LU82334A1 - Composes de pyranone substitues en position 5 et leur utilisation comme produits pharmaceutiques - Google Patents

Composes de pyranone substitues en position 5 et leur utilisation comme produits pharmaceutiques Download PDF

Info

Publication number: LU82334A1
Authority: LU; Luxembourg
Prior art keywords: group; carbon atoms; formula; compound according; compound
Prior art date: 1979-04-05

Application number

LU82334A

Other languages

English (en)

French (fr)

Inventor

B Clark

A Todd

W Ross

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.)

1979-04-05

Filing date

1980-04-04

Publication date

1981-12-02

1980-04-04 Application filed by Lilly Industries Ltd filed Critical Lilly Industries Ltd

1981-12-02 Publication of LU82334A1 publication Critical patent/LU82334A1/fr

Links

ZPSJGADGUYYRKE-UHFFFAOYSA-N 2H-pyran-2-one Chemical group O=C1C=CC=CO1 ZPSJGADGUYYRKE-UHFFFAOYSA-N 0.000 title description 4
239000003814 drug Substances 0.000 title description 4
150000001875 compounds Chemical class 0.000 claims description 82
238000000034 method Methods 0.000 claims description 43
125000004432 carbon atom Chemical group C* 0.000 claims description 41
-1 benzyloxy, hydroxy Chemical group 0.000 claims description 38
125000000217 alkyl group Chemical group 0.000 claims description 34
150000003839 salts Chemical class 0.000 claims description 20
239000002253 acid Substances 0.000 claims description 18
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 13
125000001424 substituent group Chemical group 0.000 claims description 12
125000005843 halogen group Chemical group 0.000 claims description 11
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
239000008194 pharmaceutical composition Substances 0.000 claims description 6
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
208000001718 Immediate Hypersensitivity Diseases 0.000 claims description 4
206010045240 Type I hypersensitivity Diseases 0.000 claims description 4
125000002252 acyl group Chemical group 0.000 claims description 4
125000003545 alkoxy group Chemical group 0.000 claims description 4
125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 4
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
208000010216 atopic IgE responsiveness Diseases 0.000 claims description 4
239000003937 drug carrier Substances 0.000 claims description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
125000004414 alkyl thio group Chemical group 0.000 claims description 3
229910052799 carbon Inorganic materials 0.000 claims description 3
125000000753 cycloalkyl group Chemical group 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
229910002091 carbon monoxide Inorganic materials 0.000 claims description 2
239000002552 dosage form Substances 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims description 2
150000002367 halogens Chemical class 0.000 claims description 2
239000000825 pharmaceutical preparation Substances 0.000 claims description 2
229940127557 pharmaceutical product Drugs 0.000 claims description 2
108090000623 proteins and genes Proteins 0.000 claims description 2
229910052717 sulfur Inorganic materials 0.000 claims description 2
125000004429 atom Chemical group 0.000 claims 4
101100516568 Caenorhabditis elegans nhr-7 gene Proteins 0.000 claims 1
230000009466 transformation Effects 0.000 claims 1
238000002844 melting Methods 0.000 description 57
230000008018 melting Effects 0.000 description 57
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 47
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 40
