IL31679A - History of thiazole - Google Patents

History of thiazole

Info

Publication number: IL31679A
Authority: IL; Israel
Prior art keywords: stands; hydrogen; formula; radical; carbon atoms
Prior art date: 1968-03-22

Application number

IL31679A

Other languages

English (en)

Hebrew (he)

Original Assignee

Ici 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.)

1968-03-22

Filing date

1969-02-23

Publication date

1972-08-30

1969-02-23 Application filed by Ici Ltd filed Critical Ici Ltd

1972-08-30 Publication of IL31679A publication Critical patent/IL31679A/en

Links

150000007979 thiazole derivatives Chemical class 0.000 title claims description 15
-1 alkyl radical Chemical class 0.000 claims description 44
150000001875 compounds Chemical class 0.000 claims description 41
229910052739 hydrogen Inorganic materials 0.000 claims description 38
239000001257 hydrogen Substances 0.000 claims description 38
239000000203 mixture Substances 0.000 claims description 35
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 31
125000004432 carbon atom Chemical group C* 0.000 claims description 30
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 25
150000003839 salts Chemical class 0.000 claims description 23
231100000252 nontoxic Toxicity 0.000 claims description 19
230000003000 nontoxic effect Effects 0.000 claims description 19
238000000034 method Methods 0.000 claims description 18
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
229910052783 alkali metal Inorganic materials 0.000 claims description 16
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 15
238000004519 manufacturing process Methods 0.000 claims description 14
239000000460 chlorine Substances 0.000 claims description 13
229910052801 chlorine Inorganic materials 0.000 claims description 13
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 12
150000001340 alkali metals Chemical group 0.000 claims description 10
239000007864 aqueous solution Substances 0.000 claims description 9
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 9
239000003795 chemical substances by application Substances 0.000 claims description 9
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
150000003254 radicals Chemical class 0.000 claims description 8
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 7
229910052794 bromium Inorganic materials 0.000 claims description 7
150000002431 hydrogen Chemical class 0.000 claims description 7
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 6
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 6
125000004495 thiazol-4-yl group Chemical group S1C=NC(=C1)* 0.000 claims description 6
150000003557 thiazoles Chemical class 0.000 claims description 6
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 description 5
239000002253 acid Substances 0.000 claims description 5
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 5
150000003863 ammonium salts Chemical class 0.000 claims description 5
229910052708 sodium Inorganic materials 0.000 claims description 5
239000011734 sodium Substances 0.000 claims description 5
125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 claims description 5
150000004703 alkoxides Chemical class 0.000 claims description 4
150000001408 amides Chemical class 0.000 claims description 4
150000004678 hydrides Chemical class 0.000 claims description 4
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 4
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 3
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
239000004411 aluminium Substances 0.000 claims description 3
229910052782 aluminium Inorganic materials 0.000 claims description 3
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 3
230000003110 anti-inflammatory effect Effects 0.000 claims description 3
125000001246 bromo group Chemical group Br* 0.000 claims description 3
QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims description 3
229910052731 fluorine Inorganic materials 0.000 claims description 3
239000011737 fluorine Substances 0.000 claims description 3
125000005843 halogen group Chemical group 0.000 claims description 3
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical class [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 2
229940121948 Muscarinic receptor antagonist Drugs 0.000 claims description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
229940116731 Uricosuric agent Drugs 0.000 claims description 2
