IE46676B1 - Lipofenesis-inhibiting compositions - Google Patents

Lipofenesis-inhibiting compositions

Info

Publication number: IE46676B1
Authority: IE; Ireland
Prior art keywords: carbon atoms; alkyl; hydrogen; mixture; composition
Prior art date: 1977-03-17

Application number

IE532/78A

Other languages

English (en)

Other versions

IE780532L (en

Original Assignee

Shell Int Research

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.)

1977-03-17

Filing date

1978-03-15

Publication date

1983-08-24

1977-03-17 Priority claimed from US05/778,535 external-priority patent/US4118507A/en

1977-03-21 Priority claimed from US05/779,648 external-priority patent/US4103021A/en

1978-03-15 Application filed by Shell Int Research filed Critical Shell Int Research

1978-09-17 Publication of IE780532L publication Critical patent/IE780532L/xx

1983-08-24 Publication of IE46676B1 publication Critical patent/IE46676B1/en

Links

239000000203 mixture Substances 0.000 title claims abstract description 122
230000002401 inhibitory effect Effects 0.000 title claims description 12
150000001875 compounds Chemical class 0.000 claims abstract description 86
241000124008 Mammalia Species 0.000 claims abstract description 9
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 4
239000001301 oxygen Substances 0.000 claims abstract description 4
229910052760 oxygen Inorganic materials 0.000 claims abstract description 4
239000001257 hydrogen Substances 0.000 claims description 43
229910052739 hydrogen Inorganic materials 0.000 claims description 43
125000004432 carbon atom Chemical group C* 0.000 claims description 38
125000000217 alkyl group Chemical group 0.000 claims description 35
238000000034 method Methods 0.000 claims description 32
230000004132 lipogenesis Effects 0.000 claims description 30
-1 methylsulphonylamino Chemical group 0.000 claims description 28
150000002431 hydrogen Chemical group 0.000 claims description 23
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 22
239000002253 acid Substances 0.000 claims description 21
125000001424 substituent group Chemical group 0.000 claims description 18
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 17
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
229910052801 chlorine Inorganic materials 0.000 claims description 15
150000003839 salts Chemical class 0.000 claims description 14
239000000460 chlorine Substances 0.000 claims description 13
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 13
125000000753 cycloalkyl group Chemical group 0.000 claims description 12
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
125000003545 alkoxy group Chemical group 0.000 claims description 10
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
125000001309 chloro group Chemical group Cl* 0.000 claims description 9
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
239000004480 active ingredient Substances 0.000 claims description 8
125000005843 halogen group Chemical group 0.000 claims description 8
229910052736 halogen Inorganic materials 0.000 claims description 7
150000002367 halogens Chemical group 0.000 claims description 7
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
229910052794 bromium Inorganic materials 0.000 claims description 5
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
125000000000 cycloalkoxy group Chemical group 0.000 claims 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 claims description 4
239000011737 fluorine Chemical group 0.000 claims description 4
229910052731 fluorine Inorganic materials 0.000 claims description 4
125000003884 phenylalkyl group Chemical group 0.000 claims description 4
125000003342 alkenyl group Chemical group 0.000 claims description 2
125000000304 alkynyl group Chemical group 0.000 claims description 2
125000001246 bromo group Chemical group Br* 0.000 claims description 2
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
AZFKQCNGMSSWDS-UHFFFAOYSA-N MCPA-thioethyl Chemical compound CCSC(=O)COC1=CC=C(Cl)C=C1C AZFKQCNGMSSWDS-UHFFFAOYSA-N 0.000 claims 1
HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 abstract description 11
150000002632 lipids Chemical class 0.000 abstract description 11
230000015572 biosynthetic process Effects 0.000 abstract description 7
235000012000 cholesterol Nutrition 0.000 abstract description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 130
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 118
239000002904 solvent Substances 0.000 description 82
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 72
239000000243 solution Substances 0.000 description 72
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 66
