JPS59176230A - 抗炎症作用を有するジペンゾシクロヘプテニリデン - Google Patents

抗炎症作用を有するジペンゾシクロヘプテニリデン

Info

Publication number: JPS59176230A
Authority: JP; Japan
Prior art keywords: hydrogen; formula; tetrazolyl; uncorrected; melting point
Prior art date: 1983-01-03
Legal status (The legal status 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 status listed.): Pending

Application number

JP58252492A

Other languages

English (en)

Japanese (ja)

Inventor

ミルトン・ウオルフ

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Wyeth LLC

Original Assignee

American Home Products Corp

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.)

1983-01-03

Filing date

1983-12-28

Publication date

1984-10-05

1983-12-28 Application filed by American Home Products Corp filed Critical American Home Products Corp

1984-10-05 Publication of JPS59176230A publication Critical patent/JPS59176230A/ja

Status Pending legal-status Critical Current

Links

230000003110 anti-inflammatory effect Effects 0.000 title claims description 9
150000001875 compounds Chemical class 0.000 claims description 85
239000000203 mixture Substances 0.000 claims description 55
229910052739 hydrogen Inorganic materials 0.000 claims description 39
239000001257 hydrogen Substances 0.000 claims description 39
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 30
125000003831 tetrazolyl group Chemical group 0.000 claims description 19
150000003839 salts Chemical class 0.000 claims description 16
238000000034 method Methods 0.000 claims description 13
-1 alkali metal azide Chemical class 0.000 claims description 12
239000000460 chlorine Chemical group 0.000 claims description 11
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
229910052801 chlorine Chemical group 0.000 claims description 10
229910052736 halogen Inorganic materials 0.000 claims description 10
150000002367 halogens Chemical group 0.000 claims description 10
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
125000003545 alkoxy group Chemical group 0.000 claims description 9
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
125000004432 carbon atom Chemical group C* 0.000 claims description 7
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
229910052794 bromium Chemical group 0.000 claims description 6
150000002148 esters Chemical class 0.000 claims description 5
150000001733 carboxylic acid esters Chemical class 0.000 claims description 3
229910052783 alkali metal Inorganic materials 0.000 claims description 2
UAZDIGCOBKKMPU-UHFFFAOYSA-O azanium;azide Chemical compound [NH4+].[N-]=[N+]=[N-] UAZDIGCOBKKMPU-UHFFFAOYSA-O 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims description 2
238000002360 preparation method Methods 0.000 claims description 2
YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 claims 1
229940126601 medicinal product Drugs 0.000 claims 1
238000002844 melting Methods 0.000 description 63
230000008018 melting Effects 0.000 description 62
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 48
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 48
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 47
238000000921 elemental analysis Methods 0.000 description 37
239000000243 solution Substances 0.000 description 33
239000013078 crystal Substances 0.000 description 28
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzenecarbonitrile Natural products N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 23
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 22
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
239000007787 solid Substances 0.000 description 22
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
239000003921 oil Substances 0.000 description 19
238000003756 stirring Methods 0.000 description 19
239000012153 distilled water Substances 0.000 description 16
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 16
239000000047 product Substances 0.000 description 16
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 13
239000012043 crude product Substances 0.000 description 13
XEKOWRVHYACXOJ-UHFFFAOYSA-N ethyl acetate Substances CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 13
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 12
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
239000000284 extract Substances 0.000 description 12
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 12
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
239000002253 acid Substances 0.000 description 11
238000006243 chemical reaction Methods 0.000 description 11
239000000543 intermediate Substances 0.000 description 10
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PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
239000010410 layer Substances 0.000 description 9
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 8
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 8
230000000694 effects Effects 0.000 description 8
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 8
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 8
238000012360 testing method Methods 0.000 description 8
239000005711 Benzoic acid Substances 0.000 description 7
206010061218 Inflammation Diseases 0.000 description 7
206010030113 Oedema Diseases 0.000 description 7
235000010233 benzoic acid Nutrition 0.000 description 7
239000012267 brine Substances 0.000 description 7
CJGBPPZRFOVLNI-UHFFFAOYSA-N cyclohexane;oxolane Chemical compound C1CCOC1.C1CCCCC1 CJGBPPZRFOVLNI-UHFFFAOYSA-N 0.000 description 7
230000004054 inflammatory process Effects 0.000 description 7
239000012299 nitrogen atmosphere Substances 0.000 description 7
229960005235 piperonyl butoxide Drugs 0.000 description 7
239000000741 silica gel Substances 0.000 description 7