239000000203 mixture Substances 0.000 description 38
239000000243 solution Substances 0.000 description 26
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 25
239000000047 product Substances 0.000 description 22
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
238000000354 decomposition reaction Methods 0.000 description 16
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 16
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
239000004480 active ingredient Substances 0.000 description 13
238000006243 chemical reaction Methods 0.000 description 13
239000000725 suspension Substances 0.000 description 13
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
239000003208 petroleum Substances 0.000 description 12
238000010992 reflux Methods 0.000 description 10
239000007787 solid Substances 0.000 description 10
239000012265 solid product Substances 0.000 description 10
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
239000002585 base Substances 0.000 description 7
239000003921 oil Substances 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 5
229920002472 Starch Polymers 0.000 description 5
125000001309 chloro group Chemical group Cl* 0.000 description 5
235000019698 starch Nutrition 0.000 description 5
239000012258 stirred mixture Substances 0.000 description 5
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
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 4
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 4
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 4
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 4
230000007062 hydrolysis Effects 0.000 description 4
238000006460 hydrolysis reaction Methods 0.000 description 4
239000008101 lactose Substances 0.000 description 4
HSZCZNFXUDYRKD-UHFFFAOYSA-M lithium iodide Chemical compound [Li+].[I-] HSZCZNFXUDYRKD-UHFFFAOYSA-M 0.000 description 4
235000019359 magnesium stearate Nutrition 0.000 description 4
238000000746 purification Methods 0.000 description 4
229940032147 starch Drugs 0.000 description 4
239000008107 starch Substances 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 3
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 3
JYKZIOMYJRDGJQ-UHFFFAOYSA-N 4h-pyran-2-carboxylic acid Chemical compound OC(=O)C1=CCC=CO1 JYKZIOMYJRDGJQ-UHFFFAOYSA-N 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
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 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
229910052783 alkali metal Inorganic materials 0.000 description 3
150000001408 amides Chemical class 0.000 description 3
150000001412 amines Chemical class 0.000 description 3
208000006673 asthma Diseases 0.000 description 3
239000002775 capsule Substances 0.000 description 3
229910052801 chlorine Inorganic materials 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
238000003776 cleavage reaction Methods 0.000 description 3
150000002081 enamines Chemical class 0.000 description 3
229910052500 inorganic mineral Inorganic materials 0.000 description 3
150000002576 ketones Chemical class 0.000 description 3
239000011707 mineral Substances 0.000 description 3
235000010755 mineral Nutrition 0.000 description 3
230000035479 physiological effects, processes and functions Effects 0.000 description 3
229910000027 potassium carbonate Inorganic materials 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
230000007017 scission Effects 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
239000011734 sodium Substances 0.000 description 3
