IL88365A - History of 3,3-dimethyl-7-butyl-dihydro-benzoporen and pharmaceutical preparations containing them - Google Patents

History of 3,3-dimethyl-7-butyl-dihydro-benzoporen and pharmaceutical preparations containing them

Info

Publication number: IL88365A
Authority: IL; Israel
Prior art keywords: integer; group; compounds; compound; agents
Prior art date: 1987-11-23

Application number

IL8836588A

Other languages

English (en)

Hebrew (he)

Other versions

IL88365A0 (en

Original Assignee

Procter & Gamble

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.)

1987-11-23

Filing date

1988-11-11

Publication date

1994-02-27

1988-11-11 Application filed by Procter & Gamble filed Critical Procter & Gamble

1989-06-30 Publication of IL88365A0 publication Critical patent/IL88365A0/xx

1994-02-27 Publication of IL88365A publication Critical patent/IL88365A/en

Links

239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 15
MQGORHRDTRCPCX-UHFFFAOYSA-N 7-butyl-3,3-dimethyl-3a,4-dihydro-2H-1-benzofuran Chemical class CC1(COC=2C1CC=CC=2CCCC)C MQGORHRDTRCPCX-UHFFFAOYSA-N 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 65
125000000217 alkyl group Chemical group 0.000 claims abstract description 3
229920006395 saturated elastomer Polymers 0.000 claims description 12
229910052799 carbon Inorganic materials 0.000 claims description 11
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
239000003814 drug Substances 0.000 claims description 5
150000003839 salts Chemical class 0.000 claims description 5
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 3
-1 cyclic acetal Chemical class 0.000 claims description 3
125000004122 cyclic group Chemical group 0.000 claims description 3
125000004417 unsaturated alkyl group Chemical group 0.000 claims description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 4
150000001721 carbon Chemical group 0.000 claims 3
206010061218 Inflammation Diseases 0.000 abstract description 19
230000004054 inflammatory process Effects 0.000 abstract description 19
238000000034 method Methods 0.000 abstract description 10
125000000524 functional group Chemical group 0.000 abstract description 3
125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 abstract 1
125000002485 formyl group Chemical class [H]C(*)=O 0.000 abstract 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 30
239000000203 mixture Substances 0.000 description 25
238000012360 testing method Methods 0.000 description 18
239000002260 anti-inflammatory agent Substances 0.000 description 15
239000000243 solution Substances 0.000 description 15
229940121363 anti-inflammatory agent Drugs 0.000 description 14
239000003937 drug carrier Substances 0.000 description 13
238000006243 chemical reaction Methods 0.000 description 12
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 12
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
241001465754 Metazoa Species 0.000 description 11
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 11
230000003110 anti-inflammatory effect Effects 0.000 description 11
201000010099 disease Diseases 0.000 description 11
238000002360 preparation method Methods 0.000 description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
125000004432 carbon atom Chemical group C* 0.000 description 8
239000003795 chemical substances by application Substances 0.000 description 8
239000010410 layer Substances 0.000 description 8
101150041968 CDC13 gene Proteins 0.000 description 7
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 7
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 7
239000002775 capsule Substances 0.000 description 7
239000012074 organic phase Substances 0.000 description 7
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
206010039073 rheumatoid arthritis Diseases 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 5
241000700159 Rattus Species 0.000 description 5
150000001241 acetals Chemical class 0.000 description 5
239000003435 antirheumatic agent Substances 0.000 description 5
230000037396 body weight Effects 0.000 description 5
235000010418 carrageenan Nutrition 0.000 description 5
239000000679 carrageenan Substances 0.000 description 5
229940113118 carrageenan Drugs 0.000 description 5
229910052943 magnesium sulfate Inorganic materials 0.000 description 5
201000008482 osteoarthritis Diseases 0.000 description 5
UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 5
238000005481 NMR spectroscopy Methods 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
239000000730 antalgic agent Substances 0.000 description 4
239000003963 antioxidant agent Substances 0.000 description 4
239000002221 antipyretic Substances 0.000 description 4
229940125716 antipyretic agent Drugs 0.000 description 4
YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 4
229920001525 carrageenan Polymers 0.000 description 4
229940079593 drug Drugs 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
229940124346 antiarthritic agent Drugs 0.000 description 3
235000006708 antioxidants Nutrition 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
239000002617 bone density conservation agent Substances 0.000 description 3
230000005779 cell damage Effects 0.000 description 3
208000037887 cell injury Diseases 0.000 description 3
230000006378 damage Effects 0.000 description 3
230000000694 effects Effects 0.000 description 3
125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 description 3
238000003818 flash chromatography Methods 0.000 description 3
