NO125183B - - Google Patents
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- Publication number
- NO125183B NO125183B NO1875/68A NO187568A NO125183B NO 125183 B NO125183 B NO 125183B NO 1875/68 A NO1875/68 A NO 1875/68A NO 187568 A NO187568 A NO 187568A NO 125183 B NO125183 B NO 125183B
- Authority
- NO
- Norway
- Prior art keywords
- group
- hydroxy
- denotes
- acetylphenoxy
- isopropylaminopropane
- Prior art date
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- -1 phenoxymethanesulfonyl group Chemical group 0.000 claims description 117
- 150000001875 compounds Chemical class 0.000 claims description 40
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 39
- 150000001412 amines Chemical class 0.000 claims description 29
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 28
- 239000007858 starting material Substances 0.000 claims description 22
- MMLMKHNDSNBYSQ-UHFFFAOYSA-N 1-[2-[2-hydroxy-3-(propan-2-ylamino)propoxy]phenyl]ethanone Chemical compound CC(C)NCC(O)COC1=CC=CC=C1C(C)=O MMLMKHNDSNBYSQ-UHFFFAOYSA-N 0.000 claims description 21
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 230000002378 acidificating effect Effects 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 6
- 125000000335 thiazolyl group Chemical group 0.000 claims description 6
- 125000001544 thienyl 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 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 4
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 125000002252 acyl group Chemical group 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- 150000001335 aliphatic alkanes Chemical group 0.000 claims description 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 2
- 125000005605 benzo group Chemical group 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 125000005486 naphthalic acid group Chemical group 0.000 claims description 2
- 125000001326 naphthylalkyl group Chemical group 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000001893 nitrooxy group Chemical group [O-][N+](=O)O* 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- JZEHWMUIAKALDN-UHFFFAOYSA-N 1-amino-3-phenoxypropan-2-ol Chemical class NCC(O)COC1=CC=CC=C1 JZEHWMUIAKALDN-UHFFFAOYSA-N 0.000 claims 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 claims 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 173
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 90
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 86
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 70
- 239000000203 mixture Substances 0.000 description 64
- 239000000243 solution Substances 0.000 description 60
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 48
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 34
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 34
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 33
- 239000000284 extract Substances 0.000 description 29
- 239000000543 intermediate Substances 0.000 description 26
- 238000006243 chemical reaction Methods 0.000 description 24
