PL127781B1 - Biologically active agent for utilization in stock-farming - Google Patents

Biologically active agent for utilization in stock-farming Download PDF

Info

Publication number: PL127781B1
Authority: PL; Poland
Prior art keywords: compound; group; formula; carbon atoms; mixture
Prior art date: 1977-03-17

Application number

PL1978205322A

Other languages

English (en)

Polish (pl)

Other versions

PL205322A1 (pl

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

1983-11-30

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

1979-06-04 Publication of PL205322A1 publication Critical patent/PL205322A1/xx

1983-11-30 Publication of PL127781B1 publication Critical patent/PL127781B1/pl

Links

239000013543 active substance Substances 0.000 title claims description 21
238000009313 farming Methods 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 145
125000004432 carbon atom Chemical group C* 0.000 claims description 65
125000000217 alkyl group Chemical group 0.000 claims description 52
239000002253 acid Substances 0.000 claims description 48
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 46
-1 methylsulfonylamino Chemical group 0.000 claims description 38
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 37
125000001424 substituent group Chemical group 0.000 claims description 34
239000003795 chemical substances by application Substances 0.000 claims description 28
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 25
150000001412 amines Chemical class 0.000 claims description 21
229910052801 chlorine Inorganic materials 0.000 claims description 19
239000000460 chlorine Substances 0.000 claims description 19
125000000753 cycloalkyl group Chemical group 0.000 claims description 19
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
229910052799 carbon Inorganic materials 0.000 claims description 16
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 16
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 14
125000005843 halogen group Chemical group 0.000 claims description 13
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 12
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 11
125000003884 phenylalkyl group Chemical group 0.000 claims description 11
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 10
125000003545 alkoxy group Chemical group 0.000 claims description 10
238000003975 animal breeding Methods 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 10
150000003839 salts Chemical class 0.000 claims description 10
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
229910052731 fluorine Inorganic materials 0.000 claims description 8
239000011737 fluorine Substances 0.000 claims description 8
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 7
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
125000003342 alkenyl group Chemical group 0.000 claims description 6
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 5
125000000304 alkynyl group Chemical group 0.000 claims description 5
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
125000001309 chloro group Chemical group Cl* 0.000 claims description 5
125000000000 cycloalkoxy group Chemical group 0.000 claims description 5
229910052760 oxygen Inorganic materials 0.000 claims description 5
239000001301 oxygen Substances 0.000 claims description 5
125000003277 amino group Chemical group 0.000 claims description 4
239000012433 hydrogen halide Substances 0.000 claims description 4
229910000039 hydrogen halide Inorganic materials 0.000 claims description 4
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 3
125000004429 atom Chemical group 0.000 claims description 3
125000001153 fluoro group Chemical group F* 0.000 claims description 3
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical group ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 claims description 2
SFDJOSRHYKHMOK-UHFFFAOYSA-N nitramide Chemical compound N[N+]([O-])=O SFDJOSRHYKHMOK-UHFFFAOYSA-N 0.000 claims description 2
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 2
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
229910052727 yttrium Inorganic materials 0.000 claims description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 132
239000000203 mixture Substances 0.000 description 122
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 112
239000002904 solvent Substances 0.000 description 84
239000000243 solution Substances 0.000 description 80
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 63
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 60
235000019441 ethanol Nutrition 0.000 description 47
239000000047 product Substances 0.000 description 41
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 36
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 34
238000001704 evaporation Methods 0.000 description 32
238000002844 melting Methods 0.000 description 30
230000008018 melting Effects 0.000 description 30
238000000034 method Methods 0.000 description 30
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 28
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 26
239000007788 liquid Substances 0.000 description 26
125000004494 ethyl ester group Chemical group 0.000 description 25
150000002148 esters Chemical class 0.000 description 24
239000003925 fat Substances 0.000 description 23
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 22
239000013078 crystal Substances 0.000 description 22
OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 22
238000012360 testing method Methods 0.000 description 22
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 20
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 20
210000000577 adipose tissue Anatomy 0.000 description 19
241001465754 Metazoa Species 0.000 description 18
239000000706 filtrate Substances 0.000 description 18
229910000027 potassium carbonate Inorganic materials 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
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 17
238000006243 chemical reaction Methods 0.000 description 17
239000008103 glucose Substances 0.000 description 17
239000002244 precipitate Substances 0.000 description 17
239000007787 solid Substances 0.000 description 17
230000008020 evaporation Effects 0.000 description 16
229910052739 hydrogen Inorganic materials 0.000 description 16
230000005764 inhibitory process Effects 0.000 description 16
238000010992 reflux Methods 0.000 description 16
238000009835 boiling Methods 0.000 description 14
239000003054 catalyst Substances 0.000 description 14
238000002425 crystallisation Methods 0.000 description 14
230000008025 crystallization Effects 0.000 description 14
239000000741 silica gel Substances 0.000 description 14
229910002027 silica gel Inorganic materials 0.000 description 14
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 13
239000000284 extract Substances 0.000 description 13
238000001914 filtration Methods 0.000 description 13
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 12
230000015572 biosynthetic process Effects 0.000 description 12
239000003208 petroleum Substances 0.000 description 12
238000002360 preparation method Methods 0.000 description 12
150000007513 acids Chemical class 0.000 description 11
230000004132 lipogenesis Effects 0.000 description 11
239000000126 substance Substances 0.000 description 11
241000282887 Suidae Species 0.000 description 10
239000003480 eluent Substances 0.000 description 10
229910052736 halogen Inorganic materials 0.000 description 10
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
238000011534 incubation Methods 0.000 description 9
239000010410 layer Substances 0.000 description 9
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 8
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
230000002401 inhibitory effect Effects 0.000 description 8
210000004185 liver Anatomy 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 8
238000003756 stirring Methods 0.000 description 8
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 7
150000001732 carboxylic acid derivatives Chemical class 0.000 description 7
OENICUBCLXKLJQ-UHFFFAOYSA-N ethyl 2,3-dibromopropanoate Chemical compound CCOC(=O)C(Br)CBr OENICUBCLXKLJQ-UHFFFAOYSA-N 0.000 description 7
150000002367 halogens Chemical class 0.000 description 7
210000001519 tissue Anatomy 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
238000007792 addition Methods 0.000 description 6
239000002585 base Substances 0.000 description 6
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 6
229910052794 bromium Inorganic materials 0.000 description 6
238000001035 drying Methods 0.000 description 6
ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 6
238000000605 extraction Methods 0.000 description 6
NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound 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 6
238000004519 manufacturing process Methods 0.000 description 6
150000002989 phenols Chemical class 0.000 description 6
239000000725 suspension Substances 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 5
125000005907 alkyl ester group Chemical group 0.000 description 5
229940125904 compound 1 Drugs 0.000 description 5
230000000694 effects Effects 0.000 description 5
235000019439 ethyl acetate Nutrition 0.000 description 5
239000001257 hydrogen Substances 0.000 description 5
238000005984 hydrogenation reaction Methods 0.000 description 5
229910052943 magnesium sulfate Inorganic materials 0.000 description 5
150000004702 methyl esters Chemical class 0.000 description 5
238000003786 synthesis reaction Methods 0.000 description 5
BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-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
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
229920004890 Triton X-100 Polymers 0.000 description 4
239000013504 Triton X-100 Substances 0.000 description 4
238000004458 analytical method Methods 0.000 description 4
229910001424 calcium ion Inorganic materials 0.000 description 4
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 4
150000003857 carboxamides Chemical class 0.000 description 4
230000003197 catalytic effect Effects 0.000 description 4
238000004440 column chromatography Methods 0.000 description 4
239000008101 lactose Substances 0.000 description 4
210000005228 liver tissue Anatomy 0.000 description 4
235000019341 magnesium sulphate Nutrition 0.000 description 4
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 4
239000003960 organic solvent Substances 0.000 description 4
230000002285 radioactive effect Effects 0.000 description 4
238000004064 recycling Methods 0.000 description 4
238000004809 thin layer chromatography Methods 0.000 description 4
TUADYTFWZPZZTP-UHFFFAOYSA-N 2-amino-4-methoxyphenol Chemical compound COC1=CC=C(O)C(N)=C1 TUADYTFWZPZZTP-UHFFFAOYSA-N 0.000 description 3