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 51
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 45
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 44
238000012360 testing method Methods 0.000 description 44
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 34
239000007787 solid Substances 0.000 description 32
239000000047 product Substances 0.000 description 26
VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 25
239000000706 filtrate Substances 0.000 description 24
229940073584 methylene chloride Drugs 0.000 description 24
229910000027 potassium carbonate Inorganic materials 0.000 description 22
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
210000000577 adipose tissue Anatomy 0.000 description 21
239000013078 crystal Substances 0.000 description 21
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 20
239000007788 liquid Substances 0.000 description 20
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 19
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
125000004494 ethyl ester group Chemical group 0.000 description 18
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 17
239000008103 glucose Substances 0.000 description 17
230000005764 inhibitory process Effects 0.000 description 17
OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 16
OENICUBCLXKLJQ-UHFFFAOYSA-N ethyl 2,3-dibromopropanoate Chemical compound CCOC(=O)C(Br)CBr OENICUBCLXKLJQ-UHFFFAOYSA-N 0.000 description 15
239000000284 extract Substances 0.000 description 15
238000010992 reflux Methods 0.000 description 15
150000001412 amines Chemical class 0.000 description 14
239000000741 silica gel Substances 0.000 description 14
229910002027 silica gel Inorganic materials 0.000 description 14
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 14
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 13
241001465754 Metazoa Species 0.000 description 13
229960001760 dimethyl sulfoxide Drugs 0.000 description 13
239000003480 eluent Substances 0.000 description 13
241000282898 Sus scrofa Species 0.000 description 12
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
241000700159 Rattus Species 0.000 description 11
239000003054 catalyst Substances 0.000 description 11
239000010410 layer Substances 0.000 description 11
239000003208 petroleum Substances 0.000 description 11
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
150000002148 esters Chemical class 0.000 description 10
238000011534 incubation Methods 0.000 description 10
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
229940079593 drug Drugs 0.000 description 9
239000003814 drug Substances 0.000 description 9
239000011541 reaction mixture Substances 0.000 description 9
238000001953 recrystallisation Methods 0.000 description 9
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical group N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 8
239000001117 sulphuric acid Substances 0.000 description 8
235000011149 sulphuric acid Nutrition 0.000 description 8
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 7
150000007513 acids Chemical class 0.000 description 7
210000001519 tissue Anatomy 0.000 description 7
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
150000001732 carboxylic acid derivatives Chemical class 0.000 description 6
230000000694 effects Effects 0.000 description 6
ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 6
210000004185 liver Anatomy 0.000 description 6
210000005228 liver tissue Anatomy 0.000 description 6
229920000642 polymer Polymers 0.000 description 6
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 5
238000004587 chromatography analysis Methods 0.000 description 5
239000002243 precursor Substances 0.000 description 5
238000002360 preparation method Methods 0.000 description 5
230000002285 radioactive effect Effects 0.000 description 5
229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
235000017557 sodium bicarbonate Nutrition 0.000 description 5
239000000725 suspension Substances 0.000 description 5
238000003786 synthesis reaction Methods 0.000 description 5
KVBNENBFIVLEHO-UHFFFAOYSA-N 1,2-benzoxazine-2-carboxylic acid Chemical compound C1=CC=C2C=CN(C(=O)O)OC2=C1 KVBNENBFIVLEHO-UHFFFAOYSA-N 0.000 description 4
JRLTTZUODKEYDH-UHFFFAOYSA-N 8-methylquinoline Chemical group C1=CN=C2C(C)=CC=CC2=C1 JRLTTZUODKEYDH-UHFFFAOYSA-N 0.000 description 4
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 4
BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 4
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
102000004877 Insulin Human genes 0.000 description 4
108090001061 Insulin Proteins 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
