NO175634B - - Google Patents
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- Publication number
- NO175634B NO175634B NO914567A NO914567A NO175634B NO 175634 B NO175634 B NO 175634B NO 914567 A NO914567 A NO 914567A NO 914567 A NO914567 A NO 914567A NO 175634 B NO175634 B NO 175634B
- Authority
- NO
- Norway
- Prior art keywords
- group
- pyridyl
- phenyl
- hex
- enoic acid
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims abstract description 71
- 150000003839 salts Chemical class 0.000 claims abstract description 20
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims abstract description 13
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims abstract description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 8
- 150000007529 inorganic bases Chemical class 0.000 claims abstract description 7
- 150000007530 organic bases Chemical class 0.000 claims abstract description 7
- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 7
- -1 biphenylyl Chemical group 0.000 claims description 148
- 125000004432 carbon atom Chemical group C* 0.000 claims description 31
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 27
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- 238000002360 preparation method Methods 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 239000000460 chlorine Chemical group 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 7
- 239000007858 starting material Substances 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims description 6
- 230000032050 esterification Effects 0.000 claims description 5
- 238000005886 esterification reaction Methods 0.000 claims description 5
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 5
- 125000001624 naphthyl group Chemical group 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 5
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 4
- 125000001246 bromo group Chemical group Br* 0.000 claims description 4
- 125000001041 indolyl group Chemical group 0.000 claims description 4
- 239000011777 magnesium Substances 0.000 claims description 4
- 229910052749 magnesium Inorganic materials 0.000 claims description 4
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 230000029936 alkylation Effects 0.000 claims description 3
- 238000005804 alkylation reaction Methods 0.000 claims description 3
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 2
- 230000000269 nucleophilic effect Effects 0.000 claims description 2
- 125000006239 protecting group Chemical group 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 125000004663 dialkyl amino group Chemical group 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- RIOQSEWOXXDEQQ-UHFFFAOYSA-O triphenylphosphanium Chemical compound C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-O 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 9
- RZWIIPASKMUIAC-VQTJNVASSA-N thromboxane Chemical compound CCCCCCCC[C@H]1OCCC[C@@H]1CCCCCCC RZWIIPASKMUIAC-VQTJNVASSA-N 0.000 abstract description 9
- 238000004519 manufacturing process Methods 0.000 abstract description 8
- XEYBRNLFEZDVAW-ARSRFYASSA-N dinoprostone Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O XEYBRNLFEZDVAW-ARSRFYASSA-N 0.000 abstract description 5
- 229960002986 dinoprostone Drugs 0.000 abstract description 5
- XEYBRNLFEZDVAW-UHFFFAOYSA-N prostaglandin E2 Natural products CCCCCC(O)C=CC1C(O)CC(=O)C1CC=CCCCC(O)=O XEYBRNLFEZDVAW-UHFFFAOYSA-N 0.000 abstract description 5
- 230000002785 anti-thrombosis Effects 0.000 abstract description 4
- 230000015572 biosynthetic process Effects 0.000 abstract description 4
- 239000003112 inhibitor Substances 0.000 abstract description 4
- 230000001404 mediated effect Effects 0.000 abstract description 4