208000028867 ischemia Diseases 0.000 description 3
231100000053 low toxicity Toxicity 0.000 description 3
230000000144 pharmacologic effect Effects 0.000 description 3
239000000126 substance Substances 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
150000007970 thio esters Chemical class 0.000 description 3
238000005160 1H NMR spectroscopy Methods 0.000 description 2
SKDGWNHUETZZCS-UHFFFAOYSA-N 2,3-ditert-butylphenol Chemical class CC(C)(C)C1=CC=CC(O)=C1C(C)(C)C SKDGWNHUETZZCS-UHFFFAOYSA-N 0.000 description 2
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
201000005569 Gout Diseases 0.000 description 2
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
208000022559 Inflammatory bowel disease Diseases 0.000 description 2
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
239000012359 Methanesulfonyl chloride Substances 0.000 description 2
241000699670 Mus sp. Species 0.000 description 2
240000001307 Myosotis scorpioides Species 0.000 description 2
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
201000004681 Psoriasis Diseases 0.000 description 2
208000006011 Stroke Diseases 0.000 description 2
230000009471 action Effects 0.000 description 2
150000001299 aldehydes Chemical class 0.000 description 2
150000003863 ammonium salts Chemical class 0.000 description 2
239000003524 antilipemic agent Substances 0.000 description 2
229940114079 arachidonic acid Drugs 0.000 description 2
235000021342 arachidonic acid Nutrition 0.000 description 2
238000003556 assay Methods 0.000 description 2
230000008901 benefit Effects 0.000 description 2
OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
239000001913 cellulose Substances 0.000 description 2
235000010980 cellulose Nutrition 0.000 description 2
229920002678 cellulose Polymers 0.000 description 2
238000007796 conventional method Methods 0.000 description 2
WQOXQRCZOLPYPM-UHFFFAOYSA-N dimethyl disulfide Chemical compound CSSC WQOXQRCZOLPYPM-UHFFFAOYSA-N 0.000 description 2
238000004821 distillation Methods 0.000 description 2
239000002552 dosage form Substances 0.000 description 2
235000019439 ethyl acetate Nutrition 0.000 description 2
208000007565 gingivitis Diseases 0.000 description 2
239000002955 immunomodulating agent Substances 0.000 description 2
239000004615 ingredient Substances 0.000 description 2
230000005764 inhibitory process Effects 0.000 description 2
238000002347 injection Methods 0.000 description 2
239000007924 injection Substances 0.000 description 2
230000000302 ischemic effect Effects 0.000 description 2
239000008101 lactose Substances 0.000 description 2
239000012280 lithium aluminium hydride Substances 0.000 description 2
235000019359 magnesium stearate Nutrition 0.000 description 2
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
238000012986 modification Methods 0.000 description 2
230000004048 modification Effects 0.000 description 2
231100000252 nontoxic Toxicity 0.000 description 2
230000003000 nontoxic effect Effects 0.000 description 2
239000012044 organic layer Substances 0.000 description 2
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
208000028169 periodontal disease Diseases 0.000 description 2
239000000546 pharmaceutical excipient Substances 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
239000011591 potassium Substances 0.000 description 2
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
230000002035 prolonged effect Effects 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
238000003756 stirring Methods 0.000 description 2
FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 2
230000001225 therapeutic effect Effects 0.000 description 2
230000000699 topical effect Effects 0.000 description 2
WJQOZHYUIDYNHM-UHFFFAOYSA-N 2-tert-Butylphenol Chemical compound CC(C)(C)C1=CC=CC=C1O WJQOZHYUIDYNHM-UHFFFAOYSA-N 0.000 description 1
206010001052 Acute respiratory distress syndrome Diseases 0.000 description 1
229920001817 Agar Polymers 0.000 description 1
208000035285 Allergic Seasonal Rhinitis Diseases 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
206010002199 Anaphylactic shock Diseases 0.000 description 1
241000416162 Astragalus gummifer Species 0.000 description 1
201000001320 Atherosclerosis Diseases 0.000 description 1
KUVIULQEHSCUHY-XYWKZLDCSA-N Beclometasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(Cl)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)COC(=O)CC)(OC(=O)CC)[C@@]1(C)C[C@@H]2O KUVIULQEHSCUHY-XYWKZLDCSA-N 0.000 description 1
206010065687 Bone loss Diseases 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
229920002261 Corn starch Polymers 0.000 description 1
208000011231 Crohn disease Diseases 0.000 description 1
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
206010012434 Dermatitis allergic Diseases 0.000 description 1
206010012438 Dermatitis atopic Diseases 0.000 description 1
206010012442 Dermatitis contact Diseases 0.000 description 1
206010014561 Emphysema Diseases 0.000 description 1
239000001856 Ethyl cellulose Substances 0.000 description 1
ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical class CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 1
208000009386 Experimental Arthritis Diseases 0.000 description 1
206010070840 Gastrointestinal tract irritation Diseases 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
241000282412 Homo Species 0.000 description 1
208000004575 Infectious Arthritis Diseases 0.000 description 1
206010022998 Irritability Diseases 0.000 description 1
239000003810 Jones reagent Substances 0.000 description 1
