CH620414A5 - - Google Patents

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Info

Publication number: CH620414A5
Authority: CH; Switzerland
Prior art keywords: atoms; alkyl; general formula; compound; carboxylic acids
Prior art date: 1975-06-09

Application number

CH730876A

Other languages

German (de)

English (en)

Inventor

Yutaka Kawamatsu

Takahiro Saraie

Eiko Imamiya

Yukihiko Hamuro

Original Assignee

Takeda Chemical Industries Ltd

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1975-06-09

Filing date

1976-06-09

Publication date

1980-11-28

1975-06-09 Priority claimed from GB24666/75A external-priority patent/GB1537838A/en

1975-09-29 Priority claimed from JP50118099A external-priority patent/JPS5242847A/ja

1976-04-19 Priority claimed from JP4487076A external-priority patent/JPS52128348A/ja

1976-06-09 Application filed by Takeda Chemical Industries Ltd filed Critical Takeda Chemical Industries Ltd

1980-11-28 Publication of CH620414A5 publication Critical patent/CH620414A5/de

Links

-1 vinyl compound Chemical class 0.000 claims description 46
125000004432 carbon atom Chemical group C* 0.000 claims description 38
238000006243 chemical reaction Methods 0.000 claims description 24
150000001875 compounds Chemical class 0.000 claims description 24
125000000217 alkyl group Chemical group 0.000 claims description 19
238000000034 method Methods 0.000 claims description 19
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 13
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
239000000460 chlorine Substances 0.000 claims description 8
239000012954 diazonium Substances 0.000 claims description 8
150000001989 diazonium salts Chemical class 0.000 claims description 8
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 6
229910052736 halogen Inorganic materials 0.000 claims description 6
229910052739 hydrogen Inorganic materials 0.000 claims description 6
239000001257 hydrogen Substances 0.000 claims description 6
230000007062 hydrolysis Effects 0.000 claims description 6
238000006460 hydrolysis reaction Methods 0.000 claims description 6
150000001408 amides Chemical class 0.000 claims description 5
239000003795 chemical substances by application Substances 0.000 claims description 5
230000002140 halogenating effect Effects 0.000 claims description 5
150000002367 halogens Chemical class 0.000 claims description 5
150000003839 salts Chemical class 0.000 claims description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 4
125000003884 phenylalkyl group Chemical group 0.000 claims description 4
238000002360 preparation method Methods 0.000 claims description 4
229920002554 vinyl polymer Polymers 0.000 claims description 4
125000003545 alkoxy group Chemical group 0.000 claims description 3
125000002947 alkylene group Chemical group 0.000 claims description 3
125000003118 aryl group Chemical group 0.000 claims description 3
QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 claims description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
150000001412 amines Chemical class 0.000 claims description 2
150000003863 ammonium salts Chemical class 0.000 claims description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
239000011575 calcium Substances 0.000 claims description 2
229910052791 calcium Inorganic materials 0.000 claims description 2
125000000753 cycloalkyl group Chemical group 0.000 claims description 2
125000004663 dialkyl amino group Chemical group 0.000 claims description 2
125000004986 diarylamino group Chemical group 0.000 claims description 2
150000002148 esters Chemical class 0.000 claims description 2
125000004494 ethyl ester group Chemical group 0.000 claims description 2
229910052744 lithium Inorganic materials 0.000 claims description 2
239000011777 magnesium Substances 0.000 claims description 2
229910052749 magnesium Inorganic materials 0.000 claims description 2
150000004702 methyl esters Chemical class 0.000 claims description 2