239000002904 solvent Substances 0.000 description 3
239000000829 suppository Substances 0.000 description 3
239000003826 tablet Substances 0.000 description 3
WFWKNGZODAOLEO-UHFFFAOYSA-N 1-(4-Methoxyphenyl)-2-propanone Chemical compound COC1=CC=C(CC(C)=O)C=C1 WFWKNGZODAOLEO-UHFFFAOYSA-N 0.000 description 2
KKVZPWWPLDEZRT-UHFFFAOYSA-N 1-(dimethylamino)but-3-en-2-one Chemical compound CN(C)CC(=O)C=C KKVZPWWPLDEZRT-UHFFFAOYSA-N 0.000 description 2
JMXVESGATWXZOJ-UHFFFAOYSA-N 4-(dimethylamino)-3-phenylbut-3-en-2-one Chemical compound CN(C)C=C(C(C)=O)C1=CC=CC=C1 JMXVESGATWXZOJ-UHFFFAOYSA-N 0.000 description 2
NMHKLHVESCJBEG-UHFFFAOYSA-N 4-oxo-5-phenylpyran-2-carbonitrile Chemical compound O=C1C=C(C#N)OC=C1C1=CC=CC=C1 NMHKLHVESCJBEG-UHFFFAOYSA-N 0.000 description 2
QMUAVNOJXJKPNJ-UHFFFAOYSA-N 4-oxo-5-phenylpyran-2-carboxylic acid Chemical compound O1C(C(=O)O)=CC(=O)C(C=2C=CC=CC=2)=C1 QMUAVNOJXJKPNJ-UHFFFAOYSA-N 0.000 description 2
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 2
241000700198 Cavia Species 0.000 description 2
241000700199 Cavia porcellus Species 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
108010010803 Gelatin Proteins 0.000 description 2
AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
ZSXGLVDWWRXATF-UHFFFAOYSA-N N,N-dimethylformamide dimethyl acetal Chemical compound COC(OC)N(C)C ZSXGLVDWWRXATF-UHFFFAOYSA-N 0.000 description 2
PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
150000001340 alkali metals Chemical class 0.000 description 2
230000029936 alkylation Effects 0.000 description 2
238000005804 alkylation reaction Methods 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
229910052796 boron Inorganic materials 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
239000013078 crystal Substances 0.000 description 2
125000004093 cyano group Chemical group *C#N 0.000 description 2
WYACBZDAHNBPPB-UHFFFAOYSA-N diethyl oxalate Chemical compound CCOC(=O)C(=O)OCC WYACBZDAHNBPPB-UHFFFAOYSA-N 0.000 description 2
238000004821 distillation Methods 0.000 description 2
230000000694 effects Effects 0.000 description 2
125000004185 ester group Chemical group 0.000 description 2
OKVDJUIQORRIED-UHFFFAOYSA-N ethyl 4-oxo-5-phenylpyran-2-carboxylate Chemical compound O1C(C(=O)OCC)=CC(=O)C(C=2C=CC=CC=2)=C1 OKVDJUIQORRIED-UHFFFAOYSA-N 0.000 description 2
125000004494 ethyl ester group Chemical class 0.000 description 2
229920000159 gelatin Polymers 0.000 description 2
239000008273 gelatin Substances 0.000 description 2
235000019322 gelatine Nutrition 0.000 description 2
235000011852 gelatine desserts Nutrition 0.000 description 2
239000008187 granular material Substances 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
150000004679 hydroxides Chemical class 0.000 description 2
238000002347 injection Methods 0.000 description 2
239000007924 injection Substances 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 2
TWBYWOBDOCUKOW-UHFFFAOYSA-N isonicotinic acid Chemical compound OC(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-N 0.000 description 2
210000004072 lung Anatomy 0.000 description 2
239000000463 material Substances 0.000 description 2
229910017604 nitric acid Inorganic materials 0.000 description 2
239000012299 nitrogen atmosphere Substances 0.000 description 2
231100000252 nontoxic Toxicity 0.000 description 2
230000003000 nontoxic effect Effects 0.000 description 2
230000003647 oxidation Effects 0.000 description 2
238000007254 oxidation reaction Methods 0.000 description 2