208000003456 Juvenile Arthritis Diseases 0.000 description 1
206010059176 Juvenile idiopathic arthritis Diseases 0.000 description 1
238000000023 Kugelrohr distillation Methods 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
229930195725 Mannitol Natural products 0.000 description 1
241000699666 Mus <mouse, genus> Species 0.000 description 1
GXCLVBGFBYZDAG-UHFFFAOYSA-N N-[2-(1H-indol-3-yl)ethyl]-N-methylprop-2-en-1-amine Chemical compound CN(CCC1=CNC2=C1C=CC=C2)CC=C GXCLVBGFBYZDAG-UHFFFAOYSA-N 0.000 description 1
206010030113 Oedema Diseases 0.000 description 1
235000019483 Peanut oil Nutrition 0.000 description 1
206010035664 Pneumonia Diseases 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
201000001263 Psoriatic Arthritis Diseases 0.000 description 1
208000036824 Psoriatic arthropathy Diseases 0.000 description 1
206010037423 Pulmonary oedema Diseases 0.000 description 1
206010037660 Pyrexia Diseases 0.000 description 1
208000033464 Reiter syndrome Diseases 0.000 description 1
208000013616 Respiratory Distress Syndrome Diseases 0.000 description 1
206010039085 Rhinitis allergic Diseases 0.000 description 1
DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
201000002661 Spondylitis Diseases 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
235000021355 Stearic acid Nutrition 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
229930006000 Sucrose Natural products 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
206010042496 Sunburn Diseases 0.000 description 1
240000006474 Theobroma bicolor Species 0.000 description 1
229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
241000159243 Toxicodendron radicans Species 0.000 description 1
229920001615 Tragacanth Polymers 0.000 description 1
206010052779 Transplant rejections Diseases 0.000 description 1
OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 1
208000024780 Urticaria Diseases 0.000 description 1
125000004036 acetal group Chemical group 0.000 description 1
DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 1
229960004373 acetylcholine Drugs 0.000 description 1
230000001154 acute effect Effects 0.000 description 1
201000000028 adult respiratory distress syndrome Diseases 0.000 description 1
239000008272 agar Substances 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
230000000172 allergic effect Effects 0.000 description 1
201000010105 allergic rhinitis Diseases 0.000 description 1
230000000202 analgesic effect Effects 0.000 description 1
208000003455 anaphylaxis Diseases 0.000 description 1
230000003712 anti-aging effect Effects 0.000 description 1
229940124599 anti-inflammatory drug Drugs 0.000 description 1
230000001754 anti-pyretic effect Effects 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
208000006673 asthma Diseases 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
201000008937 atopic dermatitis Diseases 0.000 description 1
208000010668 atopic eczema Diseases 0.000 description 1
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
239000008280 blood Substances 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
210000000988 bone and bone Anatomy 0.000 description 1
210000004556 brain Anatomy 0.000 description 1
206010006451 bronchitis Diseases 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000011575 calcium Substances 0.000 description 1
239000001768 carboxy methyl cellulose Substances 0.000 description 1
229920002301 cellulose acetate Polymers 0.000 description 1
210000003169 central nervous system Anatomy 0.000 description 1
HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
230000001684 chronic effect Effects 0.000 description 1
239000003086 colorant Substances 0.000 description 1
238000005056 compaction Methods 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
208000010247 contact dermatitis Diseases 0.000 description 1
235000005687 corn oil Nutrition 0.000 description 1
239000002285 corn oil Substances 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
229940099112 cornstarch Drugs 0.000 description 1
235000012343 cottonseed oil Nutrition 0.000 description 1
239000002385 cottonseed oil Substances 0.000 description 1
239000006071 cream Substances 0.000 description 1
239000012043 crude product Substances 0.000 description 1
235000001916 dieting Nutrition 0.000 description 1
230000037228 dieting effect Effects 0.000 description 1
238000007865 diluting Methods 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
238000006073 displacement reaction Methods 0.000 description 1
210000005069 ears Anatomy 0.000 description 1
HFTNNOZFRQLFQB-UHFFFAOYSA-N ethenoxy(trimethyl)silane Chemical compound C[Si](C)(C)OC=C HFTNNOZFRQLFQB-UHFFFAOYSA-N 0.000 description 1
235000019325 ethyl cellulose Nutrition 0.000 description 1
229920001249 ethyl cellulose Polymers 0.000 description 1
239000000945 filler Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
235000013305 food Nutrition 0.000 description 1
235000013355 food flavoring agent Nutrition 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
230000002496 gastric effect Effects 0.000 description 1
210000001035 gastrointestinal tract Anatomy 0.000 description 1
239000000499 gel Substances 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 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
235000011187 glycerol Nutrition 0.000 description 1
229910001385 heavy metal Inorganic materials 0.000 description 1
230000036571 hydration Effects 0.000 description 1
