DK169404B1 - Substitueret phenylamidforbindelse, fremgangsmåde til fremstilling deraf, anvendelse deraf til brug som farmaceutisk middel og farmaceutisk præparat indeholdende forbindelsen - Google Patents

Substitueret phenylamidforbindelse, fremgangsmåde til fremstilling deraf, anvendelse deraf til brug som farmaceutisk middel og farmaceutisk præparat indeholdende forbindelsen Download PDF

Info

Publication number: DK169404B1
Authority: DK; Denmark
Prior art keywords: compound; formula; alkyl; salt; compound according
Prior art date: 1986-08-08

Application number

DK413987A

Other languages

Danish (da)

English (en)

Other versions

DK413987D0 (da

DK413987A (da

Inventor

Peter Thaddeus Gallagher

Terence Alan Hicks

Graham Walter Mullier

Original Assignee

Lilly Industries Ltd

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.)

1986-08-08

Filing date

1987-08-07

Publication date

1994-10-24

1987-08-07 Application filed by Lilly Industries Ltd filed Critical Lilly Industries Ltd

1987-08-07 Publication of DK413987D0 publication Critical patent/DK413987D0/da

1988-02-09 Publication of DK413987A publication Critical patent/DK413987A/da

1994-10-24 Application granted granted Critical

1994-10-24 Publication of DK169404B1 publication Critical patent/DK169404B1/da

Links

150000001875 compounds Chemical class 0.000 title claims description 69
-1 phenylamide compound Chemical class 0.000 title claims description 21
238000000034 method Methods 0.000 title claims description 15
238000002360 preparation method Methods 0.000 title claims description 12
239000008194 pharmaceutical composition Substances 0.000 title claims description 6
150000003839 salts Chemical class 0.000 claims description 26
125000000217 alkyl group Chemical group 0.000 claims description 17
239000001257 hydrogen Substances 0.000 claims description 13
229910052739 hydrogen Inorganic materials 0.000 claims description 13
238000001816 cooling Methods 0.000 claims description 12
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
239000002253 acid Substances 0.000 claims description 8
125000004432 carbon atom Chemical group C* 0.000 claims description 7
229910052736 halogen Inorganic materials 0.000 claims description 6
150000002367 halogens Chemical class 0.000 claims description 6
150000001412 amines Chemical class 0.000 claims description 5
239000000460 chlorine Substances 0.000 claims description 5
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
229910052801 chlorine Inorganic materials 0.000 claims description 4
125000004122 cyclic group Chemical group 0.000 claims description 4
229910052799 carbon Inorganic materials 0.000 claims description 3
239000003937 drug carrier Substances 0.000 claims description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
229910021645 metal ion Inorganic materials 0.000 claims description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
125000000753 cycloalkyl group Chemical group 0.000 claims 1
UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
239000000243 solution Substances 0.000 description 17
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
239000003921 oil Substances 0.000 description 14
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
239000000203 mixture Substances 0.000 description 12
238000006243 chemical reaction Methods 0.000 description 11
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic acid anhydride Natural products CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 10
239000004480 active ingredient Substances 0.000 description 8
239000007787 solid Substances 0.000 description 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
239000000047 product Substances 0.000 description 7
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
239000002585 base Substances 0.000 description 6
238000001914 filtration Methods 0.000 description 6
238000010992 reflux Methods 0.000 description 6
238000003756 stirring Methods 0.000 description 6
239000000725 suspension Substances 0.000 description 6
229910052757 nitrogen Inorganic materials 0.000 description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
MLIREBYILWEBDM-UHFFFAOYSA-N cyanoacetic acid Chemical compound OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 description 4
238000002347 injection Methods 0.000 description 4
239000007924 injection Substances 0.000 description 4
239000007788 liquid Substances 0.000 description 4