QCCDLTOVEPVEJK-UHFFFAOYSA-N phenylacetone Chemical compound CC(=O)CC1=CC=CC=C1 QCCDLTOVEPVEJK-UHFFFAOYSA-N 0.000 description 2
YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
235000009518 sodium iodide Nutrition 0.000 description 2
229940079832 sodium starch glycolate Drugs 0.000 description 2
229920003109 sodium starch glycolate Polymers 0.000 description 2
239000008109 sodium starch glycolate Substances 0.000 description 2
239000011343 solid material Substances 0.000 description 2
125000000547 substituted alkyl group Chemical group 0.000 description 2
230000001225 therapeutic effect Effects 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
BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
UWYVPFMHMJIBHE-OWOJBTEDSA-N (e)-2-hydroxybut-2-enedioic acid Chemical compound OC(=O)\C=C(\O)C(O)=O UWYVPFMHMJIBHE-OWOJBTEDSA-N 0.000 description 1
BWKAYBPLDRWMCJ-UHFFFAOYSA-N 1,1-diethoxy-n,n-dimethylmethanamine Chemical compound CCOC(N(C)C)OCC BWKAYBPLDRWMCJ-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
OYPQDSDRQRADMD-UHFFFAOYSA-N 1-(4-butylphenyl)propan-2-one Chemical compound CCCCC1=CC=C(CC(C)=O)C=C1 OYPQDSDRQRADMD-UHFFFAOYSA-N 0.000 description 1
LSOOYAAXBIYNQY-UHFFFAOYSA-N 1-butyl-4-(2-nitroprop-1-enyl)benzene Chemical compound CCCCC1=CC=C(C=C(C)[N+]([O-])=O)C=C1 LSOOYAAXBIYNQY-UHFFFAOYSA-N 0.000 description 1
RIHXMHKNTLBIPJ-UHFFFAOYSA-N 1-nitroprop-1-ene Chemical class CC=C[N+]([O-])=O RIHXMHKNTLBIPJ-UHFFFAOYSA-N 0.000 description 1
RIZUCYSQUWMQLX-UHFFFAOYSA-N 2,3-dimethylbenzoic acid Chemical compound CC1=CC=CC(C(O)=O)=C1C RIZUCYSQUWMQLX-UHFFFAOYSA-N 0.000 description 1
NIONDZDPPYHYKY-UHFFFAOYSA-N 2-hexenoic acid Chemical class CCCC=CC(O)=O NIONDZDPPYHYKY-UHFFFAOYSA-N 0.000 description 1
UMHBEOYZDNGCOP-UHFFFAOYSA-N 2-phenyl-4h-pyran Chemical compound C1C=COC(C=2C=CC=CC=2)=C1 UMHBEOYZDNGCOP-UHFFFAOYSA-N 0.000 description 1
QFZTUWOWMRNMAH-UHFFFAOYSA-N 2h-pyran-2-carboxylic acid Chemical compound OC(=O)C1OC=CC=C1 QFZTUWOWMRNMAH-UHFFFAOYSA-N 0.000 description 1
ULRPISSMEBPJLN-UHFFFAOYSA-N 2h-tetrazol-5-amine Chemical compound NC1=NN=NN1 ULRPISSMEBPJLN-UHFFFAOYSA-N 0.000 description 1
125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
UDIRVPGJOBURPV-UHFFFAOYSA-N 4-(diethylamino)-3-phenylbut-3-en-2-one Chemical compound CCN(CC)C=C(C(C)=O)C1=CC=CC=C1 UDIRVPGJOBURPV-UHFFFAOYSA-N 0.000 description 1
KEGMAEFVJNPESF-UHFFFAOYSA-N 4-(dimethylamino)-3-(4-methoxyphenyl)but-3-en-2-one Chemical compound COC1=CC=C(C(=CN(C)C)C(C)=O)C=C1 KEGMAEFVJNPESF-UHFFFAOYSA-N 0.000 description 1
ARIREUPIXAKDAY-UHFFFAOYSA-N 4-butylbenzaldehyde Chemical compound CCCCC1=CC=C(C=O)C=C1 ARIREUPIXAKDAY-UHFFFAOYSA-N 0.000 description 1
OAHMVZYHIJQTQC-UHFFFAOYSA-N 4-cyclohexylphenol Chemical compound C1=CC(O)=CC=C1C1CCCCC1 OAHMVZYHIJQTQC-UHFFFAOYSA-N 0.000 description 1
PRBZORNPUQPRRZ-UHFFFAOYSA-N 4-oxo-5-phenoxypyran-2-carboxylic acid Chemical compound C1=CC=C(C=C1)OC2=COC(=CC2=O)C(=O)O PRBZORNPUQPRRZ-UHFFFAOYSA-N 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/34—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D309/36—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms
- C07D309/38—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms one oxygen atom in position 2 or 4, e.g. pyrones
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
- 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
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/34—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D309/36—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms
- C07D309/40—Oxygen atoms attached in positions 3 and 4, e.g. maltol

