PL83431B1 - - Google Patents
Download PDFInfo
- Publication number
- PL83431B1 PL83431B1 PL1972157362A PL15736272A PL83431B1 PL 83431 B1 PL83431 B1 PL 83431B1 PL 1972157362 A PL1972157362 A PL 1972157362A PL 15736272 A PL15736272 A PL 15736272A PL 83431 B1 PL83431 B1 PL 83431B1
- Authority
- PL
- Poland
- Prior art keywords
- biphenylyl
- fluoro
- acid
- general formula
- ketobutyric
- Prior art date
Links
- -1 4-biphenylyl Chemical group 0.000 claims description 41
- 150000001875 compounds Chemical class 0.000 claims description 18
- 239000002904 solvent Substances 0.000 claims description 14
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 150000002367 halogens Chemical group 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 150000007522 mineralic acids Chemical class 0.000 claims description 4
- 150000007524 organic acids Chemical class 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- CJDZICQLZGXQJF-UHFFFAOYSA-N 4-oxo-4-(4-phenylphenyl)butanamide Chemical class C1=CC(C(=O)CCC(=O)N)=CC=C1C1=CC=CC=C1 CJDZICQLZGXQJF-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 235000005985 organic acids Nutrition 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
- 150000002825 nitriles Chemical group 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000004193 piperazinyl group Chemical group 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 238000005576 amination reaction Methods 0.000 claims 1
- RHDGNLCLDBVESU-UHFFFAOYSA-N but-3-en-4-olide Chemical compound O=C1CC=CO1 RHDGNLCLDBVESU-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 36
- 238000002844 melting Methods 0.000 description 28
- 230000008018 melting Effects 0.000 description 28
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- 239000002253 acid Substances 0.000 description 22
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 21
- 150000001408 amides Chemical class 0.000 description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
- 239000000203 mixture Substances 0.000 description 19
- 239000000243 solution Substances 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000002244 precipitate Substances 0.000 description 14
- 238000003756 stirring Methods 0.000 description 14
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 12
- 239000000126 substance Substances 0.000 description 11
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 206010030113 Oedema Diseases 0.000 description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- 229910021529 ammonia Inorganic materials 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 8
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 241000700159 Rattus Species 0.000 description 7
- 239000005995 Aluminium silicate Substances 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 6
- 208000025865 Ulcer Diseases 0.000 description 6
- 235000012211 aluminium silicate Nutrition 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- WACQKHWOTAEEFS-UHFFFAOYSA-N cyclohexane;ethyl acetate Chemical compound CCOC(C)=O.C1CCCCC1 WACQKHWOTAEEFS-UHFFFAOYSA-N 0.000 description 6
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 229960002895 phenylbutazone Drugs 0.000 description 5
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 230000007059 acute toxicity Effects 0.000 description 4
- 231100000403 acute toxicity Toxicity 0.000 description 4
- 239000000679 carrageenan Substances 0.000 description 4
- 229940113118 carrageenan Drugs 0.000 description 4
- 235000010418 carrageenan Nutrition 0.000 description 4
- 229920001525 carrageenan Polymers 0.000 description 4
- 230000006698 induction Effects 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 230000001562 ulcerogenic effect Effects 0.000 description 4
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 4
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-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