229910002027 silica gel Inorganic materials 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
238000009835 boiling Methods 0.000 description 6
239000002904 solvent Substances 0.000 description 6
KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 6
BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 5
229960001138 acetylsalicylic acid Drugs 0.000 description 5
239000002260 anti-inflammatory agent Substances 0.000 description 5
230000001684 chronic effect Effects 0.000 description 5
238000001816 cooling Methods 0.000 description 5
150000002168 ethanoic acid esters Chemical class 0.000 description 5
238000004128 high performance liquid chromatography Methods 0.000 description 5
239000007788 liquid Substances 0.000 description 5
229920000609 methyl cellulose Polymers 0.000 description 5
239000001923 methylcellulose Substances 0.000 description 5
239000011780 sodium chloride Substances 0.000 description 5
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
150000004703 alkoxides Chemical class 0.000 description 4
125000000217 alkyl group Chemical group 0.000 description 4
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 4
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
229940121363 anti-inflammatory agent Drugs 0.000 description 4
239000012141 concentrate Substances 0.000 description 4
235000019439 ethyl acetate Nutrition 0.000 description 4
125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 4
229960000905 indomethacin Drugs 0.000 description 4
230000004968 inflammatory condition Effects 0.000 description 4
239000000463 material Substances 0.000 description 4
229910052751 metal Inorganic materials 0.000 description 4
239000002184 metal Substances 0.000 description 4
239000000126 substance Substances 0.000 description 4
239000000725 suspension Substances 0.000 description 4
KPZGRMZPZLOPBS-UHFFFAOYSA-N 1,3-dichloro-2,2-bis(chloromethyl)propane Chemical compound ClCC(CCl)(CCl)CCl KPZGRMZPZLOPBS-UHFFFAOYSA-N 0.000 description 3
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 3
238000005481 NMR spectroscopy Methods 0.000 description 3
241000700159 Rattus Species 0.000 description 3
229920002472 Starch Polymers 0.000 description 3
239000002671 adjuvant Substances 0.000 description 3
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzenecarboxaldehyde Natural products O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
239000012230 colorless oil Substances 0.000 description 3
238000009833 condensation Methods 0.000 description 3
230000005494 condensation Effects 0.000 description 3
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
238000001914 filtration Methods 0.000 description 3
210000002683 foot Anatomy 0.000 description 3
238000005259 measurement Methods 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
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VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
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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 2
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241000186359 Mycobacterium Species 0.000 description 1
206010030124 Oedema peripheral Diseases 0.000 description 1
208000008469 Peptic Ulcer Diseases 0.000 description 1
206010036030 Polyarthritis Diseases 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
ZYVVPOVJIAXSNT-UHFFFAOYSA-N [Th+4].[N-]=[N+]=[N-].[N-]=[N+]=[N-].[N-]=[N+]=[N-].[N-]=[N+]=[N-] Chemical compound [Th+4].[N-]=[N+]=[N-].[N-]=[N+]=[N-].[N-]=[N+]=[N-].[N-]=[N+]=[N-] ZYVVPOVJIAXSNT-UHFFFAOYSA-N 0.000 description 1
125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000003513 alkali Substances 0.000 description 1
239000012491 analyte Substances 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
238000003556 assay Methods 0.000 description 1
150000003935 benzaldehydes Chemical class 0.000 description 1
150000008359 benzonitriles Chemical class 0.000 description 1
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
210000001185 bone marrow Anatomy 0.000 description 1
230000031709 bromination Effects 0.000 description 1
238000005893 bromination reaction Methods 0.000 description 1
239000002775 capsule Substances 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
GYSSRZJIHXQEHQ-UHFFFAOYSA-N carboxin Chemical group S1CCOC(C)=C1C(=O)NC1=CC=CC=C1 GYSSRZJIHXQEHQ-UHFFFAOYSA-N 0.000 description 1
235000019398 chlorine dioxide Nutrition 0.000 description 1
OSVXSBDYLRYLIG-UHFFFAOYSA-N chlorine dioxide Inorganic materials O=Cl=O OSVXSBDYLRYLIG-UHFFFAOYSA-N 0.000 description 1
OQNGCCWBHLEQFN-UHFFFAOYSA-N chloroform;hexane Chemical compound ClC(Cl)Cl.CCCCCC OQNGCCWBHLEQFN-UHFFFAOYSA-N 0.000 description 1
QBWCMBCROVPCKQ-UHFFFAOYSA-N chlorous acid Chemical compound OCl=O QBWCMBCROVPCKQ-UHFFFAOYSA-N 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
208000037976 chronic inflammation Diseases 0.000 description 1
208000037893 chronic inflammatory disorder Diseases 0.000 description 1
229940110456 cocoa butter Drugs 0.000 description 1
235000019868 cocoa butter Nutrition 0.000 description 1
239000013065 commercial product Substances 0.000 description 1
230000004154 complement system Effects 0.000 description 1
229940125904 compound 1 Drugs 0.000 description 1
230000006835 compression Effects 0.000 description 1
238000007906 compression Methods 0.000 description 1
239000000470 constituent Substances 0.000 description 1
239000012050 conventional carrier Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
239000003246 corticosteroid Substances 0.000 description 1
ZXIJMRYMVAMXQP-UHFFFAOYSA-N cycloheptene Chemical compound C1CCC=CCC1 ZXIJMRYMVAMXQP-UHFFFAOYSA-N 0.000 description 1
238000007269 dehydrobromination reaction Methods 0.000 description 1