241000282887 Suidae Species 0.000 description 4
230000037396 body weight Effects 0.000 description 4
229910001424 calcium ion Inorganic materials 0.000 description 4
229910052799 carbon Inorganic materials 0.000 description 4
YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 4
238000007796 conventional method Methods 0.000 description 4
239000012259 ether extract Substances 0.000 description 4
238000001704 evaporation Methods 0.000 description 4
239000012530 fluid Substances 0.000 description 4
239000007789 gas Substances 0.000 description 4
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
229910000041 hydrogen chloride Inorganic materials 0.000 description 4
239000004615 ingredient Substances 0.000 description 4
229940125396 insulin Drugs 0.000 description 4
230000003520 lipogenic effect Effects 0.000 description 4
239000003921 oil Substances 0.000 description 4
OVHHNKPYYVQCLN-LJQANCHMSA-N (2r)-4-(6-chloronaphthalen-2-yl)sulfonyl-1-(5-methyl-6,7-dihydro-4h-[1,3]thiazolo[5,4-c]pyridine-2-carbonyl)piperazine-2-carboxamide Chemical compound C1=C(Cl)C=CC2=CC(S(=O)(=O)N3CCN([C@H](C3)C(N)=O)C(=O)C3=NC=4CCN(CC=4S3)C)=CC=C21 OVHHNKPYYVQCLN-LJQANCHMSA-N 0.000 description 3
DTVJOJFMIPUZBH-UHFFFAOYSA-N 1,2-benzoxazine-2-carboxamide Chemical compound C1=CC=C2C=CN(C(=O)N)OC2=C1 DTVJOJFMIPUZBH-UHFFFAOYSA-N 0.000 description 3
CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 3
URTUXBDUHHHBDC-UHFFFAOYSA-N 2h-chromene-2-carboxamide Chemical compound C1=CC=C2C=CC(C(=O)N)OC2=C1 URTUXBDUHHHBDC-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
241000282472 Canis lupus familiaris Species 0.000 description 3
241000282326 Felis catus Species 0.000 description 3
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 3
241001494479 Pecora Species 0.000 description 3
238000009835 boiling Methods 0.000 description 3
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
150000003857 carboxamides Chemical group 0.000 description 3
238000004440 column chromatography Methods 0.000 description 3
229940125904 compound 1 Drugs 0.000 description 3
238000000605 extraction Methods 0.000 description 3
230000004136 fatty acid synthesis Effects 0.000 description 3
238000009472 formulation Methods 0.000 description 3
239000008101 lactose Substances 0.000 description 3
ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 3
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 3
238000010626 work up procedure Methods 0.000 description 3
SWFNPENEBHAHEB-UHFFFAOYSA-N 2-amino-4-chlorophenol Chemical compound NC1=CC(Cl)=CC=C1O SWFNPENEBHAHEB-UHFFFAOYSA-N 0.000 description 2
YSUIQYOGTINQIN-UZFYAQMZSA-N 2-amino-9-[(1S,6R,8R,9S,10R,15R,17R,18R)-8-(6-aminopurin-9-yl)-9,18-difluoro-3,12-dihydroxy-3,12-bis(sulfanylidene)-2,4,7,11,13,16-hexaoxa-3lambda5,12lambda5-diphosphatricyclo[13.2.1.06,10]octadecan-17-yl]-1H-purin-6-one Chemical compound NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(S)(=O)O[C@@H]4[C@@H](COP(S)(=O)O[C@@H]2[C@@H]3F)O[C@H]([C@H]4F)N2C=NC3=C2N=CN=C3N)C(=O)N1 YSUIQYOGTINQIN-UZFYAQMZSA-N 0.000 description 2
ZMXYNJXDULEQCK-UHFFFAOYSA-N 2-amino-p-cresol Chemical compound CC1=CC=C(O)C(N)=C1 ZMXYNJXDULEQCK-UHFFFAOYSA-N 0.000 description 2
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
UVEVMKODWDQIAN-UHFFFAOYSA-N 2h-chromene-3-carboxamide Chemical compound C1=CC=C2OCC(C(=O)N)=CC2=C1 UVEVMKODWDQIAN-UHFFFAOYSA-N 0.000 description 2
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
241000283973 Oryctolagus cuniculus Species 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
229920004890 Triton X-100 Polymers 0.000 description 2
239000013504 Triton X-100 Substances 0.000 description 2
239000000908 ammonium hydroxide Substances 0.000 description 2
238000001574 biopsy Methods 0.000 description 2
239000008280 blood Substances 0.000 description 2
210000004369 blood Anatomy 0.000 description 2
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 2
150000001721 carbon Chemical group 0.000 description 2
239000003610 charcoal Substances 0.000 description 2
238000009833 condensation Methods 0.000 description 2
230000005494 condensation Effects 0.000 description 2
239000006185 dispersion Substances 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
DZFYOYRNBGNPJW-UHFFFAOYSA-N ethoxythallium Chemical compound [Tl+].CC[O-] DZFYOYRNBGNPJW-UHFFFAOYSA-N 0.000 description 2
125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 2
239000012458 free base Substances 0.000 description 2
239000008187 granular material Substances 0.000 description 2
230000003516 hyperlipidaemic effect Effects 0.000 description 2
239000005457 ice water Substances 0.000 description 2