230000002152 alkylating effect Effects 0.000 claims description 2
159000000013 aluminium salts Chemical class 0.000 claims description 2
229910000329 aluminium sulfate Inorganic materials 0.000 claims description 2
229940069428 antacid Drugs 0.000 claims description 2
239000003159 antacid agent Substances 0.000 claims description 2
239000003242 anti bacterial agent Substances 0.000 claims description 2
230000001458 anti-acid effect Effects 0.000 claims description 2
239000003429 antifungal agent Substances 0.000 claims description 2
229940121375 antifungal agent Drugs 0.000 claims description 2
125000004429 atom Chemical group 0.000 claims description 2
239000000812 cholinergic antagonist Substances 0.000 claims description 2
239000006071 cream Substances 0.000 claims description 2
125000005265 dialkylamine group Chemical group 0.000 claims description 2
239000003085 diluting agent Substances 0.000 claims description 2
125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
229910052740 iodine Inorganic materials 0.000 claims description 2
239000002085 irritant Substances 0.000 claims description 2
239000006210 lotion Substances 0.000 claims description 2
239000002674 ointment Substances 0.000 claims description 2
150000007530 organic bases Chemical class 0.000 claims description 2
239000006187 pill Substances 0.000 claims description 2
229910052700 potassium Inorganic materials 0.000 claims description 2
239000011591 potassium Substances 0.000 claims description 2
239000003542 rubefacient Substances 0.000 claims description 2
239000000829 suppository Substances 0.000 claims description 2
230000000699 topical effect Effects 0.000 claims description 2
ZNEOHLHCKGUAEB-UHFFFAOYSA-N trimethylphenylammonium Chemical compound C[N+](C)(C)C1=CC=CC=C1 ZNEOHLHCKGUAEB-UHFFFAOYSA-N 0.000 claims description 2
239000003383 uricosuric agent Substances 0.000 claims description 2
239000007900 aqueous suspension Substances 0.000 claims 2
239000003826 tablet Substances 0.000 claims 2
125000000217 alkyl group Chemical group 0.000 claims 1
229940125715 antihistaminic agent Drugs 0.000 claims 1
239000000739 antihistaminic agent Substances 0.000 claims 1
239000002585 base Substances 0.000 claims 1
239000002775 capsule Substances 0.000 claims 1
238000001311 chemical methods and process Methods 0.000 claims 1
230000000694 effects Effects 0.000 claims 1
VMWJCFLUSKZZDX-UHFFFAOYSA-N n,n-dimethylmethanamine Chemical compound [CH2]N(C)C VMWJCFLUSKZZDX-UHFFFAOYSA-N 0.000 claims 1
239000000126 substance Substances 0.000 claims 1
230000000304 vasodilatating effect Effects 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 40
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 16
239000012312 sodium hydride Substances 0.000 description 16
229910000104 sodium hydride Inorganic materials 0.000 description 16
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
239000007787 solid Substances 0.000 description 12
239000000243 solution Substances 0.000 description 12
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 10
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
239000000725 suspension Substances 0.000 description 9
229960000583 acetic acid Drugs 0.000 description 7
238000006243 chemical reaction Methods 0.000 description 7
238000001914 filtration Methods 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
238000003756 stirring Methods 0.000 description 6
IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 5
239000000284 extract Substances 0.000 description 5
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 5
229910052943 magnesium sulfate Inorganic materials 0.000 description 5
235000019341 magnesium sulphate Nutrition 0.000 description 5
238000010992 reflux Methods 0.000 description 5
229910052938 sodium sulfate Inorganic materials 0.000 description 5
235000011152 sodium sulphate Nutrition 0.000 description 5
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
238000002425 crystallisation Methods 0.000 description 4
239000006185 dispersion Substances 0.000 description 4
239000003208 petroleum Substances 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
230000003226 decolorizating effect Effects 0.000 description 3
238000000354 decomposition reaction Methods 0.000 description 3
239000012362 glacial acetic acid Substances 0.000 description 3
239000012442 inert solvent Substances 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
