PH26639A - Benzothiopyrano-Ú4,4-c¾-pyrazol-3(2H)-one derivatives - Google Patents

Benzothiopyrano-Ú4,4-c¾-pyrazol-3(2H)-one derivatives Download PDF

Info

Publication number: PH26639A
Authority: PH; Philippines
Prior art keywords: methyl; formula; mammal; compound; hydrogen
Prior art date: 1988-08-09

Application number

PH38994A

Other languages

English (en)

Inventor

John Gareth Bowen

Ian Michael Hunneyball

Roger Bernard Titman

David George Webber

Michael Henry Rockley

John Rodindale Hously

Original Assignee

Boots Co Plc

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

1989-07-25

Publication date

1992-09-04

1989-07-25 Application filed by Boots Co Plc filed Critical Boots Co Plc

1992-09-04 Publication of PH26639A publication Critical patent/PH26639A/en

Links

150000001875 compounds Chemical class 0.000 claims description 129
229910052739 hydrogen Inorganic materials 0.000 claims description 56
239000001257 hydrogen Substances 0.000 claims description 55
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 42
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 24
238000000034 method Methods 0.000 claims description 21
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 21
125000001309 chloro group Chemical group Cl* 0.000 claims description 20
150000002431 hydrogen Chemical group 0.000 claims description 20
241000124008 Mammalia Species 0.000 claims description 17
125000000217 alkyl group Chemical group 0.000 claims description 12
125000001246 bromo group Chemical group Br* 0.000 claims description 10
125000001153 fluoro group Chemical group F* 0.000 claims description 10
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 6
239000008194 pharmaceutical composition Substances 0.000 claims description 6
201000010099 disease Diseases 0.000 claims description 5
206010028980 Neoplasm Diseases 0.000 claims description 2
239000002552 dosage form Substances 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims description 2
230000009826 neoplastic cell growth Effects 0.000 claims description 2
206010039073 rheumatoid arthritis Diseases 0.000 claims description 2
201000000596 systemic lupus erythematosus Diseases 0.000 claims description 2
210000000987 immune system Anatomy 0.000 claims 3
208000035475 disorder Diseases 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 75
239000000203 mixture Substances 0.000 description 53
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 33
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 32
239000000243 solution Substances 0.000 description 27
239000003921 oil Substances 0.000 description 23
235000019198 oils Nutrition 0.000 description 23
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 20
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 19
238000012360 testing method Methods 0.000 description 19
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 16
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 13
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
125000005843 halogen group Chemical group 0.000 description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
239000000047 product Substances 0.000 description 11
239000007787 solid Substances 0.000 description 10
238000003756 stirring Methods 0.000 description 10
-1 thiopyrano[4,3-c]pyrazol-3 (2H) -one Chemical compound 0.000 description 10
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 9
229960000583 acetic acid Drugs 0.000 description 9
239000011734 sodium Substances 0.000 description 9
229910052708 sodium Inorganic materials 0.000 description 9
XBYRMPXUBGMOJC-UHFFFAOYSA-N 1,2-dihydropyrazol-3-one Chemical compound OC=1C=CNN=1 XBYRMPXUBGMOJC-UHFFFAOYSA-N 0.000 description 8
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 8
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 8
238000010438 heat treatment Methods 0.000 description 8
239000012071 phase Substances 0.000 description 8
238000010992 reflux Methods 0.000 description 8
239000000377 silicon dioxide Substances 0.000 description 8
239000002904 solvent Substances 0.000 description 8
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 7
235000019439 ethyl acetate Nutrition 0.000 description 7
239000012362 glacial acetic acid Substances 0.000 description 7
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 7
239000008096 xylene Substances 0.000 description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-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
239000003795 chemical substances by application Substances 0.000 description 6
238000001816 cooling Methods 0.000 description 6
238000001914 filtration Methods 0.000 description 6
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 6
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
239000000725 suspension Substances 0.000 description 6
230000001225 therapeutic effect Effects 0.000 description 6
RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 6
XXNOGQJZAOXWAQ-UHFFFAOYSA-N 4-chlorophenylhydrazine Chemical compound NNC1=CC=C(Cl)C=C1 XXNOGQJZAOXWAQ-UHFFFAOYSA-N 0.000 description 5
239000011521 glass Substances 0.000 description 5
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125000001424 substituent group Chemical group 0.000 description 5
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125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 4
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-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
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
239000002585 base Substances 0.000 description 4
150000007942 carboxylates Chemical class 0.000 description 4
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238000003818 flash chromatography Methods 0.000 description 4
239000010410 layer Substances 0.000 description 4
238000002156 mixing Methods 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
239000000376 reactant Substances 0.000 description 4
239000012279 sodium borohydride Substances 0.000 description 4
229910000033 sodium borohydride Inorganic materials 0.000 description 4
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
239000003981 vehicle 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
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
NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
238000011725 BALB/c mouse Methods 0.000 description 3
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
125000004414 alkyl thio group Chemical group 0.000 description 3
239000002775 capsule Substances 0.000 description 3
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 3
238000004440 column chromatography Methods 0.000 description 3
