DD265141A5 - Verfahren zur herstellung einer antiallergisch und entzuendungshemmende wirkende verbindung - Google Patents

Verfahren zur herstellung einer antiallergisch und entzuendungshemmende wirkende verbindung Download PDF

Info

Publication number: DD265141A5
Authority: DD; German Democratic Republic
Prior art keywords: compounds; hydrogen; formula; nmr; methyl
Prior art date: 1986-06-09

Application number

DD87303578A

Other languages

German (de)

English (en)

Inventor

Kitaura Yoshihiko

Ito Fumitaka

Rodney W Stevens

Asai Nobuko

Original Assignee

��@��k��

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1986-06-09

Filing date

1987-06-05

Publication date

1989-02-22

1987-06-05 Application filed by ��@��k�� filed Critical ��@��k��

1989-02-22 Publication of DD265141A5 publication Critical patent/DD265141A5/de

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 57
238000004519 manufacturing process Methods 0.000 title claims abstract 3
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 23
239000001257 hydrogen Substances 0.000 claims abstract description 23
125000000217 alkyl group Chemical group 0.000 claims abstract description 11
230000003266 anti-allergic effect Effects 0.000 claims abstract description 7
229910052760 oxygen Inorganic materials 0.000 claims abstract description 4
229910052717 sulfur Inorganic materials 0.000 claims abstract description 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 3
-1 methoxy, methyl Chemical group 0.000 claims description 16
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
125000004432 carbon atom Chemical group C* 0.000 claims description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
125000005504 styryl group Chemical group 0.000 claims description 6
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
239000000460 chlorine Substances 0.000 claims description 5
229910052801 chlorine Inorganic materials 0.000 claims description 5
230000003110 anti-inflammatory effect Effects 0.000 claims description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
XMSZANIMCDLNKA-UHFFFAOYSA-N methyl hypofluorite Chemical compound COF XMSZANIMCDLNKA-UHFFFAOYSA-N 0.000 claims description 3
125000001424 substituent group Chemical group 0.000 claims description 3
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 2
229910052731 fluorine Inorganic materials 0.000 claims description 2
239000011737 fluorine Substances 0.000 claims description 2
125000002541 furyl group Chemical group 0.000 claims description 2
125000004076 pyridyl group Chemical group 0.000 claims description 2
150000002431 hydrogen Chemical group 0.000 abstract description 8
125000003545 alkoxy group Chemical group 0.000 abstract description 2
229940121363 anti-inflammatory agent Drugs 0.000 abstract description 2
239000002260 anti-inflammatory agent Substances 0.000 abstract description 2
239000000043 antiallergic agent Substances 0.000 abstract description 2
125000001589 carboacyl group Chemical group 0.000 abstract description 2
125000000623 heterocyclic group Chemical group 0.000 abstract description 2
230000001166 anti-perspirative effect Effects 0.000 abstract 1
239000003213 antiperspirant Substances 0.000 abstract 1
125000003710 aryl alkyl group Chemical group 0.000 abstract 1
125000003118 aryl group Chemical group 0.000 abstract 1
229910052736 halogen Inorganic materials 0.000 abstract 1
150000002367 halogens Chemical class 0.000 abstract 1
238000005481 NMR spectroscopy Methods 0.000 description 19
238000006243 chemical reaction Methods 0.000 description 16
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
238000000034 method Methods 0.000 description 13
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 11
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 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
102000003820 Lipoxygenases Human genes 0.000 description 7
108090000128 Lipoxygenases Proteins 0.000 description 7
102000004005 Prostaglandin-endoperoxide synthases Human genes 0.000 description 7
108090000459 Prostaglandin-endoperoxide synthases Proteins 0.000 description 7
239000000047 product Substances 0.000 description 7
150000003839 salts Chemical class 0.000 description 7
239000000243 solution Substances 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 6
229910000041 hydrogen chloride Inorganic materials 0.000 description 6
239000002253 acid Substances 0.000 description 5
150000001299 aldehydes Chemical class 0.000 description 5
230000000172 allergic effect Effects 0.000 description 5
208000010668 atopic eczema Diseases 0.000 description 5