- 230000000144 pharmacologic effect Effects 0.000 abstract description 4
- 239000005557 antagonist Substances 0.000 abstract description 3
- 238000003786 synthesis reaction Methods 0.000 abstract description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 148
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 147
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 117
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 59
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 58
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 57
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 39
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 36
- 239000000741 silica gel Substances 0.000 description 36
- 229910002027 silica gel Inorganic materials 0.000 description 36
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 30
- 239000011541 reaction mixture Substances 0.000 description 30
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 26
- 239000000203 mixture Substances 0.000 description 26
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
- 239000012074 organic phase Substances 0.000 description 23
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 21
- 239000002904 solvent Substances 0.000 description 20
- 235000011121 sodium hydroxide Nutrition 0.000 description 19
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 14
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 14
- 239000006260 foam Substances 0.000 description 14
- 239000008346 aqueous phase Substances 0.000 description 13
- 235000015165 citric acid Nutrition 0.000 description 13
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 13
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 10
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 10
- 238000009835 boiling Methods 0.000 description 10
- 239000000126 substance Substances 0.000 description 9
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
- GHOZEBLZSATUCD-UHFFFAOYSA-N methyl 6-(4-aminophenyl)-6-pyridin-3-ylhex-5-enoate Chemical compound C=1C=CN=CC=1C(=CCCCC(=O)OC)C1=CC=C(N)C=C1 GHOZEBLZSATUCD-UHFFFAOYSA-N 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 229960000583 acetic acid Drugs 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 5
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 5
- DLQSZGMBRAFKEC-UHFFFAOYSA-N methyl 6-(3-aminophenyl)-6-pyridin-3-ylhex-5-enoate Chemical compound C=1C=CC(N)=CC=1C(=CCCCC(=O)OC)C1=CC=CN=C1 DLQSZGMBRAFKEC-UHFFFAOYSA-N 0.000 description 5
- 230000003287 optical effect Effects 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 4
- 102000008186 Collagen Human genes 0.000 description 4
- 108010035532 Collagen Proteins 0.000 description 4
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound 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
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- 229920001436 collagen Polymers 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 239000012362 glacial acetic acid Substances 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000003446 ligand Substances 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- XFSIXKNMCPNWPK-UHFFFAOYSA-N methyl 6-[3-(methylamino)phenyl]-6-pyridin-3-ylhex-5-enoate Chemical compound CNC1=CC=CC(C(=CCCCC(=O)OC)C=2C=NC=CC=2)=C1 XFSIXKNMCPNWPK-UHFFFAOYSA-N 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000006228 supernatant Substances 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- 238000011282 treatment Methods 0.000 description 4
- MLOSJPZSZWUDSK-UHFFFAOYSA-N 4-carboxybutyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCCCC(=O)O)C1=CC=CC=C1 MLOSJPZSZWUDSK-UHFFFAOYSA-N 0.000 description 3
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 230000002776 aggregation Effects 0.000 description 3
