NO834770L - Fremgangsmaate til fremstilling av nye aralkyltriazolforbindelser - Google Patents
Fremgangsmaate til fremstilling av nye aralkyltriazolforbindelserInfo
- Publication number
- NO834770L NO834770L NO834770A NO834770A NO834770L NO 834770 L NO834770 L NO 834770L NO 834770 A NO834770 A NO 834770A NO 834770 A NO834770 A NO 834770A NO 834770 L NO834770 L NO 834770L
- Authority
- NO
- Norway
- Prior art keywords
- triazole
- carboxamide
- amino
- chlorobenzyl
- formula
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims description 90
- 238000000034 method Methods 0.000 title claims description 24
- 238000002360 preparation method Methods 0.000 title claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 89
- -1 2-trifluoromethylphenyl Chemical group 0.000 claims description 85
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 58
- 150000003839 salts Chemical class 0.000 claims description 44
- 125000002947 alkylene group Chemical group 0.000 claims description 40
- 239000002253 acid Substances 0.000 claims description 38
- 125000004432 carbon atom Chemical group C* 0.000 claims description 35
- 229910052739 hydrogen Inorganic materials 0.000 claims description 34
- 239000001257 hydrogen Substances 0.000 claims description 34
- 125000003545 alkoxy group Chemical group 0.000 claims description 28
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 26
- 125000003282 alkyl amino group Chemical group 0.000 claims description 25
- 238000006243 chemical reaction Methods 0.000 claims description 22
- 239000000203 mixture Substances 0.000 claims description 21
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 21
- 239000007858 starting material Substances 0.000 claims description 20
- 125000002252 acyl group Chemical group 0.000 claims description 18
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 18
- 150000002431 hydrogen Chemical class 0.000 claims description 18
- 125000001118 alkylidene group Chemical group 0.000 claims description 17
- 150000002367 halogens Chemical group 0.000 claims description 16
- 241000534944 Thia Species 0.000 claims description 15
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- 229910052736 halogen Inorganic materials 0.000 claims description 13
- 125000003277 amino group Chemical group 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000004442 acylamino group Chemical group 0.000 claims description 7
- 125000005237 alkyleneamino group Chemical group 0.000 claims description 7
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
- 229910052740 iodine Inorganic materials 0.000 claims description 6
- QFDXECSWYQYNJR-UHFFFAOYSA-N 1-[(2-chlorophenyl)methyl]triazole-4,5-dicarboxamide Chemical compound NC(=O)C1=C(C(=O)N)N=NN1CC1=CC=CC=C1Cl QFDXECSWYQYNJR-UHFFFAOYSA-N 0.000 claims description 4
- YNHMYRUNFIQMPN-UHFFFAOYSA-N 5-amino-1-[(2-chlorophenyl)methyl]triazole-4-carboxamide Chemical compound NC1=C(C(=O)N)N=NN1CC1=CC=CC=C1Cl YNHMYRUNFIQMPN-UHFFFAOYSA-N 0.000 claims description 4
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 4
- 238000003776 cleavage reaction Methods 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 230000007017 scission Effects 0.000 claims description 4
- 125000001589 carboacyl group Chemical group 0.000 claims description 3
- 239000013067 intermediate product Substances 0.000 claims description 3
- 238000002955 isolation Methods 0.000 claims description 3