238000006703 hydration reaction Methods 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
229910052738 indium Inorganic materials 0.000 description 1
APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
230000002757 inflammatory effect Effects 0.000 description 1
230000028709 inflammatory response Effects 0.000 description 1
206010022000 influenza Diseases 0.000 description 1
208000014674 injury Diseases 0.000 description 1
230000003993 interaction Effects 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
238000010255 intramuscular injection Methods 0.000 description 1
239000007927 intramuscular injection Substances 0.000 description 1
238000007912 intraperitoneal administration Methods 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
238000010253 intravenous injection Methods 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
150000002596 lactones Chemical class 0.000 description 1
150000002617 leukotrienes Chemical class 0.000 description 1
239000007788 liquid Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
239000000463 material 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
229920000609 methyl cellulose Polymers 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
235000010981 methylcellulose Nutrition 0.000 description 1
239000013081 microcrystal Substances 0.000 description 1
238000002156 mixing Methods 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
210000000214 mouth Anatomy 0.000 description 1
201000006417 multiple sclerosis Diseases 0.000 description 1
229940035363 muscle relaxants Drugs 0.000 description 1
208000010125 myocardial infarction Diseases 0.000 description 1
239000003158 myorelaxant agent Substances 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
239000003921 oil Substances 0.000 description 1
235000019198 oils Nutrition 0.000 description 1
239000004006 olive oil Substances 0.000 description 1
235000008390 olive oil Nutrition 0.000 description 1
238000001543 one-way ANOVA Methods 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
239000000312 peanut oil Substances 0.000 description 1
JDKQTIKEGOOXTJ-UHFFFAOYSA-N pent-4-enoyl chloride Chemical compound ClC(=O)CCC=C JDKQTIKEGOOXTJ-UHFFFAOYSA-N 0.000 description 1
ASAWAIQNAGKJFT-UHFFFAOYSA-N pent-4-ynoyl chloride Chemical compound ClC(=O)CCC#C ASAWAIQNAGKJFT-UHFFFAOYSA-N 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
239000008363 phosphate buffer Substances 0.000 description 1
239000002504 physiological saline solution Substances 0.000 description 1
239000004033 plastic Substances 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229920005862 polyol Polymers 0.000 description 1
150000003077 polyols Chemical class 0.000 description 1
235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
229920000053 polysorbate 80 Polymers 0.000 description 1
229920001592 potato starch Polymers 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
235000013772 propylene glycol Nutrition 0.000 description 1
150000003180 prostaglandins Chemical class 0.000 description 1
208000005333 pulmonary edema Diseases 0.000 description 1
JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
238000011552 rat model Methods 0.000 description 1
239000002994 raw material Substances 0.000 description 1
208000002574 reactive arthritis Diseases 0.000 description 1
238000000611 regression analysis Methods 0.000 description 1
230000010410 reperfusion Effects 0.000 description 1
210000002345 respiratory system Anatomy 0.000 description 1
239000000837 restrainer Substances 0.000 description 1
201000001223 septic arthritis Diseases 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
238000000526 short-path distillation Methods 0.000 description 1
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
229940079832 sodium starch glycolate Drugs 0.000 description 1
239000008109 sodium starch glycolate Substances 0.000 description 1
229920003109 sodium starch glycolate Polymers 0.000 description 1
239000008279 sol Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
235000010356 sorbitol Nutrition 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
101150008563 spir gene Proteins 0.000 description 1
238000013222 sprague-dawley male rat Methods 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
230000003637 steroidlike Effects 0.000 description 1
210000002784 stomach Anatomy 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
238000010254 subcutaneous injection Methods 0.000 description 1
239000007929 subcutaneous injection Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
230000002194 synthesizing effect Effects 0.000 description 1
201000000596 systemic lupus erythematosus Diseases 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 1
VEPTXBCIDSFGBF-UHFFFAOYSA-M tetrabutylazanium;fluoride;trihydrate Chemical compound O.O.O.[F-].CCCC[N+](CCCC)(CCCC)CCCC VEPTXBCIDSFGBF-UHFFFAOYSA-M 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
210000001519 tissue Anatomy 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
230000008733 trauma Effects 0.000 description 1
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical group CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- 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
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/34—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/82—Benzo [b] furans; Hydrogenated benzo [b] furans 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 carbon atoms of the hetero ring
- C07D307/83—Oxygen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms

Landscapes

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

IL8836588A 1987-11-23 1988-11-11 History of 3,3-dimethyl-7-butyl-dihydro-benzoporen and pharmaceutical preparations containing them IL88365A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US07/123,756 US4849428A (en)	1987-11-23	1987-11-23	Cyclic anti-inflammatory derivatives of di-tert-butylphenol compounds, compositions and use

Publications (2)

Publication Number	Publication Date
IL88365A0 IL88365A0 (en)	1989-06-30
IL88365A true IL88365A (en)	1994-02-27

Family

ID=22410695

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL8836588A IL88365A (en)	1987-11-23	1988-11-11	History of 3,3-dimethyl-7-butyl-dihydro-benzoporen and pharmaceutical preparations containing them

Country Status (14)

Country	Link
US (1)	US4849428A (da)
EP (1)	EP0322004B1 (da)
JP (1)	JP2602931B2 (da)
KR (1)	KR970011460B1 (da)
AT (1)	ATE71623T1 (da)
AU (1)	AU621571B2 (da)
CA (1)	CA1308110C (da)
DE (1)	DE3867827D1 (da)
DK (1)	DK173367B1 (da)
IE (1)	IE61197B1 (da)
IL (1)	IL88365A (da)
NZ (1)	NZ227039A (da)
PH (1)	PH25855A (da)
ZA (1)	ZA888727B (da)

Families Citing this family (17)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4982006A (en) *	1987-12-18	1991-01-01	Norwich Eaton Pharmaceuticals, Inc.	Process for the preparation of certain substituted aromatic compounds
GB8827850D0 (en) *	1988-11-29	1988-12-29	Shell Int Research	Biocidal compounds
US5189066A (en) *	1989-11-22	1993-02-23	The Procter & Gamble Company	Pharmaceutical compositions of tebufelone
US5126487A (en) *	1991-03-26	1992-06-30	The Procter & Gamble Company	Process for the preparation of 2-alkyl-4-acyl-6-tert-butylphenol compounds
US5281420A (en) *	1992-05-19	1994-01-25	The Procter & Gamble Company	Solid dispersion compositions of tebufelone
JPH10506615A (ja) *	1994-07-27	1998-06-30	ザ、プロクター、エンド、ギャンブル、カンパニー	抗炎症剤として有用なジヒドロベンゾフラン及び関連化合物
US5674891A (en) *	1994-07-27	1997-10-07	The Procter & Gamble Company	Dihydrobenzothiophene compounds useful as anti-inflammatory agents
US5684002A (en) *	1994-09-07	1997-11-04	The Procter & Gamble Company	Dihydorbenzofuran and related compounds useful as anti-inflammatory agents
US5618835A (en) *	1996-02-01	1997-04-08	The Procter & Gamble Company	Dihydrobenzofuran and related compounds useful as anti-inflammatory agents
US5821250A (en) *	1996-02-01	1998-10-13	The Procter & Gamble Company	Dihydrobenzofuran and related compounds useful as anti-inflammatory agents
US5672620A (en) *	1996-02-01	1997-09-30	The Procter & Gamble Company	Dihydrobenzofuran and related compounds useful as anti-inflammatory agents
US5686471A (en) *	1996-02-01	1997-11-11	The Procter & Gamble Company	Dihydrobenzofuran and related compounds useful as anti-inflammatory agents
US5684031A (en) *	1996-02-01	1997-11-04	The Procter & Gamble Company	Dihydrobenzofuran and related compounds useful as anti-inflammatory agents
US5684041A (en) *	1996-02-01	1997-11-04	The Procter & Gamble Company	Dihydrobenzofuran and related compounds useful as anti-inflammatory agents
US5750543A (en) *	1996-02-01	1998-05-12	The Procter & Gamble Company	Dihydrobenzofuran and related compounds useful as anti-inflammatory agents
FR2744452B1 (fr) *	1996-02-06	1998-03-06	Cird Galderma	Composes biaryles heterocycliques, compositions pharmaceutiques et cosmetiques les contenant et utilisations
US7479507B2 (en) *	2003-01-14	2009-01-20	Adam Heller	Anti-inflammatory substituted phenols and elastomeric compositions for oral delivery of drugs

