NO860349L - Fremgangsmaate ved fremstilling av hyposensitive forbindelser. - Google Patents

Fremgangsmaate ved fremstilling av hyposensitive forbindelser.

Info

Publication number: NO860349L
Authority: NO; Norway
Prior art keywords: phenyl; aryl; alkyl; carbon atoms; hydroxy
Prior art date: 1985-02-01

Application number

NO860349A

Other languages

English (en)

Norwegian (no)

Inventor

Wan-Kit Chan

Thomas Daw-Yuan Lee

Fu-Chih Huang

Original Assignee

Usv Pharma Corp

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

1985-02-01

Filing date

1986-01-31

Publication date

1986-08-04

1986-01-31 Application filed by Usv Pharma Corp filed Critical Usv Pharma Corp

1986-08-04 Publication of NO860349L publication Critical patent/NO860349L/no

Links

150000001875 compounds Chemical class 0.000 title claims description 92
238000000034 method Methods 0.000 title claims description 29
238000002360 preparation method Methods 0.000 title claims description 16
125000000217 alkyl group Chemical group 0.000 claims description 60
125000004432 carbon atom Chemical group C* 0.000 claims description 45
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 36
125000003118 aryl group Chemical group 0.000 claims description 35
229910052739 hydrogen Inorganic materials 0.000 claims description 33
125000003282 alkyl amino group Chemical group 0.000 claims description 32
239000001257 hydrogen Substances 0.000 claims description 32
-1 allyl epoxide Chemical class 0.000 claims description 30
125000001589 carboacyl group Chemical group 0.000 claims description 28
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 28
229910052736 halogen Inorganic materials 0.000 claims description 25
150000002367 halogens Chemical class 0.000 claims description 25
239000000047 product Substances 0.000 claims description 25
125000003545 alkoxy group Chemical group 0.000 claims description 21
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 19
150000003839 salts Chemical class 0.000 claims description 19
125000003710 aryl alkyl group Chemical group 0.000 claims description 18
125000004104 aryloxy group Chemical group 0.000 claims description 18
125000004953 trihalomethyl group Chemical group 0.000 claims description 18
125000004414 alkyl thio group Chemical group 0.000 claims description 17
125000002648 azanetriyl group Chemical group *N(*)* 0.000 claims description 17
125000001424 substituent group Chemical group 0.000 claims description 16
PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims description 16
125000002947 alkylene group Chemical group 0.000 claims description 14
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 14
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 13
229910052760 oxygen Inorganic materials 0.000 claims description 13
239000001301 oxygen Substances 0.000 claims description 13
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 12
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 12
229910052717 sulfur Inorganic materials 0.000 claims description 12
239000011593 sulfur Substances 0.000 claims description 12
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 11
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 9
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 8
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 8
238000009833 condensation Methods 0.000 claims description 8
230000005494 condensation Effects 0.000 claims description 8
125000001624 naphthyl group Chemical group 0.000 claims description 8
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 7
125000004464 hydroxyphenyl group Chemical group 0.000 claims description 7
238000004519 manufacturing process Methods 0.000 claims description 7
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 7
229910052757 nitrogen Inorganic materials 0.000 claims description 7
150000004678 hydrides Chemical group 0.000 claims description 6