239000012280 lithium aluminium hydride Substances 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
239000003208 petroleum Substances 0.000 description 4
239000000843 powder Substances 0.000 description 4
159000000000 sodium salts Chemical group 0.000 description 4
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
OPXYNEYEDHAXOM-UHFFFAOYSA-N 3-oxobutanenitrile Chemical compound CC(=O)CC#N OPXYNEYEDHAXOM-UHFFFAOYSA-N 0.000 description 3
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical class NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
229920002472 Starch Polymers 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000000443 aerosol Substances 0.000 description 3
206010003246 arthritis Diseases 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
239000002552 dosage form Substances 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
150000002617 leukotrienes Chemical class 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
239000011591 potassium Substances 0.000 description 3
229910052700 potassium Inorganic materials 0.000 description 3
239000000376 reactant Substances 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
239000002904 solvent Substances 0.000 description 3
239000008107 starch Substances 0.000 description 3
235000019698 starch Nutrition 0.000 description 3
239000000126 substance Substances 0.000 description 3
WUWBDQJTQTVBSQ-UHFFFAOYSA-N 1-tert-butyl-4-isocyanatobenzene Chemical compound CC(C)(C)C1=CC=C(N=C=O)C=C1 WUWBDQJTQTVBSQ-UHFFFAOYSA-N 0.000 description 2
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
VPSMEEGFQMCUTH-UHFFFAOYSA-N 4-tert-butyl-n-methylaniline Chemical compound CNC1=CC=C(C(C)(C)C)C=C1 VPSMEEGFQMCUTH-UHFFFAOYSA-N 0.000 description 2
WRDWWAVNELMWAM-UHFFFAOYSA-N 4-tert-butylaniline Chemical compound CC(C)(C)C1=CC=C(N)C=C1 WRDWWAVNELMWAM-UHFFFAOYSA-N 0.000 description 2
ZKAQPVQEYCFRTK-UHFFFAOYSA-N 5-methyl-1,2-oxazole-4-carbonyl chloride Chemical compound CC=1ON=CC=1C(Cl)=O ZKAQPVQEYCFRTK-UHFFFAOYSA-N 0.000 description 2
VQBXUKGMJCPBMF-UHFFFAOYSA-N 5-methyl-1,2-oxazole-4-carboxylic acid Chemical compound CC=1ON=CC=1C(O)=O VQBXUKGMJCPBMF-UHFFFAOYSA-N 0.000 description 2
VWZNPDWFPULPQF-UHFFFAOYSA-N 5-methyl-n-[4-(2-methylbutan-2-yl)phenyl]-1,2-oxazole-4-carboxamide Chemical compound C1=CC(C(C)(C)CC)=CC=C1NC(=O)C1=C(C)ON=C1 VWZNPDWFPULPQF-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 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
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
241000700159 Rattus Species 0.000 description 2
239000000908 ammonium hydroxide Substances 0.000 description 2
230000003110 anti-inflammatory effect Effects 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
208000006673 asthma Diseases 0.000 description 2
208000010668 atopic eczema Diseases 0.000 description 2
239000006071 cream Substances 0.000 description 2
239000013078 crystal Substances 0.000 description 2
PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
201000010099 disease Diseases 0.000 description 2
238000001035 drying Methods 0.000 description 2
XDHWYQRLMSOZOP-UHFFFAOYSA-N ethyl 5-ethoxy-3-oxopent-4-enoate Chemical compound CCOC=CC(=O)CC(=O)OCC XDHWYQRLMSOZOP-UHFFFAOYSA-N 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
239000007903 gelatin capsule Substances 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
208000026278 immune system disease Diseases 0.000 description 2
208000027866 inflammatory disease Diseases 0.000 description 2
230000005764 inhibitory process Effects 0.000 description 2
229910052500 inorganic mineral Inorganic materials 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
239000007937 lozenge Substances 0.000 description 2
235000019359 magnesium stearate Nutrition 0.000 description 2
239000002609 medium Substances 0.000 description 2
235000010755 mineral Nutrition 0.000 description 2
239000011707 mineral Substances 0.000 description 2
NVNDYSYJDQEYDB-UHFFFAOYSA-N n-(4-tert-butylphenyl)-2-cyano-3-hydroxybut-2-enamide Chemical compound CC(O)=C(C#N)C(=O)NC1=CC=C(C(C)(C)C)C=C1 NVNDYSYJDQEYDB-UHFFFAOYSA-N 0.000 description 2
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-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
239000002244 precipitate Substances 0.000 description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
239000003826 tablet Substances 0.000 description 2
230000001225 therapeutic effect Effects 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