239000000047 product Substances 0.000 description 3
229910000029 sodium carbonate Inorganic materials 0.000 description 3
239000007858 starting material Substances 0.000 description 3
WIHGWLVPWHPMIF-UHFFFAOYSA-N 2-bromo-4-(4-bromophenyl)-1,3-thiazole Chemical compound S1C(Br)=NC(C=2C=CC(Br)=CC=2)=C1 WIHGWLVPWHPMIF-UHFFFAOYSA-N 0.000 description 2
OHDZDHHETRGNRY-UHFFFAOYSA-N 4-(4-bromophenyl)-2-methyl-1,3-thiazole Chemical compound S1C(C)=NC(C=2C=CC(Br)=CC=2)=C1 OHDZDHHETRGNRY-UHFFFAOYSA-N 0.000 description 2
VILMQRABALTXKG-UHFFFAOYSA-N 5-(4-chlorophenyl)-2-methyl-1,3-thiazole Chemical compound S1C(C)=NC=C1C1=CC=C(Cl)C=C1 VILMQRABALTXKG-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-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
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
125000000068 chlorophenyl group Chemical group 0.000 description 2
OROGSEYTTFOCAN-DNJOTXNNSA-N codeine Chemical compound C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC OROGSEYTTFOCAN-DNJOTXNNSA-N 0.000 description 2
IKMSCLUUZQEVND-UHFFFAOYSA-N diethyl 2-[4-(4-bromophenyl)-1,3-thiazol-2-yl]propanedioate Chemical compound BrC1=CC=C(C=C1)C=1N=C(SC1)C(C(=O)OCC)C(=O)OCC IKMSCLUUZQEVND-UHFFFAOYSA-N 0.000 description 2
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
ZYPQVJVSLBBPAC-UHFFFAOYSA-N dimethyl 2-[5-(4-chlorophenyl)-1,3-thiazol-2-yl]propanedioate Chemical compound ClC1=CC=C(C=C1)C1=CN=C(S1)C(C(=O)OC)C(=O)OC ZYPQVJVSLBBPAC-UHFFFAOYSA-N 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
239000008187 granular material Substances 0.000 description 2
CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
239000000463 material Substances 0.000 description 2
YNBADRVTZLEFNH-UHFFFAOYSA-N methyl nicotinate Chemical compound COC(=O)C1=CC=CN=C1 YNBADRVTZLEFNH-UHFFFAOYSA-N 0.000 description 2
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
239000012457 nonaqueous media Substances 0.000 description 2
239000008194 pharmaceutical composition Substances 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
239000011369 resultant mixture Substances 0.000 description 2
239000002904 solvent Substances 0.000 description 2
DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
WHTVZRBIWZFKQO-AWEZNQCLSA-N (S)-chloroquine Chemical compound ClC1=CC=C2C(N[C@@H](C)CCCN(CC)CC)=CC=NC2=C1 WHTVZRBIWZFKQO-AWEZNQCLSA-N 0.000 description 1
LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 1
PISMJKGQNDOCGA-UHFFFAOYSA-N 2-(1,3-thiazol-4-yl)acetic acid Chemical compound OC(=O)CC1=CSC=N1 PISMJKGQNDOCGA-UHFFFAOYSA-N 0.000 description 1
PXBSHTWLLVDXIH-UHFFFAOYSA-N 2-methyl-5-phenyl-1,3-oxazole Chemical compound O1C(C)=NC=C1C1=CC=CC=C1 PXBSHTWLLVDXIH-UHFFFAOYSA-N 0.000 description 1
PJJGZPJJTHBVMX-UHFFFAOYSA-N 5,7-Dihydroxyisoflavone Chemical compound C=1C(O)=CC(O)=C(C2=O)C=1OC=C2C1=CC=CC=C1 PJJGZPJJTHBVMX-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
BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
235000002566 Capsicum Nutrition 0.000 description 1
240000008574 Capsicum frutescens Species 0.000 description 1
229920002261 Corn starch Polymers 0.000 description 1
QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
PWWVAXIEGOYWEE-UHFFFAOYSA-N Isophenergan Chemical compound C1=CC=C2N(CC(C)N(C)C)C3=CC=CC=C3SC2=C1 PWWVAXIEGOYWEE-UHFFFAOYSA-N 0.000 description 1
235000019759 Maize starch Nutrition 0.000 description 1
229930193140 Neomycin Natural products 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
229960001138 acetylsalicylic acid Drugs 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
230000006978 adaptation Effects 0.000 description 1
150000001350 alkyl halides Chemical class 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
229910021502 aluminium hydroxide Inorganic materials 0.000 description 1
230000003444 anaesthetic effect Effects 0.000 description 1
230000000202 analgesic effect Effects 0.000 description 1
229940040526 anhydrous sodium acetate Drugs 0.000 description 1
230000001760 anti-analgesic effect Effects 0.000 description 1
230000000844 anti-bacterial effect Effects 0.000 description 1
239000002260 anti-inflammatory agent Substances 0.000 description 1
230000001754 anti-pyretic effect Effects 0.000 description 1
229940088710 antibiotic agent Drugs 0.000 description 1
239000001390 capsicum minimum Substances 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