230000009467 reduction Effects 0.000 claims description 6
238000005882 aldol condensation reaction Methods 0.000 claims description 5
125000003342 alkenyl group Chemical group 0.000 claims description 5
229910052799 carbon Inorganic materials 0.000 claims description 5
150000003857 carboxamides Chemical class 0.000 claims description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
125000006239 protecting group Chemical group 0.000 claims description 5
125000006294 amino alkylene group Chemical group 0.000 claims description 4
125000000753 cycloalkyl group Chemical group 0.000 claims description 4
125000004663 dialkyl amino group Chemical group 0.000 claims description 4
150000002576 ketones Chemical class 0.000 claims description 4
238000006467 substitution reaction Methods 0.000 claims description 4
IGXXCQFIPZSOCD-UHFFFAOYSA-N 4-[2,4-bis(phenylmethoxy)phenyl]-2-methylbut-2-en-1-ol Chemical compound C1=C(OCC=2C=CC=CC=2)C(CC=C(CO)C)=CC=C1OCC1=CC=CC=C1 IGXXCQFIPZSOCD-UHFFFAOYSA-N 0.000 claims description 3
NUSQZLLTHULKJD-UHFFFAOYSA-N 5-(1-benzylindol-3-yl)penta-2,4-dienal Chemical compound C12=CC=CC=C2C(C=CC=CC=O)=CN1CC1=CC=CC=C1 NUSQZLLTHULKJD-UHFFFAOYSA-N 0.000 claims description 3
PVUSDHZQVPIPCT-UHFFFAOYSA-N 5-(1-benzylindol-3-yl)penta-2,4-dienoic acid Chemical compound C12=CC=CC=C2C(C=CC=CC(=O)O)=CN1CC1=CC=CC=C1 PVUSDHZQVPIPCT-UHFFFAOYSA-N 0.000 claims description 3
239000007859 condensation product Substances 0.000 claims description 3
MGPVQCBFUGDXFZ-UHFFFAOYSA-N ethyl 5-(5-methoxy-1h-indol-2-yl)penta-2,4-dienoate Chemical compound COC1=CC=C2NC(C=CC=CC(=O)OCC)=CC2=C1 MGPVQCBFUGDXFZ-UHFFFAOYSA-N 0.000 claims description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
JOUAGCVYTQFOCI-UHFFFAOYSA-N 1-(1-benzylindol-3-yl)deca-1,3-dien-5-ol Chemical compound C12=CC=CC=C2C(C=CC=CC(O)CCCCC)=CN1CC1=CC=CC=C1 JOUAGCVYTQFOCI-UHFFFAOYSA-N 0.000 claims description 2
DNHXVGHKNGYKEV-UHFFFAOYSA-N 5-(1-benzylindol-3-yl)-2-ethylpenta-2,4-dienoic acid Chemical compound C12=CC=CC=C2C(C=CC=C(CC)C(O)=O)=CN1CC1=CC=CC=C1 DNHXVGHKNGYKEV-UHFFFAOYSA-N 0.000 claims description 2
125000005129 aryl carbonyl group Chemical group 0.000 claims description 2
SWABKXWGSYRMCX-UHFFFAOYSA-N ethyl 5-(1-benzyl-5-methoxyindol-3-yl)penta-2,4-dienoate Chemical compound C12=CC=C(OC)C=C2C(C=CC=CC(=O)OCC)=CN1CC1=CC=CC=C1 SWABKXWGSYRMCX-UHFFFAOYSA-N 0.000 claims description 2
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims 17
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 7
150000001728 carbonyl compounds Chemical class 0.000 claims 4
BUBODDNRTOKSDC-UHFFFAOYSA-N 5-[1-(4-chlorobenzoyl)indol-3-yl]-2-ethylpenta-2,4-dienoic acid Chemical compound C12=CC=CC=C2C(C=CC=C(CC)C(O)=O)=CN1C(=O)C1=CC=C(Cl)C=C1 BUBODDNRTOKSDC-UHFFFAOYSA-N 0.000 claims 2
229910052783 alkali metal Inorganic materials 0.000 claims 2
150000001340 alkali metals Chemical class 0.000 claims 2
125000005090 alkenylcarbonyl group Chemical group 0.000 claims 2
125000004448 alkyl carbonyl group Chemical group 0.000 claims 2
125000004076 pyridyl group Chemical group 0.000 claims 2
RCDRALDPYGQMPV-UHFFFAOYSA-N 2-(4-hydroxy-3-methylbut-2-enyl)-4-methylphenol Chemical compound OCC(C)=CCC1=CC(C)=CC=C1O RCDRALDPYGQMPV-UHFFFAOYSA-N 0.000 claims 1
PKUYVWUCWHVCDZ-UHFFFAOYSA-N 3-(1-benzylindol-3-yl)prop-2-en-1-ol Chemical compound C12=CC=CC=C2C(C=CCO)=CN1CC1=CC=CC=C1 PKUYVWUCWHVCDZ-UHFFFAOYSA-N 0.000 claims 1
IPEPVTLMGPNGOJ-UHFFFAOYSA-N 4-(4-methoxyphenyl)-2-methylbut-2-en-1-ol Chemical compound COC1=CC=C(CC=C(C)CO)C=C1 IPEPVTLMGPNGOJ-UHFFFAOYSA-N 0.000 claims 1
JQGJNOOJDOLWIQ-UHFFFAOYSA-N 5-(1-benzyl-2-methylindol-3-yl)penta-2,4-dienoic acid Chemical compound CC1=C(C=CC=CC(O)=O)C2=CC=CC=C2N1CC1=CC=CC=C1 JQGJNOOJDOLWIQ-UHFFFAOYSA-N 0.000 claims 1
XZUXOCDKDBWRLF-UHFFFAOYSA-N 5-(1-benzyl-5-chloroindol-3-yl)penta-2,4-dienoic acid Chemical compound C12=CC=C(Cl)C=C2C(C=CC=CC(=O)O)=CN1CC1=CC=CC=C1 XZUXOCDKDBWRLF-UHFFFAOYSA-N 0.000 claims 1