235000019425 dextrin Nutrition 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
238000001647 drug administration Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
201000006549 dyspepsia Diseases 0.000 description 1
OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
VEUUMBGHMNQHGO-UHFFFAOYSA-N ethyl chloroacetate Chemical compound CCOC(=O)CCl VEUUMBGHMNQHGO-UHFFFAOYSA-N 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
235000013355 food flavoring agent Nutrition 0.000 description 1
239000007789 gas Substances 0.000 description 1
210000004211 gastric acid Anatomy 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
239000008103 glucose Substances 0.000 description 1
150000002343 gold Chemical class 0.000 description 1
PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
239000010931 gold Substances 0.000 description 1
229910052737 gold Inorganic materials 0.000 description 1
KWHDXJHBFYQOTK-UHFFFAOYSA-N heptane;toluene Chemical compound CCCCCCC.CC1=CC=CC=C1 KWHDXJHBFYQOTK-UHFFFAOYSA-N 0.000 description 1
210000000548 hind-foot Anatomy 0.000 description 1
239000012456 homogeneous solution Substances 0.000 description 1
235000020256 human milk Nutrition 0.000 description 1
210000004251 human milk Anatomy 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
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
230000002757 inflammatory effect Effects 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
LRDFRRGEGBBSRN-UHFFFAOYSA-N isobutyronitrile Chemical compound CC(C)C#N LRDFRRGEGBBSRN-UHFFFAOYSA-N 0.000 description 1
239000000644 isotonic solution Substances 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000008101 lactose Substances 0.000 description 1
229940059904 light mineral oil Drugs 0.000 description 1
229910003002 lithium salt Inorganic materials 0.000 description 1
159000000002 lithium salts Chemical class 0.000 description 1
238000011866 long-term treatment Methods 0.000 description 1
210000004698 lymphocyte Anatomy 0.000 description 1
ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
239000001095 magnesium carbonate Substances 0.000 description 1
229910000021 magnesium carbonate Inorganic materials 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
OHZZTXYKLXZFSZ-UHFFFAOYSA-I manganese(3+) 5,10,15-tris(1-methylpyridin-1-ium-4-yl)-20-(1-methylpyridin-4-ylidene)porphyrin-22-ide pentachloride Chemical compound [Cl-].[Cl-].[Cl-].[Cl-].[Cl-].[Mn+3].C1=CN(C)C=CC1=C1C(C=C2)=NC2=C(C=2C=C[N+](C)=CC=2)C([N-]2)=CC=C2C(C=2C=C[N+](C)=CC=2)=C(C=C2)N=C2C(C=2C=C[N+](C)=CC=2)=C2N=C1C=C2 OHZZTXYKLXZFSZ-UHFFFAOYSA-I 0.000 description 1
238000004949 mass spectrometry Methods 0.000 description 1
239000000155 melt Substances 0.000 description 1
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
229910052753 mercury Inorganic materials 0.000 description 1
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
230000001333 moisturizer Effects 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
206010033675 panniculitis Diseases 0.000 description 1
239000001814 pectin Substances 0.000 description 1
235000010987 pectin Nutrition 0.000 description 1
229920001277 pectin Polymers 0.000 description 1
208000011906 peptic ulcer disease Diseases 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 1
IUGYQRQAERSCNH-UHFFFAOYSA-M pivalate Chemical compound CC(C)(C)C([O-])=O IUGYQRQAERSCNH-UHFFFAOYSA-M 0.000 description 1
208000030428 polyarticular arthritis Diseases 0.000 description 1
229920000137 polyphosphoric acid Polymers 0.000 description 1
238000004393 prognosis Methods 0.000 description 1
238000011084 recovery Methods 0.000 description 1
230000004044 response Effects 0.000 description 1
238000006798 ring closing metathesis reaction Methods 0.000 description 1
150000003902 salicylic acid esters Chemical class 0.000 description 1
239000012266 salt solution Substances 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
238000000526 short-path distillation Methods 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000007619 statistical method Methods 0.000 description 1
230000004936 stimulating effect Effects 0.000 description 1
210000004304 subcutaneous tissue Anatomy 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
239000013589 supplement Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
208000011580 syndromic disease Diseases 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000007885 tablet disintegrant Substances 0.000 description 1
150000003536 tetrazoles Chemical group 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
239000002966 varnish Substances 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
239000003643 water by type Substances 0.000 description 1
239000001993 wax Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/30—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings
- C07C57/38—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings polycyclic
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D257/04—Five-membered rings
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/52—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen
- C07C57/62—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings and other rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/72—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings and other rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C63/00—Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings
- C07C63/68—Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings containing halogen
- C07C63/72—Polycyclic acids
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/01—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups
- C07C65/105—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups polycyclic