VAJVDSVGBWFCLW-UHFFFAOYSA-N 3-Phenyl-1-propanol Chemical compound OCCCC1=CC=CC=C1 VAJVDSVGBWFCLW-UHFFFAOYSA-N 0.000 description 4
YGCZTXZTJXYWCO-UHFFFAOYSA-N 3-phenylpropanal Chemical compound O=CCCC1=CC=CC=C1 YGCZTXZTJXYWCO-UHFFFAOYSA-N 0.000 description 4
241000124008 Mammalia Species 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
229940114079 arachidonic acid Drugs 0.000 description 4
235000021342 arachidonic acid Nutrition 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
230000000694 effects Effects 0.000 description 4
230000004968 inflammatory condition Effects 0.000 description 4
150000003180 prostaglandins Chemical class 0.000 description 4
FPNNPEPPWHRWNZ-UHFFFAOYSA-N 6-(3-phenylpropylamino)-3h-1,3-benzoxazol-2-one Chemical compound C1=C2OC(=O)NC2=CC=C1NCCCC1=CC=CC=C1 FPNNPEPPWHRWNZ-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
229910052784 alkaline earth metal Inorganic materials 0.000 description 3
125000003282 alkyl amino group Chemical group 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
239000003085 diluting agent Substances 0.000 description 3
150000002617 leukotrienes Chemical class 0.000 description 3
229940094443 oxytocics prostaglandins Drugs 0.000 description 3
229910000033 sodium borohydride Inorganic materials 0.000 description 3
239000012279 sodium borohydride Substances 0.000 description 3
239000002904 solvent Substances 0.000 description 3
239000000126 substance Substances 0.000 description 3
JPUYXUBUJJDJNL-UHFFFAOYSA-N 5-amino-1,3-dihydroindol-2-one Chemical compound NC1=CC=C2NC(=O)CC2=C1 JPUYXUBUJJDJNL-UHFFFAOYSA-N 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
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
229910019142 PO4 Inorganic materials 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
208000007536 Thrombosis Diseases 0.000 description 2
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
239000004480 active ingredient Substances 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
239000007900 aqueous suspension Substances 0.000 description 2
208000006673 asthma Diseases 0.000 description 2
239000002585 base Substances 0.000 description 2
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
230000037396 body weight Effects 0.000 description 2
239000012267 brine Substances 0.000 description 2
239000002775 capsule Substances 0.000 description 2
239000003638 chemical reducing agent Substances 0.000 description 2
238000007796 conventional method Methods 0.000 description 2
239000012024 dehydrating agents‎ Substances 0.000 description 2
125000001153 fluoro group Chemical group F* 0.000 description 2
150000002391 heterocyclic compounds Chemical class 0.000 description 2
239000012442 inert solvent Substances 0.000 description 2
208000030603 inherited susceptibility to asthma Diseases 0.000 description 2
239000003112 inhibitor Substances 0.000 description 2
230000002401 inhibitory effect Effects 0.000 description 2
238000001990 intravenous administration Methods 0.000 description 2
239000008101 lactose 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
239000002207 metabolite Substances 0.000 description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
239000002808 molecular sieve Substances 0.000 description 2
239000008194 pharmaceutical composition Substances 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
239000010452 phosphate Substances 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
239000002243 precursor Substances 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical group [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
239000000725 suspension Substances 0.000 description 2
208000024891 symptom Diseases 0.000 description 2
239000003826 tablet Substances 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
150000003595 thromboxanes Chemical class 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
BXQNSPXDWSNUKE-UHFFFAOYSA-N 1,3-benzothiazole 1-oxide Chemical class C1=CC=C2S(=O)C=NC2=C1 BXQNSPXDWSNUKE-UHFFFAOYSA-N 0.000 description 1
150000000183 1,3-benzoxazoles Chemical class 0.000 description 1
ZIIUUSVHCHPIQD-UHFFFAOYSA-N 2,4,6-trimethyl-N-[3-(trifluoromethyl)phenyl]benzenesulfonamide Chemical compound CC1=CC(C)=CC(C)=C1S(=O)(=O)NC1=CC=CC(C(F)(F)F)=C1 ZIIUUSVHCHPIQD-UHFFFAOYSA-N 0.000 description 1
IQVAERDLDAZARL-UHFFFAOYSA-N 2-phenylpropanal Chemical compound O=CC(C)C1=CC=CC=C1 IQVAERDLDAZARL-UHFFFAOYSA-N 0.000 description 1
CSDQQAQKBAQLLE-UHFFFAOYSA-N 4-(4-chlorophenyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical compound C1=CC(Cl)=CC=C1C1C(C=CS2)=C2CCN1 CSDQQAQKBAQLLE-UHFFFAOYSA-N 0.000 description 1