- 239000011541 reaction mixture Substances 0.000 description 23
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 20
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 20
- 239000007787 solid Substances 0.000 description 19
- 238000003756 stirring Methods 0.000 description 15
- VCJHWSHVJVUYQC-UHFFFAOYSA-N 1-[2-(oxiran-2-ylmethoxy)phenyl]ethanone Chemical compound CC(=O)C1=CC=CC=C1OCC1OC1 VCJHWSHVJVUYQC-UHFFFAOYSA-N 0.000 description 12
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- 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 9
- VJRITMATACIYAF-UHFFFAOYSA-N benzenesulfonohydrazide Chemical compound NNS(=O)(=O)C1=CC=CC=C1 VJRITMATACIYAF-UHFFFAOYSA-N 0.000 description 9
- 238000001816 cooling Methods 0.000 description 9
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 9
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 8
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 150000002118 epoxides Chemical class 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- SRVJKTDHMYAMHA-WUXMJOGZSA-N thioacetazone Chemical compound CC(=O)NC1=CC=C(\C=N\NC(N)=S)C=C1 SRVJKTDHMYAMHA-WUXMJOGZSA-N 0.000 description 8
- 239000010410 layer Substances 0.000 description 7
- SMQUZDBALVYZAC-UHFFFAOYSA-N ortho-hydroxybenzaldehyde Natural products OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- 238000004809 thin layer chromatography Methods 0.000 description 7
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 6
- 238000011065 in-situ storage Methods 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
- 238000000354 decomposition reaction Methods 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 239000003208 petroleum Substances 0.000 description 5
- MAZUHAMDUYFWSV-UHFFFAOYSA-N 1-(2-methoxyphenyl)-2,2-dimethylpropan-1-one Chemical compound COC1=CC=CC=C1C(=O)C(C)(C)C MAZUHAMDUYFWSV-UHFFFAOYSA-N 0.000 description 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 4
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 4
- 239000011777 magnesium Substances 0.000 description 4
- 229910052749 magnesium Inorganic materials 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 239000001632 sodium acetate Substances 0.000 description 4
- 235000017281 sodium acetate Nutrition 0.000 description 4
- YUFYDTPPHKTEOD-UHFFFAOYSA-N (2-methoxyphenyl)-pyridin-4-ylmethanone Chemical compound COC1=CC=CC=C1C(=O)C1=CC=NC=C1 YUFYDTPPHKTEOD-UHFFFAOYSA-N 0.000 description 3
- DATBOQDYGBLGAR-UHFFFAOYSA-N 1-(2-hydroxyphenyl)-2,2-dimethylpropan-1-one Chemical compound CC(C)(C)C(=O)C1=CC=CC=C1O DATBOQDYGBLGAR-UHFFFAOYSA-N 0.000 description 3
- OCMGKHDHUIJXLD-UHFFFAOYSA-N 1-(2-methoxyphenyl)-4-methylpentan-1-ol Chemical compound COC1=CC=CC=C1C(O)CCC(C)C OCMGKHDHUIJXLD-UHFFFAOYSA-N 0.000 description 3
- UMHOMJHXZRYGLO-UHFFFAOYSA-N 1-(2-methoxyphenyl)-4-methylpentan-1-one Chemical compound COC1=CC=CC=C1C(=O)CCC(C)C UMHOMJHXZRYGLO-UHFFFAOYSA-N 0.000 description 3
- FGKCXXCWFBSRHT-UHFFFAOYSA-N 1-[5-chloro-2-(oxiran-2-ylmethoxy)phenyl]propan-1-one Chemical compound CCC(=O)C1=CC(Cl)=CC=C1OCC1OC1 FGKCXXCWFBSRHT-UHFFFAOYSA-N 0.000 description 3