YUQPJMAOUVWWOM-UHFFFAOYSA-N 4-cyclohexyl-2-nitrophenol Chemical compound C1=C([N+]([O-])=O)C(O)=CC=C1C1CCCCC1 YUQPJMAOUVWWOM-UHFFFAOYSA-N 0.000 description 3
YBUGOACXDPDUIR-UHFFFAOYSA-N 4-methoxy-2-nitrophenol Chemical compound COC1=CC=C(O)C([N+]([O-])=O)=C1 YBUGOACXDPDUIR-UHFFFAOYSA-N 0.000 description 3
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 3
241000282472 Canis lupus familiaris Species 0.000 description 3
241000282326 Felis catus Species 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
102000004877 Insulin Human genes 0.000 description 3
108090001061 Insulin Proteins 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
241001494479 Pecora Species 0.000 description 3
150000001408 amides Chemical class 0.000 description 3
150000001735 carboxylic acids Chemical class 0.000 description 3
239000003153 chemical reaction reagent Substances 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
238000009833 condensation Methods 0.000 description 3
230000005494 condensation Effects 0.000 description 3
238000007796 conventional method Methods 0.000 description 3
238000001816 cooling Methods 0.000 description 3
230000004136 fatty acid synthesis Effects 0.000 description 3
239000007789 gas Substances 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
229940125396 insulin Drugs 0.000 description 3
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 3
239000003921 oil Substances 0.000 description 3
235000019198 oils Nutrition 0.000 description 3
230000035484 reaction time Effects 0.000 description 3
239000011347 resin Substances 0.000 description 3
229920005989 resin Polymers 0.000 description 3
239000011734 sodium Substances 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
239000007858 starting material Substances 0.000 description 3
LGIWCQVLZIYRAR-UHFFFAOYSA-N 2-amino-4-cyclohexylphenol Chemical compound C1=C(O)C(N)=CC(C2CCCCC2)=C1 LGIWCQVLZIYRAR-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
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 2
QOVDNTCLOUTNGU-UHFFFAOYSA-N 6-chloro-4-hydroxy-n-prop-2-enyl-2h-chromene-2-carboxamide Chemical compound C1=C(Cl)C=C2C(O)=CC(C(=O)NCC=C)OC2=C1 QOVDNTCLOUTNGU-UHFFFAOYSA-N 0.000 description 2
UAETUFOUFXVDJX-UHFFFAOYSA-N 6-cyclohexyl-n-prop-2-enyl-3,4-dihydro-2h-chromene-2-carboxamide Chemical compound C=1C=C2OC(C(=O)NCC=C)CCC2=CC=1C1CCCCC1 UAETUFOUFXVDJX-UHFFFAOYSA-N 0.000 description 2
ROWKJAVDOGWPAT-UHFFFAOYSA-N Acetoin Chemical compound CC(O)C(C)=O ROWKJAVDOGWPAT-UHFFFAOYSA-N 0.000 description 2
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
241000124008 Mammalia Species 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
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238000010521 absorption reaction Methods 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
238000007259 addition reaction Methods 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
150000004703 alkoxides Chemical group 0.000 description 1
229920000180 alkyd Polymers 0.000 description 1
150000001350 alkyl halides Chemical class 0.000 description 1
239000011260 aqueous acid Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
GOLCXWYRSKYTSP-UHFFFAOYSA-N arsenic trioxide Inorganic materials O1[As]2O[As]1O2 GOLCXWYRSKYTSP-UHFFFAOYSA-N 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
XRWSZZJLZRKHHD-WVWIJVSJSA-N asunaprevir Chemical compound O=C([C@@H]1C[C@H](CN1C(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)(C)C)OC1=NC=C(C2=CC=C(Cl)C=C21)OC)N[C@]1(C(=O)NS(=O)(=O)C2CC2)C[C@H]1C=C XRWSZZJLZRKHHD-WVWIJVSJSA-N 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
150000001562 benzopyrans Chemical class 0.000 description 1
KGNDCEVUMONOKF-UGPLYTSKSA-N benzyl n-[(2r)-1-[(2s,4r)-2-[[(2s)-6-amino-1-(1,3-benzoxazol-2-yl)-1,1-dihydroxyhexan-2-yl]carbamoyl]-4-[(4-methylphenyl)methoxy]pyrrolidin-1-yl]-1-oxo-4-phenylbutan-2-yl]carbamate Chemical compound C1=CC(C)=CC=C1CO[C@H]1CN(C(=O)[C@@H](CCC=2C=CC=CC=2)NC(=O)OCC=2C=CC=CC=2)[C@H](C(=O)N[C@@H](CCCCN)C(O)(O)C=2OC3=CC=CC=C3N=2)C1 KGNDCEVUMONOKF-UGPLYTSKSA-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
238000001574 biopsy Methods 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000002775 capsule Substances 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
125000005392 carboxamide group Chemical group NC(=O)* 0.000 description 1
239000000969 carrier Substances 0.000 description 1
YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Substances ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
UXTMROKLAAOEQO-UHFFFAOYSA-N chloroform;ethanol Chemical compound CCO.ClC(Cl)Cl UXTMROKLAAOEQO-UHFFFAOYSA-N 0.000 description 1
JJBKVCQUFIBRFK-UHFFFAOYSA-N chloromethane;methanol Chemical compound OC.ClC JJBKVCQUFIBRFK-UHFFFAOYSA-N 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
229940125797 compound 12 Drugs 0.000 description 1
229940126543 compound 14 Drugs 0.000 description 1
229940126142 compound 16 Drugs 0.000 description 1
229940125782 compound 2 Drugs 0.000 description 1
229940125810 compound 20 Drugs 0.000 description 1
229940126086 compound 21 Drugs 0.000 description 1
229940126208 compound 22 Drugs 0.000 description 1
229940125833 compound 23 Drugs 0.000 description 1
229940125961 compound 24 Drugs 0.000 description 1
229940125846 compound 25 Drugs 0.000 description 1
229940125851 compound 27 Drugs 0.000 description 1
229940127204 compound 29 Drugs 0.000 description 1