238000010348 incorporation Methods 0.000 description 2
239000003112 inhibitor Substances 0.000 description 2
239000007924 injection Substances 0.000 description 2
238000002347 injection Methods 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
230000001404 mediated effect Effects 0.000 description 2
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
150000004702 methyl esters Chemical class 0.000 description 2
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 2
PNMWAHCSBXANLU-UHFFFAOYSA-N n-prop-2-enyl-2,3-dihydro-1,4-benzodioxine-3-carboxamide Chemical class C1=CC=C2OC(C(=O)NCC=C)COC2=C1 PNMWAHCSBXANLU-UHFFFAOYSA-N 0.000 description 2
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 2
150000002989 phenols Chemical class 0.000 description 2
239000000902 placebo Substances 0.000 description 2
229940068196 placebo Drugs 0.000 description 2
229910003446 platinum oxide Inorganic materials 0.000 description 2
239000000843 powder Substances 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
238000003345 scintillation counting Methods 0.000 description 2
239000000377 silicon dioxide Substances 0.000 description 2
JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 2
239000011343 solid material Substances 0.000 description 2
239000012265 solid product Substances 0.000 description 2
239000012258 stirred mixture Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
238000002627 tracheal intubation Methods 0.000 description 2
150000003626 triacylglycerols Chemical class 0.000 description 2
UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 2
238000005303 weighing Methods 0.000 description 2
HJTAZXHBEBIQQX-UHFFFAOYSA-N 1,5-bis(chloromethyl)naphthalene Chemical compound C1=CC=C2C(CCl)=CC=CC2=C1CCl HJTAZXHBEBIQQX-UHFFFAOYSA-N 0.000 description 1
HMBHAQMOBKLWRX-UHFFFAOYSA-N 2,3-dihydro-1,4-benzodioxine-3-carboxylic acid Chemical compound C1=CC=C2OC(C(=O)O)COC2=C1 HMBHAQMOBKLWRX-UHFFFAOYSA-N 0.000 description 1
VLZVIIYRNMWPSN-UHFFFAOYSA-N 2-Amino-4-nitrophenol Chemical compound NC1=CC([N+]([O-])=O)=CC=C1O VLZVIIYRNMWPSN-UHFFFAOYSA-N 0.000 description 1
BHTKIYIEMXRHGL-UHFFFAOYSA-N 2-amino-4-(trifluoromethyl)phenol Chemical compound NC1=CC(C(F)(F)F)=CC=C1O BHTKIYIEMXRHGL-UHFFFAOYSA-N 0.000 description 1
LGIWCQVLZIYRAR-UHFFFAOYSA-N 2-amino-4-cyclohexylphenol Chemical compound C1=C(O)C(N)=CC(C2CCCCC2)=C1 LGIWCQVLZIYRAR-UHFFFAOYSA-N 0.000 description 1
XZEDEVRSUANQEM-UHFFFAOYSA-N 2-nitro-4-(trifluoromethyl)phenol Chemical compound OC1=CC=C(C(F)(F)F)C=C1[N+]([O-])=O XZEDEVRSUANQEM-UHFFFAOYSA-N 0.000 description 1
IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical compound OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 description 1
CMLFRMDBDNHMRA-UHFFFAOYSA-N 2h-1,2-benzoxazine Chemical compound C1=CC=C2C=CNOC2=C1 CMLFRMDBDNHMRA-UHFFFAOYSA-N 0.000 description 1
SFLFCQJQOIZMHF-UHFFFAOYSA-N 3,4-dihydro-2h-chromene-2-carboxylic acid Chemical compound C1=CC=C2OC(C(=O)O)CCC2=C1 SFLFCQJQOIZMHF-UHFFFAOYSA-N 0.000 description 1
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
YUQPJMAOUVWWOM-UHFFFAOYSA-N 4-cyclohexyl-2-nitrophenol Chemical compound C1=C([N+]([O-])=O)C(O)=CC=C1C1CCCCC1 YUQPJMAOUVWWOM-UHFFFAOYSA-N 0.000 description 1
YBUGOACXDPDUIR-UHFFFAOYSA-N 4-methoxy-2-nitrophenol Chemical compound COC1=CC=C(O)C([N+]([O-])=O)=C1 YBUGOACXDPDUIR-UHFFFAOYSA-N 0.000 description 1
CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 description 1
PZUNFDRVVXRIDQ-UHFFFAOYSA-N 6-chloro-4-hydroxy-3,4-dihydro-2h-chromene-3-carbonitrile Chemical compound C1=C(Cl)C=C2C(O)C(C#N)COC2=C1 PZUNFDRVVXRIDQ-UHFFFAOYSA-N 0.000 description 1
RJNYIXPGUIVGJT-UHFFFAOYSA-N 6-chloro-4-oxo-2,3-dihydrochromene-2-carboxylic acid Chemical compound ClC1=CC=C2OC(C(=O)O)CC(=O)C2=C1 RJNYIXPGUIVGJT-UHFFFAOYSA-N 0.000 description 1
ZELQTBVMQLHKBN-UHFFFAOYSA-N 6-cyclohexyl-3,4-dihydro-2h-chromene-2-carboxylic acid Chemical compound C=1C=C2OC(C(=O)O)CCC2=CC=1C1CCCCC1 ZELQTBVMQLHKBN-UHFFFAOYSA-N 0.000 description 1
ZYRDNNPPLSXOHV-UHFFFAOYSA-N 6-phenyl-3,4-dihydro-2h-chromene-2-carboxylic acid Chemical compound C=1C=C2OC(C(=O)O)CCC2=CC=1C1=CC=CC=C1 ZYRDNNPPLSXOHV-UHFFFAOYSA-N 0.000 description 1
VFTOHJFKIJLYKN-UHFFFAOYSA-N 7-nitro-9h-fluoren-2-ol Chemical group [O-][N+](=O)C1=CC=C2C3=CC=C(O)C=C3CC2=C1 VFTOHJFKIJLYKN-UHFFFAOYSA-N 0.000 description 1
241000283690 Bos taurus Species 0.000 description 1
241000283707 Capra Species 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
241000283086 Equidae Species 0.000 description 1
241000283074 Equus asinus Species 0.000 description 1
241001331845 Equus asinus x caballus Species 0.000 description 1