- 238000004220 aggregation Methods 0.000 description 3
- 210000004369 blood Anatomy 0.000 description 3
- 239000008280 blood Substances 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- IZEKFCXSFNUWAM-UHFFFAOYSA-N dipyridamole Chemical compound C=12N=C(N(CCO)CCO)N=C(N3CCCCC3)C2=NC(N(CCO)CCO)=NC=1N1CCCCC1 IZEKFCXSFNUWAM-UHFFFAOYSA-N 0.000 description 3
- 239000011888 foil Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- FOYWNSCCNCUEPU-UHFFFAOYSA-N mopidamol Chemical compound C12=NC(N(CCO)CCO)=NC=C2N=C(N(CCO)CCO)N=C1N1CCCCC1 FOYWNSCCNCUEPU-UHFFFAOYSA-N 0.000 description 3
- GGQLSDSHNXUAHS-UHFFFAOYSA-N n-[3-[3-[2-(3-acetamidophenyl)pyridine-3-carbonyl]pyridin-2-yl]phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC(C=2C(=CC=CN=2)C(=O)C=2C(=NC=CC=2)C=2C=C(NC(C)=O)C=CC=2)=C1 GGQLSDSHNXUAHS-UHFFFAOYSA-N 0.000 description 3
- JIZCJZSHXYYOQJ-UHFFFAOYSA-N n-[4-[3-[2-(4-acetamidophenyl)pyridine-3-carbonyl]pyridin-2-yl]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1C1=NC=CC=C1C(=O)C1=CC=CN=C1C1=CC=C(NC(C)=O)C=C1 JIZCJZSHXYYOQJ-UHFFFAOYSA-N 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 210000004623 platelet-rich plasma Anatomy 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 3
- 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 2
- UQTWEWWEIMWOGT-UHFFFAOYSA-N 1-[3-[1-acetyl-2-[3-(methylamino)phenyl]-2h-pyridine-3-carbonyl]-2-[3-(methylamino)phenyl]-2h-pyridin-1-yl]ethanone Chemical compound CNC1=CC=CC(C2C(=CC=CN2C(C)=O)C(=O)C=2C(N(C=CC=2)C(C)=O)C=2C=C(NC)C=CC=2)=C1 UQTWEWWEIMWOGT-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- NAMYKGVDVNBCFQ-UHFFFAOYSA-N 2-bromopropane Chemical compound CC(C)Br NAMYKGVDVNBCFQ-UHFFFAOYSA-N 0.000 description 2
- GOLXRNDWAUTYKT-UHFFFAOYSA-N 3-(1H-indol-3-yl)propanoic acid Chemical compound C1=CC=C2C(CCC(=O)O)=CNC2=C1 GOLXRNDWAUTYKT-UHFFFAOYSA-N 0.000 description 2
- WALNEXXMLYRUSW-UHFFFAOYSA-N 4-(5-methyl-3-piperazin-1-ylisoquinolin-1-yl)-1,4-thiazinane 1-oxide Chemical compound C1=C2C(C)=CC=CC2=C(N2CCS(=O)CC2)N=C1N1CCNCC1 WALNEXXMLYRUSW-UHFFFAOYSA-N 0.000 description 2
- FJVLPEHOJLUUNW-UHFFFAOYSA-N 4-chloro-n-[4-[3-[2-[4-[(4-chlorophenyl)sulfonylamino]phenyl]pyridine-3-carbonyl]pyridin-2-yl]phenyl]benzenesulfonamide Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)NC1=CC=C(C=2C(=CC=CN=2)C(=O)C=2C(=NC=CC=2)C=2C=CC(NS(=O)(=O)C=3C=CC(Cl)=CC=3)=CC=2)C=C1 FJVLPEHOJLUUNW-UHFFFAOYSA-N 0.000 description 2
- ZLYBFBAHAQEEQQ-UHFFFAOYSA-N 4-chlorobenzenesulfonyl chloride Chemical compound ClC1=CC=C(S(Cl)(=O)=O)C=C1 ZLYBFBAHAQEEQQ-UHFFFAOYSA-N 0.000 description 2
- FCMPXMPGPDNMDD-UHFFFAOYSA-N 6-(3-acetamidophenyl)-6-pyridin-3-ylhex-5-enoic acid Chemical compound CC(=O)NC1=CC=CC(C(=CCCCC(O)=O)C=2C=NC=CC=2)=C1 FCMPXMPGPDNMDD-UHFFFAOYSA-N 0.000 description 2
- ZOGKMYQBZYBWLU-UHFFFAOYSA-N 6-(4-acetamidophenyl)-6-pyridin-3-ylhex-5-enoic acid Chemical compound C1=CC(NC(=O)C)=CC=C1C(=CCCCC(O)=O)C1=CC=CN=C1 ZOGKMYQBZYBWLU-UHFFFAOYSA-N 0.000 description 2
- USKSSUIWVBMHGS-UHFFFAOYSA-N 6-[4-(3,4-dichlorophenyl)sulfinylbutoxy]-3,4-dihydro-1h-quinolin-2-one Chemical compound C1=C2CCC(O)=NC2=CC=C1OCCCCS(=O)C1=CC=C(Cl)C(Cl)=C1 USKSSUIWVBMHGS-UHFFFAOYSA-N 0.000 description 2
- RUZWQDOCRWZSJB-UHFFFAOYSA-N 6-[4-[(4-chlorophenyl)sulfonyl-propan-2-ylamino]phenyl]-6-pyridin-3-ylhex-5-enoic acid Chemical compound C=1C=C(Cl)C=CC=1S(=O)(=O)N(C(C)C)C(C=C1)=CC=C1C(=CCCCC(O)=O)C1=CC=CN=C1 RUZWQDOCRWZSJB-UHFFFAOYSA-N 0.000 description 2
- NOPNHMSYLBTLME-UHFFFAOYSA-N 6-[4-[(4-methylphenyl)sulfonylamino]phenyl]-6-pyridin-3-ylhex-5-enoic acid Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC1=CC=C(C(=CCCCC(O)=O)C=2C=NC=CC=2)C=C1 NOPNHMSYLBTLME-UHFFFAOYSA-N 0.000 description 2