Family Cites Families (17)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE1922815A1 (de) *	1969-05-05	1970-11-12	Merck Anlagen Gmbh	Phenolaether und Phenolester als Stabilisatoren
US3829446A (en) *	1970-10-15	1974-08-13	Pfizer	Oxobenzofuran intermediates
US3862133A (en) *	1973-04-30	1975-01-21	Goodrich Co B F	Gamma-lactones of o-hydroxyphenylacetic acids
US4013690A (en) *	1974-02-05	1977-03-22	Sandoz Ltd.	Organic compounds
DE2608697A1 (de) *	1975-03-12	1976-09-23	Sandoz Ag	Neue organische verbindungen, ihre herstellung und verwendung
US4130666A (en) *	1977-05-16	1978-12-19	Riker Laboratories, Inc.	Anti-inflammatory method
DE2803544A1 (de) *	1978-01-27	1979-08-02	Sandoz Ag	Neue benzofuran- und benzoxepinderivate
GB2042562B (en) *	1979-02-05	1983-05-11	Sandoz Ltd	Stabilising polymers
DE2931672A1 (de) *	1979-08-04	1981-02-26	Basf Ag	Substituierte 2,3-dihydrobenzofurylmethylester, verfahren zu ihrer herstellung und ihre verwendung zur bekaempfung von schaedlingen
US4440784A (en) *	1981-02-05	1984-04-03	Kanegafuchi Chemical Industry Company, Ltd.	Anti-inflammatory, analgesic, and antipyretic pharmaceutical composition
US4431656A (en) *	1981-02-05	1984-02-14	Kanegafuchi Chemical Industry Company Limited	3,5-di-Tert-butylstyrene derivatives, salts thereof, and pharmaceutical compositions containing the same as an active ingredient
US4514415A (en) *	1981-10-28	1985-04-30	Ciba Geigy Corporation	Benzofuran-2(3H)-ones used as anti-inflammatory agents
JPH0623194B2 (ja) *	1985-03-23	1994-03-30	鐘淵化学工業株式会社	新規ラクタム誘導体及び抗炎症剤
US4711903A (en) *	1986-01-31	1987-12-08	G. D. Searle & Co.	Phenolic thioethers as inhibitors of 5-lipoxygenase
US4708966A (en) *	1986-06-27	1987-11-24	The Procter & Gamble Company	Novel anti-inflammatory agents, pharmaceutical compositions and methods for reducing inflammation
US4911754A (en) *	1987-07-16	1990-03-27	American Cyanamid Company	Herbicidally active aryloxy saturated 5-membered benzo fused hetero-cyclic compounds
JPH0654315A (ja) *	1992-07-31	1994-02-25	Canon Inc	動画像符号化方法及び装置