- SWFQXPINDMWJFF-UHFFFAOYSA-N 1-[(2-chlorophenyl)methyl]-5-(dimethylamino)triazole-4-carboxamide Chemical compound CN(C)C1=C(C(N)=O)N=NN1CC1=CC=CC=C1Cl SWFQXPINDMWJFF-UHFFFAOYSA-N 0.000 claims description 2
- VWEVISZLGUYTRM-UHFFFAOYSA-N 1-[(2-chlorophenyl)methyl]-5-formamidotriazole-4-carboxamide Chemical compound O=CNC1=C(C(=O)N)N=NN1CC1=CC=CC=C1Cl VWEVISZLGUYTRM-UHFFFAOYSA-N 0.000 claims description 2
- FRCWDCMFWBONID-UHFFFAOYSA-N 1-[(2-chlorophenyl)methyl]-5-methyltriazole-4-carboxamide Chemical compound CC1=C(C(N)=O)N=NN1CC1=CC=CC=C1Cl FRCWDCMFWBONID-UHFFFAOYSA-N 0.000 claims description 2
- WRHZXKNJPWHHMF-UHFFFAOYSA-N 1-[(2-chlorophenyl)methyl]-n,n-dimethyltriazole-4-carboxamide Chemical compound N1=NC(C(=O)N(C)C)=CN1CC1=CC=CC=C1Cl WRHZXKNJPWHHMF-UHFFFAOYSA-N 0.000 claims description 2
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical class C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 claims description 2
- MULICVVLWANMHH-UHFFFAOYSA-N 5-amino-1-[(2,6-dichlorophenyl)methyl]triazole-4-carboxamide Chemical compound NC1=C(C(=O)N)N=NN1CC1=C(Cl)C=CC=C1Cl MULICVVLWANMHH-UHFFFAOYSA-N 0.000 claims description 2
- JUXIQMCKKHYJOM-UHFFFAOYSA-N 5-methyl-1-[(2-methylphenyl)methyl]triazole-4-carboxamide Chemical compound CC1=C(C(N)=O)N=NN1CC1=CC=CC=C1C JUXIQMCKKHYJOM-UHFFFAOYSA-N 0.000 claims description 2
- BZULNGXUURANDL-UHFFFAOYSA-N [1-[(2-chlorophenyl)methyl]triazol-4-yl]-piperidin-1-ylmethanone Chemical compound ClC1=CC=CC=C1CN1N=NC(C(=O)N2CCCCC2)=C1 BZULNGXUURANDL-UHFFFAOYSA-N 0.000 claims description 2
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- XLGJAYCAWUZGCE-UHFFFAOYSA-N n-[5-carbamoyl-3-[(2-chlorophenyl)methyl]triazol-4-yl]-4-methylpiperazine-1-carboxamide Chemical compound C1CN(C)CCN1C(=O)NC1=C(C(N)=O)N=NN1CC1=CC=CC=C1Cl XLGJAYCAWUZGCE-UHFFFAOYSA-N 0.000 claims description 2
- YWOWBPIGSXHKQH-UHFFFAOYSA-N 1-[(2-chlorophenyl)methyl]-5-methoxytriazole-4-carboxamide Chemical compound COC1=C(C(N)=O)N=NN1CC1=CC=CC=C1Cl YWOWBPIGSXHKQH-UHFFFAOYSA-N 0.000 claims 1
- YKDSRHNYPYHUDB-UHFFFAOYSA-N 1-[(3-chlorophenyl)methyl]triazole-4-carboxamide Chemical compound N1=NC(C(=O)N)=CN1CC1=CC=CC(Cl)=C1 YKDSRHNYPYHUDB-UHFFFAOYSA-N 0.000 claims 1
- QQQUFMKPWGTYGD-UHFFFAOYSA-N 5-amino-1-[(2,3-dimethylphenyl)methyl]triazole-4-carboxamide Chemical compound CC1=CC=CC(CN2C(=C(C(N)=O)N=N2)N)=C1C QQQUFMKPWGTYGD-UHFFFAOYSA-N 0.000 claims 1
- QFDGCLTXHHYQNU-UHFFFAOYSA-N 5-amino-1-[(2-bromophenyl)methyl]triazole-4-carboxamide Chemical compound NC1=C(C(=O)N)N=NN1CC1=CC=CC=C1Br QFDGCLTXHHYQNU-UHFFFAOYSA-N 0.000 claims 1
- ZDNVWYVKSXRJRO-UHFFFAOYSA-N 5-amino-1-[(3-chlorophenyl)methyl]triazole-4-carboxamide Chemical compound NC1=C(C(=O)N)N=NN1CC1=CC=CC(Cl)=C1 ZDNVWYVKSXRJRO-UHFFFAOYSA-N 0.000 claims 1
- LWEBZLFLPFCROT-UHFFFAOYSA-N 5-amino-1-[(3-methylphenyl)methyl]triazole-4-carboxamide Chemical compound CC1=CC=CC(CN2C(=C(C(N)=O)N=N2)N)=C1 LWEBZLFLPFCROT-UHFFFAOYSA-N 0.000 claims 1
- FZDOUHCDMALQPA-UHFFFAOYSA-N 5-amino-1-[(5-chloro-2-methylphenyl)methyl]triazole-4-carboxamide Chemical compound CC1=CC=C(Cl)C=C1CN1C(N)=C(C(N)=O)N=N1 FZDOUHCDMALQPA-UHFFFAOYSA-N 0.000 claims 1
- MHAZBPOOLJNYEX-UHFFFAOYSA-N 5-amino-1-[[2-(trifluoromethyl)phenyl]methyl]triazole-4-carboxamide Chemical compound NC1=C(C(=O)N)N=NN1CC1=CC=CC=C1C(F)(F)F MHAZBPOOLJNYEX-UHFFFAOYSA-N 0.000 claims 1
