DD287039A5 - Verfahren zur herstellung von (1)benzothiopyrano/4,3-c/pyrazolen - Google Patents

Verfahren zur herstellung von (1)benzothiopyrano/4,3-c/pyrazolen Download PDF

Info

Publication number: DD287039A5
Authority: DD; German Democratic Republic
Prior art keywords: methyl; hydrogen; formula; compounds; trifluoromethyl
Prior art date: 1988-08-09

Application number

DD89331552A

Other languages

German (de)

English (en)

Inventor

John G Bowen

Michael H Hockley

John R Housley

Ian M Hunneyball

Roger B Titman

David G Webber

Original Assignee

��@��@��@��k��

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.)

1988-08-09

Filing date

1989-08-07

Publication date

1991-02-14

1989-08-07 Application filed by ��@��@��@��k�� filed Critical ��@��@��@��k��

1991-02-14 Publication of DD287039A5 publication Critical patent/DD287039A5/de

Links

238000004519 manufacturing process Methods 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 105
238000000034 method Methods 0.000 claims abstract description 19
238000002360 preparation method Methods 0.000 claims abstract description 6
229910052739 hydrogen Inorganic materials 0.000 claims description 81
239000001257 hydrogen Substances 0.000 claims description 81
150000002431 hydrogen Chemical group 0.000 claims description 51
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 43
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 42
229910052736 halogen Inorganic materials 0.000 claims description 36
150000002367 halogens Chemical class 0.000 claims description 36
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 27
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 19
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 10
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 8
238000006243 chemical reaction Methods 0.000 claims description 8
125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 6
125000000217 alkyl group Chemical group 0.000 claims description 6
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 5
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 5
125000004414 alkyl thio group Chemical group 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 2
230000003647 oxidation Effects 0.000 claims description 2
238000007254 oxidation reaction Methods 0.000 claims description 2
125000004356 hydroxy functional group Chemical group O* 0.000 claims 7
125000001475 halogen functional group Chemical group 0.000 claims 1
230000002519 immonomodulatory effect Effects 0.000 abstract description 4
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 69
XBYRMPXUBGMOJC-UHFFFAOYSA-N 1,2-dihydropyrazol-3-one Chemical compound OC=1C=CNN=1 XBYRMPXUBGMOJC-UHFFFAOYSA-N 0.000 description 53
239000000203 mixture Substances 0.000 description 40
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 32
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239000000460 chlorine Substances 0.000 description 30
239000000243 solution Substances 0.000 description 28
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
206010012434 Dermatitis allergic Diseases 0.000 description 20
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 19
239000003921 oil Substances 0.000 description 19
235000019198 oils Nutrition 0.000 description 19
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 17
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 16
-1 for example Chemical group 0.000 description 14
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
238000002844 melting Methods 0.000 description 12
230000008018 melting Effects 0.000 description 12
239000000047 product Substances 0.000 description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
229910052801 chlorine Inorganic materials 0.000 description 11
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 11
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 10
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 10
238000003756 stirring Methods 0.000 description 10
229960000583 acetic acid Drugs 0.000 description 9
238000009835 boiling Methods 0.000 description 9
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
239000007787 solid Substances 0.000 description 9
125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 description 8