229910052760 oxygen Inorganic materials 0.000 claims description 2
239000001301 oxygen Substances 0.000 claims description 2
229910052700 potassium Inorganic materials 0.000 claims description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
229910052717 sulfur Inorganic materials 0.000 claims description 2
239000011593 sulfur Substances 0.000 claims description 2
150000001735 carboxylic acids Chemical class 0.000 claims 5
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims 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 claims 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
150000003857 carboxamides Chemical class 0.000 claims 1
125000005843 halogen group Chemical group 0.000 claims 1
125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
239000011591 potassium Substances 0.000 claims 1
239000011734 sodium Substances 0.000 claims 1
229910052708 sodium Inorganic materials 0.000 claims 1
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 30
238000002329 infrared spectrum Methods 0.000 description 20
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 19
239000002904 solvent Substances 0.000 description 17
239000000243 solution Substances 0.000 description 16
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
239000000203 mixture Substances 0.000 description 14
101150041968 CDC13 gene Proteins 0.000 description 13
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 13
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
239000007788 liquid Substances 0.000 description 12
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 11
229910000041 hydrogen chloride Inorganic materials 0.000 description 11
OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 11
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
239000000047 product Substances 0.000 description 9
238000003756 stirring Methods 0.000 description 9
239000002253 acid Substances 0.000 description 8
BERDEBHAJNAUOM-UHFFFAOYSA-N copper(i) oxide Chemical compound [Cu]O[Cu] BERDEBHAJNAUOM-UHFFFAOYSA-N 0.000 description 8
239000000126 substance Substances 0.000 description 7
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
239000003054 catalyst Substances 0.000 description 6
238000001816 cooling Methods 0.000 description 6
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 6
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
238000004458 analytical method Methods 0.000 description 5
235000019441 ethanol Nutrition 0.000 description 5
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 4
238000000921 elemental analysis Methods 0.000 description 4
150000004820 halides Chemical class 0.000 description 4
238000001953 recrystallisation Methods 0.000 description 4
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 4
ZVSCENGNXWPDPL-UHFFFAOYSA-N 2-methyl-2-phenylpropan-1-ol Chemical compound OCC(C)(C)C1=CC=CC=C1 ZVSCENGNXWPDPL-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 3
150000001450 anions Chemical class 0.000 description 3
229910052801 chlorine Inorganic materials 0.000 description 3
201000005577 familial hyperlipidemia Diseases 0.000 description 3
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
150000002828 nitro derivatives Chemical class 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
235000019260 propionic acid Nutrition 0.000 description 3
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 3
230000035484 reaction time Effects 0.000 description 3
239000007858 starting material Substances 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
ZIOMJGCTBNSXIK-UHFFFAOYSA-N 2-(4-aminophenoxy)-2-methyl-1-phenylpropan-1-one Chemical compound C=1C=CC=CC=1C(=O)C(C)(C)OC1=CC=C(N)C=C1 ZIOMJGCTBNSXIK-UHFFFAOYSA-N 0.000 description 2
PFCHFHIRKBAQGU-UHFFFAOYSA-N 3-hexanone Chemical compound CCCC(=O)CC PFCHFHIRKBAQGU-UHFFFAOYSA-N 0.000 description 2
CZGCEKJOLUNIFY-UHFFFAOYSA-N 4-Chloronitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C=C1 CZGCEKJOLUNIFY-UHFFFAOYSA-N 0.000 description 2