- QGRSHNKPXCGFFD-UHFFFAOYSA-N [5-amino-1-[(2-chlorophenyl)methyl]triazol-4-yl]-piperidin-1-ylmethanone Chemical compound NC1=C(N=NN1CC1=C(C=CC=C1)Cl)C(=O)N1CCCCC1 QGRSHNKPXCGFFD-UHFFFAOYSA-N 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 98
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 48
- 238000002844 melting Methods 0.000 description 42
- 230000008018 melting Effects 0.000 description 42
- 235000019441 ethanol Nutrition 0.000 description 39
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- 239000000243 solution Substances 0.000 description 29
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 20
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- 239000003795 chemical substances by application Substances 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 15
- 239000011734 sodium Substances 0.000 description 15
- 229910052708 sodium Inorganic materials 0.000 description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 14
- 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 14
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 14
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 238000010992 reflux Methods 0.000 description 10
- BOSNISRGGXSMHE-UHFFFAOYSA-N 1-(azidomethyl)-2-chlorobenzene Chemical compound ClC1=CC=CC=C1CN=[N+]=[N-] BOSNISRGGXSMHE-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 239000013543 active substance Substances 0.000 description 9
- 229910052783 alkali metal Inorganic materials 0.000 description 9
- 238000002425 crystallisation Methods 0.000 description 9
- 230000008025 crystallization Effects 0.000 description 9
- 239000002585 base Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical group C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 6
- 125000005907 alkyl ester group Chemical group 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 235000011121 sodium hydroxide Nutrition 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical group O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 230000002378 acidificating effect Effects 0.000 description 5
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 5
- 150000001340 alkali metals Chemical class 0.000 description 5
- 229910021529 ammonia Inorganic materials 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 150000003973 alkyl amines Chemical class 0.000 description 4
- 125000005281 alkyl ureido group Chemical group 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
- 238000009833 condensation Methods 0.000 description 4
- 230000005494 condensation Effects 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 description 4
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 4
- 239000011707 mineral Substances 0.000 description 4
- 235000010755 mineral Nutrition 0.000 description 4
- 239000000825 pharmaceutical preparation Substances 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- TVDRLUFPNNVBEC-UHFFFAOYSA-N 1-[(2-chlorophenyl)methyl]triazole-4-carboxylic acid Chemical compound N1=NC(C(=O)O)=CN1CC1=CC=CC=C1Cl TVDRLUFPNNVBEC-UHFFFAOYSA-N 0.000 description 3
- OSKSVLBJJXQUPI-UHFFFAOYSA-N 2h-triazole-4-carboxamide Chemical compound NC(=O)C1=CNN=N1 OSKSVLBJJXQUPI-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- 229920002261 Corn starch Polymers 0.000 description 3
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 3
- 229920002472 Starch Polymers 0.000 description 3
- 150000008065 acid anhydrides Chemical class 0.000 description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 3