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239000000377 silicon dioxide Substances 0.000 description 8
239000011734 sodium Substances 0.000 description 8
229910052708 sodium Inorganic materials 0.000 description 8
239000008096 xylene Substances 0.000 description 8
125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 7
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 7
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 7
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 7
125000001309 chloro group Chemical group Cl* 0.000 description 7
238000001816 cooling Methods 0.000 description 7
235000019439 ethyl acetate Nutrition 0.000 description 7
239000011737 fluorine Substances 0.000 description 7
229910052731 fluorine Inorganic materials 0.000 description 7
238000010438 heat treatment Methods 0.000 description 7
125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
239000011541 reaction mixture Substances 0.000 description 7
125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 6
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 6
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 6
229910052794 bromium Inorganic materials 0.000 description 6
238000001914 filtration Methods 0.000 description 6
239000012362 glacial acetic acid Substances 0.000 description 6
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 6
239000012071 phase Substances 0.000 description 6
239000000376 reactant Substances 0.000 description 6
239000002904 solvent Substances 0.000 description 6
RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 6
241000699666 Mus <mouse, genus> Species 0.000 description 5
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
239000011521 glass Substances 0.000 description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
239000000843 powder Substances 0.000 description 5
125000001424 substituent group Chemical group 0.000 description 5
230000001225 therapeutic effect Effects 0.000 description 5
125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 4
XXNOGQJZAOXWAQ-UHFFFAOYSA-N 4-chlorophenylhydrazine Chemical compound NNC1=CC=C(Cl)C=C1 XXNOGQJZAOXWAQ-UHFFFAOYSA-N 0.000 description 4
LOMVENUNSWAXEN-UHFFFAOYSA-N Methyl oxalate Chemical compound COC(=O)C(=O)OC LOMVENUNSWAXEN-UHFFFAOYSA-N 0.000 description 4
241000699670 Mus sp. Species 0.000 description 4
201000010099 disease Diseases 0.000 description 4
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
239000000284 extract Substances 0.000 description 4
238000003818 flash chromatography Methods 0.000 description 4
239000010410 layer Substances 0.000 description 4
239000003208 petroleum Substances 0.000 description 4
239000000725 suspension Substances 0.000 description 4
SJHPCNCNNSSLPL-CSKARUKUSA-N (4e)-4-(ethoxymethylidene)-2-phenyl-1,3-oxazol-5-one Chemical compound O1C(=O)C(=C/OCC)\N=C1C1=CC=CC=C1 SJHPCNCNNSSLPL-CSKARUKUSA-N 0.000 description 3
125000004178 (C1-C4) alkyl group Chemical group 0.000 description 3
125000004209 (C1-C8) alkyl group Chemical group 0.000 description 3
NHBKXEKEPDILRR-UHFFFAOYSA-N 2,3-bis(butanoylsulfanyl)propyl butanoate Chemical compound CCCC(=O)OCC(SC(=O)CCC)CSC(=O)CCC NHBKXEKEPDILRR-UHFFFAOYSA-N 0.000 description 3
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
239000002585 base Substances 0.000 description 3
238000004440 column chromatography Methods 0.000 description 3
238000002425 crystallisation Methods 0.000 description 3
210000003298 dental enamel Anatomy 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
239000002955 immunomodulating agent Substances 0.000 description 3
239000012299 nitrogen atmosphere Substances 0.000 description 3
238000010992 reflux Methods 0.000 description 3
239000012279 sodium borohydride Substances 0.000 description 3
229910000033 sodium borohydride Inorganic materials 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
238000011282 treatment Methods 0.000 description 3
TWLGLTREQVCPRA-UHFFFAOYSA-N 2-ethyl-2,3-dihydrothiochromen-4-one Chemical compound C1=CC=C2SC(CC)CC(=O)C2=C1 TWLGLTREQVCPRA-UHFFFAOYSA-N 0.000 description 2
YSYYFHVHCXBCCS-UHFFFAOYSA-N 2-methyl-2,3-dihydrothiochromen-4-one Chemical compound C1=CC=C2SC(C)CC(=O)C2=C1 YSYYFHVHCXBCCS-UHFFFAOYSA-N 0.000 description 2