FUFVKLQESJNNAN-RIMUKSHESA-M chembl1200851 Chemical compound [Br-].O([C@H]1C[C@H]2CC[C@@H](C1)[N+]2(C)C)C(=O)C(O)C1=CC=CC=C1 FUFVKLQESJNNAN-RIMUKSHESA-M 0.000 description 1
239000002026 chloroform extract Substances 0.000 description 1
229960003677 chloroquine Drugs 0.000 description 1
WHTVZRBIWZFKQO-UHFFFAOYSA-N chloroquine Natural products ClC1=CC=C2C(NC(C)CCCN(CC)CC)=CC=NC2=C1 WHTVZRBIWZFKQO-UHFFFAOYSA-N 0.000 description 1
229960004126 codeine Drugs 0.000 description 1
239000000356 contaminant Substances 0.000 description 1
238000010908 decantation Methods 0.000 description 1
CBICJNRWSHCWDC-UHFFFAOYSA-N diethyl 2-[5-(4-chlorophenyl)-1,3-thiazol-2-yl]propanedioate Chemical compound ClC1=CC=C(C=C1)C1=CN=C(S1)C(C(=O)OCC)C(=O)OCC CBICJNRWSHCWDC-UHFFFAOYSA-N 0.000 description 1
238000010828 elution Methods 0.000 description 1
238000000605 extraction Methods 0.000 description 1
LPEPZBJOKDYZAD-UHFFFAOYSA-N flufenamic acid Chemical compound OC(=O)C1=CC=CC=C1NC1=CC=CC(C(F)(F)F)=C1 LPEPZBJOKDYZAD-UHFFFAOYSA-N 0.000 description 1
229960004369 flufenamic acid Drugs 0.000 description 1
238000007429 general method Methods 0.000 description 1
150000002391 heterocyclic compounds Chemical class 0.000 description 1
229960003246 homatropine methylbromide Drugs 0.000 description 1
OROGSEYTTFOCAN-UHFFFAOYSA-N hydrocodone Natural products C1C(N(CCC234)C)C2C=CC(O)C3OC2=C4C1=CC=C2OC OROGSEYTTFOCAN-UHFFFAOYSA-N 0.000 description 1
229950009183 ibufenac Drugs 0.000 description 1
CYWFCPPBTWOZSF-UHFFFAOYSA-N ibufenac Chemical compound CC(C)CC1=CC=C(CC(O)=O)C=C1 CYWFCPPBTWOZSF-UHFFFAOYSA-N 0.000 description 1
229960000905 indomethacin Drugs 0.000 description 1
230000003993 interaction Effects 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
239000007788 liquid Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
229960003464 mefenamic acid Drugs 0.000 description 1
239000000155 melt Substances 0.000 description 1
HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 1
150000004702 methyl esters Chemical group 0.000 description 1
229960001238 methylnicotinate Drugs 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
238000005648 named reaction Methods 0.000 description 1
229960004927 neomycin Drugs 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
229960000649 oxyphenbutazone Drugs 0.000 description 1
HFHZKZSRXITVMK-UHFFFAOYSA-N oxyphenbutazone Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=C(O)C=C1 HFHZKZSRXITVMK-UHFFFAOYSA-N 0.000 description 1
229960005489 paracetamol Drugs 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
229960002895 phenylbutazone Drugs 0.000 description 1
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 1
CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
OIGNJSKKLXVSLS-VWUMJDOOSA-N prednisolone Chemical compound O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OIGNJSKKLXVSLS-VWUMJDOOSA-N 0.000 description 1
229960005205 prednisolone Drugs 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
DBABZHXKTCFAPX-UHFFFAOYSA-N probenecid Chemical compound CCCN(CCC)S(=O)(=O)C1=CC=C(C(O)=O)C=C1 DBABZHXKTCFAPX-UHFFFAOYSA-N 0.000 description 1
229960003081 probenecid Drugs 0.000 description 1
229960003910 promethazine Drugs 0.000 description 1
MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000011084 recovery Methods 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
150000003385 sodium Chemical class 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
150000003456 sulfonamides Chemical class 0.000 description 1
239000001117 sulphuric acid Substances 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
GKCBAIGFKIBETG-UHFFFAOYSA-N tetracaine Chemical compound CCCCNC1=CC=C(C(=O)OCCN(C)C)C=C1 GKCBAIGFKIBETG-UHFFFAOYSA-N 0.000 description 1
229960002372 tetracaine Drugs 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
JIVZKJJQOZQXQB-UHFFFAOYSA-N tolazoline Chemical compound C=1C=CC=CC=1CC1=NCCN1 JIVZKJJQOZQXQB-UHFFFAOYSA-N 0.000 description 1
229960002312 tolazoline Drugs 0.000 description 1
239000005526 vasoconstrictor agent Substances 0.000 description 1
239000003071 vasodilator agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/08—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D277/12—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D277/30—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
- C07D471/14—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Thiazole And Isothizaole Compounds (AREA)