- 235000011114 ammonium hydroxide Nutrition 0.000 description 3
- 150000008064 anhydrides Chemical group 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000008120 corn starch Substances 0.000 description 3
- 229940099112 cornstarch Drugs 0.000 description 3
- BGOUMNLLIGEMFC-UHFFFAOYSA-N dimethyl 1-[(2-chlorophenyl)methyl]triazole-4,5-dicarboxylate Chemical compound COC(=O)C1=C(C(=O)OC)N=NN1CC1=CC=CC=C1Cl BGOUMNLLIGEMFC-UHFFFAOYSA-N 0.000 description 3
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 239000008101 lactose Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 125000001477 organic nitrogen group Chemical group 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 3
- 235000019698 starch Nutrition 0.000 description 3
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical class SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
- AUHZEENZYGFFBQ-UHFFFAOYSA-N 1,3,5-trimethylbenzene Chemical compound CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 2
- SOYANKPFXHJUCE-UHFFFAOYSA-N 1,4-dioxane-2-carbaldehyde Chemical compound O=CC1COCCO1 SOYANKPFXHJUCE-UHFFFAOYSA-N 0.000 description 2
- DISKVNRGMSADDG-UHFFFAOYSA-N 1-(azidomethyl)-2-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1CN=[N+]=[N-] DISKVNRGMSADDG-UHFFFAOYSA-N 0.000 description 2
- OTNOZELYEDJCQH-UHFFFAOYSA-N 1-(azidomethyl)-3-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC(CN=[N+]=[N-])=C1 OTNOZELYEDJCQH-UHFFFAOYSA-N 0.000 description 2
- WYFWUPTWYUKGQM-UHFFFAOYSA-N 1-(azidomethyl)-3-chlorobenzene Chemical compound ClC1=CC=CC(CN=[N+]=[N-])=C1 WYFWUPTWYUKGQM-UHFFFAOYSA-N 0.000 description 2
- CWTFFDYHIPDZAG-UHFFFAOYSA-N 1-[(2-chlorophenyl)methyl]-5-methoxytriazole-4-carboxylic acid Chemical compound COC1=C(C(O)=O)N=NN1CC1=CC=CC=C1Cl CWTFFDYHIPDZAG-UHFFFAOYSA-N 0.000 description 2
- CKKQEIIHQZWBHC-UHFFFAOYSA-N 1-[(2-chlorophenyl)methyl]-5-methyltriazole-4-carboxylic acid Chemical compound CC1=C(C(O)=O)N=NN1CC1=CC=CC=C1Cl CKKQEIIHQZWBHC-UHFFFAOYSA-N 0.000 description 2
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- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
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- 125000004915 dibutylamino group Chemical group C(CCC)N(CCCC)* 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- PFBUKDPBVNJDEW-UHFFFAOYSA-N dichlorocarbene Chemical class Cl[C]Cl PFBUKDPBVNJDEW-UHFFFAOYSA-N 0.000 description 1
- HNGGSWPHMZXFNN-UHFFFAOYSA-N dimethyl 2h-triazole-4,5-dicarboxylate Chemical compound COC(=O)C1=NNN=C1C(=O)OC HNGGSWPHMZXFNN-UHFFFAOYSA-N 0.000 description 1
- VHILMKFSCRWWIJ-UHFFFAOYSA-N dimethyl acetylenedicarboxylate Chemical compound COC(=O)C#CC(=O)OC VHILMKFSCRWWIJ-UHFFFAOYSA-N 0.000 description 1
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- 125000001072 heteroaryl group Chemical group 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
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- 150000004677 hydrates Chemical class 0.000 description 1
- BICAGYDGRXJYGD-UHFFFAOYSA-N hydrobromide;hydrochloride Chemical compound Cl.Br BICAGYDGRXJYGD-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 1
- 239000003978 infusion fluid Substances 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- SYZHAGPAUUOSEZ-UHFFFAOYSA-N iodosilicon Chemical compound I[Si] SYZHAGPAUUOSEZ-UHFFFAOYSA-N 0.000 description 1