- ZZRGOEMPMJRGPN-UHFFFAOYSA-N 1-amino-3-[(2-methoxyphenyl)methyl]thiourea Chemical compound COC1=CC=CC=C1CNC(=S)NN ZZRGOEMPMJRGPN-UHFFFAOYSA-N 0.000 description 3
- UJTTUOLQLCQZEA-UHFFFAOYSA-N 9h-fluoren-9-ylmethyl n-(4-hydroxybutyl)carbamate Chemical compound C1=CC=C2C(COC(=O)NCCCCO)C3=CC=CC=C3C2=C1 UJTTUOLQLCQZEA-UHFFFAOYSA-N 0.000 description 3
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000003610 charcoal Substances 0.000 description 3
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N dimethylmethane Natural products CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 231100000252 nontoxic Toxicity 0.000 description 3
- 230000003000 nontoxic effect Effects 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- 238000007514 turning Methods 0.000 description 3
- HJIAMFHSAAEUKR-UHFFFAOYSA-N (2-hydroxyphenyl)-phenylmethanone Chemical compound OC1=CC=CC=C1C(=O)C1=CC=CC=C1 HJIAMFHSAAEUKR-UHFFFAOYSA-N 0.000 description 2
- RRHUALAXDWPXRI-UHFFFAOYSA-N (2-hydroxyphenyl)-pyridin-4-ylmethanone Chemical compound OC1=CC=CC=C1C(=O)C1=CC=NC=C1 RRHUALAXDWPXRI-UHFFFAOYSA-N 0.000 description 2
- XTGCUDZCCIRWHL-UHFFFAOYSA-N 1-(5-chloro-2-hydroxyphenyl)ethanone Chemical compound CC(=O)C1=CC(Cl)=CC=C1O XTGCUDZCCIRWHL-UHFFFAOYSA-N 0.000 description 2
- WPKZNLBCKHWPID-UHFFFAOYSA-N 1-[2-(oxiran-2-ylmethoxy)phenyl]-N-phenylmethoxymethanimine Chemical compound C(C1=CC=CC=C1)ON=CC1=C(OCC2CO2)C=CC=C1 WPKZNLBCKHWPID-UHFFFAOYSA-N 0.000 description 2
- FZJQSFPAKZCCMK-UHFFFAOYSA-N 1-[2-[3-(cyclohexylamino)-2-hydroxypropoxy]phenyl]ethanone Chemical compound CC(=O)C1=CC=CC=C1OCC(O)CNC1CCCCC1 FZJQSFPAKZCCMK-UHFFFAOYSA-N 0.000 description 2
- HTDQSWDEWGSAMN-UHFFFAOYSA-N 1-bromo-2-methoxybenzene Chemical compound COC1=CC=CC=C1Br HTDQSWDEWGSAMN-UHFFFAOYSA-N 0.000 description 2
- WSKCRBSHOIAZBQ-UHFFFAOYSA-N 2-(2-chlorophenyl)acetohydrazide Chemical compound NNC(=O)CC1=CC=CC=C1Cl WSKCRBSHOIAZBQ-UHFFFAOYSA-N 0.000 description 2
- PKZJLOCLABXVMC-UHFFFAOYSA-N 2-Methoxybenzaldehyde Chemical compound COC1=CC=CC=C1C=O PKZJLOCLABXVMC-UHFFFAOYSA-N 0.000 description 2
- AILWISDLOFOZHA-UHFFFAOYSA-N 3,5-dichloro-4-methoxybenzohydrazide Chemical compound COC1=C(Cl)C=C(C(=O)NN)C=C1Cl AILWISDLOFOZHA-UHFFFAOYSA-N 0.000 description 2
- FJBLNCPJAVARBR-UHFFFAOYSA-N 3,5-dihydroxybenzohydrazide Chemical compound NNC(=O)C1=CC(O)=CC(O)=C1 FJBLNCPJAVARBR-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- CHGGEJXIEILEFU-UHFFFAOYSA-N CC(C)NCC(O)COC1=C(C=CC=C1)C(C)=NO Chemical compound CC(C)NCC(O)COC1=C(C=CC=C1)C(C)=NO CHGGEJXIEILEFU-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- 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 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical class NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- VNJKIQCYNCQEOW-UHFFFAOYSA-N [2-(oxiran-2-ylmethoxy)phenyl]-phenylmethanone Chemical compound C=1C=CC=C(OCC2OC2)C=1C(=O)C1=CC=CC=C1 VNJKIQCYNCQEOW-UHFFFAOYSA-N 0.000 description 2