- 230000003110 anti-inflammatory effect Effects 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 231100001274 therapeutic index Toxicity 0.000 description 3
- 231100000397 ulcer Toxicity 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- TYEYBOSBBBHJIV-UHFFFAOYSA-N 2-oxobutanoic acid Chemical compound CCC(=O)C(O)=O TYEYBOSBBBHJIV-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 230000002322 anti-exudative effect Effects 0.000 description 2
- UZBQIPPOMKBLAS-UHFFFAOYSA-N diethylazanide Chemical compound CC[N-]CC UZBQIPPOMKBLAS-UHFFFAOYSA-N 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 2
- YLGXILFCIXHCMC-JHGZEJCSSA-N methyl cellulose Chemical compound COC1C(OC)C(OC)C(COC)O[C@H]1O[C@H]1C(OC)C(OC)C(OC)OC1COC YLGXILFCIXHCMC-JHGZEJCSSA-N 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 2
- 230000001012 protector Effects 0.000 description 2
- 239000013049 sediment Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 210000002784 stomach Anatomy 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- HBGALFVDRUBTCE-UHFFFAOYSA-N 1,2-dichloroethane;propan-2-one Chemical compound CC(C)=O.ClCCCl HBGALFVDRUBTCE-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 1
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- PNPCRKVUWYDDST-UHFFFAOYSA-N 3-chloroaniline Chemical compound NC1=CC=CC(Cl)=C1 PNPCRKVUWYDDST-UHFFFAOYSA-N 0.000 description 1
- XCFZGTNKAXCMQO-UHFFFAOYSA-N 4-[4-(2,3-dichlorophenyl)phenyl]-4-oxobutanoic acid Chemical compound C1=CC(C(=O)CCC(=O)O)=CC=C1C1=CC=CC(Cl)=C1Cl XCFZGTNKAXCMQO-UHFFFAOYSA-N 0.000 description 1
- IMPPGHMHELILKG-UHFFFAOYSA-N 4-ethoxyaniline Chemical compound CCOC1=CC=C(N)C=C1 IMPPGHMHELILKG-UHFFFAOYSA-N 0.000 description 1
- AQDPGGRHNBRJKL-UHFFFAOYSA-N 4-oxo-4-(4-phenylphenyl)-n-propan-2-ylbutanamide Chemical compound C1=CC(C(=O)CCC(=O)NC(C)C)=CC=C1C1=CC=CC=C1 AQDPGGRHNBRJKL-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- APTHNDOPFRDPBL-UHFFFAOYSA-N C(C)NC(CCC(=O)C1=CC=C(C=C1)C1=C(C=CC=C1)F)=O Chemical compound C(C)NC(CCC(=O)C1=CC=C(C=C1)C1=C(C=CC=C1)F)=O APTHNDOPFRDPBL-UHFFFAOYSA-N 0.000 description 1
- UFACTWDSFYNOFG-UHFFFAOYSA-N C(CC)NC(CCC(=O)C1=CC=C(C=C1)C1=C(C=CC=C1)F)=O Chemical compound C(CC)NC(CCC(=O)C1=CC=C(C=C1)C1=C(C=CC=C1)F)=O UFACTWDSFYNOFG-UHFFFAOYSA-N 0.000 description 1
- WSSCHGLBRMRWRG-UHFFFAOYSA-N CCCNC(CCC(C(C=C1)=CC=C1C(C=CC=C1)=C1[N+]([O-])=O)=O)=O Chemical compound CCCNC(CCC(C(C=C1)=CC=C1C(C=CC=C1)=C1[N+]([O-])=O)=O)=O WSSCHGLBRMRWRG-UHFFFAOYSA-N 0.000 description 1
- XTYXOHHSCXNLEU-UHFFFAOYSA-N CNC(CCC(C(C=C1)=CC=C1C(C=CC=C1)=C1F)=O)=O Chemical compound CNC(CCC(C(C=C1)=CC=C1C(C=CC=C1)=C1F)=O)=O XTYXOHHSCXNLEU-UHFFFAOYSA-N 0.000 description 1
- NOTFZGFABLVTIG-UHFFFAOYSA-N Cyclohexylethyl acetate Chemical compound CC(=O)OCCC1CCCCC1 NOTFZGFABLVTIG-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- IDWFXUSABXKHKN-UHFFFAOYSA-N FC1=C(C=CC=C1)C1=CC=C(C=C1)C(CCC(=O)N)=O Chemical compound FC1=C(C=CC=C1)C1=CC=C(C=C1)C(CCC(=O)N)=O IDWFXUSABXKHKN-UHFFFAOYSA-N 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 206010020751 Hypersensitivity Diseases 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
- 206010022998 Irritability Diseases 0.000 description 1
- CCWPBBZEVLGEKP-UHFFFAOYSA-N NC(CCC(C(C=C1)=CC=C1C(C=C1)=CC=C1Cl)=O)=O Chemical compound NC(CCC(C(C=C1)=CC=C1C(C=C1)=CC=C1Cl)=O)=O CCWPBBZEVLGEKP-UHFFFAOYSA-N 0.000 description 1
- YYBVODDRQNXDHC-UHFFFAOYSA-N O=C(CCC(N1CCCCC1)=O)C(C=C1)=CC=C1C(C=CC=C1)=C1F Chemical compound O=C(CCC(N1CCCCC1)=O)C(C=C1)=CC=C1C(C=CC=C1)=C1F YYBVODDRQNXDHC-UHFFFAOYSA-N 0.000 description 1
- WRBDLAZXPNXXNL-UHFFFAOYSA-N O=C(CCC(N1CCOCC1)=O)C(C=C1)=CC=C1C(C=CC=C1)=C1F Chemical compound O=C(CCC(N1CCOCC1)=O)C(C=C1)=CC=C1C(C=CC=C1)=C1F WRBDLAZXPNXXNL-UHFFFAOYSA-N 0.000 description 1