238000007309 Fischer-Speier esterification reaction Methods 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
239000003810 Jones reagent Substances 0.000 description 1
QXKHYNVANLEOEG-UHFFFAOYSA-N Methoxsalen Chemical group C1=CC(=O)OC2=C1C=C1C=COC1=C2OC QXKHYNVANLEOEG-UHFFFAOYSA-N 0.000 description 1
241000772415 Neovison vison Species 0.000 description 1
JBZRLVKMCLOFLG-UHFFFAOYSA-N O=S=Cl Chemical compound O=S=Cl JBZRLVKMCLOFLG-UHFFFAOYSA-N 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
229920001938 Vegetable gum Polymers 0.000 description 1
ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
210000000702 aorta abdominal Anatomy 0.000 description 1
GOLCXWYRSKYTSP-UHFFFAOYSA-N arsenic trioxide Inorganic materials O1[As]2O[As]1O2 GOLCXWYRSKYTSP-UHFFFAOYSA-N 0.000 description 1
239000002585 base Substances 0.000 description 1
AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
NEDMOHHWRPHBAL-UHFFFAOYSA-N benzyl pyrrolidin-1-ium-2-carboxylate;chloride Chemical compound Cl.C1CCNC1C(=O)OCC1=CC=CC=C1 NEDMOHHWRPHBAL-UHFFFAOYSA-N 0.000 description 1
239000002775 capsule Substances 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
239000000969 carrier Substances 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 1
239000012043 crude product Substances 0.000 description 1
HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
USPLDBATMHXKKD-UHFFFAOYSA-N dichloromethane;pentane Chemical compound ClCCl.CCCCC USPLDBATMHXKKD-UHFFFAOYSA-N 0.000 description 1
235000015872 dietary supplement Nutrition 0.000 description 1
238000001647 drug administration Methods 0.000 description 1
229940000406 drug candidate Drugs 0.000 description 1
239000008157 edible vegetable oil Substances 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000003777 experimental drug Substances 0.000 description 1
201000005577 familial hyperlipidemia Diseases 0.000 description 1
235000013305 food Nutrition 0.000 description 1
230000002496 gastric effect Effects 0.000 description 1
239000000499 gel Substances 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
239000003979 granulating agent Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
239000007943 implant Substances 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
239000007928 intraperitoneal injection Substances 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 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
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000012263 liquid product Substances 0.000 description 1
244000144972 livestock Species 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
230000008018 melting Effects 0.000 description 1
238000002844 melting Methods 0.000 description 1
SPAAUUYJRNLHLI-UHFFFAOYSA-N methyl 6-chloro-3,4-dihydro-2h-chromene-3-carboxylate Chemical compound C1=C(Cl)C=C2CC(C(=O)OC)COC2=C1 SPAAUUYJRNLHLI-UHFFFAOYSA-N 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
210000002445 nipple Anatomy 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
238000010183 spectrum analysis Methods 0.000 description 1
238000012453 sprague-dawley rat model Methods 0.000 description 1
230000000087 stabilizing effect Effects 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
238000007619 statistical method Methods 0.000 description 1
ZRRGOUHITGRLBA-UHFFFAOYSA-N stattic Chemical compound [O-][N+](=O)C1=CC=C2C=CS(=O)(=O)C2=C1 ZRRGOUHITGRLBA-UHFFFAOYSA-N 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
239000000758 substrate Substances 0.000 description 1
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000006188 syrup Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
PGAPATLGJSQQBU-UHFFFAOYSA-M thallium(i) bromide Chemical compound [Tl]Br PGAPATLGJSQQBU-UHFFFAOYSA-M 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
239000012485 toluene extract Substances 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
MDYZKJNTKZIUSK-UHFFFAOYSA-N tyloxapol Chemical compound O=C.C1CO1.CC(C)(C)CC(C)(C)C1=CC=C(O)C=C1 MDYZKJNTKZIUSK-UHFFFAOYSA-N 0.000 description 1
239000011345 viscous material Substances 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
- C07D265/34—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings
- C07D265/36—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings condensed with one six-membered ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
- C07D311/66—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
- C07D319/14—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems
- C07D319/16—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D319/20—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring with substituents attached to the hetero ring