YHVOIOHYFBIDKB-UHFFFAOYSA-N 5-(1-benzylindol-3-yl)-2-propylpenta-2,4-dienoic acid Chemical compound C12=CC=CC=C2C(C=CC=C(CCC)C(O)=O)=CN1CC1=CC=CC=C1 YHVOIOHYFBIDKB-UHFFFAOYSA-N 0.000 claims 1
UIGCDEZZKQPJAY-UHFFFAOYSA-N 5-[1-(pyridin-2-ylmethyl)indol-3-yl]penta-2,4-dienoic acid Chemical compound N1=C(C=CC=C1)CN1C=C(C2=CC=CC=C12)C=CC=CC(=O)O UIGCDEZZKQPJAY-UHFFFAOYSA-N 0.000 claims 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 1
TWQWHQMYXACNCG-UHFFFAOYSA-N ethyl 4-[5-(1-benzylindol-3-yl)penta-2,4-dienoylamino]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1NC(=O)C=CC=CC(C1=CC=CC=C11)=CN1CC1=CC=CC=C1 TWQWHQMYXACNCG-UHFFFAOYSA-N 0.000 claims 1
LJWJSLJBXIYPON-UHFFFAOYSA-N ethyl 5-(1-benzyl-5-phenylmethoxyindol-3-yl)penta-2,4-dienoate Chemical compound C12=CC=C(OCC=3C=CC=CC=3)C=C2C(C=CC=CC(=O)OCC)=CN1CC1=CC=CC=C1 LJWJSLJBXIYPON-UHFFFAOYSA-N 0.000 claims 1
SDZZBCJDYRCYQJ-UHFFFAOYSA-N ethyl 5-(1-benzylindol-3-yl)-2-ethylpenta-2,4-dienoate Chemical compound C12=CC=CC=C2C(C=CC=C(CC)C(=O)OCC)=CN1CC1=CC=CC=C1 SDZZBCJDYRCYQJ-UHFFFAOYSA-N 0.000 claims 1
125000005493 quinolyl group Chemical group 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 66
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 62
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 30
239000000203 mixture Substances 0.000 description 24
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 22
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
239000000243 solution Substances 0.000 description 21
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
230000000694 effects Effects 0.000 description 19
238000006243 chemical reaction Methods 0.000 description 16
238000012360 testing method Methods 0.000 description 15
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
239000000872 buffer Substances 0.000 description 14
238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 14
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
229940114079 arachidonic acid Drugs 0.000 description 12
235000021342 arachidonic acid Nutrition 0.000 description 11
210000001519 tissue Anatomy 0.000 description 11
108010058864 Phospholipases A2 Proteins 0.000 description 10
102000006447 Phospholipases A2 Human genes 0.000 description 10
150000002617 leukotrienes Chemical class 0.000 description 10
239000000843 powder Substances 0.000 description 10
102000004190 Enzymes Human genes 0.000 description 9
108090000790 Enzymes Proteins 0.000 description 9
239000007788 liquid Substances 0.000 description 9
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 8
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 8
102000014384 Type C Phospholipases Human genes 0.000 description 8
108010079194 Type C Phospholipases Proteins 0.000 description 8
239000002253 acid Substances 0.000 description 8
238000004440 column chromatography Methods 0.000 description 8
238000002425 crystallisation Methods 0.000 description 8
230000008025 crystallization Effects 0.000 description 8
238000000746 purification Methods 0.000 description 8
239000000126 substance Substances 0.000 description 8
WTJKGGKOPKCXLL-RRHRGVEJSA-N phosphatidylcholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC WTJKGGKOPKCXLL-RRHRGVEJSA-N 0.000 description 7
239000000758 substrate Substances 0.000 description 7
239000000725 suspension Substances 0.000 description 7
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
XNRNNGPBEPRNAR-JQBLCGNGSA-N thromboxane B2 Chemical compound CCCCC[C@H](O)\C=C\[C@H]1OC(O)C[C@H](O)[C@@H]1C\C=C/CCCC(O)=O XNRNNGPBEPRNAR-JQBLCGNGSA-N 0.000 description 7
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 6
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
239000013078 crystal Substances 0.000 description 6
235000021588 free fatty acids Nutrition 0.000 description 6