- RXCXXXIESIJGNB-UHFFFAOYSA-N O=C1OC(C(C=C2)=CC=C2C(C=CC=C2)=C2F)=CC1 Chemical compound O=C1OC(C(C=C2)=CC=C2C(C=CC=C2)=C2F)=CC1 RXCXXXIESIJGNB-UHFFFAOYSA-N 0.000 description 1
- XUDKTMWTHZCNMS-UHFFFAOYSA-N O=C1OC(C(C=C2)=CC=C2C2=CC(Cl)=CC=C2)=CC1 Chemical compound O=C1OC(C(C=C2)=CC=C2C2=CC(Cl)=CC=C2)=CC1 XUDKTMWTHZCNMS-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 241000906446 Theraps Species 0.000 description 1
- RYKIURSPRVPERI-UHFFFAOYSA-N [N+](=O)([O-])C1=C(C=CC=C1)C1=CC=C(C=C1)C1=CCC(O1)=O Chemical compound [N+](=O)([O-])C1=C(C=CC=C1)C1=CC=C(C=C1)C1=CCC(O1)=O RYKIURSPRVPERI-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 208000026935 allergic disease Diseases 0.000 description 1
- 230000007815 allergy Effects 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000003501 anti-edematous effect Effects 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 230000000573 anti-seizure effect Effects 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- LZLOFGMGFADIKQ-UHFFFAOYSA-N benzene;1,4-dioxane Chemical compound C1COCCO1.C1=CC=CC=C1 LZLOFGMGFADIKQ-UHFFFAOYSA-N 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- BRYSLIOQYFVAJD-UHFFFAOYSA-N cyclohexane;1,2-dichloroethane Chemical compound ClCCCl.C1CCCCC1 BRYSLIOQYFVAJD-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000012024 dehydrating agents‎ Substances 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 208000000718 duodenal ulcer Diseases 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- ZPAKPRAICRBAOD-UHFFFAOYSA-N fenbufen Chemical class C1=CC(C(=O)CCC(=O)O)=CC=C1C1=CC=CC=C1 ZPAKPRAICRBAOD-UHFFFAOYSA-N 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 210000001156 gastric mucosa Anatomy 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 230000009931 harmful effect Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- XZOQSETVVCIPMZ-UHFFFAOYSA-N n-(3-chlorophenyl)-4-oxo-4-(4-phenylphenyl)butanamide Chemical compound ClC1=CC=CC(NC(=O)CCC(=O)C=2C=CC(=CC=2)C=2C=CC=CC=2)=C1 XZOQSETVVCIPMZ-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000001175 peptic effect Effects 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000000391 smoking effect Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/32—Oxygen atoms
- C07D307/33—Oxygen atoms in position 2, the oxygen atom being in its keto or unsubstituted enol form
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Obesity (AREA)
- Diabetes (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Hematology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Furan Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2141925A DE2141925A1 (de) | 1971-08-20 | 1971-08-20 | Neue 4-(4-biphenylyl)-4-oxo-buttersaeureamide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL83431B1 true PL83431B1 (OSRAM) | 1975-12-31 |
Family
ID=5817371
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1972157362A PL83431B1 (OSRAM) | 1971-08-20 | 1972-08-19 |
Country Status (10)
| Country | Link |
|---|---|
| JP (1) | JPS4829749A (OSRAM) |
| AT (5) | AT323722B (OSRAM) |
| AU (1) | AU4575272A (OSRAM) |
| DD (1) | DD99990A5 (OSRAM) |
| DE (1) | DE2141925A1 (OSRAM) |
| ES (6) | ES410835A1 (OSRAM) |
| HU (1) | HU163806B (OSRAM) |
| PL (1) | PL83431B1 (OSRAM) |
| RO (1) | RO59404A (OSRAM) |
| ZA (1) | ZA725709B (OSRAM) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS51119170A (en) * | 1975-04-10 | 1976-10-19 | Shimakura Kogyosho:Kk | Process and apparatus for producing a toothbrush |
-
1971
- 1971-08-20 DE DE2141925A patent/DE2141925A1/de active Pending
-
1972
- 1972-08-10 AT AT690473A patent/AT323722B/de not_active IP Right Cessation
- 1972-08-10 AT AT690573A patent/AT323723B/de not_active IP Right Cessation
- 1972-08-10 AT AT690572A patent/AT318583B/de not_active IP Right Cessation
- 1972-08-10 AT AT690373A patent/AT323721B/de not_active IP Right Cessation
- 1972-08-10 AT AT690673A patent/AT323724B/de not_active IP Right Cessation