IL31679A 1968-03-22 1969-02-23 History of thiazole IL31679A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB03989/68A GB1192701A (en)	1968-03-22	1968-03-22	Novel Thiazole Derivatives, the preparation thereof and Compositions containing the same

Publications (1)

Publication Number	Publication Date
IL31679A true IL31679A (en)	1972-08-30

Family

ID=10033003

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL31679A IL31679A (en)	1968-03-22	1969-02-23	History of thiazole

Country Status (15)

Country	Link
US (1)	US3661920A (da)
AT (1)	AT284841B (da)
BE (1)	BE730284A (da)
BR (1)	BR6807374D0 (da)
CA (1)	CA948199A (da)
CH (2)	CH513907A (da)
CS (3)	CS154268B2 (da)
DE (1)	DE1913472A1 (da)
DK (3)	DK125251B (da)
ES (1)	ES365089A1 (da)
FR (1)	FR2004544A1 (da)
GB (1)	GB1192701A (da)
IE (1)	IE32967B1 (da)
IL (1)	IL31679A (da)
NL (1)	NL6903963A (da)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2703542C2 (de) *	1977-01-26	1985-09-26	Schering AG, 1000 Berlin und 4709 Bergkamen	Thiazolylzimtsäurenitrile, Insektenbekämpfungsmittel enthaltend diese Verbindungen sowie Verfahren zu ihrer Herstellung
US4153703A (en) *	1977-06-30	1979-05-08	Uniroyal, Inc.	Method of controlling insects and acarids with certain aryl-substituted thiazoles
US4197306A (en) *	1977-06-30	1980-04-08	Uniroyal, Inc.	Aryl-substituted thiazoles
DE2801794A1 (de)	1978-01-17	1979-07-19	Basf Ag	Verfahren zur herstellung von thiazolderivaten und neue thiazole
DE2920183A1 (de) *	1979-05-17	1981-04-30	Schering Ag Berlin Und Bergkamen, 1000 Berlin	Thiazolyliden-oxo-propionitrile, insektizide mittel enthaltend diese verbindungen sowie verfahren zu ihrer herstellung
US4346094A (en) *	1980-09-22	1982-08-24	Eli Lilly And Company	3-Aryl-5-isothiazolecarboxylic acids and related compounds used to lower uric acid levels
US5077305A (en) *	1990-02-13	1991-12-31	Bristol-Myers Squibb Co.	Thiazole carboxylic acids and esters
CA2036192A1 (en)	1990-02-13	1991-08-14	Nicholas Meanwell	Heterocyclic carboxylic acids and esters
DE10331675A1 (de) *	2003-07-14	2005-02-10	Bayer Cropscience Ag	Hetarylsubstituierte Pyrazolidindion-Derivate
EP2200649A4 (en) *	2007-10-19	2012-09-26	Univ California	COMPOSITIONS AND METHODS FOR TREATING CNS INFUSION, PSYCHOSIS, DELIRE, PTSD OR PTSS

1968
- 1968-03-22 GB GB03989/68A patent/GB1192701A/en not_active Expired
- 1968-03-23 BR BR207374/68A patent/BR6807374D0/pt unknown
1969
- 1969-02-17 US US799963A patent/US3661920A/en not_active Expired - Lifetime
- 1969-02-18 IE IE209/69A patent/IE32967B1/xx unknown
- 1969-02-23 IL IL31679A patent/IL31679A/en unknown
- 1969-02-24 CA CA043,831A patent/CA948199A/en not_active Expired
- 1969-03-14 AT AT251269A patent/AT284841B/de not_active IP Right Cessation
- 1969-03-14 NL NL6903963A patent/NL6903963A/xx unknown
- 1969-03-17 DE DE19691913472 patent/DE1913472A1/de active Pending
- 1969-03-18 CS CS810072*1A patent/CS154268B2/cs unknown
- 1969-03-18 CS CS193669A patent/CS154266B2/cs unknown
- 1969-03-18 CS CS809972*1A patent/CS154267B2/cs unknown
- 1969-03-21 FR FR6908408A patent/FR2004544A1/fr not_active Withdrawn
- 1969-03-21 BE BE730284D patent/BE730284A/xx unknown
- 1969-03-21 CH CH434369A patent/CH513907A/de not_active IP Right Cessation
- 1969-03-21 DK DK157569AA patent/DK125251B/da unknown
- 1969-03-21 CH CH806371A patent/CH553209A/xx not_active IP Right Cessation
- 1969-03-22 ES ES365089A patent/ES365089A1/es not_active Expired
1970
- 1970-09-30 DK DK498970AA patent/DK122393B/da unknown
- 1970-09-30 DK DK498870AA patent/DK125326B/da unknown