1987
- 1987-11-23 US US07/123,756 patent/US4849428A/en not_active Expired - Lifetime
1988
- 1988-11-11 IL IL8836588A patent/IL88365A/en not_active IP Right Cessation
- 1988-11-17 PH PH37827A patent/PH25855A/en unknown
- 1988-11-18 EP EP88202593A patent/EP0322004B1/en not_active Expired - Lifetime
- 1988-11-18 AT AT88202593T patent/ATE71623T1/de not_active IP Right Cessation
- 1988-11-18 DE DE8888202593T patent/DE3867827D1/de not_active Expired - Lifetime
- 1988-11-22 IE IE349188A patent/IE61197B1/en not_active IP Right Cessation
- 1988-11-22 NZ NZ227039A patent/NZ227039A/xx unknown
- 1988-11-22 AU AU25771/88A patent/AU621571B2/en not_active Ceased
- 1988-11-22 CA CA000583746A patent/CA1308110C/en not_active Expired - Lifetime
- 1988-11-22 ZA ZA888727A patent/ZA888727B/xx unknown
- 1988-11-23 KR KR1019880015404A patent/KR970011460B1/ko not_active Expired - Fee Related
- 1988-11-23 DK DK198806530A patent/DK173367B1/da not_active IP Right Cessation
- 1988-11-24 JP JP63297155A patent/JP2602931B2/ja not_active Expired - Fee Related

Also Published As

Publication number	Publication date
ZA888727B (en)	1989-08-30
NZ227039A (en)	1990-10-26
JPH01250372A (ja)	1989-10-05
JP2602931B2 (ja)	1997-04-23
IL88365A0 (en)	1989-06-30
AU2577188A (en)	1989-05-25
KR890008123A (ko)	1989-07-08
ATE71623T1 (de)	1992-02-15
IE883491L (en)	1989-05-23
DE3867827D1 (de)	1992-02-27
EP0322004B1 (en)	1992-01-15
DK653088A (da)	1989-05-24
DK653088D0 (da)	1988-11-23
KR970011460B1 (ko)	1997-07-11
IE61197B1 (en)	1994-10-19
DK173367B1 (da)	2000-08-21
AU621571B2 (en)	1992-03-19
PH25855A (en)	1991-12-02
US4849428A (en)	1989-07-18
CA1308110C (en)	1992-09-29
EP0322004A1 (en)	1989-06-28

Legal Events

Date	Code	Title	Description
2003-01-12	KB	Patent renewed
2007-07-24	MM9K	Patent not in force due to non-payment of renewal fees

Publication	Publication Date	Title
AU612979B2 (en)	1991-07-25	Novel anti-inflammatory agents, pharmaceutical compositions and methods for reducing inflammation
EP0322004B1 (en)	1992-01-15	Cyclic anti-inflammatory derivatives of di-tert-butylphenol compounds
CA1316932C (en)	1993-04-27	Methods and compositions for inhibiting lipoxygenase
US4833164A (en)	1989-05-23	2-substituted-1-naphthols, pharmaceutical compositions of, and their use as 5-lipoxygenase inhibitors
US4847303A (en)	1989-07-11	Tert-butylphenyl compounds useful as anti-inflammatory agents
US5112864A (en)	1992-05-12	PLA2 inhibitors as antiinflammatories
JPH11504657A (ja)	1999-04-27	フラン―およびチオフェンカルボチオアミド誘導体，それらの製造，ならびにｈｉｖ―１およびｈｉｖ―１突然変異株の複製の阻害剤としてのそれらの使用
US4801611A (en)	1989-01-31	5-lipoxygenase inhibitors
US5162365A (en)	1992-11-10	5-lipoxygenase inhibitors
US4576962A (en)	1986-03-18	Prostaglandin analogues
US5036105A (en)	1991-07-30	5-lipoxygenase inhibitors
US4985442A (en)	1991-01-15	2-substituted-1-naphthols as 5-lipoxygenase inhibitors
US5229421A (en)	1993-07-20	Methods and compositions for inhibiting lipoxygenase
EP0177927A1 (en)	1986-04-16	3-Hydroxybenzo[b]thiophene-2-sulfide derivatives as specific-5-lipoxygenase inhibitors
US5026759A (en)	1991-06-25	2-substituted-1-naphthols as 5-lipoxygenase inhibitors
WO1980000964A1 (en)	1980-05-15	Anti-inflammatory agents including 2-carbonyl-3-hydroxy-2-alkenonitriles
JPH03204882A (ja)	1991-09-06	Ｎ―アルケニルベンゾ［ｂ］チエノ［３，２―ｂ］オキサジン―２，４―ジオン
NZ277986A (en)	1998-03-25	Di-tertiary-butylphenol ketone derivatives as anti-inflammatory agents