229940125877 compound 31 Drugs 0.000 description 1
229940125898 compound 5 Drugs 0.000 description 1
239000013068 control sample Substances 0.000 description 1
239000012043 crude product Substances 0.000 description 1
238000005520 cutting process Methods 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
125000001316 cycloalkyl alkyl group Chemical group 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
238000007865 diluting Methods 0.000 description 1
238000004821 distillation Methods 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
239000008157 edible vegetable oil Substances 0.000 description 1
150000002081 enamines Chemical class 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
DZFYOYRNBGNPJW-UHFFFAOYSA-N ethoxythallium Chemical compound [Tl+].CC[O-] DZFYOYRNBGNPJW-UHFFFAOYSA-N 0.000 description 1
FVHKEEWXGIIDHB-UHFFFAOYSA-N ethyl 5-phenyl-1-benzofuran-2-carboxylate Chemical compound C=1C=C2OC(C(=O)OCC)=CC2=CC=1C1=CC=CC=C1 FVHKEEWXGIIDHB-UHFFFAOYSA-N 0.000 description 1
230000001747 exhibiting effect Effects 0.000 description 1
235000021323 fish oil Nutrition 0.000 description 1
235000004426 flaxseed Nutrition 0.000 description 1
239000012530 fluid Substances 0.000 description 1
238000009472 formulation Methods 0.000 description 1
238000005194 fractionation Methods 0.000 description 1
239000012458 free base Substances 0.000 description 1
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 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
238000005469 granulation Methods 0.000 description 1
230000003179 granulation Effects 0.000 description 1
125000005842 heteroatom Chemical group 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
GFAZHVHNLUBROE-UHFFFAOYSA-N hydroxymethyl propionaldehyde Natural products CCC(=O)CO GFAZHVHNLUBROE-UHFFFAOYSA-N 0.000 description 1
239000012535 impurity Substances 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
230000000977 initiatory effect Effects 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 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
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
239000012263 liquid product Substances 0.000 description 1
235000004213 low-fat Nutrition 0.000 description 1
230000002934 lysing effect Effects 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
229910052753 mercury Inorganic materials 0.000 description 1
YVUZUKYBUMROPQ-UHFFFAOYSA-N mercury zinc Chemical compound [Zn].[Hg] YVUZUKYBUMROPQ-UHFFFAOYSA-N 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
BHGADZKHWXCHKX-UHFFFAOYSA-N methane;potassium Chemical compound C.[K] BHGADZKHWXCHKX-UHFFFAOYSA-N 0.000 description 1
ROXQOUUAPQUMLN-UHFFFAOYSA-N methyl 2,3-dibromopropanoate Chemical compound COC(=O)C(Br)CBr ROXQOUUAPQUMLN-UHFFFAOYSA-N 0.000 description 1
229940050176 methyl chloride Drugs 0.000 description 1
GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
239000010413 mother solution Substances 0.000 description 1
NZMAJUHVSZBJHL-UHFFFAOYSA-N n,n-dibutylformamide Chemical compound CCCCN(C=O)CCCC NZMAJUHVSZBJHL-UHFFFAOYSA-N 0.000 description 1
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
238000006396 nitration reaction Methods 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
YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
239000006187 pill Substances 0.000 description 1
235000015277 pork Nutrition 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
238000003825 pressing Methods 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
230000000630 rising effect Effects 0.000 description 1
239000012266 salt solution Substances 0.000 description 1
238000010956 selective crystallization Methods 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 1
229910001948 sodium oxide Inorganic materials 0.000 description 1
PFUVRDFDKPNGAV-UHFFFAOYSA-N sodium peroxide Chemical compound [Na+].[Na+].[O-][O-] PFUVRDFDKPNGAV-UHFFFAOYSA-N 0.000 description 1
NASFKTWZWDYFER-UHFFFAOYSA-N sodium;hydrate Chemical compound O.[Na] NASFKTWZWDYFER-UHFFFAOYSA-N 0.000 description 1
OTNVGWMVOULBFZ-UHFFFAOYSA-N sodium;hydrochloride Chemical compound [Na].Cl OTNVGWMVOULBFZ-UHFFFAOYSA-N 0.000 description 1
230000003595 spectral effect Effects 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
239000000758 substrate Substances 0.000 description 1
150000003462 sulfoxides Chemical class 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 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
229910052716 thallium Inorganic materials 0.000 description 1
BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical compound [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 0.000 description 1
PGAPATLGJSQQBU-UHFFFAOYSA-M thallium(i) bromide Chemical compound [Tl]Br PGAPATLGJSQQBU-UHFFFAOYSA-M 0.000 description 1
239000012485 toluene extract Substances 0.000 description 1
238000002627 tracheal intubation Methods 0.000 description 1
238000009966 trimming Methods 0.000 description 1
210000000689 upper leg Anatomy 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1
238000005406 washing Methods 0.000 description 1
238000005303 weighing 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)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (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)
Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
Plural Heterocyclic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