BFWGZWGLZIWCCW-UHFFFAOYSA-N 5'-(3-phenylpropylamino)spiro[1,3-dioxolane-2,3'-1h-indole]-2'-one Chemical compound C1=C2C3(OCCO3)C(=O)NC2=CC=C1NCCCC1=CC=CC=C1 BFWGZWGLZIWCCW-UHFFFAOYSA-N 0.000 description 1
JQKZSACVBHBOLG-UHFFFAOYSA-N 5'-aminospiro[1,3-dioxolane-2,3'-1h-indole]-2'-one Chemical compound C12=CC(N)=CC=C2NC(=O)C21OCCO2 JQKZSACVBHBOLG-UHFFFAOYSA-N 0.000 description 1
NBBRLIBUUQMZIV-UHFFFAOYSA-N 5-amino-6-methoxy-3-methyl-1h-benzimidazol-2-one Chemical compound C1=C(N)C(OC)=CC2=C1N(C)C(=O)N2 NBBRLIBUUQMZIV-UHFFFAOYSA-N 0.000 description 1
BHBQNWPJDGIAOE-UHFFFAOYSA-N 5-fluoro-6-(3-phenylpropylamino)-3h-1,3-benzoxazol-2-one Chemical compound FC1=CC=2NC(=O)OC=2C=C1NCCCC1=CC=CC=C1 BHBQNWPJDGIAOE-UHFFFAOYSA-N 0.000 description 1
CIOQNUSPTLYSMU-UHFFFAOYSA-N 5-methyl-6-(3-phenylpropylamino)-3h-1,3-benzoxazol-2-one Chemical compound CC1=CC=2NC(=O)OC=2C=C1NCCCC1=CC=CC=C1 CIOQNUSPTLYSMU-UHFFFAOYSA-N 0.000 description 1
QSELIJIQZIWRSK-UHFFFAOYSA-N 6-(3-phenylpropylamino)-3h-1,3-benzothiazol-2-one Chemical compound C1=C2SC(=O)NC2=CC=C1NCCCC1=CC=CC=C1 QSELIJIQZIWRSK-UHFFFAOYSA-N 0.000 description 1
VZSRROFDELKSGA-UHFFFAOYSA-N 6-(5-phenylpentylamino)-3h-1,3-benzoxazol-2-one Chemical compound C1=C2OC(=O)NC2=CC=C1NCCCCCC1=CC=CC=C1 VZSRROFDELKSGA-UHFFFAOYSA-N 0.000 description 1
XFIIXJLWGOSKMF-UHFFFAOYSA-N 6-[methyl(3-phenylpropyl)amino]-3h-1,3-benzoxazol-2-one;hydrochloride Chemical compound Cl.C=1C=C2NC(=O)OC2=CC=1N(C)CCCC1=CC=CC=C1 XFIIXJLWGOSKMF-UHFFFAOYSA-N 0.000 description 1
FPNLXQSOWBNXCN-UHFFFAOYSA-N 6-amino-3-methyl-1,3-benzoxazol-2-one Chemical compound C1=C(N)C=C2OC(=O)N(C)C2=C1 FPNLXQSOWBNXCN-UHFFFAOYSA-N 0.000 description 1
CLYCLRFHPKKUBR-UHFFFAOYSA-N 6-amino-3h-1,3-benzothiazol-2-one Chemical compound NC1=CC=C2N=C(O)SC2=C1 CLYCLRFHPKKUBR-UHFFFAOYSA-N 0.000 description 1
STLPJYGZOIEDAJ-UHFFFAOYSA-N 6-amino-3h-1,3-benzoxazol-2-one Chemical group NC1=CC=C2NC(=O)OC2=C1 STLPJYGZOIEDAJ-UHFFFAOYSA-N 0.000 description 1
CLCPWTXGFUIRJE-UHFFFAOYSA-N 7-amino-3h-1,3-benzoxazol-2-one Chemical compound NC1=CC=CC2=C1OC(=O)N2 CLCPWTXGFUIRJE-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
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 1
206010002198 Anaphylactic reaction Diseases 0.000 description 1
BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
229920002261 Corn starch Polymers 0.000 description 1
RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 1
102000004190 Enzymes Human genes 0.000 description 1
108090000790 Enzymes Proteins 0.000 description 1
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
241000282412 Homo Species 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
206010020751 Hypersensitivity Diseases 0.000 description 1
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 1
ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 description 1
JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 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
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
102000015439 Phospholipases Human genes 0.000 description 1
108010064785 Phospholipases Proteins 0.000 description 1
ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
210000000683 abdominal cavity Anatomy 0.000 description 1
238000009825 accumulation Methods 0.000 description 1
229960001138 acetylsalicylic acid Drugs 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000004931 aggregating effect Effects 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
229910000102 alkali metal hydride Inorganic materials 0.000 description 1
150000008046 alkali metal hydrides Chemical class 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
230000002152 alkylating effect Effects 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
208000026935 allergic disease Diseases 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
230000000202 analgesic effect Effects 0.000 description 1
230000036783 anaphylactic response Effects 0.000 description 1
208000003455 anaphylaxis Diseases 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
230000004872 arterial blood pressure Effects 0.000 description 1
125000005418 aryl aryl group Chemical group 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
229940077388 benzenesulfonate Drugs 0.000 description 1
125000005605 benzo group Chemical group 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
239000000969 carrier Substances 0.000 description 1
241001233037 catfish Species 0.000 description 1
238000004113 cell culture Methods 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