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Life Sciences & Earth Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Pain & Pain Management (AREA)
Pharmacology & Pharmacy (AREA)
Rheumatology (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

JP58252492A 1983-01-03 1983-12-28 抗炎症作用を有するジペンゾシクロヘプテニリデン Pending JPS59176230A (ja)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US45494183A	1983-01-03	1983-01-03
US454941		1983-01-03

Publications (1)

Publication Number	Publication Date
JPS59176230A true JPS59176230A (ja)	1984-10-05

Family

ID=23806706

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP58252492A Pending JPS59176230A (ja)	1983-01-03	1983-12-28	抗炎症作用を有するジペンゾシクロヘプテニリデン

Country Status (9)

Country	Link
EP (1)	EP0115690A1 (2)
JP (1)	JPS59176230A (2)
KR (1)	KR840007398A (2)
AU (1)	AU2258683A (2)
DK (1)	DK1384A (2)
GB (1)	GB2132618A (2)
GR (1)	GR81689B (2)
PT (1)	PT77911B (2)
ZA (1)	ZA839509B (2)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
HU195800B (en) *	1983-10-13	1988-07-28	Sandoz Ltd	Process for producing 4h-benzo/4,5/cylopenta/1,2-b/ thiofene derivatives and pharmaceutical compositions containing them
DE19941211A1 (de)	1999-08-30	2001-03-08	Haarmann & Reimer Gmbh	Herstellung von Dibenzosuberenon-Derivaten durch katralytische Dehydrierung
DE102005022020A1 (de) *	2005-05-12	2006-11-23	Merckle Gmbh	Dibenzocycloheptanverbindungen und pharmazeutische Mittel, welche diese Verbindungen enthalten