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
206010020751 Hypersensitivity Diseases 0.000 description 2
206010070834 Sensitisation Diseases 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
239000003377 acid catalyst Substances 0.000 description 2
208000026935 allergic disease Diseases 0.000 description 2
125000005605 benzo group Chemical group 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
208000010247 contact dermatitis Diseases 0.000 description 2
229910052802 copper Inorganic materials 0.000 description 2
239000010949 copper Substances 0.000 description 2
LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
239000012259 ether extract Substances 0.000 description 2
230000001900 immune effect Effects 0.000 description 2
230000028993 immune response Effects 0.000 description 2
229910052740 iodine Inorganic materials 0.000 description 2
239000007788 liquid Substances 0.000 description 2
NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
XCOFWPBVKOWSNQ-UHFFFAOYSA-N methyl 2-(2,6-dimethyl-4-oxo-2,3-dihydrothiochromen-3-yl)-2-oxoacetate Chemical compound C1=C(C)C=C2C(=O)C(C(=O)C(=O)OC)C(C)SC2=C1 XCOFWPBVKOWSNQ-UHFFFAOYSA-N 0.000 description 2
PEUSUINVFUYCHO-UHFFFAOYSA-N methyl 2-(6-fluoro-4-oxo-2,3-dihydrothiochromen-3-yl)-2-oxoacetate Chemical compound C1=C(F)C=C2C(=O)C(C(=O)C(=O)OC)CSC2=C1 PEUSUINVFUYCHO-UHFFFAOYSA-N 0.000 description 2
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
239000008194 pharmaceutical composition Substances 0.000 description 2
150000003217 pyrazoles Chemical class 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
230000004044 response Effects 0.000 description 2
238000007363 ring formation reaction Methods 0.000 description 2
230000008313 sensitization Effects 0.000 description 2
239000012312 sodium hydride Substances 0.000 description 2
229910000104 sodium hydride Inorganic materials 0.000 description 2
239000012265 solid product Substances 0.000 description 2
239000012258 stirred mixture Substances 0.000 description 2
238000011200 topical administration Methods 0.000 description 2
LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 2
JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical class OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
RBTMKXZTRMUGLR-UHFFFAOYSA-N 2,6-dimethyl-2,3-dihydrothiochromen-4-one Chemical compound CC1=CC=C2SC(C)CC(=O)C2=C1 RBTMKXZTRMUGLR-UHFFFAOYSA-N 0.000 description 1
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
BVGWYHPPUHSKIU-UHFFFAOYSA-N 2-(3,4-dichlorophenyl)-3a-methyl-4h-thiochromeno[4,3-c]pyrazol-3-one Chemical compound O=C1C2(C)CSC3=CC=CC=C3C2=NN1C1=CC=C(Cl)C(Cl)=C1 BVGWYHPPUHSKIU-UHFFFAOYSA-N 0.000 description 1
SQNLOVYIZFSMTR-UHFFFAOYSA-N 2-(4-bromo-3-chlorophenyl)-3a-methyl-4h-thiochromeno[4,3-c]pyrazol-3-one Chemical compound O=C1C2(C)CSC3=CC=CC=C3C2=NN1C1=CC=C(Br)C(Cl)=C1 SQNLOVYIZFSMTR-UHFFFAOYSA-N 0.000 description 1
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
ONJRTQUWKRDCTA-UHFFFAOYSA-N 2h-thiochromene Chemical compound C1=CC=C2C=CCSC2=C1 ONJRTQUWKRDCTA-UHFFFAOYSA-N 0.000 description 1
KJTRXVXWSSPHRV-UHFFFAOYSA-N 4-benzoyl-5-methyl-2-phenyl-1h-pyrazol-3-one Chemical compound O=C1C(C(=O)C=2C=CC=CC=2)=C(C)NN1C1=CC=CC=C1 KJTRXVXWSSPHRV-UHFFFAOYSA-N 0.000 description 1
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
NUERIQOWHSTEEB-UHFFFAOYSA-N 4-methyl-2-[4-(trifluoromethyl)phenyl]thiochromeno[4,3-c]pyrazol-3-one Chemical compound O=C1C2=C(C)SC3=CC=CC=C3C2=NN1C1=CC=C(C(F)(F)F)C=C1 NUERIQOWHSTEEB-UHFFFAOYSA-N 0.000 description 1
NBBGHADNMPMHST-UHFFFAOYSA-N 6-fluoro-2,3-dihydrothiochromen-4-one Chemical compound S1CCC(=O)C2=CC(F)=CC=C21 NBBGHADNMPMHST-UHFFFAOYSA-N 0.000 description 1
208000023275 Autoimmune disease Diseases 0.000 description 1
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206010012442 Dermatitis contact Diseases 0.000 description 1
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238000004566 IR spectroscopy Methods 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
206010028980 Neoplasm Diseases 0.000 description 1
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DBNLGTYGKCMLLR-UHFFFAOYSA-N [4-(trifluoromethyl)phenyl]hydrazine Chemical compound NNC1=CC=C(C(F)(F)F)C=C1 DBNLGTYGKCMLLR-UHFFFAOYSA-N 0.000 description 1