229910052943 magnesium sulfate Inorganic materials 0.000 description 6
235000019341 magnesium sulphate Nutrition 0.000 description 6
239000012044 organic layer Substances 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
239000000741 silica gel Substances 0.000 description 6
229910002027 silica gel Inorganic materials 0.000 description 6
239000002904 solvent Substances 0.000 description 6
230000001225 therapeutic effect Effects 0.000 description 6
KGIJOOYOSFUGPC-CABOLEKPSA-N 5-HETE Natural products CCCCC\C=C/C\C=C/C\C=C/C=C/[C@H](O)CCCC(O)=O KGIJOOYOSFUGPC-CABOLEKPSA-N 0.000 description 5
KGIJOOYOSFUGPC-MSFIICATSA-N 5-Hydroxyeicosatetraenoic acid Chemical compound CCCCCC=CCC=CCC=C\C=C\[C@@H](O)CCCC(O)=O KGIJOOYOSFUGPC-MSFIICATSA-N 0.000 description 5
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
102000003820 Lipoxygenases Human genes 0.000 description 5
108090000128 Lipoxygenases Proteins 0.000 description 5
239000006185 dispersion Substances 0.000 description 5
238000000605 extraction Methods 0.000 description 5
IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical group CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 5
125000004356 hydroxy functional group Chemical group O* 0.000 description 5
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 5
239000003921 oil Substances 0.000 description 5
235000019198 oils Nutrition 0.000 description 5
FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 4
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
102100022364 Polyunsaturated fatty acid 5-lipoxygenase Human genes 0.000 description 4
230000009471 action Effects 0.000 description 4
150000001298 alcohols Chemical class 0.000 description 4
150000001299 aldehydes Chemical class 0.000 description 4
208000006673 asthma Diseases 0.000 description 4
239000002775 capsule Substances 0.000 description 4
ZTUGAZKZXITUQZ-UHFFFAOYSA-N ethyl 5-(1-benzylindol-3-yl)penta-2,4-dienoate Chemical compound C12=CC=CC=C2C(C=CC=CC(=O)OCC)=CN1CC1=CC=CC=C1 ZTUGAZKZXITUQZ-UHFFFAOYSA-N 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
125000000623 heterocyclic group Chemical group 0.000 description 4
239000003112 inhibitor Substances 0.000 description 4
230000002401 inhibitory effect Effects 0.000 description 4
239000010410 layer Substances 0.000 description 4
239000000463 material Substances 0.000 description 4
239000011780 sodium chloride Substances 0.000 description 4
229910000104 sodium hydride Inorganic materials 0.000 description 4
238000003756 stirring Methods 0.000 description 4
239000003826 tablet Substances 0.000 description 4
PXGPLTODNUVGFL-BRIYLRKRSA-N (E,Z)-(1R,2R,3R,5S)-7-(3,5-Dihydroxy-2-((3S)-(3-hydroxy-1-octenyl))cyclopentyl)-5-heptenoic acid Chemical compound CCCCC[C@H](O)C=C[C@H]1[C@H](O)C[C@H](O)[C@@H]1CC=CCCCC(O)=O PXGPLTODNUVGFL-BRIYLRKRSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
206010002198 Anaphylactic reaction Diseases 0.000 description 3
108010093579 Arachidonate 5-lipoxygenase Proteins 0.000 description 3
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102000015439 Phospholipases Human genes 0.000 description 3
108010064785 Phospholipases Proteins 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
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KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
230000036783 anaphylactic response Effects 0.000 description 3
208000003455 anaphylaxis Diseases 0.000 description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
239000006227 byproduct Substances 0.000 description 3
239000001110 calcium chloride Substances 0.000 description 3
235000011148 calcium chloride Nutrition 0.000 description 3
229910001628 calcium chloride Inorganic materials 0.000 description 3
229910002092 carbon dioxide Inorganic materials 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
230000008602 contraction Effects 0.000 description 3