KIZXRDIROMPMKU-UHFFFAOYSA-N AL-294 Chemical compound C1=CC(CC(Cl)C(=O)OCC)=CC=C1OCC(C)(C)C1=CC=CC=C1 KIZXRDIROMPMKU-UHFFFAOYSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
229910021591 Copper(I) chloride Inorganic materials 0.000 description 2
229910021592 Copper(II) chloride Inorganic materials 0.000 description 2
JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 2
241000124008 Mammalia Species 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical class OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
239000002585 base Substances 0.000 description 2
238000009835 boiling Methods 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
229940125890 compound Ia Drugs 0.000 description 2
OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 2
QTMDXZNDVAMKGV-UHFFFAOYSA-L copper(ii) bromide Chemical compound [Cu+2].[Br-].[Br-] QTMDXZNDVAMKGV-UHFFFAOYSA-L 0.000 description 2
206010012601 diabetes mellitus Diseases 0.000 description 2
230000000055 hyoplipidemic effect Effects 0.000 description 2
230000002218 hypoglycaemic effect Effects 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
KPSSIOMAKSHJJG-UHFFFAOYSA-N neopentyl alcohol Chemical compound CC(C)(C)CO KPSSIOMAKSHJJG-UHFFFAOYSA-N 0.000 description 2
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 2
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
239000012312 sodium hydride Substances 0.000 description 2
229910000104 sodium hydride Inorganic materials 0.000 description 2
235000010288 sodium nitrite Nutrition 0.000 description 2
KUPSZFGCEDEEDL-UHFFFAOYSA-M sodium;2-chloro-3-[4-(2-methyl-2-phenylpropoxy)phenyl]propanoate Chemical compound [Na+].C=1C=CC=CC=1C(C)(C)COC1=CC=C(CC(Cl)C([O-])=O)C=C1 KUPSZFGCEDEEDL-UHFFFAOYSA-M 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical class OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
ZAOUOBFZAWXHFB-UHFFFAOYSA-N 1-(2,2-dimethylpropoxy)-4-nitrobenzene Chemical compound CC(C)(C)COC1=CC=C([N+]([O-])=O)C=C1 ZAOUOBFZAWXHFB-UHFFFAOYSA-N 0.000 description 1
SNUMJBFQBPXHEH-UHFFFAOYSA-N 1-(2-methyl-2-phenylpropoxy)-4-nitrobenzene Chemical compound C=1C=CC=CC=1C(C)(C)COC1=CC=C([N+]([O-])=O)C=C1 SNUMJBFQBPXHEH-UHFFFAOYSA-N 0.000 description 1
WFQDTOYDVUWQMS-UHFFFAOYSA-N 1-fluoro-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(F)C=C1 WFQDTOYDVUWQMS-UHFFFAOYSA-N 0.000 description 1
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
QMOSZSHTSOWPRX-UHFFFAOYSA-N 2-bromo-2-methyl-1-phenylpropan-1-one Chemical compound CC(C)(Br)C(=O)C1=CC=CC=C1 QMOSZSHTSOWPRX-UHFFFAOYSA-N 0.000 description 1
QCYIUWPQWBEKSP-UHFFFAOYSA-N 2-chloro-3-[4-(2-methyl-1-oxo-1-phenylpropan-2-yl)oxyphenyl]propanoic acid Chemical compound C=1C=CC=CC=1C(=O)C(C)(C)OC1=CC=C(CC(Cl)C(O)=O)C=C1 QCYIUWPQWBEKSP-UHFFFAOYSA-N 0.000 description 1
HLGRMVDRQKCDBT-UHFFFAOYSA-N 2-chloro-3-[4-(2-methyl-2-phenylpropoxy)phenyl]propanoic acid Chemical compound C=1C=CC=CC=1C(C)(C)COC1=CC=C(CC(Cl)C(O)=O)C=C1 HLGRMVDRQKCDBT-UHFFFAOYSA-N 0.000 description 1
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
GLLRNGJPGZMVCL-UHFFFAOYSA-N 4-(2-methyl-2-phenylpropoxy)aniline Chemical compound C=1C=CC=CC=1C(C)(C)COC1=CC=C(N)C=C1 GLLRNGJPGZMVCL-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
LGMGYMBBFKTKRS-UHFFFAOYSA-N C(CC)(=O)OC1=CC=C(C=C1)OCC(C)(C1=CC=CC=C1)C Chemical compound C(CC)(=O)OC1=CC=C(C=C1)OCC(C)(C1=CC=CC=C1)C LGMGYMBBFKTKRS-UHFFFAOYSA-N 0.000 description 1
101100328518 Caenorhabditis elegans cnt-1 gene Proteins 0.000 description 1
239000005749 Copper compound Substances 0.000 description 1
229910021589 Copper(I) bromide Inorganic materials 0.000 description 1
229910021590 Copper(II) bromide Inorganic materials 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
208000001840 Dandruff Diseases 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
241000530268 Lycaena heteronea Species 0.000 description 1
101000740206 Mus musculus Sal-like protein 1 Proteins 0.000 description 1