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- LWLPYZUDBNFNAH-UHFFFAOYSA-M magnesium;butane;bromide Chemical compound [Mg+2].[Br-].CCC[CH2-] LWLPYZUDBNFNAH-UHFFFAOYSA-M 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 229960002510 mandelic acid Drugs 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
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- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
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- 238000002156 mixing Methods 0.000 description 1
- 125000006518 morpholino carbonyl group Chemical group [H]C1([H])OC([H])([H])C([H])([H])N(C(*)=O)C1([H])[H] 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical compound O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 description 1
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- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
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- 239000003921 oil Substances 0.000 description 1
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- 125000000962 organic group Chemical group 0.000 description 1
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- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
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- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000004208 shellac Substances 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 235000013874 shellac Nutrition 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 1
- 235000014214 soft drink Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000003797 solvolysis reaction Methods 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000003459 sulfonic acid esters Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000003613 toluenes Chemical class 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- MJXUZAHRGOEWSQ-UHFFFAOYSA-N trimethyl(triazol-1-yl)silane Chemical class C[Si](C)(C)N1C=CN=N1 MJXUZAHRGOEWSQ-UHFFFAOYSA-N 0.000 description 1
- SEDZOYHHAIAQIW-UHFFFAOYSA-N trimethylsilyl azide Chemical compound C[Si](C)(C)N=[N+]=[N-] SEDZOYHHAIAQIW-UHFFFAOYSA-N 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C247/00—Compounds containing azido groups
-
- 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
- A61P25/08—Antiepileptics; Anticonvulsants
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/04—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pain & Pain Management (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biomedical Technology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH752682 | 1982-12-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO834770L true NO834770L (no) | 1984-06-25 |
Family
ID=4326531
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO834770A NO834770L (no) | 1982-12-23 | 1983-12-22 | Fremgangsmaate til fremstilling av nye aralkyltriazolforbindelser |
Country Status (14)
| Country | Link |
|---|---|
| EP (1) | EP0114347A3 (en)) |
| JP (1) | JPS59118775A (en)) |
| AU (1) | AU566730B2 (en)) |
| DD (1) | DD216456A5 (en)) |
| DK (1) | DK591983A (en)) |
| ES (3) | ES528267A0 (en)) |
| FI (1) | FI834666A7 (en)) |
| GR (1) | GR79452B (en)) |
| HU (1) | HU191388B (en)) |
| IL (1) | IL70508A (en)) |
| NO (1) | NO834770L (en)) |
| NZ (1) | NZ206696A (en)) |
| PT (1) | PT77867B (en)) |
| ZA (1) | ZA839478B (en)) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3578499D1 (de) * | 1984-02-02 | 1990-08-09 | Merck & Co Inc | 5-(amino oder substituiertes amino)-1,2,3-triazole. |