150000002148 esters Chemical group 0.000 description 3
HWJHWSBFPPPIPD-UHFFFAOYSA-N ethoxyethane;propan-2-one Chemical compound CC(C)=O.CCOCC HWJHWSBFPPPIPD-UHFFFAOYSA-N 0.000 description 3
239000011521 glass Substances 0.000 description 3
229960001340 histamine Drugs 0.000 description 3
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 3
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 3
230000004968 inflammatory condition Effects 0.000 description 3
239000004615 ingredient Substances 0.000 description 3
230000005764 inhibitory process Effects 0.000 description 3
239000012280 lithium aluminium hydride Substances 0.000 description 3
239000002609 medium Substances 0.000 description 3
230000004060 metabolic process Effects 0.000 description 3
244000005700 microbiome Species 0.000 description 3
230000037361 pathway Effects 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
230000004044 response Effects 0.000 description 3
230000000717 retained effect Effects 0.000 description 3
239000012312 sodium hydride Substances 0.000 description 3
238000004611 spectroscopical analysis Methods 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
238000001665 trituration Methods 0.000 description 3
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IPCARISCJBUPJR-UHFFFAOYSA-N ethyl 5-[1-(4-chlorobenzoyl)-5-methoxyindol-2-yl]penta-2,4-dienoate Chemical compound CCOC(=O)C=CC=CC1=CC2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 IPCARISCJBUPJR-UHFFFAOYSA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
230000001747 exhibiting effect Effects 0.000 description 1
238000013265 extended release Methods 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
235000013305 food Nutrition 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
239000012458 free base Substances 0.000 description 1
238000004108 freeze drying Methods 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
229960003180 glutathione Drugs 0.000 description 1
229940096919 glycogen Drugs 0.000 description 1
150000004795 grignard reagents Chemical class 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
235000001050 hortel pimenta Nutrition 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
239000001863 hydroxypropyl cellulose Substances 0.000 description 1
235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
238000000099 in vitro assay Methods 0.000 description 1
239000003701 inert diluent Substances 0.000 description 1
208000027866 inflammatory disease Diseases 0.000 description 1
230000004054 inflammatory process Effects 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
CDAISMWEOUEBRE-GPIVLXJGSA-N inositol Chemical compound O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@@H]1O CDAISMWEOUEBRE-GPIVLXJGSA-N 0.000 description 1
229960000367 inositol Drugs 0.000 description 1
230000035987 intoxication Effects 0.000 description 1
231100000566 intoxication Toxicity 0.000 description 1
238000011835 investigation Methods 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
239000011630 iodine Substances 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
238000002955 isolation Methods 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000007951 isotonicity adjuster Substances 0.000 description 1
125000000468 ketone group Chemical group 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000000787 lecithin Substances 0.000 description 1
235000010445 lecithin Nutrition 0.000 description 1
229940067606 lecithin Drugs 0.000 description 1
VNYSSYRCGWBHLG-AMOLWHMGSA-N leukotriene B4 Chemical compound CCCCC\C=C/C[C@@H](O)\C=C\C=C\C=C/[C@@H](O)CCCC(O)=O VNYSSYRCGWBHLG-AMOLWHMGSA-N 0.000 description 1
XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 1
229960004488 linolenic acid Drugs 0.000 description 1
235000019421 lipase Nutrition 0.000 description 1
229910003002 lithium salt Inorganic materials 0.000 description 1
