FI66833C - Foerfarande och mellanprodukt foer framstaellning av fenylalkylkarboxylsyraderivat - Google Patents

Foerfarande och mellanprodukt foer framstaellning av fenylalkylkarboxylsyraderivat Download PDF

Info

Publication number: FI66833C
Authority: FI; Finland
Prior art keywords: mixture; hydrogen; water; added; methyl
Prior art date: 1975-06-24

Application number

FI761833A

Other languages

English (en)

Finnish (fi)

Swedish (sv)

Other versions

FI761833A7 (da

FI66833B (fi

Inventor

Endre Palosi

Georgely Heja

Dezso Korbonits

Csaba Goenczi

Pal Kiss

Rudolf Szebeni

Nee Bako Erzsebet Molnar

Original Assignee

Chinoin Gyogyszer Es Vegyeszet

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.)

1975-06-24

Filing date

1976-06-23

Publication date

1984-12-10

1976-06-23 Application filed by Chinoin Gyogyszer Es Vegyeszet filed Critical Chinoin Gyogyszer Es Vegyeszet

1976-12-25 Publication of FI761833A7 publication Critical patent/FI761833A7/fi

1984-08-31 Publication of FI66833B publication Critical patent/FI66833B/fi

1984-12-10 Application granted granted Critical

1984-12-10 Publication of FI66833C publication Critical patent/FI66833C/fi

Links

OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 48
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 37
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 30
229910052739 hydrogen Inorganic materials 0.000 claims description 28
KLBIUKJOZFWCLW-UHFFFAOYSA-N thallium(iii) nitrate Chemical compound [Tl+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O KLBIUKJOZFWCLW-UHFFFAOYSA-N 0.000 claims description 24
239000001257 hydrogen Substances 0.000 claims description 19
239000002253 acid Substances 0.000 claims description 16
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
238000000034 method Methods 0.000 claims description 16
150000001875 compounds Chemical class 0.000 claims description 12
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
238000006243 chemical reaction Methods 0.000 claims description 10
238000002360 preparation method Methods 0.000 claims description 10
-1 phenoxy, benzoyl Chemical group 0.000 claims description 9
125000000217 alkyl group Chemical group 0.000 claims description 8
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
150000003839 salts Chemical class 0.000 claims description 7
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 claims description 6
229910052736 halogen Chemical group 0.000 claims description 5
150000002367 halogens Chemical group 0.000 claims description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 claims description 4
UEXCJVNBTNXOEH-UHFFFAOYSA-N Ethynylbenzene Chemical group C#CC1=CC=CC=C1 UEXCJVNBTNXOEH-UHFFFAOYSA-N 0.000 claims description 3
230000007062 hydrolysis Effects 0.000 claims description 3
238000006460 hydrolysis reaction Methods 0.000 claims description 3
230000002378 acidificating effect Effects 0.000 claims 1
150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 38
239000000203 mixture Substances 0.000 description 37
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
239000000243 solution Substances 0.000 description 25
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 18
239000011541 reaction mixture Substances 0.000 description 18
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 16
238000003756 stirring Methods 0.000 description 16
239000000706 filtrate Substances 0.000 description 13
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 12
239000012044 organic layer Substances 0.000 description 11
239000000047 product Substances 0.000 description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 9
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 9
238000009835 boiling Methods 0.000 description 8
FYWSTUCDSVYLPV-UHFFFAOYSA-N nitrooxythallium Chemical compound [Tl+].[O-][N+]([O-])=O FYWSTUCDSVYLPV-UHFFFAOYSA-N 0.000 description 8
229910052938 sodium sulfate Inorganic materials 0.000 description 8
235000011152 sodium sulphate Nutrition 0.000 description 8
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