229940099112 cornstarch Drugs 0.000 description 1
239000012043 crude product Substances 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
239000003814 drug Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
150000004675 formic acid derivatives Chemical class 0.000 description 1
235000021588 free fatty acids Nutrition 0.000 description 1
230000002496 gastric effect Effects 0.000 description 1
229940050410 gluconate Drugs 0.000 description 1
125000001072 heteroaryl group Chemical group 0.000 description 1
239000002638 heterogeneous catalyst Substances 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
230000009610 hypersensitivity Effects 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
238000007912 intraperitoneal administration Methods 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
125000005647 linker group Chemical group 0.000 description 1
239000007937 lozenge Substances 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000012528 membrane Substances 0.000 description 1
230000004060 metabolic process Effects 0.000 description 1
229910052987 metal hydride Inorganic materials 0.000 description 1
150000004681 metal hydrides Chemical class 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000011259 mixed solution Substances 0.000 description 1
239000000203 mixture Substances 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
239000011368 organic material Substances 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
201000008482 osteoarthritis Diseases 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000012071 phase Substances 0.000 description 1
150000003904 phospholipids Chemical class 0.000 description 1
230000001766 physiological effect Effects 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
DJEHXEMURTVAOE-UHFFFAOYSA-M potassium bisulfite Chemical compound [K+].OS([O-])=O DJEHXEMURTVAOE-UHFFFAOYSA-M 0.000 description 1
229940099427 potassium bisulfite Drugs 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
235000010259 potassium hydrogen sulphite Nutrition 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
230000002265 prevention Effects 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
150000003815 prostacyclins Chemical class 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000000376 reactant Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
230000004044 response Effects 0.000 description 1
206010039073 rheumatoid arthritis Diseases 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
230000028327 secretion Effects 0.000 description 1
208000017520 skin disease Diseases 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
AVERBMQHYOZACV-UHFFFAOYSA-M sodium;7-chloro-4-[(3,4-dichlorophenyl)carbamoyl]-1,1-dioxo-2,3-dihydro-1$l^{6}-benzothiepin-5-olate;hydrate Chemical compound O.[Na+].C1CS(=O)(=O)C2=CC=C(Cl)C=C2C([O-])=C1C(=O)NC1=CC=C(Cl)C(Cl)=C1 AVERBMQHYOZACV-UHFFFAOYSA-M 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
235000011150 stannous chloride Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000008174 sterile solution Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
RZWIIPASKMUIAC-VQTJNVASSA-N thromboxane Chemical compound CCCCCCCC[C@H]1OCCC[C@@H]1CCCCCCC RZWIIPASKMUIAC-VQTJNVASSA-N 0.000 description 1
AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
235000021122 unsaturated fatty acids Nutrition 0.000 description 1
150000004670 unsaturated fatty acids Chemical class 0.000 description 1
229910052727 yttrium Inorganic materials 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/58—Benzoxazoles; Hydrogenated benzoxazoles 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 in position 2
- 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]
- 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
- A61P37/08—Antiallergic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/32—Oxygen atoms
- C07D209/34—Oxygen atoms in position 2
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles 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 in position 2
- C07D235/26—Oxygen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles 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 in position 2
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Immunology (AREA)
Pain & Pain Management (AREA)
Rheumatology (AREA)
Pulmonology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Thiazole And Isothizaole Compounds (AREA)
Indole Compounds (AREA)
External Artificial Organs (AREA)
Fats And Perfumes (AREA)
Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
Hydrogenated Pyridines (AREA)