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical class CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
229910003074 TiCl4 Inorganic materials 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
ZSLFECMJERXWSY-UHFFFAOYSA-K aluminum;2-chloro-3-[4-(2-methyl-2-phenylpropoxy)phenyl]propanoate Chemical compound [Al+3].C=1C=CC=CC=1C(C)(C)COC1=CC=C(CC(Cl)C([O-])=O)C=C1.C=1C=CC=CC=1C(C)(C)COC1=CC=C(CC(Cl)C([O-])=O)C=C1.C=1C=CC=CC=1C(C)(C)COC1=CC=C(CC(Cl)C([O-])=O)C=C1 ZSLFECMJERXWSY-UHFFFAOYSA-K 0.000 description 1
239000003472 antidiabetic agent Substances 0.000 description 1
229940125708 antidiabetic agent Drugs 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
239000002775 capsule Substances 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
150000001768 cations Chemical class 0.000 description 1
125000000068 chlorophenyl group Chemical group 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
150000001880 copper compounds Chemical class 0.000 description 1
229910000365 copper sulfate Inorganic materials 0.000 description 1
XTVVROIMIGLXTD-UHFFFAOYSA-N copper(II) nitrate Chemical compound [Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O XTVVROIMIGLXTD-UHFFFAOYSA-N 0.000 description 1
ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
NKNDPYCGAZPOFS-UHFFFAOYSA-M copper(i) bromide Chemical compound Br[Cu] NKNDPYCGAZPOFS-UHFFFAOYSA-M 0.000 description 1
DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 1
OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
125000004473 dialkylaminocarbonyl group Chemical group 0.000 description 1
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000003480 eluent Substances 0.000 description 1
239000012156 elution solvent Substances 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
238000004508 fractional distillation Methods 0.000 description 1
239000008187 granular material Substances 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
238000002955 isolation Methods 0.000 description 1
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
ICZLSNFVMHZDCJ-UHFFFAOYSA-N n-[4-(2-methyl-1-oxo-1-phenylpropan-2-yl)oxyphenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1OC(C)(C)C(=O)C1=CC=CC=C1 ICZLSNFVMHZDCJ-UHFFFAOYSA-N 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
229910000069 nitrogen hydride Inorganic materials 0.000 description 1
231100000926 not very toxic Toxicity 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
238000010979 pH adjustment Methods 0.000 description 1
239000008188 pellet Substances 0.000 description 1
125000004344 phenylpropyl group Chemical group 0.000 description 1
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
239000000843 powder Substances 0.000 description 1
QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
229940080818 propionamide Drugs 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
238000010992 reflux Methods 0.000 description 1
238000000638 solvent extraction Methods 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical compound BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-N 0.000 description 1
XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
125000003944 tolyl group Chemical group 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/46—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups containing any of the groups, X being a hetero atom, Y being any atom, e.g. acylureas
- C07C275/48—Y being a hydrogen or a carbon atom
- C07C275/50—Y being a hydrogen or an acyclic carbon atom
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/27—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups
- C07C205/35—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C205/36—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system
- C07C205/37—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system the oxygen atom of at least one of the etherified hydroxy groups being further bound to an acyclic carbon atom