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Engineering & Computer Science (AREA)
Pharmacology & Pharmacy (AREA)
Pulmonology (AREA)
Animal Behavior & Ethology (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Immunology (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Catalysts (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pyrane Compounds (AREA)

LU82334A 1979-04-05 1980-04-04 Composes de pyranone substitues en position 5 et leur utilisation comme produits pharmaceutiques LU82334A1 (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB7912063		1979-04-05
GB7912063		1979-04-05

Publications (1)

Publication Number	Publication Date
LU82334A1 true LU82334A1 (fr)	1981-12-02

Family

ID=10504372

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
LU82334A LU82334A1 (fr)	1979-04-05	1980-04-04	Composes de pyranone substitues en position 5 et leur utilisation comme produits pharmaceutiques

Country Status (32)

Country	Link
US (1)	US4364956A (de)
JP (1)	JPS55133376A (de)
AR (1)	AR225918A1 (de)
AT (1)	AT368499B (de)
AU (1)	AU535315B2 (de)
BE (1)	BE882644A (de)
CA (1)	CA1142944A (de)
CH (1)	CH646967A5 (de)
CS (1)	CS214826B2 (de)
DD (1)	DD150002A5 (de)
DE (1)	DE3012597A1 (de)
DK (1)	DK142180A (de)
ES (1)	ES490122A0 (de)
FI (1)	FI801020A7 (de)
FR (1)	FR2453168A1 (de)
GB (2)	GB2047697B (de)
GR (1)	GR67760B (de)
HU (1)	HU184257B (de)
IE (1)	IE49581B1 (de)
IL (1)	IL59748A (de)
IT (1)	IT1143086B (de)
LU (1)	LU82334A1 (de)
NL (1)	NL8002025A (de)
NZ (1)	NZ193343A (de)
PH (1)	PH14895A (de)
PL (1)	PL123700B1 (de)
PT (1)	PT71050A (de)
RO (1)	RO81048A (de)
SE (1)	SE8002515L (de)
SU (1)	SU976850A3 (de)
YU (1)	YU92080A (de)
ZA (1)	ZA801977B (de)

Families Citing this family (17)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4603144A (en) *	1984-08-16	1986-07-29	G. D. Searle & Co.	Kojic acid ether-ester derivatives
DE3600287A1 (de)	1986-01-08	1987-07-16	Bayer Ag	1-arylpyrazole
JPH0778059B2 (ja) *	1986-03-11	1995-08-23	ダイセル化学工業株式会社	ピロン−３−カルボキサミド誘導体及び除草剤
DE3831695A1 (de) *	1988-09-17	1990-03-22	Hoechst Ag	Elaiophylinderivate, verfahren zu ihrer herstellung ihre verwendung als arzneimittel und sie enthaltende arzneimittel
US5747424A (en) *	1989-09-11	1998-05-05	Rhone-Poulenc Agriculture Ltd.	Herbicidal 4-substituted isoxazol
US5656573A (en) *	1989-09-11	1997-08-12	Rhone-Poulenc Agriculture Ltd.	Herbicidal 4-substituted isoxazoles
US5650533A (en) *	1989-09-11	1997-07-22	Rhone-Poulenc Agriculture Ltd.	Intermediates to herbicidal 4-substituted isoxazoles
GB8920519D0 (en) *	1989-09-11	1989-10-25	Rhone Poulenc Ltd	New compositions of matter
DE4031723A1 (de) *	1990-10-06	1992-04-09	Basf Ag	Verfahren zur herstellung von (alpha),(beta)-ungesaettigten carbonylverbindungen
TW587079B (en)	1998-09-25	2004-05-11	Almirall Prodesfarma Ag	2-phenylpyran-4-one derivatives
AR029489A1 (es) *	2000-03-10	2003-07-02	Euro Celtique Sa	Piridinas, pirimidinas, pirazinas, triazinas sustituidas por arilo, composiciones farmaceuticas y el uso de las mismas para la manufactura de un medicamento
PE20011333A1 (es)	2000-03-16	2002-01-16	Almirall Prodesfarma Ag	Derivados de 2-fenilpiran-4-ona como inhibidores de ciclooxigenasa 2
AR036873A1 (es)	2001-09-07	2004-10-13	Euro Celtique Sa	Piridinas aril sustituidas a, composiciones farmaceuticas y el uso de las mismas para la preparacion de un medicamento
AR037233A1 (es)	2001-09-07	2004-11-03	Euro Celtique Sa	Piridinas aril sustituidas, composiciones farmaceuticas y el uso de dichos compuestos para la elaboracion de un medicamento
US20090053641A1 (en) *	2005-03-24	2009-02-26	Kazuyoshi Kuroda	Charge control agent and related art
KR100904972B1 (ko) *	2005-03-24	2009-06-26	오리엔트 가가쿠 고교 가부시키가이샤	부전하 부여성 하전 제어제, 정전하상 현상용 토너 및 하전 제어 방법
CN107108429B (zh)	2015-12-23	2022-08-19	联邦科学与工业研究组织	化合物

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4065290A (en) *	1975-07-03	1977-12-27	Eli Lilly And Company	Herbicidal β-phenyl-4-piperidinones
US4060533A (en) *	1976-06-25	1977-11-29	Sandoz, Inc.	Pyranone carboxamides