150000004668 long chain fatty acids Chemical class 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
XWCQLLDGXBLGMD-UHFFFAOYSA-M magnesium;pentane;bromide Chemical compound [Mg+2].[Br-].CCCC[CH2-] XWCQLLDGXBLGMD-UHFFFAOYSA-M 0.000 description 1
239000001630 malic acid Substances 0.000 description 1
235000011090 malic acid Nutrition 0.000 description 1
150000002697 manganese compounds Chemical class 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
239000012528 membrane Substances 0.000 description 1
239000002207 metabolite Substances 0.000 description 1
229910052987 metal hydride Inorganic materials 0.000 description 1
150000004681 metal hydrides Chemical class 0.000 description 1
235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
239000000041 non-steroidal anti-inflammatory agent Substances 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
239000007968 orange flavor Substances 0.000 description 1
239000010502 orange oil Substances 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
239000002245 particle Substances 0.000 description 1
230000007310 pathophysiology Effects 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
229960003742 phenol Drugs 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
150000003904 phospholipids Chemical class 0.000 description 1
229920005862 polyol Polymers 0.000 description 1
150000003077 polyols Chemical class 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
229920001592 potato starch Polymers 0.000 description 1
238000011533 pre-incubation Methods 0.000 description 1
239000002243 precursor Substances 0.000 description 1
230000002335 preservative effect Effects 0.000 description 1
150000003138 primary alcohols Chemical class 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
239000002599 prostaglandin synthase inhibitor Substances 0.000 description 1
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
230000002285 radioactive effect Effects 0.000 description 1
238000011084 recovery Methods 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
230000000284 resting effect Effects 0.000 description 1
CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
229940081974 saccharin Drugs 0.000 description 1
235000019204 saccharin Nutrition 0.000 description 1
239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
239000000523 sample Substances 0.000 description 1
239000012723 sample buffer Substances 0.000 description 1
238000003345 scintillation counting Methods 0.000 description 1
230000007017 scission Effects 0.000 description 1
CDAISMWEOUEBRE-UHFFFAOYSA-N scyllo-inosotol Natural products OC1C(O)C(O)C(O)C(O)C1O CDAISMWEOUEBRE-UHFFFAOYSA-N 0.000 description 1
150000003333 secondary alcohols Chemical class 0.000 description 1
ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
239000004208 shellac Substances 0.000 description 1
229940113147 shellac Drugs 0.000 description 1
235000013874 shellac Nutrition 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
210000002460 smooth muscle Anatomy 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
239000004334 sorbic acid Substances 0.000 description 1
235000010199 sorbic acid Nutrition 0.000 description 1
229940075582 sorbic acid Drugs 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
230000001954 sterilising effect Effects 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
RTKIYNMVFMVABJ-UHFFFAOYSA-L thimerosal Chemical compound [Na+].CC[Hg]SC1=CC=CC=C1C([O-])=O RTKIYNMVFMVABJ-UHFFFAOYSA-L 0.000 description 1
229940033663 thimerosal Drugs 0.000 description 1
229930192474 thiophene Natural products 0.000 description 1
150000003595 thromboxanes Chemical class 0.000 description 1
230000009466 transformation Effects 0.000 description 1
238000001291 vacuum drying Methods 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
239000009637 wintergreen oil Substances 0.000 description 1