239000008346 aqueous phase Substances 0.000 description 6
239000000725 suspension Substances 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 4
125000003435 aroyl group Chemical group 0.000 description 4
239000000543 intermediate Substances 0.000 description 4
239000003208 petroleum Substances 0.000 description 4
239000002904 solvent Substances 0.000 description 4
SDEOCRNJMPHIDU-UHFFFAOYSA-N 1-(2-methylpropyl)-4-prop-1-ynylbenzene Chemical group CC#CC1=CC=C(CC(C)C)C=C1 SDEOCRNJMPHIDU-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 3
125000004104 aryloxy group Chemical group 0.000 description 3
238000001816 cooling Methods 0.000 description 3
235000019441 ethanol Nutrition 0.000 description 3
125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 3
239000010410 layer Substances 0.000 description 3
239000007858 starting material Substances 0.000 description 3
PDHSXDCMCANTPE-UHFFFAOYSA-N 1-(1-chloroprop-1-enyl)-3-phenoxybenzene Chemical compound CC=C(Cl)C1=CC=CC(OC=2C=CC=CC=2)=C1 PDHSXDCMCANTPE-UHFFFAOYSA-N 0.000 description 2
DPRGJQPMWFNAFJ-UHFFFAOYSA-N 1-(3-phenoxyphenyl)propan-1-one Chemical compound CCC(=O)C1=CC=CC(OC=2C=CC=CC=2)=C1 DPRGJQPMWFNAFJ-UHFFFAOYSA-N 0.000 description 2
GPZIKPBHFMNTOH-UHFFFAOYSA-N 1-[4-(2-methylpropyl)phenyl]propan-1-one Chemical compound CCC(=O)C1=CC=C(CC(C)C)C=C1 GPZIKPBHFMNTOH-UHFFFAOYSA-N 0.000 description 2
RUPJOPCERIEGFU-UHFFFAOYSA-N 1-ethynyl-3-phenoxybenzene Chemical group C#CC1=CC=CC(OC=2C=CC=CC=2)=C1 RUPJOPCERIEGFU-UHFFFAOYSA-N 0.000 description 2
OBTDVRGUJLGMIN-UHFFFAOYSA-N 1-phenoxy-3-prop-1-ynylbenzene Chemical group CC#CC1=CC=CC(OC=2C=CC=CC=2)=C1 OBTDVRGUJLGMIN-UHFFFAOYSA-N 0.000 description 2
FHJFIDHAAZZYAQ-UHFFFAOYSA-N 2-fluoro-1-phenyl-4-prop-1-ynylbenzene Chemical group FC1=CC(C#CC)=CC=C1C1=CC=CC=C1 FHJFIDHAAZZYAQ-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 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
NFQDPEZMYRBUCU-UHFFFAOYSA-N [2-chloro-4-(1-chloroprop-1-enyl)phenyl]-thiophen-2-ylmethanone Chemical compound ClC1=CC(C(Cl)=CC)=CC=C1C(=O)C1=CC=CS1 NFQDPEZMYRBUCU-UHFFFAOYSA-N 0.000 description 2
NTZHARCRPHIAGJ-UHFFFAOYSA-N [3-(1-chloroprop-1-enyl)phenyl]-phenylmethanone Chemical compound CC=C(Cl)C1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 NTZHARCRPHIAGJ-UHFFFAOYSA-N 0.000 description 2
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
125000003710 aryl alkyl group Chemical group 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
239000005457 ice water Substances 0.000 description 2
YNZYUHPFNYBBFF-UHFFFAOYSA-N methyl 2-[4-(2-methylpropyl)phenyl]propanoate Chemical compound COC(=O)C(C)C1=CC=C(CC(C)C)C=C1 YNZYUHPFNYBBFF-UHFFFAOYSA-N 0.000 description 2
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
239000012071 phase Substances 0.000 description 2
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
238000010992 reflux Methods 0.000 description 2
238000000926 separation method Methods 0.000 description 2
239000011734 sodium Substances 0.000 description 2
BTFBUHBMTIPXPE-UHFFFAOYSA-N (2-chloro-4-prop-1-ynylphenyl)-thiophen-2-ylmethanone Chemical compound ClC1=CC(C#CC)=CC=C1C(=O)C1=CC=CS1 BTFBUHBMTIPXPE-UHFFFAOYSA-N 0.000 description 1
IPHWOCLLPTVXOY-UHFFFAOYSA-N (4-prop-1-ynylphenyl)-thiophen-2-ylmethanone Chemical compound C1=CC(C#CC)=CC=C1C(=O)C1=CC=CS1 IPHWOCLLPTVXOY-UHFFFAOYSA-N 0.000 description 1
RSWQGTWDERENIR-UHFFFAOYSA-N (4-prop-2-ynylphenyl)-thiophen-2-ylmethanone Chemical group C1(=CC=CS1)C(=O)C1=CC=C(C=C1)CC#C RSWQGTWDERENIR-UHFFFAOYSA-N 0.000 description 1
125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
SGDQDYNGZNZGIZ-UHFFFAOYSA-N 1-(1-chloroprop-1-enyl)-4-(2-methylpropyl)benzene Chemical compound CC=C(Cl)C1=CC=C(CC(C)C)C=C1 SGDQDYNGZNZGIZ-UHFFFAOYSA-N 0.000 description 1
KSQSNIADOOKZAT-UHFFFAOYSA-N 1-(3-benzoylphenyl)propan-1-one Chemical compound CCC(=O)C1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 KSQSNIADOOKZAT-UHFFFAOYSA-N 0.000 description 1
FZCDBGYCFVKRDV-UHFFFAOYSA-N 1-(3-phenoxyphenyl)ethanone Chemical compound CC(=O)C1=CC=CC(OC=2C=CC=CC=2)=C1 FZCDBGYCFVKRDV-UHFFFAOYSA-N 0.000 description 1