210000001015 abdomen Anatomy 0.000 description 1
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YIYBQIKDCADOSF-UHFFFAOYSA-N alpha-Butylen-alpha-carbonsaeure Natural products CCC=CC(O)=O YIYBQIKDCADOSF-UHFFFAOYSA-N 0.000 description 1
BIVUUOPIAYRCAP-UHFFFAOYSA-N aminoazanium;chloride Chemical compound Cl.NN BIVUUOPIAYRCAP-UHFFFAOYSA-N 0.000 description 1
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125000001246 bromo group Chemical group Br* 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000002775 capsule Substances 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
150000007942 carboxylates Chemical class 0.000 description 1
OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
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125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
CAIKKJIIZHDMSX-UHFFFAOYSA-N ethyl 2-sulfanylbenzoate Chemical compound CCOC(=O)C1=CC=CC=C1S CAIKKJIIZHDMSX-UHFFFAOYSA-N 0.000 description 1
ZVQYUHGDKOBQFR-UHFFFAOYSA-N ethyl 3-oxo-4h-thiochromene-2-carboxylate Chemical compound C1=CC=C2CC(=O)C(C(=O)OCC)SC2=C1 ZVQYUHGDKOBQFR-UHFFFAOYSA-N 0.000 description 1
CZMPMGZGVDXHHO-UHFFFAOYSA-N ethyl 4-oxo-2,3-dihydrothiochromene-3-carboxylate Chemical compound C1=CC=C2C(=O)C(C(=O)OCC)CSC2=C1 CZMPMGZGVDXHHO-UHFFFAOYSA-N 0.000 description 1
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HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 description 1
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230000003308 immunostimulating effect Effects 0.000 description 1
229960003444 immunosuppressant agent Drugs 0.000 description 1
239000003018 immunosuppressive agent Substances 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
238000002372 labelling Methods 0.000 description 1
239000003446 ligand Substances 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
206010025135 lupus erythematosus Diseases 0.000 description 1
238000004949 mass spectrometry Methods 0.000 description 1
239000000463 material Substances 0.000 description 1
201000001441 melanoma Diseases 0.000 description 1
MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
SIMJFIJGYJLEBW-UHFFFAOYSA-N methyl 2-(2-methyl-4-oxo-2,3-dihydrothiochromen-3-yl)-2-oxoacetate Chemical compound C1=CC=C2C(=O)C(C(=O)C(=O)OC)C(C)SC2=C1 SIMJFIJGYJLEBW-UHFFFAOYSA-N 0.000 description 1
WZQJPWCPIWRQKI-UHFFFAOYSA-N methyl 2-ethyl-4-oxo-2,3-dihydrothiochromene-3-carboxylate Chemical compound C1=CC=C2C(=O)C(C(=O)OC)C(CC)SC2=C1 WZQJPWCPIWRQKI-UHFFFAOYSA-N 0.000 description 1
QJRRYPJPZJNOQI-UHFFFAOYSA-N methyl 6-fluoro-4-oxo-2,3-dihydrothiochromene-3-carboxylate Chemical compound C1=C(F)C=C2C(=O)C(C(=O)OC)CSC2=C1 QJRRYPJPZJNOQI-UHFFFAOYSA-N 0.000 description 1
239000012022 methylating agents‎ Substances 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
239000011259 mixed solution Substances 0.000 description 1
125000000896 monocarboxylic acid group Chemical group 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
239000004006 olive oil Substances 0.000 description 1
235000008390 olive oil Nutrition 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
229920000137 polyphosphoric acid Polymers 0.000 description 1
229920000053 polysorbate 80 Polymers 0.000 description 1
238000012746 preparative thin layer chromatography Methods 0.000 description 1
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
206010039073 rheumatoid arthritis Diseases 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
208000017520 skin disease Diseases 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
238000004611 spectroscopical analysis Methods 0.000 description 1
230000001629 suppression Effects 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000006188 syrup Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 1
239000012485 toluene extract Substances 0.000 description 1
YIYBQIKDCADOSF-ONEGZZNKSA-N trans-pent-2-enoic acid Chemical compound CC\C=C\C(O)=O YIYBQIKDCADOSF-ONEGZZNKSA-N 0.000 description 1
238000005303 weighing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Immunology (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)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