Classifications

- 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
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/12—Radicals substituted by oxygen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/23—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing hydroxy or O-metal groups
- 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
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- 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
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D209/22—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with an aralkyl radical attached to the ring nitrogen atom
- 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
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D209/26—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with an acyl radical attached to the ring nitrogen atom

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Indole Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Polysaccharides And Polysaccharide Derivatives (AREA)

NO860349A 1985-02-01 1986-01-31 Fremgangsmaate ved fremstilling av hyposensitive forbindelser. NO860349L (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US69759485A	1985-02-01	1985-02-01
US06/821,063 US4758586A (en)	1985-02-01	1986-01-21	Indolyl compounds and hyposensitivity use thereof

Publications (1)

Publication Number	Publication Date
NO860349L true NO860349L (no)	1986-08-04

Family

ID=27106043

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO860349A NO860349L (no)	1985-02-01	1986-01-31	Fremgangsmaate ved fremstilling av hyposensitive forbindelser.

Country Status (6)

Country	Link
US (1)	US4758586A (fr)
EP (1)	EP0189936A2 (fr)
AU (1)	AU5296486A (fr)
DK (1)	DK48886A (fr)
FI (1)	FI860479A7 (fr)
NO (1)	NO860349L (fr)

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4708966A (en) *	1986-06-27	1987-11-24	The Procter & Gamble Company	Novel anti-inflammatory agents, pharmaceutical compositions and methods for reducing inflammation
DE3639402A1 (de) *	1986-11-18	1988-05-19	Siemens Ag	Verfahren zur herstellung einer mehrschichtigen leiterplatte sowie danach hergestellte leiterplatte
GB8628467D0 (en) *	1986-11-28	1987-01-07	Wellcome Found	Pesticidal compounds
US5380732A (en) *	1986-11-28	1995-01-10	Roussel-Uclaf	Pesticidal compounds
DE68907095T2 (de) *	1988-03-21	1994-01-05	Boehringer Ingelheim Pharma	Verbindungen zur Verhinderung der Biosynthese von der Lipoxygenase abgeleiteten Metaboliten der Arachidonsäure.
JPH0764841B2 (ja) *	1990-10-03	1995-07-12	ファイザー製薬株式会社	インドール誘導体およびその用途
US5977125A (en) *	1994-10-31	1999-11-02	Eisai Co., Ltd.	Mono-or polyenic carboxylic acid derivatives
GB2295151B (en) *	1994-11-18	1998-12-09	Nmc	Polymerization of substituted heterocyclic monomers
CA2245524A1 (fr) *	1996-02-02	1997-08-07	Wei Han	Agents antidiabetiques
US5859051A (en) *	1996-02-02	1999-01-12	Merck & Co., Inc.	Antidiabetic agents
GB9614366D0 (en) *	1996-07-09	1996-09-04	Smithkline Beecham Spa	Novel compounds
GB9614347D0 (en) *	1996-07-09	1996-09-04	Smithkline Beecham Spa	Novel compounds
AU6886896A (en) *	1996-08-28	1998-03-19	Farmacon, Inc.	Phenylbutanol derivatives, methods for their preparation and pharmaceutical compositions thereof
US6160000A (en) *	1996-12-23	2000-12-12	Merck & Co., Inc.	Antidiabetic agents based on aryl and heteroarylacetic acids
US6090839A (en) *	1996-12-23	2000-07-18	Merck & Co., Inc.	Antidiabetic agents

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3271416A (en) *	1961-10-24	1966-09-06	Merck & Co Inc	Indolyl aliphatic acids
US4536505A (en) *	1983-05-17	1985-08-20	Ciba-Geigy Corporation	Certain N-(pyridyl) indoles