1980
- 1980-03-31 IL IL59748A patent/IL59748A/xx unknown
- 1980-03-31 ES ES490122A patent/ES490122A0/es active Granted
- 1980-04-01 DK DK142180A patent/DK142180A/da not_active IP Right Cessation
- 1980-04-01 FI FI801020A patent/FI801020A7/fi not_active Application Discontinuation
- 1980-04-01 PH PH23844A patent/PH14895A/en unknown
- 1980-04-01 AU AU57031/80A patent/AU535315B2/en not_active Expired - Fee Related
- 1980-04-01 SE SE8002515A patent/SE8002515L/xx not_active Application Discontinuation
- 1980-04-01 DE DE19803012597 patent/DE3012597A1/de not_active Withdrawn
- 1980-04-02 FR FR8007447A patent/FR2453168A1/fr active Granted
- 1980-04-02 HU HU80785A patent/HU184257B/hu unknown
- 1980-04-02 IE IE671/80A patent/IE49581B1/en unknown
- 1980-04-02 PT PT71050A patent/PT71050A/pt unknown
- 1980-04-02 CH CH258980A patent/CH646967A5/fr not_active IP Right Cessation
- 1980-04-02 NZ NZ193343A patent/NZ193343A/xx unknown
- 1980-04-02 AT AT0181880A patent/AT368499B/de not_active IP Right Cessation
- 1980-04-02 GR GR61605A patent/GR67760B/el unknown
- 1980-04-02 ZA ZA00801977A patent/ZA801977B/xx unknown
- 1980-04-03 YU YU00920/80A patent/YU92080A/xx unknown
- 1980-04-03 BE BE6/47126A patent/BE882644A/fr not_active IP Right Cessation
- 1980-04-03 GB GB8011365A patent/GB2047697B/en not_active Expired
- 1980-04-03 DD DD80220217A patent/DD150002A5/de unknown
- 1980-04-03 GB GB08312570A patent/GB2123814B/en not_active Expired
- 1980-04-03 PL PL1980223229A patent/PL123700B1/pl unknown
- 1980-04-03 CA CA000349145A patent/CA1142944A/en not_active Expired
- 1980-04-04 IT IT48348/80A patent/IT1143086B/it active
- 1980-04-04 JP JP4455080A patent/JPS55133376A/ja active Pending
- 1980-04-04 LU LU82334A patent/LU82334A1/fr unknown
- 1980-04-04 SU SU802905747A patent/SU976850A3/ru active
- 1980-04-04 NL NL8002025A patent/NL8002025A/nl not_active Application Discontinuation
- 1980-04-04 CS CS802358A patent/CS214826B2/cs unknown
- 1980-04-05 RO RO80100749A patent/RO81048A/ro unknown
- 1980-04-07 AR AR280568A patent/AR225918A1/es active
1981
- 1981-09-17 US US06/303,307 patent/US4364956A/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
AT368499B (de)	1982-10-11
ES8104268A1 (es)	1981-04-01
SE8002515L (sv)	1980-10-06
ATA181880A (de)	1982-02-15
CH646967A5 (fr)	1984-12-28
IT1143086B (it)	1986-10-22
ZA801977B (en)	1981-07-29
AR225918A1 (es)	1982-05-14
FR2453168A1 (fr)	1980-10-31
GB8312570D0 (en)	1983-06-08
DD150002A5 (de)	1981-08-12
DK142180A (da)	1980-10-06
IL59748A (en)	1983-11-30
BE882644A (fr)	1980-10-03
FI801020A7 (fi)	1981-01-01
GB2123814A (en)	1984-02-08
AU5703180A (en)	1980-10-09
GB2047697A (en)	1980-12-03
DE3012597A1 (de)	1980-10-16
ES490122A0 (es)	1981-04-01
RO81048B (ro)	1983-01-30
PL223229A1 (de)	1981-01-30
HU184257B (en)	1984-07-30
RO81048A (ro)	1983-02-01
CA1142944A (en)	1983-03-15
FR2453168B1 (de)	1983-08-12
NZ193343A (en)	1982-03-23
AU535315B2 (en)	1984-03-15
JPS55133376A (en)	1980-10-17
GB2123814B (en)	1984-08-01
GB2047697B (en)	1983-10-19
YU92080A (en)	1983-02-28
US4364956A (en)	1982-12-21
PH14895A (en)	1982-01-08
SU976850A3 (ru)	1982-11-23
PT71050A (en)	1980-05-01
PL123700B1 (en)	1982-11-30
IL59748A0 (en)	1980-06-30
GR67760B (de)	1981-09-22
NL8002025A (nl)	1980-10-07
IE49581B1 (en)	1985-10-30
IE800671L (en)	1980-10-05
IT8048348A0 (it)	1980-04-04
CS214826B2 (en)	1982-06-25