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
BE633316A (2) *
GB1053843A (2) *	1963-09-16
US4267192A (en) *	1980-03-11	1981-05-12	American Home Products Corporation	Method for treating inflammation

1983
- 1983-12-20 AU AU22586/83A patent/AU2258683A/en not_active Abandoned
- 1983-12-21 GB GB08334019A patent/GB2132618A/en not_active Withdrawn
- 1983-12-21 EP EP83307839A patent/EP0115690A1/en not_active Withdrawn
- 1983-12-21 ZA ZA839509A patent/ZA839509B/xx unknown
- 1983-12-28 JP JP58252492A patent/JPS59176230A/ja active Pending
- 1983-12-29 GR GR73391A patent/GR81689B/el unknown
- 1983-12-30 KR KR1019830006313A patent/KR840007398A/ko not_active Withdrawn
- 1983-12-30 PT PT77911A patent/PT77911B/pt unknown
1984
- 1984-01-02 DK DK1384A patent/DK1384A/da not_active Application Discontinuation

Also Published As

Publication number	Publication date
PT77911B (en)	1986-04-11
GB2132618A (en)	1984-07-11
DK1384D0 (da)	1984-01-02
GB8334019D0 (en)	1984-02-01
EP0115690A1 (en)	1984-08-15
AU2258683A (en)	1984-07-05
KR840007398A (ko)	1984-12-07
ZA839509B (en)	1985-08-28
PT77911A (en)	1984-01-01
DK1384A (da)	1984-07-04
GR81689B (2)	1984-12-12

Publication	Publication Date	Title
EP0918514B1 (en)	2005-12-28	Triaryl methane compounds for the treatment of cancer, actinic keratosis and kaposi's sarcoma
US4861798A (en)	1989-08-29	Lipoxygenase inhibitory compounds
JPS582936B2 (ja)	1983-01-19	５↓−アロイルピロ−ル酢酸およびその塩類の製法
US4172151A (en)	1979-10-23	Anti-inflammatory method
JPH0223537B2 (2)	1990-05-24
JPH0153671B2 (2)	1989-11-15
US6028103A (en)	2000-02-22	Triaryl methane compounds and analogues thereof useful for the treatment or prevention of sickle cell disease or diseases characterized by abnormal cell proliferation
JPS5920655B2 (ja)	1984-05-15	新ナフタレン誘導体の製法
US4375479A (en)	1983-03-01	Indanyl derivatives and use
JPH0222271A (ja)	1990-01-25	共役γ−オキシブテノライド化合物およびこれを有効成分とする抗潰瘍剤
JPH0222059B2 (2)	1990-05-17
US4055595A (en)	1977-10-25	Substituted aryloxy-3,3,3-trifluoro-2-propionic acids, esters and salts thereof
JPH04334358A (ja)	1992-11-20	縮合ベンゼンオキシ酢酸誘導体
US4273785A (en)	1981-06-16	Benzaldehydes, alkanophenones, and benzophenones and derivatives thereof containing a 4-monoalkylamino group
JPS623145B2 (2)	1987-01-23
JP3694774B2 (ja)	2005-09-14	フェニルカルボン酸誘導体
JPS5973516A (ja)	1984-04-25	抗炎症剤
JPH0246035B2 (2)	1990-10-12
CA1052788A (fr)	1979-04-17	Procede d'obtention de nouveaux acetamides n-substitues et les composes ainsi obtenus
IE881060L (en)	1988-10-10	Improvements in or relating to leukotriene antagonists
GB2132618A (en)	1984-07-11	Dibenzocycloheptenylidenes
JPS6013730A (ja)	1985-01-24	テルフエニル誘導体
JPH0422912B2 (2)	1992-04-20
US4011344A (en)	1977-03-08	Iminodimethylene di-tert-alkylophenones and phenols
JPS6011440A (ja)	1985-01-21	新ベンゾフエノン