DD87303578A 1986-06-09 1987-06-05 Verfahren zur herstellung einer antiallergisch und entzuendungshemmende wirkende verbindung DD265141A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP13347086		1986-06-09

Publications (1)

Publication Number	Publication Date
DD265141A5 true DD265141A5 (de)	1989-02-22

Family

ID=15105525

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD87303578A DD265141A5 (de)	1986-06-09	1987-06-05	Verfahren zur herstellung einer antiallergisch und entzuendungshemmende wirkende verbindung

Country Status (21)

Country	Link
EP (1)	EP0249407B1 (fr)
JP (1)	JPH0623199B2 (fr)
KR (1)	KR900000552B1 (fr)
CN (1)	CN1015334B (fr)
AT (1)	ATE60596T1 (fr)
AU (1)	AU586337B2 (fr)
CA (1)	CA1305151C (fr)
DD (1)	DD265141A5 (fr)
DE (1)	DE3767778D1 (fr)
DK (1)	DK288287A (fr)
ES (1)	ES2031892T3 (fr)
FI (1)	FI87924C (fr)
GR (1)	GR3001584T3 (fr)
HU (1)	HU198451B (fr)
IE (1)	IE60015B1 (fr)
NO (1)	NO168246C (fr)
PL (1)	PL150631B1 (fr)
PT (1)	PT85035B (fr)
SU (1)	SU1757464A3 (fr)
YU (1)	YU45423B (fr)
ZA (1)	ZA874046B (fr)

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4720297A (en) *	1985-09-27	1988-01-19	Sumitomo Chemical Company, Limited	Benzothiazolones, and their production and use as herbicides
JPH0283376A (ja) *	1988-09-19	1990-03-23	Pfizer Pharmaceut Co Ltd	ベンゾオキサゾロン誘導体および抗アレルギー又は抗炎症組成物
IL93473A0 (en) *	1989-02-28	1990-11-29	Pfizer	Antiinflammatory benzoxazolones
JPH0678327B2 (ja) *	1989-07-20	1994-10-05	ファイザー製薬株式会社	４，５，６，７，―四置換ベンゾオキサゾロン類
JPH0729998B2 (ja) *	1990-01-22	1995-04-05	ファイザー製薬株式会社	新規ベンゾキノン化合物およびその組成物
WO1997012613A1 (fr) *	1995-10-05	1997-04-10	Warner-Lambert Company	Procede de traitement et de prevention des inflammations et de l'atherosclerose
US5972980A (en) *	1995-10-05	1999-10-26	Warner-Lambert Company	Method for treating and preventing inflammation and atherosclerosis
US6001866A (en) *	1995-10-05	1999-12-14	Warner-Lambert Company	Method for treating and preventing inflammation and atherosclerosis
WO2002070478A1 (fr)	2001-03-06	2002-09-12	Astrazeneca Ab	Dérivés indolone capable de dégrader des vaisseaux
DE10210779A1 (de) *	2002-03-12	2003-10-09	Merck Patent Gmbh	Cyclische Amide
TW200508197A (en) *	2003-03-31	2005-03-01	Ucb Sa	Indolone-acetamide derivatives, processes for preparing them and their uses
US7270805B1 (en) *	2006-03-30	2007-09-18	Conopco, Inc.	Skin lightening agents, compositions and methods
WO2010090680A1 (fr) *	2008-12-15	2010-08-12	Wyeth Llc	Agonistes de cb2 de type oxindole substitué
CA2845284C (fr) *	2011-08-18	2018-03-06	Dr. Reddy's Laboratories Ltd.	Composes amines heterocycliques substitues comme inhibiteurs de la proteine de transfert d'ester cholesterylique (cetp)
WO2013174508A1 (fr) *	2012-05-21	2013-11-28	Dr. August Wolff Gmbh & Co. Kg Arzneimittel	Nouvelles 1,3-benzoxazol-2(3h)-ones et leur utilisation comme médicaments et produits cosmétiques
EP3932395A1 (fr) *	2020-07-03	2022-01-05	Dr. August Wolff GmbH & Co. KG Arzneimittel	Émulsion stable contenant un ingrédient pharmaceutique actif à base de n(3-méthyl-2-oxo-2,3-dihydrobenzo[d]oxazol-5-yl)dodécanamide, production et utilisation