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Epidemiology (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Medicinal Chemistry (AREA)
Public Health (AREA)
Pharmacology & Pharmacy (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)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
Plural Heterocyclic Compounds (AREA)

IE532/78A 1977-03-17 1978-03-15 Lipofenesis-inhibiting compositions IE46676B1 (en)

Applications Claiming Priority (5)

Application Number	Priority Date	Filing Date	Title
US77881677A	1977-03-17	1977-03-17
US77853477A	1977-03-17	1977-03-17
US05/778,535 US4118507A (en)	1977-03-17	1977-03-17	Benzodioxincarboxamide lipogenesis inhibitors
US05/779,648 US4103021A (en)	1977-03-21	1977-03-21	Method of lowering blood lipid levels in mammals
US79175877A	1977-04-28	1977-04-28

Publications (2)

Publication Number	Publication Date
IE780532L IE780532L (en)	1978-09-17
IE46676B1 true IE46676B1 (en)	1983-08-24

Family

ID=27542199

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IE532/78A IE46676B1 (en)	1977-03-17	1978-03-15	Lipofenesis-inhibiting compositions

Country Status (11)

Country	Link
JP (1)	JPS53116377A (fr)
BE (1)	BE864918A (fr)
DD (1)	DD137714A5 (fr)
DE (1)	DE2811236A1 (fr)
DK (1)	DK117478A (fr)
FR (1)	FR2424741A1 (fr)
GB (3)	GB1598128A (fr)
IE (1)	IE46676B1 (fr)
LU (1)	LU79238A1 (fr)
NL (1)	NL7802921A (fr)
PL (1)	PL127781B1 (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4205079A (en) *	1978-10-16	1980-05-27	Shell Oil Company	Benzodioxincarboxamides
US4208424A (en) *	1979-04-26	1980-06-17	Shell Oil Company	Lipogenesis inhibition by certain esters of substituted benzodioxincarboxylic acids
EP0019955A1 (fr) *	1979-05-16	1980-12-10	Shell Internationale Researchmaatschappij B.V.	Dérivés d'acide benzofuranne-carboxylique, leur préparation et leur utilisation dans des compositions inhibant la lipogenèse
FR2763335B1 (fr) *	1997-05-16	2000-11-24	Adir	Nouveaux composes heterocycliques substitues, leur procede de preparation et les compositions pharmaceutiques qui les contiennent

1978
- 1978-03-15 GB GB31590/78A patent/GB1598128A/en not_active Expired
- 1978-03-15 LU LU79238A patent/LU79238A1/fr unknown
- 1978-03-15 GB GB10303/78A patent/GB1598126A/en not_active Expired
- 1978-03-15 BE BE185951A patent/BE864918A/fr not_active IP Right Cessation
- 1978-03-15 PL PL1978205322A patent/PL127781B1/pl unknown
- 1978-03-15 GB GB31589/78A patent/GB1598127A/en not_active Expired
- 1978-03-15 DK DK117478A patent/DK117478A/da not_active Application Discontinuation
- 1978-03-15 FR FR7807462A patent/FR2424741A1/fr not_active Withdrawn
- 1978-03-15 DD DD78204196A patent/DD137714A5/xx unknown
- 1978-03-15 DE DE19782811236 patent/DE2811236A1/de not_active Withdrawn
- 1978-03-15 IE IE532/78A patent/IE46676B1/en unknown
- 1978-03-15 JP JP2877678A patent/JPS53116377A/ja active Pending
- 1978-03-17 NL NL7802921A patent/NL7802921A/xx not_active Application Discontinuation