- ZYTXYUKRQOQMQR-UHFFFAOYSA-N [2-[2-hydroxy-3-(propan-2-ylamino)propoxy]phenyl]-phenylmethanone Chemical compound CC(C)NCC(O)COC1=CC=CC=C1C(=O)C1=CC=CC=C1 ZYTXYUKRQOQMQR-UHFFFAOYSA-N 0.000 description 2
- UCTWMZQNUQWSLP-UHFFFAOYSA-N adrenaline Chemical compound CNCC(O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 229940040526 anhydrous sodium acetate Drugs 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 239000002026 chloroform extract Substances 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 150000003840 hydrochlorides Chemical class 0.000 description 2
- RNVFYQUEEMZKLR-UHFFFAOYSA-N methyl 3,5-dihydroxybenzoate Chemical compound COC(=O)C1=CC(O)=CC(O)=C1 RNVFYQUEEMZKLR-UHFFFAOYSA-N 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- 150000002923 oximes Chemical class 0.000 description 2
- 230000003285 pharmacodynamic effect Effects 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 1
- PXJACNDVRNAFHD-UHFFFAOYSA-N (2-methoxyphenyl)methanamine Chemical compound COC1=CC=CC=C1CN PXJACNDVRNAFHD-UHFFFAOYSA-N 0.000 description 1
- OSKGYRIYNMZFSJ-UHFFFAOYSA-N (3,4-dichlorophenyl) acetate Chemical compound CC(=O)OC1=CC=C(Cl)C(Cl)=C1 OSKGYRIYNMZFSJ-UHFFFAOYSA-N 0.000 description 1
- OTXHZHQQWQTQMW-UHFFFAOYSA-N (diaminomethylideneamino)azanium;hydrogen carbonate Chemical compound OC([O-])=O.N[NH2+]C(N)=N OTXHZHQQWQTQMW-UHFFFAOYSA-N 0.000 description 1
- OEHUHOINFSQPQL-UHFFFAOYSA-N 1-(2-ethanehydrazonoylphenoxy)-3-(propan-2-ylamino)propan-2-ol Chemical compound CC(C)NCC(O)COC1=CC=CC=C1C(C)=NN OEHUHOINFSQPQL-UHFFFAOYSA-N 0.000 description 1
- BKSKHRCXEMBCAX-UHFFFAOYSA-N 1-(2-hydroxyphenyl)-4-methylpentan-1-one Chemical compound CC(C)CCC(=O)C1=CC=CC=C1O BKSKHRCXEMBCAX-UHFFFAOYSA-N 0.000 description 1
- CJFYGRLJDKWMDI-UHFFFAOYSA-N 1-(3,5-dichloro-2-hydroxyphenyl)ethanone Chemical compound CC(=O)C1=CC(Cl)=CC(Cl)=C1O CJFYGRLJDKWMDI-UHFFFAOYSA-N 0.000 description 1
- LGPWDDRVASDGCO-UHFFFAOYSA-N 1-[2-(N-hydroxy-C-methylcarbonimidoyl)-4-methoxyphenoxy]-3-(propan-2-ylamino)propan-2-ol Chemical compound COC1=CC(C(C)=NO)=C(OCC(O)CNC(C)C)C=C1 LGPWDDRVASDGCO-UHFFFAOYSA-N 0.000 description 1
- DCPPEJKHXFATCY-UHFFFAOYSA-N 1-[2-(N-hydroxy-C-methylcarbonimidoyl)-4-phenylphenoxy]-3-(propan-2-ylamino)propan-2-ol Chemical compound CC(C)NCC(O)COC1=C(C=C(C=C1)C1=CC=CC=C1)C(C)=NO DCPPEJKHXFATCY-UHFFFAOYSA-N 0.000 description 1
- WPCODBUUAISDJS-UHFFFAOYSA-N 1-[3,5-dichloro-2-[2-hydroxy-3-(propan-2-ylamino)propoxy]phenyl]ethanone Chemical compound CC(C)NCC(O)COC1=C(C=C(Cl)C=C1Cl)C(C)=O WPCODBUUAISDJS-UHFFFAOYSA-N 0.000 description 1
- PFGKJALEHXBNRC-UHFFFAOYSA-N 1-[4-chloro-2-(N-hydroxy-C-methylcarbonimidoyl)phenoxy]-3-(propan-2-ylamino)propan-2-ol Chemical compound CC(C)NCC(O)COC1=C(C=C(Cl)C=C1)C(C)=NO PFGKJALEHXBNRC-UHFFFAOYSA-N 0.000 description 1
- HDUWTOPVFBPLPX-UHFFFAOYSA-N 1-amino-3-(2-ethoxyethyl)thiourea Chemical compound CCOCCNC(=S)NN HDUWTOPVFBPLPX-UHFFFAOYSA-N 0.000 description 1
- ZTRUHAVBRPABTK-UHFFFAOYSA-N 1-amino-3-benzylthiourea Chemical compound NNC(=S)NCC1=CC=CC=C1 ZTRUHAVBRPABTK-UHFFFAOYSA-N 0.000 description 1