| FI93544C (fi) * | 1985-04-18 | 1995-04-25 | Ciba Geigy Ag | Menetelmä fluorattujen, antikonvulsiivisesti vaikuttavien 1-bentsyyli-1H-1,2,3-triatsoliyhdisteiden valmistamiseksi |
| US5359078A (en) * | 1989-05-19 | 1994-10-25 | The United States Of America As Represented By The Department Of Health And Human Services | Signal transduction inhibitor compounds |
| US5498620A (en) * | 1989-05-19 | 1996-03-12 | The United States Of America As Represented By The Department Of Health And Human Services | Signal transduction inhibitor 1,2,3-triazolo compounds |
| US5880129A (en) * | 1989-05-19 | 1999-03-09 | The United States Of America As Represented By The Department Of Health And Human Services | Methods of inhibiting invasion and metastasis of malignant solid tumors |
| WO1997040025A1 (en) * | 1996-04-19 | 1997-10-30 | Novo Nordisk A/S | Solid phase and combinatorial synthesis of substituted 1,2,3-triazoles and of arrays of substituted 1,2,3-triazoles |
| TW526195B (en) | 1997-06-10 | 2003-04-01 | Novartis Ag | Crystal modifications of 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxamide and their use |
| GB0507298D0 (en) | 2005-04-11 | 2005-05-18 | Novartis Ag | Organic compounds |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL50699A0 (en) * | 1975-10-28 | 1976-12-31 | Ici America Inc | Triazole derivatives |
| CH632291A5 (de) * | 1978-01-10 | 1982-09-30 | Sandoz Ag | Organische azoverbindungen. |
| CH639376A5 (en) * | 1979-02-14 | 1983-11-15 | Sandoz Ag | Process for preparing disperse dyes of the triazolylazo class |
-
1983
- 1983-12-19 FI FI834666A patent/FI834666A7/fi not_active Application Discontinuation
- 1983-12-20 EP EP83112847A patent/EP0114347A3/de not_active Withdrawn
- 1983-12-21 DD DD83258352A patent/DD216456A5/de unknown
- 1983-12-21 ZA ZA839478A patent/ZA839478B/xx unknown
- 1983-12-21 PT PT77867A patent/PT77867B/pt unknown
- 1983-12-21 IL IL70508A patent/IL70508A/xx unknown
- 1983-12-21 ES ES528267A patent/ES528267A0/es active Granted
- 1983-12-21 GR GR73317A patent/GR79452B/el unknown
- 1983-12-22 NO NO834770A patent/NO834770L/no unknown
- 1983-12-22 HU HU834423A patent/HU191388B/hu unknown
- 1983-12-22 DK DK591983A patent/DK591983A/da not_active Application Discontinuation
- 1983-12-22 JP JP58241096A patent/JPS59118775A/ja active Pending
- 1983-12-22 AU AU22807/83A patent/AU566730B2/en not_active Ceased
- 1983-12-22 NZ NZ206696A patent/NZ206696A/en unknown
-
1985
- 1985-05-29 ES ES543624A patent/ES8608496A1/es not_active Expired
- 1985-05-29 ES ES543623A patent/ES8608495A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| EP0114347A2 (de) | 1984-08-01 |
| ZA839478B (en) | 1984-08-29 |
| NZ206696A (en) | 1986-02-21 |
| ES8608495A1 (es) | 1986-06-16 |
| EP0114347A3 (de) | 1986-01-29 |
| ES8601930A1 (es) | 1985-11-16 |
| GR79452B (en)) | 1984-10-30 |
| AU566730B2 (en) | 1987-10-29 |
| JPS59118775A (ja) | 1984-07-09 |
| ES543623A0 (es) | 1986-06-16 |
| AU2280783A (en) | 1984-06-28 |
| DK591983A (da) | 1984-06-24 |
| IL70508A (en) | 1988-03-31 |
| ES8608496A1 (es) | 1986-06-16 |
| FI834666A0 (fi) | 1983-12-19 |
| FI834666A7 (fi) | 1984-06-24 |
| DK591983D0 (da) | 1983-12-22 |
| ES528267A0 (es) | 1985-11-16 |
| DD216456A5 (de) | 1984-12-12 |
| HU191388B (en) | 1987-02-27 |
| PT77867B (en) | 1986-05-08 |
| ES543624A0 (es) | 1986-06-16 |
| IL70508A0 (en) | 1984-03-30 |
| PT77867A (en) | 1984-01-01 |
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