238000002425 crystallisation Methods 0.000 description 3
229960001760 dimethyl sulfoxide Drugs 0.000 description 3
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 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
230000002519 immonomodulatory effect Effects 0.000 description 3
235000019271 petrolatum Nutrition 0.000 description 3
239000000546 pharmaceutical excipient Substances 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
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239000012258 stirred mixture Substances 0.000 description 3
239000001117 sulphuric acid Substances 0.000 description 3
235000011149 sulphuric acid Nutrition 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
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 2
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
125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 2
BLNAVINUTYEKLP-UHFFFAOYSA-N 3-methyl-4-oxo-2h-thiochromene-3-carboxamide Chemical compound C1=CC=C2C(=O)C(C)(C(N)=O)CSC2=C1 BLNAVINUTYEKLP-UHFFFAOYSA-N 0.000 description 2
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 2
206010012434 Dermatitis allergic Diseases 0.000 description 2
239000004264 Petrolatum Substances 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 2
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125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
230000001900 immune effect Effects 0.000 description 2
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239000007788 liquid Substances 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
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
KDUXYDNCQDFIOQ-UHFFFAOYSA-N methyl 2-(2-ethyl-4-oxo-2,3-dihydrothiochromen-3-yl)-2-oxoacetate Chemical compound C1=CC=C2C(=O)C(C(=O)C(=O)OC)C(CC)SC2=C1 KDUXYDNCQDFIOQ-UHFFFAOYSA-N 0.000 description 2
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KCYJAVFZHACRFI-UHFFFAOYSA-N 2,4-dihydro-1h-thiochromeno[4,3-c]pyrazol-3-one Chemical class C1SC2=CC=CC=C2C2=C1C(=O)NN2 KCYJAVFZHACRFI-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
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229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
239000012043 crude product Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
229940045803 cuprous chloride Drugs 0.000 description 1
125000004093 cyano group Chemical group *C#N 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
239000003814 drug Substances 0.000 description 1
238000000921 elemental analysis Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
DLZDAQNJFZIIFR-UHFFFAOYSA-N ethyl 2-methyl-4-oxo-2,3-dihydrothiochromene-3-carboxylate Chemical compound C1=CC=C2C(=O)C(C(=O)OCC)C(C)SC2=C1 DLZDAQNJFZIIFR-UHFFFAOYSA-N 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
ZVXVXLASNKQPJV-UHFFFAOYSA-N ethyl 4-oxothiochromene-3-carboxylate Chemical compound C1=CC=C2C(=O)C(C(=O)OCC)=CSC2=C1 ZVXVXLASNKQPJV-UHFFFAOYSA-N 0.000 description 1
125000004705 ethylthio group Chemical group C(C)S* 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000012530 fluid Substances 0.000 description 1
238000009472 formulation Methods 0.000 description 1
239000012458 free base Substances 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
239000003349 gelling agent Substances 0.000 description 1
239000011491 glass wool Substances 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
230000004727 humoral immunity Effects 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
230000008105 immune reaction Effects 0.000 description 1
230000003308 immunostimulating effect Effects 0.000 description 1
229960003444 immunosuppressant agent Drugs 0.000 description 1
239000003018 immunosuppressive agent Substances 0.000 description 1
238000012750 in vivo screening Methods 0.000 description 1
239000003701 inert diluent Substances 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
210000003734 kidney Anatomy 0.000 description 1
239000003446 ligand Substances 0.000 description 1
229940057995 liquid paraffin Drugs 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
238000004949 mass spectrometry Methods 0.000 description 1
239000011159 matrix material Substances 0.000 description 1
201000001441 melanoma Diseases 0.000 description 1
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 1
ZWZRNSSMZLNWRI-UHFFFAOYSA-N methyl 2-methyl-4-oxo-2,3-dihydrothiochromene-3-carboxylate Chemical compound C1=CC=C2C(=O)C(C(=O)OC)C(C)SC2=C1 ZWZRNSSMZLNWRI-UHFFFAOYSA-N 0.000 description 1
MFQBTQNMUMJOTM-UHFFFAOYSA-N methyl 3-methyl-4-oxo-2h-thiochromene-3-carboxylate Chemical compound C1=CC=C2C(=O)C(C(=O)OC)(C)CSC2=C1 MFQBTQNMUMJOTM-UHFFFAOYSA-N 0.000 description 1
WFCYDMXWNSWTSI-UHFFFAOYSA-N methyl 6-chloro-3-methyl-4-oxo-2h-thiochromene-3-carboxylate Chemical compound C1=C(Cl)C=C2C(=O)C(C(=O)OC)(C)CSC2=C1 WFCYDMXWNSWTSI-UHFFFAOYSA-N 0.000 description 1
239000012022 methylating agents‎ Substances 0.000 description 1
238000003801 milling Methods 0.000 description 1
239000012046 mixed solvent 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
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
235000008390 olive oil Nutrition 0.000 description 1
239000004006 olive oil Substances 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000012188 paraffin wax Substances 0.000 description 1
235000019809 paraffin wax Nutrition 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000002245 particle 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
239000002831 pharmacologic agent Substances 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
229920001223 polyethylene glycol Polymers 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
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
150000003217 pyrazoles Chemical class 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
230000001235 sensitizing effect Effects 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
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
238000012306 spectroscopic technique Methods 0.000 description 1
239000008174 sterile solution Substances 0.000 description 1
239000008223 sterile water Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
238000013268 sustained release Methods 0.000 description 1
239000012730 sustained-release form Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 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
229940124597 therapeutic agent Drugs 0.000 description 1
239000012485 toluene extract Substances 0.000 description 1
238000011200 topical administration Methods 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
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
239000001993 wax Substances 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)