FCJNODBVCAQFTP-UHFFFAOYSA-N 1-phenyl-2-prop-2-ynylbenzene Chemical group C#CCC1=CC=CC=C1C1=CC=CC=C1 FCJNODBVCAQFTP-UHFFFAOYSA-N 0.000 description 1
LEMRHTTWKDVQEI-UHFFFAOYSA-N 2-(3-phenoxyphenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(OC=2C=CC=CC=2)=C1 LEMRHTTWKDVQEI-UHFFFAOYSA-N 0.000 description 1
CMWTZPSULFXXJA-UHFFFAOYSA-N 2-(6-methoxy-2-naphthalenyl)propanoic acid Chemical compound C1=C(C(C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-UHFFFAOYSA-N 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
229910002651 NO3 Inorganic materials 0.000 description 1
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
PKOBTMHCMFVQPQ-UHFFFAOYSA-N [4-(1-chloroprop-1-enyl)phenyl]-thiophen-2-ylmethanone Chemical compound C1=CC(C(Cl)=CC)=CC=C1C(=O)C1=CC=CS1 PKOBTMHCMFVQPQ-UHFFFAOYSA-N 0.000 description 1
238000005903 acid hydrolysis reaction Methods 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
150000001336 alkenes Chemical class 0.000 description 1
230000003110 anti-inflammatory effect Effects 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000003125 aqueous solvent Substances 0.000 description 1
239000002585 base Substances 0.000 description 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
QBWCMBCROVPCKQ-UHFFFAOYSA-N chlorous acid Chemical compound OCl=O QBWCMBCROVPCKQ-UHFFFAOYSA-N 0.000 description 1
238000004042 decolorization Methods 0.000 description 1
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
238000004821 distillation Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
238000004880 explosion Methods 0.000 description 1
238000000605 extraction Methods 0.000 description 1
SYTBZMRGLBWNTM-UHFFFAOYSA-N flurbiprofen Chemical compound FC1=CC(C(C(O)=O)C)=CC=C1C1=CC=CC=C1 SYTBZMRGLBWNTM-UHFFFAOYSA-N 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
KXUHSQYYJYAXGZ-UHFFFAOYSA-N isobutylbenzene Chemical compound CC(C)CC1=CC=CC=C1 KXUHSQYYJYAXGZ-UHFFFAOYSA-N 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
DDBREPKUVSBGFI-UHFFFAOYSA-N phenobarbital Chemical compound C=1C=CC=CC=1C1(CC)C(=O)NC(=O)NC1=O DDBREPKUVSBGFI-UHFFFAOYSA-N 0.000 description 1
XKSZRKFJTJZDBY-UHFFFAOYSA-N phenyl-(2-prop-1-ynylphenyl)methanone Chemical group CC#CC1=CC=CC=C1C(=O)C1=CC=CC=C1 XKSZRKFJTJZDBY-UHFFFAOYSA-N 0.000 description 1
NAFYIVBGSAMIFS-UHFFFAOYSA-N phenyl-(3-prop-1-ynylphenyl)methanone Chemical compound CC#CC1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 NAFYIVBGSAMIFS-UHFFFAOYSA-N 0.000 description 1
DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
MWWATHDPGQKSAR-UHFFFAOYSA-N propyne Chemical group CC#C MWWATHDPGQKSAR-UHFFFAOYSA-N 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000006748 scratching Methods 0.000 description 1
230000002393 scratching effect Effects 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
MDKGKXOCJGEUJW-UHFFFAOYSA-N suprofen Chemical compound C1=CC(C(C(O)=O)C)=CC=C1C(=O)C1=CC=CS1 MDKGKXOCJGEUJW-UHFFFAOYSA-N 0.000 description 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
229910052716 thallium Inorganic materials 0.000 description 1
BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical compound [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
238000001665 trituration Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/22—Radicals substituted by doubly bound hetero atoms, or by two hetero atoms other than halogen singly bound to the same carbon atom
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/30—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/52—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen
- C07C57/58—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
- C07C59/66—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings
- C07C59/68—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings the oxygen atom of the ether group being bound to a non-condensed six-membered aromatic ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/76—Unsaturated compounds containing keto groups
- C07C59/84—Unsaturated compounds containing keto groups containing six membered aromatic rings