235000012431 wafers Nutrition 0.000 description 2
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 2
TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 1
LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
GDSHKRFBTKLMRH-UHFFFAOYSA-N 1-(1-methylcyclopropyl)-4-nitrobenzene Chemical compound C=1C=C([N+]([O-])=O)C=CC=1C1(C)CC1 GDSHKRFBTKLMRH-UHFFFAOYSA-N 0.000 description 1
IQFYYKKMVGJFEH-OFKYTIFKSA-N 1-[(2r,4s,5r)-4-hydroxy-5-(tritiooxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione Chemical compound C1[C@H](O)[C@@H](CO[3H])O[C@H]1N1C(=O)NC(=O)C(C)=C1 IQFYYKKMVGJFEH-OFKYTIFKSA-N 0.000 description 1
HBOMLICNUCNMMY-KJFJCRTCSA-N 1-[(4s,5s)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione Chemical compound O=C1NC(=O)C(C)=CN1C1O[C@H](CO)[C@@H](N=[N+]=[N-])C1 HBOMLICNUCNMMY-KJFJCRTCSA-N 0.000 description 1
IOHPVZBSOKLVMN-UHFFFAOYSA-N 2-(2-phenylethyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1CCC1=CC=CC=C1 IOHPVZBSOKLVMN-UHFFFAOYSA-N 0.000 description 1
JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 1
JHLMKJXIUGFOBC-UHFFFAOYSA-N 2-cyano-3-hydroxy-n-[4-(1-methylcyclopropyl)phenyl]but-2-enamide Chemical compound C1=CC(NC(=O)C(C#N)=C(O)C)=CC=C1C1(C)CC1 JHLMKJXIUGFOBC-UHFFFAOYSA-N 0.000 description 1
BNABQPWNGFHUNB-UHFFFAOYSA-N 2-cyano-3-hydroxy-n-[4-(2-methylhexan-2-yl)phenyl]but-2-enamide Chemical compound CCCCC(C)(C)C1=CC=C(NC(=O)C(C#N)=C(C)O)C=C1 BNABQPWNGFHUNB-UHFFFAOYSA-N 0.000 description 1
JHIXIEPXRPNJJG-UHFFFAOYSA-N 2-cyano-3-hydroxy-n-[4-(2-methylpentan-2-yl)phenyl]but-2-enamide Chemical compound CCCC(C)(C)C1=CC=C(NC(=O)C(C#N)=C(C)O)C=C1 JHIXIEPXRPNJJG-UHFFFAOYSA-N 0.000 description 1
MMKGNFNMTJTNMG-UHFFFAOYSA-N 2-phenylbut-2-enamide Chemical class CC=C(C(N)=O)C1=CC=CC=C1 MMKGNFNMTJTNMG-UHFFFAOYSA-N 0.000 description 1
AEIOZWYBDBVCGW-UHFFFAOYSA-N 2-tert-butylaniline Chemical compound CC(C)(C)C1=CC=CC=C1N AEIOZWYBDBVCGW-UHFFFAOYSA-N 0.000 description 1
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DCIDLPBHZKXLJD-UHFFFAOYSA-N 4-(1-methylcyclopropyl)aniline Chemical compound C=1C=C(N)C=CC=1C1(C)CC1 DCIDLPBHZKXLJD-UHFFFAOYSA-N 0.000 description 1
RQUPXQYTWVIBIV-UHFFFAOYSA-N 4-(2-methylbutan-2-yl)aniline Chemical compound CCC(C)(C)C1=CC=C(N)C=C1 RQUPXQYTWVIBIV-UHFFFAOYSA-N 0.000 description 1
UHPGPCHPULHMAC-UHFFFAOYSA-N 4-(2-methylhexan-2-yl)aniline Chemical compound CCCCC(C)(C)C1=CC=C(N)C=C1 UHPGPCHPULHMAC-UHFFFAOYSA-N 0.000 description 1
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WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
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239000012948 isocyanate Substances 0.000 description 1
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CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
150000002545 isoxazoles Chemical class 0.000 description 1
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PYSUERPZDAIPFH-UHFFFAOYSA-N n-(4-tert-butylphenyl)-n,5-dimethyl-1,2-oxazole-4-carboxamide Chemical compound C=1C=C(C(C)(C)C)C=CC=1N(C)C(=O)C=1C=NOC=1C PYSUERPZDAIPFH-UHFFFAOYSA-N 0.000 description 1
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 1
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229910000027 potassium carbonate Inorganic materials 0.000 description 1
229910001414 potassium ion Inorganic materials 0.000 description 1
230000003334 potential effect Effects 0.000 description 1
229940069328 povidone Drugs 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 1
229960003415 propylparaben Drugs 0.000 description 1
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238000007142 ring opening reaction Methods 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000012056 semi-solid material Substances 0.000 description 1
208000017520 skin disease Diseases 0.000 description 1
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
239000011343 solid material Substances 0.000 description 1
239000008247 solid mixture Substances 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
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239000001119 stannous chloride Substances 0.000 description 1
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239000007858 starting material Substances 0.000 description 1
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QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
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Classifications

- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- 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
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members 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 ring carbon atoms
- C07D261/14—Nitrogen atoms
- C07D261/16—Benzene-sulfonamido isoxazoles

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Immunology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
Engineering & Computer Science (AREA)
Animal Behavior & Ethology (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Transplantation (AREA)
Pain & Pain Management (AREA)
Rheumatology (AREA)
Dermatology (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)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Hydrogenated Pyridines (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

DK413987A 1986-08-08 1987-08-07 Substitueret phenylamidforbindelse, fremgangsmåde til fremstilling deraf, anvendelse deraf til brug som farmaceutisk middel og farmaceutisk præparat indeholdende forbindelsen DK169404B1 (da)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB868619432A GB8619432D0 (en)	1986-08-08	1986-08-08	Pharmaceutical compounds
GB8619432		1986-08-08

Publications (3)

Publication Number	Publication Date
DK413987D0 DK413987D0 (da)	1987-08-07
DK413987A DK413987A (da)	1988-02-09
DK169404B1 true DK169404B1 (da)	1994-10-24

Family

ID=10602473

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DK413987A DK169404B1 (da)	1986-08-08	1987-08-07	Substitueret phenylamidforbindelse, fremgangsmåde til fremstilling deraf, anvendelse deraf til brug som farmaceutisk middel og farmaceutisk præparat indeholdende forbindelsen

Country Status (23)

Country	Link
US (1)	US4892963A (de)
EP (1)	EP0257882B1 (de)
JP (1)	JPS63239259A (de)
KR (2)	KR880002823A (de)
CN (1)	CN1015256B (de)
AR (2)	AR244660A1 (de)
AT (1)	ATE65494T1 (de)
AU (1)	AU604737B2 (de)
CA (1)	CA1317964C (de)
DE (1)	DE3771611D1 (de)
DK (1)	DK169404B1 (de)
EG (1)	EG18269A (de)
ES (1)	ES2031510T3 (de)
GB (1)	GB8619432D0 (de)
GR (1)	GR3002714T3 (de)
HU (1)	HU197559B (de)
IL (1)	IL83432A (de)
MX (1)	MX174371B (de)
NZ (1)	NZ221352A (de)
PH (1)	PH22821A (de)
PT (1)	PT85476B (de)
RU (1)	RU1771472C (de)
ZA (1)	ZA875813B (de)