PH38994A 1988-08-09 1989-07-25 Benzothiopyrano-Ú4,4-c¾-pyrazol-3(2H)-one derivatives PH26639A (en)

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
PH26639A true PH26639A (en)	1992-09-04

Family

ID=10641840

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
PH38994A PH26639A (en)	1988-08-09	1989-07-25	Benzothiopyrano-Ú4,4-c¾-pyrazol-3(2H)-one derivatives

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)	DK85290A (da)
FI (1)	FI901754A0 (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
WO1998009969A1 (en) *	1996-09-05	1998-03-12	Astra Pharmaceuticals Ltd.	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 ZA ZA895645A patent/ZA895645B/xx unknown
- 1989-07-25 PH PH38994A patent/PH26639A/en unknown
- 1989-07-28 KR KR1019900700730A patent/KR900701794A/ko not_active Withdrawn
- 1989-07-28 EP EP89307726A patent/EP0354694A1/en not_active Withdrawn
- 1989-07-28 AU AU40426/89A patent/AU625915B2/en not_active Ceased
- 1989-07-28 FI FI901754A patent/FI901754A0/fi not_active IP Right Cessation
- 1989-07-28 WO PCT/GB1989/000860 patent/WO1990001482A1/en not_active Ceased
- 1989-07-28 JP JP1508301A patent/JPH03500417A/ja active Pending
- 1989-07-28 HU HU894573A patent/HU205763B/hu not_active IP Right Cessation
- 1989-08-02 MX MX1704289A patent/MX17042A/es unknown
- 1989-08-07 NZ NZ230232A patent/NZ230232A/xx unknown
- 1989-08-07 DD DD89331552A patent/DD287039A5/de not_active IP Right Cessation
- 1989-08-07 YU YU01552/89A patent/YU155289A/xx unknown
- 1989-08-09 PT PT91409A patent/PT91409A/pt unknown
1990
- 1990-04-05 DK DK085290A patent/DK85290A/da not_active Application Discontinuation

Also Published As

Publication number	Publication date
HUT58743A (en)	1992-03-30
FI901754A7 (fi)	1990-04-06
NZ230232A (en)	1991-10-25
AU625915B2 (en)	1992-07-16
ZA895645B (en)	1990-04-25
YU155289A (en)	1991-10-31
WO1990001482A1 (en)	1990-02-22
JPH03500417A (ja)	1991-01-31
DD287039A5 (de)	1991-02-14
KR900701794A (ko)	1990-12-04
GB8818895D0 (en)	1988-09-14
DK85290D0 (da)	1990-04-05
HU894573D0 (en)	1991-05-28
MX17042A (es)	1994-01-31
PT91409A (pt)	1990-03-08
DK85290A (da)	1990-04-05
HU205763B (en)	1992-06-29
FI901754A0 (fi)	1990-04-06
AU4042689A (en)	1990-03-05
EP0354694A1 (en)	1990-02-14

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