- BGCDDMALTCVQBP-UHFFFAOYSA-N 1-amino-3-pyridin-2-ylurea Chemical compound NNC(=O)NC1=CC=CC=N1 BGCDDMALTCVQBP-UHFFFAOYSA-N 0.000 description 1
- YXZFFTJAHVMMLF-UHFFFAOYSA-N 1-bromo-3-methylbutane Chemical compound CC(C)CCBr YXZFFTJAHVMMLF-UHFFFAOYSA-N 0.000 description 1
- RQEUFEKYXDPUSK-UHFFFAOYSA-N 1-phenylethylamine Chemical compound CC(N)C1=CC=CC=C1 RQEUFEKYXDPUSK-UHFFFAOYSA-N 0.000 description 1
- JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 description 1
- NTOIKDYVJIWVSU-UHFFFAOYSA-N 2,3-dihydroxy-2,3-bis(4-methylbenzoyl)butanedioic acid Chemical compound C1=CC(C)=CC=C1C(=O)C(O)(C(O)=O)C(O)(C(O)=O)C(=O)C1=CC=C(C)C=C1 NTOIKDYVJIWVSU-UHFFFAOYSA-N 0.000 description 1
- WXTMDXOMEHJXQO-UHFFFAOYSA-N 2,5-dihydroxybenzoic acid Chemical class OC(=O)C1=CC(O)=CC=C1O WXTMDXOMEHJXQO-UHFFFAOYSA-N 0.000 description 1
- HZKXFLZMKWMMNG-UHFFFAOYSA-N 2-(oxiran-2-ylmethoxy)benzaldehyde Chemical compound O=CC1=CC=CC=C1OCC1OC1 HZKXFLZMKWMMNG-UHFFFAOYSA-N 0.000 description 1
- KMVZDSQHLDGKGV-UHFFFAOYSA-N 2-chlorobenzenesulfonyl chloride Chemical compound ClC1=CC=CC=C1S(Cl)(=O)=O KMVZDSQHLDGKGV-UHFFFAOYSA-N 0.000 description 1
- JHWIEAWILPSRMU-UHFFFAOYSA-N 2-methyl-3-pyrimidin-4-ylpropanoic acid Chemical compound OC(=O)C(C)CC1=CC=NC=N1 JHWIEAWILPSRMU-UHFFFAOYSA-N 0.000 description 1
- WDNBURPWRNALGP-UHFFFAOYSA-N 3,4-Dichlorophenol Chemical compound OC1=CC=C(Cl)C(Cl)=C1 WDNBURPWRNALGP-UHFFFAOYSA-N 0.000 description 1
- SHPKLAWJDWHSCJ-UHFFFAOYSA-N 3,5-Dichlor-4-methoxy-benzoesaeure-methylester Natural products COC(=O)C1=CC(Cl)=C(OC)C(Cl)=C1 SHPKLAWJDWHSCJ-UHFFFAOYSA-N 0.000 description 1
- OINWZUJVEXUHCC-UHFFFAOYSA-N 3-chlorobenzenesulfonyl chloride Chemical compound ClC1=CC=CC(S(Cl)(=O)=O)=C1 OINWZUJVEXUHCC-UHFFFAOYSA-N 0.000 description 1
- PTVZQOAHCSKAAS-UHFFFAOYSA-N 4-methyl-3-thiosemicarbazide Chemical compound CNC(=S)NN PTVZQOAHCSKAAS-UHFFFAOYSA-N 0.000 description 1
- QIZPONOMFWAPRR-UHFFFAOYSA-N 4-phenoxybenzenesulfonyl chloride Chemical compound C1=CC(S(=O)(=O)Cl)=CC=C1OC1=CC=CC=C1 QIZPONOMFWAPRR-UHFFFAOYSA-N 0.000 description 1
- WECUIGDEWBNQJJ-UHFFFAOYSA-N 4-phenylbutan-2-amine Chemical compound CC(N)CCC1=CC=CC=C1 WECUIGDEWBNQJJ-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 206010002383 Angina Pectoris Diseases 0.000 description 1
- MVPKMJFWWAAJGI-UHFFFAOYSA-N CC(C)NCC(O)COC1=C(C=C(C)C=C1)C(C)=NO Chemical compound CC(C)NCC(O)COC1=C(C=C(C)C=C1)C(C)=NO MVPKMJFWWAAJGI-UHFFFAOYSA-N 0.000 description 1
- CYSNOOHXGAGKHI-UHFFFAOYSA-N CC(C)NCC(O)COC1=C(C=CC(=C1)C1=CC=CC=C1)C(C)=NO Chemical compound CC(C)NCC(O)COC1=C(C=CC(=C1)C1=CC=CC=C1)C(C)=NO CYSNOOHXGAGKHI-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 125000005281 alkyl ureido group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000003288 anthiarrhythmic effect Effects 0.000 description 1
- 206010003119 arrhythmia Diseases 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001860 citric acid derivatives Chemical class 0.000 description 1