PL1978205322A 1977-03-17 1978-03-15 Biologically active agent for utilization in stock-farming PL127781B1 (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
PL205322A1 PL205322A1 (pl)	1979-06-04
PL127781B1 true PL127781B1 (en)	1983-11-30

Family

ID=27542199

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
PL1978205322A PL127781B1 (en)	1977-03-17	1978-03-15	Biologically active agent for utilization in stock-farming

Country Status (11)

Country	Link
JP (1)	JPS53116377A (de)
BE (1)	BE864918A (de)
DD (1)	DD137714A5 (de)
DE (1)	DE2811236A1 (de)
DK (1)	DK117478A (de)
FR (1)	FR2424741A1 (de)
GB (3)	GB1598126A (de)
IE (1)	IE46676B1 (de)
LU (1)	LU79238A1 (de)
NL (1)	NL7802921A (de)
PL (1)	PL127781B1 (de)

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 (de) *	1979-05-16	1980-12-10	Shell Internationale Researchmaatschappij B.V.	Benzofurancarbonsäure-Derivate, ihre Herstellung und ihre Verwendung in Lipogenese inhibierenden Zusammensetzungen
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 DK DK117478A patent/DK117478A/da not_active Application Discontinuation
- 1978-03-15 DE DE19782811236 patent/DE2811236A1/de not_active Withdrawn
- 1978-03-15 FR FR7807462A patent/FR2424741A1/fr not_active Withdrawn
- 1978-03-15 JP JP2877678A patent/JPS53116377A/ja active Pending
- 1978-03-15 GB GB10303/78A patent/GB1598126A/en not_active Expired
- 1978-03-15 GB GB31589/78A patent/GB1598127A/en not_active Expired
- 1978-03-15 BE BE185951A patent/BE864918A/xx not_active IP Right Cessation
- 1978-03-15 DD DD78204196A patent/DD137714A5/de unknown
- 1978-03-15 GB GB31590/78A patent/GB1598128A/en not_active Expired
- 1978-03-15 PL PL1978205322A patent/PL127781B1/pl unknown
- 1978-03-15 LU LU79238A patent/LU79238A1/xx unknown
- 1978-03-15 IE IE532/78A patent/IE46676B1/en unknown
- 1978-03-17 NL NL7802921A patent/NL7802921A/xx not_active Application Discontinuation