DD89331552A 1988-08-09 1989-08-07 Verfahren zur herstellung von (1)benzothiopyrano/4,3-c/pyrazolen DD287039A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB888818895A GB8818895D0 (en)	1988-08-09	1988-08-09	Therapeutic agents

Publications (1)

Publication Number	Publication Date
DD287039A5 true DD287039A5 (de)	1991-02-14

Family

ID=10641840

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD89331552A DD287039A5 (de)	1988-08-09	1989-08-07	Verfahren zur herstellung von (1)benzothiopyrano/4,3-c/pyrazolen

Country Status (16)

Country	Link
EP (1)	EP0354694A1 (da)
JP (1)	JPH03500417A (da)
KR (1)	KR900701794A (da)
AU (1)	AU625915B2 (da)
DD (1)	DD287039A5 (da)
DK (1)	DK85290D0 (da)
FI (1)	FI901754A7 (da)
GB (1)	GB8818895D0 (da)
HU (1)	HU205763B (da)
MX (1)	MX17042A (da)
NZ (1)	NZ230232A (da)
PH (1)	PH26639A (da)
PT (1)	PT91409A (da)
WO (1)	WO1990001482A1 (da)
YU (1)	YU155289A (da)
ZA (1)	ZA895645B (da)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA2263586A1 (en) *	1996-09-05	1998-03-12	Eifion Phillips	Novel aryl-pyridazines
SE0102404D0 (sv) *	2001-07-04	2001-07-04	Active Biotech Ab	Novel immunomodulating compounds
US6642249B2 (en)	2001-07-04	2003-11-04	Active Biotech Ab	Immunomodulating compounds

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4268516A (en) *	1978-10-11	1981-05-19	Pfizer Inc.	[1]Benzothiopyrano[4,3-c]pyrazoles as immunoregulatory agents

1988
- 1988-08-09 GB GB888818895A patent/GB8818895D0/en active Pending
1989
- 1989-07-25 PH PH38994A patent/PH26639A/en unknown
- 1989-07-25 ZA ZA895645A patent/ZA895645B/xx unknown
- 1989-07-28 WO PCT/GB1989/000860 patent/WO1990001482A1/en not_active Ceased
- 1989-07-28 EP EP89307726A patent/EP0354694A1/en not_active Withdrawn
- 1989-07-28 HU HU894573A patent/HU205763B/hu not_active IP Right Cessation
- 1989-07-28 KR KR1019900700730A patent/KR900701794A/ko not_active Withdrawn
- 1989-07-28 AU AU40426/89A patent/AU625915B2/en not_active Ceased
- 1989-07-28 FI FI901754A patent/FI901754A7/fi not_active IP Right Cessation
- 1989-07-28 JP JP1508301A patent/JPH03500417A/ja active Pending
- 1989-08-02 MX MX1704289A patent/MX17042A/es unknown
- 1989-08-07 DD DD89331552A patent/DD287039A5/de not_active IP Right Cessation
- 1989-08-07 YU YU01552/89A patent/YU155289A/xx unknown
- 1989-08-07 NZ NZ230232A patent/NZ230232A/xx unknown
- 1989-08-09 PT PT91409A patent/PT91409A/pt unknown
1990
- 1990-04-05 DK DK085290A patent/DK85290D0/da not_active Application Discontinuation