- 208000029078 coronary artery disease Diseases 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 229940042396 direct acting antivirals thiosemicarbazones Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 1
- BRWIZMBXBAOCCF-UHFFFAOYSA-N hydrazinecarbothioamide Chemical compound NNC(N)=S BRWIZMBXBAOCCF-UHFFFAOYSA-N 0.000 description 1
- 230000001077 hypotensive effect Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 150000003893 lactate salts Chemical class 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- WJGVYRMMIIWBAU-UHFFFAOYSA-M magnesium;2-methylbutane;bromide Chemical compound [Mg+2].[Br-].CC(C)C[CH2-] WJGVYRMMIIWBAU-UHFFFAOYSA-M 0.000 description 1
- VXWPONVCMVLXBW-UHFFFAOYSA-M magnesium;carbanide;iodide Chemical compound [CH3-].[Mg+2].[I-] VXWPONVCMVLXBW-UHFFFAOYSA-M 0.000 description 1
- FCPRDUXJWIUVPZ-UHFFFAOYSA-M magnesium;methoxybenzene;bromide Chemical compound [Mg+2].[Br-].COC1=CC=CC=[C-]1 FCPRDUXJWIUVPZ-UHFFFAOYSA-M 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- KHBWTRFWQROKJZ-UHFFFAOYSA-N methyl 2-(2-chlorophenyl)acetate Chemical compound COC(=O)CC1=CC=CC=C1Cl KHBWTRFWQROKJZ-UHFFFAOYSA-N 0.000 description 1
- RNQAAVNGCJFEJE-UHFFFAOYSA-N methyl 4-(dimethylamino)benzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(N(C)C)C=C1 RNQAAVNGCJFEJE-UHFFFAOYSA-N 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 210000004165 myocardium Anatomy 0.000 description 1
- XHFGWHUWQXTGAT-UHFFFAOYSA-N n-methylpropan-2-amine Chemical compound CNC(C)C XHFGWHUWQXTGAT-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 229960002748 norepinephrine Drugs 0.000 description 1
- SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229910001392 phosphorus oxide Inorganic materials 0.000 description 1
- GPHQHTOMRSGBNZ-UHFFFAOYSA-N pyridine-4-carbonitrile Chemical compound N#CC1=CC=NC=C1 GPHQHTOMRSGBNZ-UHFFFAOYSA-N 0.000 description 1
- 150000003873 salicylate salts Chemical class 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- FDRCDNZGSXJAFP-UHFFFAOYSA-M sodium chloroacetate Chemical compound [Na+].[O-]C(=O)CCl FDRCDNZGSXJAFP-UHFFFAOYSA-M 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 230000002889 sympathetic effect Effects 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- IMWMFJMYEKHYKG-UHFFFAOYSA-N tert-butyl n-(2-oxooxolan-3-yl)carbamate Chemical compound CC(C)(C)OC(=O)NC1CCOC1=O IMWMFJMYEKHYKG-UHFFFAOYSA-N 0.000 description 1
- VSAISIQCTGDGPU-UHFFFAOYSA-N tetraphosphorus hexaoxide Chemical compound O1P(O2)OP3OP1OP2O3 VSAISIQCTGDGPU-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 150000003584 thiosemicarbazones Chemical class 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical group CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
- C07D213/53—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/72—Hydrazones
-
- 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
- C07C45/004—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with organometalhalides
-
- 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
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/29—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups
- C07C45/292—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups with chromium derivatives
-
- 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
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/54—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition of compounds containing doubly bound oxygen atoms, e.g. esters
-
- 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
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/673—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/84—Ketones containing a keto group bound to a six-membered aromatic ring containing ether groups, groups, groups, or groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
- C07D213/46—Oxygen atoms
- C07D213/50—Ketonic radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
- C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
- C07D303/22—Ethers with hydroxy compounds containing no oxirane rings with monohydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
- C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
- C07D303/24—Ethers with hydroxy compounds containing no oxirane rings with polyhydroxy compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2273567 | 1967-05-16 | ||
| GB5851667 | 1967-12-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO125183B true NO125183B (de) | 1972-07-31 |
Family
ID=26256090
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO1875/68A NO125183B (de) | 1967-05-16 | 1968-05-14 |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US3875149A (de) |
| AT (2) | AT289826B (de) |
| BE (1) | BE715205A (de) |
| CH (1) | CH489467A (de) |
| DE (1) | DE1768468A1 (de) |
| DK (1) | DK127060B (de) |
| ES (1) | ES353917A1 (de) |
| FR (2) | FR1570087A (de) |
| GB (1) | GB1231783A (de) |
| IE (1) | IE32174B1 (de) |
| IL (1) | IL30001A (de) |
| IS (1) | IS860B6 (de) |
| MT (1) | MTP557B (de) |
| NL (1) | NL6806946A (de) |
| NO (1) | NO125183B (de) |
| SE (1) | SE369894B (de) |
| SU (2) | SU443509A3 (de) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1501632A (en) * | 1974-06-28 | 1978-02-22 | Cm Ind | Aromatic ketones having cardiovascular activity |
| US4201790A (en) * | 1975-06-20 | 1980-05-06 | May & Baker Limited | Benzophenone derivatives |
| JPS58116450A (ja) * | 1981-12-29 | 1983-07-11 | Nippon Soda Co Ltd | ５−フエニルシクロヘキセノン誘導体、その製造方法及び選択的除草剤 |
| DE3237400A1 (de) * | 1982-10-08 | 1984-04-12 | Bayer Ag, 5090 Leverkusen | Substituierte 1-hydroxyethyl-triazolyl-derivate |
| DE3309595A1 (de) * | 1983-03-17 | 1984-09-20 | Basf Ag, 6700 Ludwigshafen | Neue aminopropanolderivate von 1-(2-hydroxy-phenyl)-3-phenyl-propanolen, verfahren zu ihrer herstellung und diese enthaltende therapeutische mittel |
| FI832377A0 (fi) * | 1983-06-29 | 1983-06-29 | Star Oy Ab | Nytt foerfarande foer framstaellning av (r)-, (s)-eller (r,s)-1-(4'-alkylamido-2'-acetyl) fenoxi-3-alkylamino-2-propanoler |
| DE3856166T2 (de) * | 1987-09-29 | 1998-08-06 | Banyu Pharma Co Ltd | N-Acylaminosäurederivate und deren Verwendung |