Also Published As

Publication number	Publication date
IE46676B1 (en)	1983-08-24
FR2424741A1 (fr)	1979-11-30
GB1598126A (en)	1981-09-16
DK117478A (da)	1978-09-18
GB1598128A (en)	1981-09-16
DE2811236A1 (de)	1978-09-28
NL7802921A (nl)	1978-09-19
GB1598127A (en)	1981-09-16
PL205322A1 (pl)	1979-06-04
JPS53116377A (en)	1978-10-11
IE780532L (en)	1978-09-17
DD137714A5 (de)	1979-09-19
BE864918A (fr)	1978-09-15
LU79238A1 (fr)	1978-10-17

Publication	Publication Date	Title
EP2132206B1 (de)	2015-04-01	Substituierte 4-aryl-1,4-dihydro-1,6-naphthyridinamide und ihre verwendung
US3340266A (en)	1967-09-05	(3-amino-2-hydroxypropoxy)-benzoheterocyclic derivatives
US4048317A (en)	1977-09-13	Chroman derivatives
HUT58310A (en)	1992-02-28	Anti-atherosclerotic and anti-thrombotic 1-benzopyran-4-one- and 2-amino-1,3-benzoxazin-4-one derivatives, process for producing them and pharmaceutical compositions containing them
HU193624B (en)	1987-11-30	Process for production of new tieno-triasolo-/1,4/-diazephino-amides of carbonic acid
PL70430B1 (en)	1974-02-28	Phenylaminoethanol derivatives[gb1200886a]
US4251537A (en)	1981-02-17	Hypotensive 3,4-dihydro-2,2-dimethyl-4-amino-2H-benzo[b]pyran-3-ols
US4147780A (en)	1979-04-03	α-Amino-phosphonous acids for inhibiting bacteria and yeast
JPH0314574A (ja)	1991-01-23	中枢神経系に作用する新規クロマン誘導体、その製造方法およびこれを含有する調剤組成物
US2924603A (en)	1960-02-09	Aralkylbenzmorphan derivatives
FR2554719A1 (fr)	1985-05-17	Medicaments a base de nouveaux derives de la vinyl-6 furo-(3,4-c)-pyridine
PL127781B1 (en)	1983-11-30	Biologically active agent for utilization in stock-farming
CA1084918A (en)	1980-09-02	New, in 11-position substituted 5,11-dihydro-6h- pyrido 2,3-b - 1,4 benzodiazepine-6-ones, processes for their preparation and pharmaceutical compositions containing such compounds
US4395559A (en)	1983-07-26	2,3-Indoledione derivatives
HUT58726A (en)	1992-03-30	Process for producing chromane derivatives and pharmaceutical compositions containing them
US3706755A (en)	1972-12-19	Certain 4(3-(4-(phenyl)-3,6-dihydro-1(2h)pyridyl)-2 - hydroxy-propoxy)-benzophenones
EP0005298A1 (de)	1979-11-14	Ester von substituierten 8-Hydroxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepinen, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Präparate
DK160556B (da)	1991-03-25	Benzodioxinpyrrolderivater, fremgangsmaade til fremstilling deraf samt farmaceutiske praeparater indeholdende disse
LU82419A1 (fr)	1980-07-31	Pyrido(1,2-a)pyrimidines substituees
EP0043736B1 (de)	1984-04-25	Propanolamin-Derivate, ihre Salze, Verfahren zu ihrer Herstellung und pharmazeutische Präparate
HU179951B (en)	1983-01-28	Process for preparing 1,2,4-oxadiazolin-5-one derivatives and pharmaceutical compositions containing thereof
US4769367A (en)	1988-09-06	Heterocyclic amino compounds
US3700691A (en)	1972-10-24	3,3-disubstituted-3,4-dihydrobenzodioxepins
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US3944560A (en)	1976-03-16	3-Hydroxy-3-(1,2,5-thiadiazolyloxyalkanol)-3,4-dihydro-2H-1,5-benzodioxepin products