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CH730876A 1975-06-09 1976-06-09 CH620414A5 (sv)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
GB24666/75A GB1537838A (en)	1975-06-09	1975-06-09	Alpha-chlorocarboxylic acids
JP50118099A JPS5242847A (en)	1975-09-29	1975-09-29	Process for preparation of alpha-chlorocarboxylic acids
JP4487076A JPS52128348A (en)	1976-04-19	1976-04-19	Alpha-chlorocarboxylic acid derivatives and their preparation

Publications (1)

Publication Number	Publication Date
CH620414A5 true CH620414A5 (sv)	1980-11-28

Family

ID=27258358

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH730876A CH620414A5 (sv)	1975-06-09	1976-06-09

Country Status (15)

Country	Link
US (1)	US4080505A (sv)
AU (1)	AU500421B2 (sv)
BE (1)	BE842692A (sv)
CA (1)	CA1078403A (sv)
CH (1)	CH620414A5 (sv)
DE (1)	DE2625163A1 (sv)
DK (1)	DK251276A (sv)
ES (1)	ES448647A1 (sv)
FI (1)	FI761637A7 (sv)
FR (1)	FR2333771A1 (sv)
GR (1)	GR60269B (sv)
NL (1)	NL7606250A (sv)
NO (1)	NO761940L (sv)
PT (1)	PT65179B (sv)
SE (1)	SE7606441L (sv)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5657775A (en) *	1979-10-17	1981-05-20	Takeda Chem Ind Ltd	Thiazole derivative
AR017346A1 (es) *	1997-10-16	2001-09-05	Fmc Corp	PROCEDIMIENTO PARA LA PREPARACIoN DE UN HERBICIDA DE TRIAZOLINONA Y PROCEDIMIENTO PARA LA PREPARACIoN DE COMPUESTOS INTERMEDIARIOS.
GB0405033D0 (en) *	2004-03-05	2004-04-07	Karobio Ab	Novel pharmaceutical compositions
EP2266949B1 (en) *	2009-06-10	2013-05-29	Gregoria, Liberata	"Fast, high-efficiency quantitative synthesis of paracetamol"

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IL45396A0 (en) *	1973-08-23	1974-11-29	Beecham Group Ltd	Pharmaceutical compositions containing aryl aralkyl ether and thioether derivatives,certain such novel compounds and their preparation

1976
- 1976-06-03 PT PT65179A patent/PT65179B/pt unknown
- 1976-06-03 US US05/692,577 patent/US4080505A/en not_active Expired - Lifetime
- 1976-06-04 DE DE19762625163 patent/DE2625163A1/de not_active Withdrawn
- 1976-06-08 SE SE7606441A patent/SE7606441L/sv unknown
- 1976-06-08 BE BE167710A patent/BE842692A/xx unknown
- 1976-06-08 NO NO761940A patent/NO761940L/no unknown
- 1976-06-08 AU AU14726/76A patent/AU500421B2/en not_active Expired
- 1976-06-08 GR GR50929A patent/GR60269B/el unknown
- 1976-06-08 CA CA254,290A patent/CA1078403A/en not_active Expired
- 1976-06-08 FR FR7617253A patent/FR2333771A1/fr active Granted
- 1976-06-08 DK DK251276A patent/DK251276A/da unknown
- 1976-06-09 NL NL7606250A patent/NL7606250A/xx not_active Application Discontinuation
- 1976-06-09 CH CH730876A patent/CH620414A5/de not_active IP Right Cessation
- 1976-06-09 FI FI761637A patent/FI761637A7/fi not_active Application Discontinuation
1977
- 1977-06-08 ES ES448647A patent/ES448647A1/es not_active Expired

Also Published As

Publication number	Publication date
US4080505A (en)	1978-03-21
ES448647A1 (es)	1977-12-01
PT65179B (en)	1977-11-18
NL7606250A (nl)	1976-12-13
AU1472676A (en)	1977-12-15
BE842692A (fr)	1976-12-08
GR60269B (en)	1978-04-20
NO761940L (sv)	1976-12-10
SE7606441L (sv)	1976-12-10
FI761637A7 (sv)	1976-12-10
DE2625163A1 (de)	1976-12-30
PT65179A (en)	1976-07-01
DK251276A (da)	1976-12-10
CA1078403A (en)	1980-05-27
FR2333771A1 (fr)	1977-07-01
AU500421B2 (en)	1979-05-24
FR2333771B1 (sv)	1982-09-24