- 1972-08-18 ZA ZA725709A patent/ZA725709B/xx unknown
- 1972-08-18 AU AU45752/72A patent/AU4575272A/en not_active Expired
- 1972-08-18 HU HUTO883A patent/HU163806B/hu unknown
- 1972-08-18 DD DD165129A patent/DD99990A5/xx unknown
- 1972-08-18 RO RO71986A patent/RO59404A/ro unknown
- 1972-08-19 PL PL1972157362A patent/PL83431B1/pl unknown
- 1972-08-19 JP JP47083254A patent/JPS4829749A/ja active Pending
-
1973
- 1973-01-20 ES ES410835A patent/ES410835A1/es not_active Expired
- 1973-01-20 ES ES410836A patent/ES410836A1/es not_active Expired
- 1973-01-20 ES ES410834A patent/ES410834A1/es not_active Expired
- 1973-01-20 ES ES410833A patent/ES410833A1/es not_active Expired
- 1973-01-20 ES ES410832A patent/ES410832A1/es not_active Expired
- 1973-01-20 ES ES410837A patent/ES410837A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| ES410834A1 (es) | 1975-12-16 |
| ES410836A1 (es) | 1975-12-16 |
| JPS4829749A (OSRAM) | 1973-04-19 |
| AT318583B (de) | 1974-10-25 |
| DD99990A5 (OSRAM) | 1973-09-05 |
| AT323724B (de) | 1975-07-25 |
| DE2141925A1 (de) | 1973-03-08 |
| ES410833A1 (es) | 1975-12-01 |
| ES410832A1 (es) | 1975-12-01 |
| AU4575272A (en) | 1974-02-21 |
| ES410837A1 (es) | 1975-12-01 |
| AT323721B (de) | 1975-07-25 |
| ES410835A1 (es) | 1975-12-16 |
| HU163806B (OSRAM) | 1973-10-27 |
| RO59404A (OSRAM) | 1976-06-15 |
| AT323722B (de) | 1975-07-25 |
| AT323723B (de) | 1975-07-25 |
| ZA725709B (en) | 1974-04-24 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4233302A (en) | Amine derivatives and pharmaceutical compositions containing them | |
| US4374990A (en) | Cyclic diamine derivatives | |
| US3865840A (en) | Process of preparing 1,4-diloweralkyl-3-loweralkoxy-carbonyl-2-acetates | |
| DE3340967C2 (de) | Aminderivate, Salze derselben, Verfahren zur Herstellung derselben sowie Anti-Ulcusmittel mit einem Gehalt derselben | |
| CH678427A5 (OSRAM) | ||
| PL126032B1 (en) | Process for preparing novel derivatives of 5-phenyl-2-hydroxytetrahydrofuran | |
| EP0028483B1 (en) | 1,2,4-triazole derivatives, processes for the preparation thereof and pharmaceutical compositions containing them | |
| EP0012866B1 (en) | New 3h-naphtho(1,2-d)imidazoles, processes for preparing them, compounds for use as antiinflammatory and antimicrobial agents and compositions for that use containing them | |
| GB1561411A (en) | 2-phenoxyphenyl pyrrolidines and pharmaceutical compositions containing them | |
| US3665011A (en) | Substituted phenylacetic acids and esters thereof | |
| US4115569A (en) | Cyclic diamine derivatives | |
| EP0001699B1 (en) | Derivatives of furyl compounds, their preparation and pharmaceutical compositions containing them | |
| EP0005559B1 (de) | Phenylaminothiophenessigsäuren, Verfahren zu ihrer Herstellung und sie enthaltende Arzneimittel | |
| PL83431B1 (OSRAM) | ||
| US3972994A (en) | Disubstituted azabicycloalkanes | |
| US4208420A (en) | New benzo [d] thiazole derivatives, process for their preparation and their therapeutic applications | |
| US5298503A (en) | N-(isoquinolin-5-ylsulphonyl) azacycloalkanes | |
| US4157340A (en) | N,N'-[Bis(N-cyanoguanyl)]cystamine derivatives | |
| DE68909757T2 (de) | Indanderivate, Verfahren zu ihrer Herstellung und erhaltene Zwischenprodukte, ihre Verwendung als Arzneimittel und diese enthaltende pharmazeutische Zusammensetzungen. | |
| US4599346A (en) | Propan-2-ol derivatives, a process for their production and medicaments containing these compounds | |
| US3939267A (en) | 4-Ethers of 3-amino-5-sulfamoylbenzoic acids | |
| GB2087869A (en) | Piperazine derivatives | |
| DK152843B (da) | Analogifremgangsmaade til fremstilling af n-substituerede 4-(3-trifluormethylphenyl)-1,2,3,6-tetrahydropyridiner og farmaceutisk acceptable salte deraf | |
| US4048321A (en) | Disubstituted azabicycloalkanes | |
| US3982018A (en) | 4-Ethers of 3-amino-5-sulfamoylbenzoic acids |