| US6613942B1 (en) | 1997-07-01 | 2003-09-02 | Novo Nordisk A/S | Glucagon antagonists/inverse agonists |
| JP5070797B2 (ja) * | 2005-12-08 | 2012-11-14 | Ｊｎｃ株式会社 | 側方オキシラン化合物およびその重合体 |
| US8034815B2 (en) | 2007-01-11 | 2011-10-11 | Critical Outcome Technologies, Inc. | Compounds and method for treatment of cancer |
| CA2710039C (en) | 2007-12-26 | 2018-07-03 | Critical Outcome Technologies, Inc. | Semicarbazones, thiosemicarbazones and related compounds and methods for treatment of cancer |
| WO2010006438A1 (en) | 2008-07-17 | 2010-01-21 | Critical Outcome Technologies Inc. | Thiosemicarbazone inhibitor compounds and cancer treatment methods |
| CA2999435A1 (en) | 2010-04-01 | 2011-10-06 | Critical Outcome Technologies Inc. | Compounds and method for treatment of hiv |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2774766A (en) * | 1954-09-08 | 1956-12-18 | Hoffmann La Roche | Basic ethers |
| BE754604A (fr) * | 1969-08-08 | 1971-02-08 | Boehringer Sohn Ingelheim | Le 1-(2-nitrilophenoxy)-2-hydroxy-3-ethyl-aminopropane et ses sels |
-
1967
- 1967-05-16 GB GB2273567A patent/GB1231783A/en not_active Expired
-
1968
- 1968-05-13 SU SU1331581A patent/SU443509A3/ru active
- 1968-05-13 SU SU1241053A patent/SU449484A3/ru active
- 1968-05-14 DK DK224468AA patent/DK127060B/da unknown
- 1968-05-14 IS IS1741A patent/IS860B6/is unknown
- 1968-05-14 SE SE06518/68A patent/SE369894B/xx unknown
- 1968-05-14 NO NO1875/68A patent/NO125183B/no unknown
- 1968-05-15 FR FR151931A patent/FR1570087A/fr not_active Expired
- 1968-05-15 IE IE582/68A patent/IE32174B1/xx unknown
- 1968-05-15 MT MT557A patent/MTP557B/xx unknown
- 1968-05-15 BE BE715205D patent/BE715205A/xx unknown
- 1968-05-15 IL IL30001A patent/IL30001A/en unknown
- 1968-05-15 FR FR151932A patent/FR7616M/fr not_active Expired
- 1968-05-16 DE DE19681768468 patent/DE1768468A1/de active Pending
- 1968-05-16 NL NL6806946A patent/NL6806946A/xx unknown
- 1968-05-16 AT AT00822/70A patent/AT289826B/de not_active IP Right Cessation
- 1968-05-16 CH CH722668A patent/CH489467A/fr not_active IP Right Cessation
- 1968-05-16 AT AT470768A patent/AT286262B/de not_active IP Right Cessation
- 1968-05-16 ES ES353917A patent/ES353917A1/es not_active Expired
-
1972
- 1972-12-19 US US316508A patent/US3875149A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| FR1570087A (fr) | 1969-06-06 |
| ES353917A1 (es) | 1969-10-16 |
| IL30001A0 (en) | 1968-07-25 |
| IS860B6 (is) | 1974-05-22 |
| GB1231783A (en) | 1971-05-12 |
| CH489467A (fr) | 1970-04-30 |
| AT289826B (de) | 1971-03-15 |
| IE32174L (en) | 1968-11-16 |
| IL30001A (en) | 1973-07-30 |
| SU443509A3 (ru) | 1974-09-15 |
| AT286262B (de) | 1970-12-10 |
| MTP557B (en) | 1969-01-04 |
| FR7616M (fr) | 1970-01-19 |
| IS1741A7 (is) | 1968-11-17 |
| SE369894B (de) | 1974-09-23 |
| NL6806946A (de) | 1968-11-18 |
| US3875149A (en) | 1975-04-01 |
| DK127060B (da) | 1973-09-17 |
| BE715205A (fr) | 1968-11-18 |
| DE1768468A1 (de) | 1971-07-01 |
| SU449484A3 (ru) | 1974-11-05 |
| IE32174B1 (en) | 1973-05-02 |
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