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DE2814556C2 (de)	1987-03-12	Substituierte Phenylessigsäurederivate, Verfahren zu deren Herstellung und sie enthaltende pharmazeutische Zusammensetzungen
DE2205815A1 (de)	1973-08-16	Piperazinderivate und verfahren zu ihrer herstellung
EP0007019A1 (de)	1980-01-23	Neue 5-Phenylpyrazol-Derivate und ihre Salze; Verfahren zu deren Herstellung und diese Verbindungen enthaltende Arzneimittel
EP0176846A2 (de)	1986-04-09	3-Amino-2-benzoyl-acrylsäurederivate und ein Verfahren zu ihrer Herstellung
DD200152A5 (de)	1983-03-23	Verfahren zur herstellung neuer 2-aminobenzoesaeure-derivate
EP0165422A1 (de)	1985-12-27	Neue substituierte Bis(4-aminophenyl)sulfone, ihre Herstellung und ihre Verwendung als Arzneimittel
DD280323A5 (de)	1990-07-04	Herstellung von zwischenprodukten der oxophthalazinyl-essigsaeuren mit benzothiazol- oder anderen heterocyclischen seitenketten
DE69024546T2 (de)	1996-08-29	Verfahren zur herstellung von amidoxim-derivaten
DE2637098A1 (de)	1977-02-24	Phenoxyalkylcarbonsaeurederivate und verfahren zu ihrer herstellung
EP0317845A2 (de)	1989-05-31	Substituierte Hydroxylamine
DE68903263T2 (de)	1993-05-19	Substituierte aromatische verbindungen mit zentraler nervensystem-wirkung.
DE3038593C2 (sv)	1988-11-10
WO2016146607A1 (de)	2016-09-22	Verfahren zur herstellung von (4s)-4-[4-cyano-2-(methylsulfonyl)phenyl]-3,6-dimethyl-2-oxo-1-[3-(trifluormethyl)phenyl]-1,2,3,4-tetrahydro pyrimidin-5-carbonitril
EP1636199A2 (de)	2006-03-22	Verfahren zur herstellung von phenylessig derivaten
CH620414A5 (sv)	1980-11-28
CH574921A5 (en)	1976-04-30	Anti-inflammatory alpha-aminophenyl carboxylic acids
CH638525A5 (de)	1983-09-30	3-(tetrazol-5-yl)-1-azaxanthone und verfahren zu ihrer herstellung.
EP0088282A1 (de)	1983-09-14	Neue Indanyl-Derivate, ihre Herstellung und Verwendung
EP0091044B1 (de)	1986-06-18	Verfahren zur Herstellung von 4-Hydroxy-3-(heterocyclocarbamoyl)-2H-1,2-benzothiazin-1,1-dioxiden
EP0014390A1 (de)	1980-08-20	2-Amino-8-cyclopropyl-5-oxo-5,8-dihydro-pyrido (2,3-d) pyrimidin-6-carbonsäuren, sie enthaltende Arzneimittel sowie Verfahren zu ihrer Herstellung
DE2825194C2 (sv)	1989-01-26
DE3816634A1 (de)	1988-11-24	Cyclobuten-3,4-dion-zwischenverbindungen, verfahren zu ihrer herstellung und ihre verwendung
EP0427161B1 (de)	1994-04-20	Picolylselenobenzamide von Aminopyridinen, Anilinen und Picolylaminen
DE2065698A1 (de)	1974-12-12	Verfahren zur herstellung von 2isopropyl-6-methyl-4(3h)-pyrimidon

Legal Events

Date	Code	Title	Description
1984-02-29	PL	Patent ceased
2024-10-31	PL	Patent ceased