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Heterocyclic Compounds Containing Sulfur Atoms (AREA)

FI761833A 1975-06-24 1976-06-23 Foerfarande och mellanprodukt foer framstaellning av fenylalkylkarboxylsyraderivat FI66833C (fi)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
HUCI001595		1975-06-24
HU75CI1595A HU173576B (hu)	1975-06-24	1975-06-24	Sposob poluchenija zamehhjonnykh fenil-alkil-karbonovykh kislot

Publications (3)

Publication Number	Publication Date
FI761833A7 FI761833A7 (da)	1976-12-25
FI66833B FI66833B (fi)	1984-08-31
FI66833C true FI66833C (fi)	1984-12-10

Family

ID=10994574

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
FI761833A FI66833C (fi)	1975-06-24	1976-06-23	Foerfarande och mellanprodukt foer framstaellning av fenylalkylkarboxylsyraderivat

Country Status (10)

Country	Link
JP (1)	JPS5236642A (da)
CH (1)	CH613936A5 (da)
DK (1)	DK281576A (da)
ES (1)	ES449023A1 (da)
FI (1)	FI66833C (da)
GB (1)	GB1552202A (da)
HU (1)	HU173576B (da)
NL (1)	NL7606830A (da)
SE (1)	SE432588B (da)
SU (1)	SU927109A3 (da)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
YU39220B (en) *	1976-10-18	1984-08-31	Lek Tovarna Farmacevtskih	Process for preparing 2-(3-benzoylphenyl)-propionic acid
JPS5535056A (en) *	1978-09-04	1980-03-11	Hamari Yakuhin Kogyo Kk	3-substituted acetophenone and its preparation
JPS5561132A (en) *	1978-10-31	1980-05-08	Nippon Technical Co Ltd	Channel selector of electronic tuning receiver
US4528114A (en) *	1981-12-18	1985-07-09	Hoffmann-La Roche Inc.	Acetylenes
DE3802619C1 (da) *	1988-01-29	1989-09-07	Hoechst Ag, 6230 Frankfurt, De