Also Published As

Publication number	Publication date
ZA895645B (en)	1990-04-25
AU4042689A (en)	1990-03-05
HU205763B (en)	1992-06-29
HUT58743A (en)	1992-03-30
GB8818895D0 (en)	1988-09-14
KR900701794A (ko)	1990-12-04
FI901754A0 (fi)	1990-04-06
NZ230232A (en)	1991-10-25
AU625915B2 (en)	1992-07-16
PH26639A (en)	1992-09-04
DK85290A (da)	1990-04-05
MX17042A (es)	1994-01-31
EP0354694A1 (en)	1990-02-14
PT91409A (pt)	1990-03-08
DK85290D0 (da)	1990-04-05
WO1990001482A1 (en)	1990-02-22
HU894573D0 (en)	1991-05-28
FI901754A7 (fi)	1990-04-06
JPH03500417A (ja)	1991-01-31
YU155289A (en)	1991-10-31

Legal Events

Date	Code	Title	Description
2000-03-02	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
DE69309670T2 (de)	1997-11-20	Heterocyclische carbonsäure-derivate, die an rar rezeptoren binden können
DE3855388T2 (de)	1997-02-13	7-Piperazinyl- oder 7-Morpholino-4-oxo-Chinolin-3- carbonsäurederivate, ihre Herstellung und ihre Verwendung als antimikrobielle Mittel
DE69433401T2 (de)	2004-09-16	Gefässverengende dihydrobenzopyranderivate
DE69708142T2 (de)	2002-07-11	1-phenylpyrozol-verbindungen und ihre medizinische anwendung
CH641350A5 (de)	1984-02-29	Pharmazeutische zusammensetzung zur verwendung als antihistaminicum, auf der basis eines carbostyrilderivates.
EP0314154A2 (de)	1989-05-03	Tetrahydro-furo- und -thieno[2,3-c]pyridine, ihre Verwendung als Arzneimittel und Verfahren zu ihrer Herstellung
DE69712084T2 (de)	2002-11-28	Aminothiazole derivate, ihre herstellung und sie enthaltenden pharmazeutischen zusammensetzungen
DE69524428T2 (de)	2002-05-23	Dihydrobenzofuran und verwandte verbindungen als entzündungshemmende mittel
DE3724164A1 (de)	1988-01-28	Neue 1,4-benzodiazepine, ihre herstellung und verwendung
DE4430639A1 (de)	1996-03-07	Verwendung von 5-substituierten Pyridin- und Hexahydrochinolin-3-carbonsäurederivaten
EP0053767B1 (de)	1984-09-12	Tricyclische Cytosinderivate zur Verwendung in Arzneimitteln und Verfahren zu ihrer Herstellung
DD253823A5 (de)	1988-02-03	Verfahren zur herstellung neuartiger thienopyridone
DE3533331A1 (de)	1987-03-26	Pyridothiazolderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
DE68925270T2 (de)	1996-06-13	Pyrrolo[3,2-e]pyrazolo[1,5-a]pyrimidinderivate und diese enthaltende Arzneimittel
DD244133A5 (de)	1987-03-25	Verfahren zur herstellung von substituierten 2-oxindolen als analgetische und entzuendungshemmende mittel
DE68906200T2 (de)	1993-08-05	Kondensierte pyrazol-3-oxo-propannitril-derivate und verfahren zu deren herstellung.
DE69201302T2 (de)	1995-09-28	Therapeutische zusammenstellungen auf der basis von 1,2-dithiole-3-thionderivaten.
EP0406656B1 (de)	1995-01-11	Chromanderivate
DE2730832A1 (de)	1978-01-19	Thieno-(2,3-c)- und -(3,2-c)pyridine, verfahren zu ihrer herstellung und sie enthaltende arzneimittel
EP0621037B1 (de)	1999-07-07	Pyrido-pyrimidindione, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel
DE3040950A1 (de)	1981-05-14	Pyridothienotriazine, verfahren zu ihrer herstellung und sie enthaltende antiallergiemittel
AT400845B (de)	1996-03-25	Neue thienothiazinderivate, ein verfahren zu ihrer herstellung und ihre verwendung
DE2807381A1 (de)	1978-08-24	Pharmazeutische zusammensetzung mit einem gehalt an einem 1,3,5-triazin- 2,6-dion
EP0489327A1 (de)	1992-06-10	Chromanderivate
DD287039A5 (de)	1991-02-14	Verfahren zur herstellung von (1)benzothiopyrano/4,3-c/pyrazolen