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3017977A1 (de) *	1980-05-10	1981-11-19	Dr. Karl Thomae Gmbh, 7950 Biberach	Neue substituierte 2(3h)-benzothiazolone
DE3042481A1 (de) *	1980-11-11	1982-06-16	A. Nattermann & Cie GmbH, 5000 Köln	(omega)-(2-oxo-benzazolinyl)-alkansaeure-derivate, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische praeparate
GB8325370D0 (en) *	1983-09-22	1983-10-26	Fujisawa Pharmaceutical Co	Benzoxazoline and benzothiazoline derivatives
US4569942A (en) *	1984-05-04	1986-02-11	Pfizer Inc.	N,3-Disubstituted 2-oxindole-1-carboxamides as analgesic and antiinflammatory agents
US4690943A (en) *	1984-09-19	1987-09-01	Pfizer Inc.	Analgesic and antiinflammatory 1,3-diacyl-2-oxindole compounds

1987
- 1987-06-04 DK DK288287A patent/DK288287A/da not_active Application Discontinuation
- 1987-06-05 DD DD87303578A patent/DD265141A5/de not_active IP Right Cessation
- 1987-06-05 AU AU73878/87A patent/AU586337B2/en not_active Ceased
- 1987-06-05 DE DE8787304983T patent/DE3767778D1/de not_active Expired - Lifetime
- 1987-06-05 AT AT87304983T patent/ATE60596T1/de not_active IP Right Cessation
- 1987-06-05 CA CA000538939A patent/CA1305151C/fr not_active Expired - Lifetime
- 1987-06-05 IE IE150587A patent/IE60015B1/en not_active IP Right Cessation
- 1987-06-05 ZA ZA874046A patent/ZA874046B/xx unknown
- 1987-06-05 ES ES87304983T patent/ES2031892T3/es not_active Expired - Lifetime
- 1987-06-05 EP EP87304983A patent/EP0249407B1/fr not_active Expired - Lifetime
- 1987-06-05 NO NO872382A patent/NO168246C/no unknown
- 1987-06-08 JP JP62142779A patent/JPH0623199B2/ja not_active Expired - Lifetime
- 1987-06-08 FI FI872555A patent/FI87924C/fi not_active IP Right Cessation
- 1987-06-08 KR KR1019870005780A patent/KR900000552B1/ko not_active Expired
- 1987-06-08 HU HU872613A patent/HU198451B/hu not_active IP Right Cessation
- 1987-06-08 CN CN87104099A patent/CN1015334B/zh not_active Expired
- 1987-06-08 PT PT85035A patent/PT85035B/pt unknown
- 1987-06-08 SU SU874202723A patent/SU1757464A3/ru active
- 1987-06-08 YU YU1049/87A patent/YU45423B/xx unknown
- 1987-06-08 PL PL1987266132A patent/PL150631B1/pl unknown
1991
- 1991-03-08 GR GR91400282T patent/GR3001584T3/el unknown

Also Published As

Publication number	Publication date
DK288287D0 (da)	1987-06-04
HUT48209A (en)	1989-05-29
CA1305151C (fr)	1992-07-14
GR3001584T3 (en)	1992-11-23
NO168246B (no)	1991-10-21
AU586337B2 (en)	1989-07-06
KR880000413A (ko)	1988-03-25
PL266132A1 (en)	1988-06-23
FI87924C (fi)	1993-03-10
AU7387887A (en)	1987-12-10
PL150631B1 (en)	1990-06-30
EP0249407B1 (fr)	1991-01-30
ATE60596T1 (de)	1991-02-15
PT85035B (pt)	1990-03-08
CN87104099A (zh)	1988-02-10
NO872382D0 (no)	1987-06-05
FI87924B (fi)	1992-11-30
KR900000552B1 (ko)	1990-01-31
JPS63107958A (ja)	1988-05-12
HU198451B (en)	1989-10-30
ES2031892T3 (es)	1996-07-16
FI872555L (fi)	1987-12-10
FI872555A0 (fi)	1987-06-08
NO168246C (no)	1992-01-29
DK288287A (da)	1987-12-10
ZA874046B (en)	1989-01-25
IE871505L (en)	1987-12-09
EP0249407A2 (fr)	1987-12-16
SU1757464A3 (ru)	1992-08-23
CN1015334B (zh)	1992-01-29
IE60015B1 (en)	1994-05-18
EP0249407A3 (en)	1988-10-19
DE3767778D1 (de)	1991-03-07
YU45423B (en)	1992-05-28
JPH0623199B2 (ja)	1994-03-30
NO872382L (no)	1987-12-10
PT85035A (en)	1987-07-01
YU104987A (en)	1988-08-31

