RO RO7100070105A patent/RO62418A/ro unknown
- 1971-04-28 RO RO70106A patent/RO57681A/ro unknown
- 1971-04-28 SU SU1820134A patent/SU440824A3/ru active
- 1971-04-28 SU SU1649251A patent/SU398031A3/ru active
- 1971-04-29 CH CH29975A patent/CH579023A5/xx not_active IP Right Cessation
- 1971-04-29 CH CH29875A patent/CH579022A5/xx not_active IP Right Cessation
- 1971-04-29 CS CS722324A patent/CS194665B2/cs unknown
- 1971-04-29 NL NLAANVRAGE7105946,A patent/NL169462C/xx not_active IP Right Cessation
- 1971-04-29 CS CS3115A patent/CS170545B2/cs unknown
- 1971-04-29 CH CH29775A patent/CH570968A5/xx not_active IP Right Cessation
- 1971-04-29 CH CH632271A patent/CH561169A5/xx not_active IP Right Cessation
- 1971-04-29 YU YU1080/71A patent/YU35571B/xx unknown
- 1971-04-29 CS CS2325A patent/CS175428B2/cs unknown
- 1971-04-30 FR FR7115627A patent/FR2092123B1/fr not_active Expired
- 1971-04-30 NO NO1615/71A patent/NO133708C/no unknown
- 1971-04-30 IL IL36743A patent/IL36743A/xx unknown
- 1971-04-30 ES ES390778A patent/ES390778A1/es not_active Expired
- 1971-04-30 GB GB1244371A patent/GB1354451A/en not_active Expired
- 1971-04-30 BG BG019046A patent/BG21016A3/xx unknown
- 1971-04-30 BG BG017446A patent/BG18601A3/xx unknown
- 1971-04-30 AT AT375071A patent/AT317171B/de active
- 1971-04-30 SE SE7105652A patent/SE374355B/xx unknown
- 1971-04-30 PL PL1971177491A patent/PL91964B1/pl unknown
- 1971-04-30 HU HUBO1290A patent/HU162545B/hu unknown
- 1971-04-30 IE IE545/71A patent/IE35608B1/xx unknown
- 1971-04-30 FI FI1212/71A patent/FI53571C/fi active
- 1971-04-30 AT AT518373A patent/AT317173B/de not_active IP Right Cessation
- 1971-04-30 BG BG019045A patent/BG19589A3/xx unknown
- 1971-04-30 AT AT518573A patent/AT317175B/de not_active IP Right Cessation
- 1971-04-30 BG BG22776A patent/BG21017A3/xx unknown
- 1971-04-30 AT AT518273A patent/AT317172B/de not_active IP Right Cessation
- 1971-04-30 PL PL1971177492A patent/PL90714B1/pl unknown
- 1971-04-30 PL PL1971147865A patent/PL85189B1/pl unknown
- 1971-04-30 AT AT518473A patent/AT317174B/de active
- 1971-04-30 ZA ZA712788A patent/ZA712788B/xx unknown
- 1971-04-30 AT AT518673A patent/AT317176B/de not_active IP Right Cessation
- 1971-04-30 BG BG019047A patent/BG19131A3/xx unknown
- 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 ES402637A patent/ES402637A1/es not_active Expired
- 1972-05-12 ES ES402636A patent/ES402636A1/es not_active Expired
- 1972-05-12 ES ES402638A patent/ES402638A1/es not_active Expired
-
1978
- 1978-10-26 YU YU2498/78A patent/YU36285B/xx unknown
- 1978-10-26 YU YU2499/78A patent/YU36286B/xx unknown
- 1978-10-26 YU YU02500/78A patent/YU36482B/xx unknown
-
1980
- 1980-06-16 YU YU1590/80A patent/YU37114B/xx unknown
- 1980-09-17 JP JP12902980A patent/JPS5655352A/ja active Granted
- 1980-09-17 JP JP55129028A patent/JPS589090B2/ja not_active Expired
- 1980-09-17 JP JP12902780A patent/JPS5655350A/ja active Granted
-
1981
- 1981-02-20 YU YU00433/81A patent/YU43381A/xx unknown
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