1986
- 1986-01-21 US US06/821,063 patent/US4758586A/en not_active Expired - Fee Related
- 1986-01-31 EP EP86101291A patent/EP0189936A2/fr not_active Withdrawn
- 1986-01-31 AU AU52964/86A patent/AU5296486A/en not_active Abandoned
- 1986-01-31 NO NO860349A patent/NO860349L/no unknown
- 1986-01-31 DK DK48886A patent/DK48886A/da not_active Application Discontinuation
- 1986-02-03 FI FI860479A patent/FI860479A7/fi not_active Application Discontinuation

Also Published As

Publication number	Publication date
DK48886A (da)	1986-08-02
US4758586A (en)	1988-07-19
FI860479A0 (fi)	1986-02-03
EP0189936A2 (fr)	1986-08-06
FI860479A7 (fi)	1986-08-02
DK48886D0 (da)	1986-01-31
AU5296486A (en)	1986-08-07

Publication	Publication Date	Title
NO860349L (no)	1986-08-04	Fremgangsmaate ved fremstilling av hyposensitive forbindelser.
EP3230278B1 (fr)	2019-12-11	Nouveaux composés méthyl-pipéridine servant à inhiber la prostaglandine e2 synthase-1 microsomale
US7915448B2 (en)	2011-03-29	Substituted sulfonylaminoarylmethyl cyclopropanecarboxamide as VR1 receptor antagonists
US4661596A (en)	1987-04-28	Quinolinyl (or pyridinyl) methoxy substituted naphthalene compounds as antiallergic agents
NO861306L (no)	1986-10-06	Fremgangsmaate ved fremstilling av terapeutisk virksomme hydroxamatforbindelser.
US11661400B2 (en)	2023-05-30	NADPH oxidase inhibitors, pharmaceutical composition comprising the same, and application thereof
EP0051917B1 (fr)	1986-02-19	Dérivés de benzofuranne-éthanolamine, leurs procédés de préparation et leur usage en médicine
NO166938B (no)	1991-06-10	Analogifremgangsmaate for fremstilling av terapeutisk aktive fenoxyeddiksyrederivater.
NO169438B (no)	1992-03-16	Analogifremgangsmaate for fremstilling av terapeutisk aktive tetrazolforbindelser
EP0309541B1 (fr)	1992-01-02	Sulfonyle carboxamides
NO164414B (no)	1990-06-25	Analogifremgangsmaate for fremstilling av terapeutisk aktive leukotrien-antagonister.
NO155240B (no)	1986-11-24	Analogifremgangsmaate for fremstilling av terapeutisk aktive aroyl (propionyl- eller butyryl)-l-prolinderivater.
US4751235A (en)	1988-06-14	Anti-atherosclerotic indolizine derivatives
US4845100A (en)	1989-07-04	Carbostyril derivatives and salts thereof, processes for preparing the same and cardiotonic composition containing the same
JP6333355B2 (ja)	2018-05-30	Ｇｐｒ１２０のアゴニストとして有用な二環式ピロール誘導体
KR100230639B1 (ko)	1999-11-15	카르보스티릴 유도체
US5750524A (en)	1998-05-12	Remedy for hyperlipidemia
US4567279A (en)	1986-01-28	Diarylhydroxy alkanones and alkenones antiallergy agents
US4341781A (en)	1982-07-27	Pyridazopyridazine derivatives
JPH0368554A (ja)	1991-03-25	４―フェニルメチル―１ｈ―インドールの誘導体、それらの製造法及び中間体、それらの薬剤としての使用並びにそれを含有する組成物
US4175137A (en)	1979-11-20	Etherified cycloalkanols
US4528392A (en)	1985-07-09	Aromatic compounds as antiallergic agents
FR2491064A1 (fr)	1982-04-02	Quinolones, leurs procedes de preparation et composition therapeutique les contenant
NO154493B (no)	1986-06-23	Analogifremgangsmaate for fremstilling av nye, terapeutisk aktive 1-substituerte-3-cycloalkyl-sulfonyl-pyrrolidin-2,5-dion-derivater.
JP6360569B2 (ja)	2018-07-18	Ｇｐｒ１２０のアゴニストとして有用な二環式ピロール誘導体