Families Citing this family (22)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5268382A (en) *	1985-09-27	1993-12-07	Hoechst Aktiengesellschaft	Medicaments to combat autoimmune diseases, in particular systemic lupus erythematosus
DE3534440A1 (de) *	1985-09-27	1987-04-02	Hoechst Ag	Arzneimittel gegen chronische graft-versus-host-krankheiten sowie gegen autoimmunerkrankungen, insbesondere systemischen lupus erythematodes
US4975462A (en) *	1988-07-29	1990-12-04	Bristol-Myers Company	Antiarthritic α-arylcarbamoyl cyanoacetic acid derivatives
US5583150A (en) *	1989-08-18	1996-12-10	Alcon Laboratories, Inc.	5-methyl-isoxazole-4-carboxylic acid anilides and 2-hydroxyethylidene-cyano acetic anilides for the treatment of ocular diseases
DD297328A5 (de) *	1989-08-18	1992-01-09	��@��k��Kk��	5-methyl-isoxalol-4-carbonsaeureanilide und 2 hydroxyethyliden-cyanoessigsaeureanilide zur behandlung von augenerkrankungen
US5001124A (en) *	1990-02-02	1991-03-19	Syntex (U.S.A.) Inc.	4-isoxazolecarboxamide derivatives
US5108999A (en) *	1990-02-02	1992-04-28	Syntex (U.S.A.) Inc.	4-isoxazolecarboxamide derivatives
JPH04211048A (ja) *	1990-03-05	1992-08-03	Mitsubishi Kasei Corp	チオカルバモイルアセトニトリル誘導体
ES2102367T3 (es) *	1990-05-18	1997-08-01	Hoechst Ag	Amidas de acidos isoxazol-4-carboxilicos y amidas de acidos hidroxialquiliden-cianoaceticos, medicamentos que contienen estos compuestos y su utilizacion.
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1986
- 1986-08-08 GB GB868619432A patent/GB8619432D0/en active Pending
1987
- 1987-08-02 EG EG448/87A patent/EG18269A/xx active
- 1987-08-03 PH PH35615A patent/PH22821A/en unknown
- 1987-08-04 IL IL83432A patent/IL83432A/xx not_active IP Right Cessation
- 1987-08-04 PT PT85476A patent/PT85476B/pt not_active IP Right Cessation
- 1987-08-05 CA CA000543739A patent/CA1317964C/en not_active Expired - Fee Related
- 1987-08-05 NZ NZ221352A patent/NZ221352A/xx unknown
- 1987-08-06 DE DE8787306988T patent/DE3771611D1/de not_active Expired - Fee Related
- 1987-08-06 RU SU874203189A patent/RU1771472C/ru active
- 1987-08-06 AT AT87306988T patent/ATE65494T1/de active
- 1987-08-06 ZA ZA875813A patent/ZA875813B/xx unknown
- 1987-08-06 ES ES198787306988T patent/ES2031510T3/es not_active Expired - Lifetime
- 1987-08-06 EP EP87306988A patent/EP0257882B1/de not_active Expired - Lifetime
- 1987-08-06 MX MX007668A patent/MX174371B/es unknown
- 1987-08-07 KR KR1019870008651A patent/KR880002823A/ko not_active Ceased
- 1987-08-07 HU HU873604A patent/HU197559B/hu not_active IP Right Cessation
- 1987-08-07 CN CN87105516A patent/CN1015256B/zh not_active Expired
- 1987-08-07 US US07/083,538 patent/US4892963A/en not_active Expired - Fee Related
- 1987-08-07 AU AU76681/87A patent/AU604737B2/en not_active Ceased
- 1987-08-07 JP JP62198006A patent/JPS63239259A/ja active Pending
- 1987-08-07 DK DK413987A patent/DK169404B1/da not_active IP Right Cessation
- 1987-08-07 KR KR1019870008650A patent/KR880002815A/ko not_active Ceased
- 1987-08-07 AR AR87308368A patent/AR244660A1/es active
1991
- 1991-09-12 GR GR91401318T patent/GR3002714T3/el unknown
1992
- 1992-11-20 AR AR92323708A patent/AR247876A1/es active