Also Published As

Publication number	Publication date
IE780532L (en)	1978-09-17
LU79238A1 (fr)	1978-10-17
GB1598128A (en)	1981-09-16
DE2811236A1 (de)	1978-09-28
DD137714A5 (de)	1979-09-19
JPS53116377A (en)	1978-10-11
PL127781B1 (en)	1983-11-30
NL7802921A (nl)	1978-09-19
FR2424741A1 (fr)	1979-11-30
DK117478A (da)	1978-09-18
PL205322A1 (pl)	1979-06-04
GB1598127A (en)	1981-09-16
BE864918A (fr)	1978-09-15
GB1598126A (en)	1981-09-16

Publication	Publication Date	Title
ZA200104455B (en)	2002-05-30	3-Substituted-4-Arylquinolin-2-one derivatives as potassium channel modulators.
KR900006744B1 (ko)	1990-09-20	천식, 관절염 및 관련질환 상태의 치료에 있어서의 치환된 테트랄린, 크로만 및 관련 화합물
JP2001511767A (ja)	2001-08-14	糖尿病薬
HU223076B1 (hu)	2004-03-01	HIV-reverz transzkriptáz inhibitor hatású benzoxazinon-származékok, ezeket tartalmazó gyógyászati készítmények, a vegyületek alkalmazása és eljárás a 6-klór-4-(ciklopropil-etinil)-4-trifluor-metil-1,4-dihidro-2H-3,1-benzoxazin-2-on előállítására
CA2045256A1 (fr)	1991-12-23	Chalcones, leur procede de preparation et les compositions pharmaceutiques qui les contiennent
NO167916B (no)	1991-09-16	Analogifremgangsmaate for fremstilling av terapeutisk aktive tiolaktam-n-eddiksyrederivater
IE46676B1 (en)	1983-08-24	Lipofenesis-inhibiting compositions
US6110961A (en)	2000-08-29	Phenoxathin derivatives as inhibitors of monoamine oxidase
US5569669A (en)	1996-10-29	Alkylaminoindane compounds
US4395414A (en)	1983-07-26	Substituted quinolinone-alkanecarboxylic acids and medicaments containing them, having a hyperglycaemic action
US4103021A (en)	1978-07-25	Method of lowering blood lipid levels in mammals
EP0013788B1 (fr)	1983-04-27	Octahydro-2H-pyrrolo-(3,4-g)quinoléines, procédé pour leur préparation et compositions pharmaceutiques les contenant
US4118507A (en)	1978-10-03	Benzodioxincarboxamide lipogenesis inhibitors
US5641785A (en)	1997-06-24	Oxazoloquinolinone derivatives, their preparation and their therapeutic application as inhibitors of monoamine oxidase
US4205079A (en)	1980-05-27	Benzodioxincarboxamides
JPS62135423A (ja)	1987-06-18	低酸素症改善剤
JPH01313464A (ja)	1989-12-18	血糖低下剤であるアルキルピペラジニルピリジン
US4164576A (en)	1979-08-14	Benzoxazine carboxamides
US4180572A (en)	1979-12-25	Lipogenesis control by esters of benzoxazinecarboxylic acids
CA1140856A (fr)	1983-02-08	Preparation inhibant la lipogenese et procede de preparation
FR2565586A1 (fr)	1985-12-13	Derives de la naphtoxazine, leur preparation, leur application comme medicaments et compositions pharmaceutiques les contenant
US4308276A (en)	1981-12-29	Inhibiting lipogenesis with benzoxathiincarboxamides
EP0061341B1 (fr)	1986-04-30	Hexahydroindazolo isoquinoléines substituées en 6
JP3195455B2 (ja)	2001-08-06	キノリン−３−酢酸誘導体、その製造法と用途
JPH03232858A (ja)	1991-10-16	１，８―ナフタル酸イミド誘導体とその製法及び用途