Publication	Publication Date	Title
CH643546A5 (fr)	1984-06-15	Procede pour la preparation de derives d'hydantoine.
CH646967A5 (fr)	1984-12-28	Composes de pyranone et compositions pharmaceutiques les comprenant.
EP0399856B1 (de)	1995-08-09	Pteridin-4 (3H)-onen, Verfahren zu ihrer Herstellung und sie enthaltende Medikamente
CH653025A5 (fr)	1985-12-13	Oxazolidine-2,4-diones substituees en position 5 douees d'activite hypoglycemique.
EP0465323A1 (de)	1992-01-08	Pyrimidinderivate, Angiotensin-II-Rezeptorantagonisten, Verfahren zu deren Herstellung, diese enthaltende pharmazeutische Zusammenstellungen
EP0248734A1 (de)	1987-12-09	Benzo[b]thiophen und Benzo[b]furancarboxamid-Derivate, ihre Verfahren zur Herstellung und sie enthaltende Arzneimittel
EP0621255A1 (de)	1994-10-26	Substituierte Phenoxy-isobuttersäuren und ihre Ester
CA2055326A1 (fr)	1992-05-15	Derives de la n-benzoyl proline, leur procede de preparation et les compositions pharmaceutiques qui les contiennent
MC1334A1 (fr)	1981-04-21	Derives de triazolopyridazine
EP0109866B1 (de)	1987-08-19	Sulfonylharnstoff-Derivate, Verfahren zur Herstellung und pharmazeutische Zusammenstellungen die sie enthalten
EP0410834A1 (de)	1991-01-30	4,1,2-Benzoxadiazin-Derivate enthaltende Arzneimittel, Derivate und Verfahren zu deren Herstellung
EP0418933A1 (de)	1991-03-27	Alkadienderivate, ihre Herstellungen und sie enthaltende Arzneimittel und Zwischenprodukte
EP0566446A1 (de)	1993-10-20	Indan-1,3-Dion und Indan-1,2,3-Trionderivate, Verfahren zu ihrer Herstellung und ihrer therapeutische Verwendung
EP0374041A1 (de)	1990-06-20	2-Benzothiazolamin-Derivate enthaltende Arzneimittel, Verbindungen und ihre Herstellung
CH645370A5 (fr)	1984-09-28	Composes de pyranone et compositions pharmaceutiques les contenant.
LU81676A1 (fr)	1981-04-17	Nouveaux derives d'aurones,leur procede de preparation et leur utilisation comme produits pharmaceutiques
CA1152992A (fr)	1983-08-30	Amino-alcoxy pyrazoles, procede pour leur preparation, et medicaments les contenant
EP0196943B1 (de)	1990-01-24	8-Thiotetrahydrochinoleinderivate und deren Salze
BE779775A (fr)	1972-08-24	Derives de l'uree, procede pour les preparer et leurs applications
FR2772766A1 (fr)	1999-06-25	Nouveaux composes heterocycliques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent
FR2636327A1 (fr)	1990-03-16	Derives de quinoleine, leurs procedes de preparation et les medicaments les contenant
LU81832A1 (fr)	1980-05-07	Nouveaux derives d'acyl-1h-1,2,4-triazoles et leur procede de preparation
EP0412014A1 (de)	1991-02-06	Benzothiazinderivate, ihre Herstellung und ihre Verwendungen als Arzneimittel oder als Zwischenprodukte zur Synthese von Arzneimitteln
EP0161235A2 (de)	1985-11-13	Thienopyridinonderivate, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutiche Zubereitungen
BE826816R (fr)	1975-09-18	Nouveaux thiadiazoles, leur preparation et medicaments les contenant