Also Published As

Publication number	Publication date
AR244660A1 (es)	1993-11-30
CA1317964C (en)	1993-05-18
NZ221352A (en)	1989-10-27
MX174371B (es)	1994-05-11
IL83432A0 (en)	1988-01-31
ATE65494T1 (de)	1991-08-15
HUT44523A (en)	1988-03-28
AU7668187A (en)	1988-02-11
ES2031510T3 (es)	1992-12-16
CN87105516A (zh)	1988-02-24
US4892963A (en)	1990-01-09
EG18269A (en)	1992-12-30
GR3002714T3 (en)	1993-01-25
JPS63239259A (ja)	1988-10-05
KR880002823A (ko)	1988-05-11
DK413987D0 (da)	1987-08-07
GB8619432D0 (en)	1986-09-17
KR880002815A (ko)	1988-05-11
EP0257882B1 (de)	1991-07-24
DE3771611D1 (de)	1991-08-29
MX7668A (es)	1993-08-01
EP0257882A1 (de)	1988-03-02
PH22821A (en)	1989-01-19
AU604737B2 (en)	1991-01-03
ZA875813B (en)	1989-04-26
CN1015256B (zh)	1992-01-01
DK413987A (da)	1988-02-09
IL83432A (en)	1992-06-21
RU1771472C (ru)	1992-10-23
AR247876A1 (es)	1995-04-28
PT85476B (pt)	1990-06-29
PT85476A (en)	1987-09-01
HU197559B (en)	1989-04-28

Legal Events

Date	Code	Title	Description
1994-10-24	B1	Patent granted (law 1993)
1996-04-15	PBP	Patent lapsed

Publication	Publication Date	Title
DK169404B1 (da)	1994-10-24	Substitueret phenylamidforbindelse, fremgangsmåde til fremstilling deraf, anvendelse deraf til brug som farmaceutisk middel og farmaceutisk præparat indeholdende forbindelsen
AU2019233698B2 (en)	2023-01-19	Novel calcium salt polymorphs as anti-inflammatory, immunomodulatory and anti-proliferatory agents
NO174043B (no)	1993-11-29	Analogifremgangsmaate for fremstilling av terapeutisk aktive mettede fettsyreamider
EP0506532A1 (de)	1992-09-30	Indolderivate, Verfahren zu deren Herstellung und diese enthaltende Arzneimittel
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JP6023322B2 (ja)	2016-11-09	２−シアノフェニルボロン酸およびそのエステルの製造プロセス
EP0413667B1 (de)	1993-09-29	Halogenalkylphenyl-Alkohole, -Ketone und deren Hydrate
JPH08259559A (ja)	1996-10-08	抗−神経変性活性１０−アミノ脂肪族−ジベンゾ［ｂ，ｆ］オキセピン類
JPH02306947A (ja)	1990-12-20	キラルβ―アミノ酸の製造方法
JPH0813808B2 (ja)	1996-02-14	２−アミノアルキル−５−アリールアルキル−１，３−ジオキサン誘導体、その製造方法およびそれを含有する医薬
HUT57712A (en)	1991-12-30	Process for producing urea derivatives and pharmaceutical compositions comprising such compounds as active ingredient
JPWO1995009160A1 (ja)	1996-02-27	ベンゾラクタム誘導体
JP6884857B2 (ja)	2021-06-09	フェニルアラニン類化合物の製造方法
JPH02169571A (ja)	1990-06-29	置換アリルアミン誘導体
JPH10316617A (ja)	1998-12-02	新規なフタル酸誘導体
US4511566A (en)	1985-04-16	2-N-Cycloalkylmethyl 3-oxo 5,6-diaryl-as-triazines
JP2009518380A (ja)	2009-05-07	２−クロロエトキシ−酢酸−ｎ，ｎ−ジメチルアミドの製法
JPH05294921A (ja)	1993-11-09	新規なフェニル置換シクロアルキル尿素誘導体および組成物
US4003932A (en)	1977-01-18	Aminoalkylethers
EP0006864B1 (de)	1981-12-30	Neues zwischenprodukt für die herstellung therapeutisch wirksamer pyridinverbindungen und verfahren zu dessen herstellung
JP3855686B2 (ja)	2006-12-13	３，３−ジアルコキシ−２−ヒドロキシイミノ誘導体及びその製造法
JPH0576473B2 (de)	1993-10-22
JPS62178585A (ja)	1987-08-05	１−〔３−（２−ヒドロキシ−３−アルキルアミノプロポキシ）−２−チエニル〕−３−フエニル−１−プロパノン及びそれらの酸付加塩並びにそれらの製造法及びそれらを含む薬学的組成物
US20070027198A1 (en)	2007-02-01	Crystal of heterocyclic compound