Also Published As

Publication number	Publication date
BE730284A (da)	1969-09-22
GB1192701A (en)	1970-05-20
US3661920A (en)	1972-05-09
CS154268B2 (da)	1974-03-29
BR6807374D0 (pt)	1973-02-08
NL6903963A (da)	1969-09-24
IE32967L (en)	1969-09-22
FR2004544A1 (da)	1969-11-28
DK122393B (da)	1972-02-28
CH553209A (de)	1974-08-30
ES365089A1 (es)	1971-01-01
CH513907A (de)	1971-10-15
DK125326B (da)	1973-02-05
IE32967B1 (en)	1974-02-06
CA948199A (en)	1974-05-28
DE1913472A1 (de)	1969-11-06
CS154267B2 (da)	1974-03-29
CS154266B2 (da)	1974-03-29
AT284841B (de)	1970-09-25
DK125251B (da)	1973-01-22

Publication	Publication Date	Title
US3413305A (en)	1968-11-26	2-phenyl-3[para(beta-pyrrolidino ethoxy)-phenyl]-6-methoxy benzo[b]thiophene
JP2655692B2 (ja)	1997-09-24	スルホンアミドチエニルカルボン酸化合物
JP4523273B2 (ja)	2010-08-11	テトラヒドロキノリン誘導体
US3538107A (en)	1970-11-03	Aryl-thiazolyl-acetic acid derivatives
JPH01157983A (ja)	1989-06-21	テトラヒドロ−フロ及び−チェノ〔２，３−ｃ〕ピリジン類、該化合物を含む医薬製剤及びその製造法
DE69419917T2 (de)	2000-02-24	Indazolderivate
DE69125308T2 (de)	1997-07-10	Indolderivate
US3445473A (en)	1969-05-20	3-anilino-thiophene-4-carboxylic acids,esters,and amides
DE2537070C2 (da)	1987-06-25
US3661920A (en)	1972-05-09	Phenyl-thiazole-malonic acid derivatives
RU2236405C2 (ru)	2004-09-20	Полициклические тиазолидин-2-илиденовые амины, содержащие их лекарственные средства и способ получения лекарственного средства
US2423709A (en)	1947-07-08	X-aryl thiazole
JPH0244306B2 (da)	1990-10-03
US3379729A (en)	1968-04-23	Piperazinyldibenzothiepins
US4134900A (en)	1979-01-16	5,6-Dihydro-4-oxo-4H-thieno[2,3-b]thiopyran-5-carboxamides, and process for the preparation thereof
JPH0222059B2 (da)	1990-05-17
US3560525A (en)	1971-02-02	5-phenyl-2-furanacetic acids,5-phenyl-2-thiopheneacetic acids,and their derivatives
PT85477B (pt)	1990-06-29	Processo para a preparacao de derivados heterociclicos substituidos de fenil butenamida
AU2114600A (en)	2000-07-24	Tetrahydroindazole derivatives as ligands for gaba-a alpha 5 receptors
IL31991A (en)	1971-12-29	A fertile history and theology
JPH0365338B2 (da)	1991-10-11
US3691202A (en)	1972-09-12	Phenyl-thienyl- and phenyl-furyl malonic acid derivatives
EP0009142A1 (de)	1980-04-02	Neue 4-Hydroxy-2H(1)benzothieno(2,3-e)-1,2-thiazin-3-carboxamid-1,1-dioxide sowie deren Salze, deren Verwendung und Verfahren zu ihrer Herstellung
DE3017977A1 (de)	1981-11-19	Neue substituierte 2(3h)-benzothiazolone
JPH03261778A (ja)	1991-11-21	新規ベンゾフラン誘導体、尿酸排泄剤及びその製法