1975
- 1975-06-24 HU HU75CI1595A patent/HU173576B/hu unknown
1976
- 1976-06-18 ES ES449023A patent/ES449023A1/es not_active Expired
- 1976-06-22 SE SE7607167A patent/SE432588B/xx unknown
- 1976-06-23 DK DK281576A patent/DK281576A/da not_active Application Discontinuation
- 1976-06-23 FI FI761833A patent/FI66833C/fi not_active IP Right Cessation
- 1976-06-23 GB GB26189/76A patent/GB1552202A/en not_active Expired
- 1976-06-23 JP JP51073372A patent/JPS5236642A/ja active Pending
- 1976-06-23 NL NL7606830A patent/NL7606830A/xx not_active Application Discontinuation
- 1976-06-24 SU SU762375571A patent/SU927109A3/ru active
- 1976-06-24 CH CH811576A patent/CH613936A5/xx not_active IP Right Cessation

Also Published As

Publication number	Publication date
CH613936A5 (en)	1979-10-31
SU927109A3 (ru)	1982-05-07
FI761833A7 (da)	1976-12-25
HU173576B (hu)	1979-06-28
SE432588B (sv)	1984-04-09
ES449023A1 (es)	1977-12-01
DK281576A (da)	1976-12-25
FI66833B (fi)	1984-08-31
GB1552202A (en)	1979-09-12
JPS5236642A (en)	1977-03-22
NL7606830A (nl)	1976-12-28
SE7607167L (sv)	1976-12-25

Legal Events

Date	Code	Title	Description
2004-08-31	MM	Patent lapsed	Owner name: CHINOIN GYOGUSZER ES VEGYESZETI TERMEKEK

Publication	Publication Date	Title
FI66833C (fi)	1984-12-10	Foerfarande och mellanprodukt foer framstaellning av fenylalkylkarboxylsyraderivat
DK163056B (da)	1992-01-13	Analogifremgangsmaade til fremstilling af alfa-sulfonyloxyketonacetaler
US4675418A (en)	1987-06-23	Process for preparing alkanoic acids or esters thereof by rearrangement of alpha-halo-ketones in protic medium and in the presence of a non-noble metal salt
US4317920A (en)	1982-03-02	Arylacetic acid derivatives
US4154743A (en)	1979-05-15	3-Oxobenzofuranyl-2-idenyl, haloacetic acids
US4393008A (en)	1983-07-12	2-Cyano-2-(3-phenoxy-phenyl)-propionic acid amide and preparation thereof
JPH0670064B2 (ja)	1994-09-07	二環性イミダゾ−ル誘導体
EP0026505B1 (en)	1982-09-15	7,8-substituted-1-phenyl-2,3,4,5-tetrahydro-1-h-3-benzazepines
EP0309626B1 (en)	1992-05-06	Process for the preparation of dibenzothiepin derivative
HU190101B (en)	1986-08-28	Process for preparing 2,2-dimethyl-3-aryl-cyclopropane-carboxylic acid derivatives
JP2719742B2 (ja)	1998-02-25	フェニルチアゾール誘導体
US4891433A (en)	1990-01-02	Process for the preparation of dibenzothiepin derivative
US3442890A (en)	1969-05-06	Substituted 3-benzazocin-16-ones
US4385004A (en)	1983-05-24	Esters of ortho-allylphenol useful for the preparation of arylacetic acid derivatives
US4465855A (en)	1984-08-14	Process for the preparation of arylacetic acid derivatives
HU198073B (en)	1989-07-28	Process for producing (+)-3-(3-pyridyl)-1h, 3h-pyrrolo (1,2-c/thiazole-7-carboxylic acid
JPS6284064A (ja)	1987-04-17	３−パ−フルオロアルキル−５−ヒドロキシイソオキサゾ−ル類
CY1193A (en)	1983-10-07	Process for preparing thiazoles
HU204265B (en)	1991-12-30	Process for producing thienyl-chloro-acetamide
FI62049B (fi)	1982-07-30	Foerfarande foer framstaellning av indanderivat
JP2549997B2 (ja)	1996-10-30	新規ハロケタール化合物
JPS644508B2 (da)	1989-01-25
US4453005A (en)	1984-06-05	Process for preparing substituted phenylalkenoic acids
FI66343B (fi)	1984-06-29	Foerfarande foer framstaellning av alfa-naftylpropionsyraderivat
JPS584698B2 (ja)	1983-01-27	２−（３−ベンゾイルフエニル）プロピオン酸の製造方法