Legal Events

Date	Code	Title	Description
1998-08-27	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
DE69013836T2 (de)	1995-03-23	Benzimidazolverbindungen und deren Anwendung.
DE69725465T2 (de)	2004-05-06	6-phenylpyridyl-2-amin-derivate verwendbar als nos-inhibitoren
DE69200378T2 (de)	1995-03-09	Indolderivate, Verfahren zu deren Herstellung und diese enthaltende Arzneimittel.
EP0026848B1 (fr)	1983-05-04	Dérivés de tétraline, leur préparation et médicaments contenant ces composés
DE69524246T2 (de)	2002-06-27	1,2,3,4-Tetrahydroquinoxalindion Derivate und ihre Verwendung als Glutamat Rezeptor Antagonisten
DE3047142C2 (de)	1985-09-26	Basische 1,7,7-Trimethylbicyclo[2,2,1]heptyläther, Verfahren zur Herstellung derselben und diese enthaltende Arzneimittel
DE3026201C2 (fr)	1990-11-08
DE3522604A1 (de)	1987-01-08	Neue feste formen von 2-(gamma)thoxy-4-(n-(1-(2-piperidino-phenyl)-3-methyl-1-butyl)-aminocarbonylmethyl)-benzoesaeure, diese formen enthaltende arzneimittel und verfahren zu ihrer herstellung
DE69101449T2 (de)	1994-07-14	1,3-Dicarbonylverbindungen und ihre Verwendung.
DE3617183A1 (de)	1987-05-27	Substituierte benzylether
EP0183159A2 (fr)	1986-06-04	1-Hétéroaryl-4-aryl-pyrazolin-5-ones pour application en tant que médicaments
DE69530988T2 (de)	2003-12-04	Benzimidazolderivate mit dopaminerger wirkung
DD264919A5 (de)	1989-02-15	Verfahren zur herstellung von 5-hydroxy-3-aminochromanen
DE69105278T2 (de)	1995-04-06	Neue aminobenzosultamderivate und ihre verwendung als lipoxygenase hemmer.
DE3100575A1 (de)	1982-09-02	"neue benzoesaeuren, ihre herstellung und ihre verwendung als arzneimittel"
DE3856501T2 (de)	2004-04-29	Schlafverbesserungsmittel
EP0297380B1 (fr)	1994-10-05	Indolylpropanols, procédé pour leur préparation, leur utilisation ainsi que les préparations contenant ces composés
EP0185909B1 (fr)	1990-02-21	Composés de 5-alkyl-1-phényl-2-pipérazinoalkylpyrazolin-3-one ainsi que procédés et produits intermédiaires pour leur préparation et médicaments comprenant ces composés
DE69014798T2 (de)	1995-04-27	Thionaphthalen-derivate, verfahren zur herstellung und antiallergisches mittel daraus.
EP0425906A2 (fr)	1991-05-08	Cycloalkano[b]dihydroindol- et -indolsulfonamides substituées
DE69227596T2 (de)	1999-04-08	Alkoxyphenylalkylaminderivat
CH645368A5 (de)	1984-09-28	2-hydroxy-5-(1-hydroxy-2-piperazinylethyl)benzoesaeure-derivate sowie verfahren zu deren herstellung.
EP0018360A1 (fr)	1980-11-12	N-(5-méthoxybenzofuran-2-ylcarbonyl)-N'-benzylpipérazine et procédé pour sa préparation.
EP0389425B1 (fr)	1995-04-26	Benzothiopyranylamines
DE3300522C2 (fr)	1992-01-09