- OUINBUSJKORLMO-UHFFFAOYSA-N 7-[4-[(4-chlorophenyl)sulfonylamino]phenyl]-7-pyridin-3-ylhept-6-enoic acid Chemical compound C=1C=CN=CC=1C(=CCCCCC(=O)O)C(C=C1)=CC=C1NS(=O)(=O)C1=CC=C(Cl)C=C1 OUINBUSJKORLMO-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 108010058207 Anistreplase Proteins 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 108010017384 Blood Proteins Proteins 0.000 description 2
- 102000004506 Blood Proteins Human genes 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
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- QJZUKDFHGGYHMC-UHFFFAOYSA-N pyridine-3-carbaldehyde Chemical compound O=CC1=CC=CN=C1 QJZUKDFHGGYHMC-UHFFFAOYSA-N 0.000 description 1
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- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
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- 230000009885 systemic effect Effects 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/89—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/54—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
- C07D213/55—Acids; Esters
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Paper (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4037112A DE4037112A1 (de) | 1990-11-22 | 1990-11-22 | Neue pyridylderivate, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| NO914567D0 NO914567D0 (no) | 1991-11-21 |
| NO914567L NO914567L (no) | 1992-05-25 |
| NO175634B true NO175634B (pt) | 1994-08-01 |
| NO175634C NO175634C (no) | 1994-11-09 |
Family
ID=6418696
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO914567A NO175634C (no) | 1990-11-22 | 1991-11-21 | Analogifremgangsmåte for fremstilling av terapeutisk aktive pyridylderivater |
Country Status (19)
| Country | Link |
|---|---|
| EP (1) | EP0487095B1 (pt) |
| JP (1) | JPH04275273A (pt) |
| KR (1) | KR920009799A (pt) |
| AT (1) | ATE134619T1 (pt) |
| AU (1) | AU640063B2 (pt) |
| CA (1) | CA2055950A1 (pt) |
| DE (2) | DE4037112A1 (pt) |
| DK (1) | DK0487095T3 (pt) |
| ES (1) | ES2084756T3 (pt) |
| FI (1) | FI915484A (pt) |
| GR (1) | GR3019783T3 (pt) |
| HU (1) | HU213676B (pt) |
| IE (1) | IE74248B1 (pt) |
| IL (1) | IL100097A (pt) |
| NO (1) | NO175634C (pt) |
| NZ (1) | NZ240677A (pt) |
| PT (1) | PT99571B (pt) |
| RU (1) | RU2028292C1 (pt) |
| ZA (1) | ZA919205B (pt) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4216364A1 (de) * | 1991-12-14 | 1993-11-25 | Thomae Gmbh Dr K | Neue Pyridylderivate, diese Verbindungen enthaltende Arzneimittel und Verfahren zu ihrer Herstellung |
| TWI290549B (en) * | 2000-06-02 | 2007-12-01 | Astrazeneca Ab | Process for the preparation of cyclopropyl carboxylic acid ester and derivatives |
| DE10225635C1 (de) * | 2002-06-07 | 2003-12-24 | Aventis Pharma Gmbh | N-Benzoylureido-Zimtsäurederivate, Verfahren zu deren Herstellung und deren Verwendung |
| FI20055498A0 (fi) * | 2005-09-16 | 2005-09-16 | Biotie Therapies Corp | Sulfonamidijohdannaisia |
| EP2928860A1 (en) * | 2012-12-10 | 2015-10-14 | H. Lundbeck A/S | New positive allosteric modulators of nicotinic acetylcholine receptor |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4518602A (en) * | 1982-10-07 | 1985-05-21 | Takeda Chemical Industries, Ltd. | Vinyl carboxylic acid derivatives, their production and use as inhibitors of thromboxane synthetase |
| GB8708233D0 (en) * | 1987-04-07 | 1987-05-13 | Smith Kline French Lab | Pharmaceutically active compounds |
| DE3932403A1 (de) * | 1989-05-12 | 1991-04-11 | Thomae Gmbh Dr K | Neue arylsulfonamide, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung |
-
1990
- 1990-11-22 DE DE4037112A patent/DE4037112A1/de not_active Withdrawn
-
1991
- 1991-11-19 AU AU87964/91A patent/AU640063B2/en not_active Ceased
- 1991-11-20 IL IL10009791A patent/IL100097A/en not_active IP Right Cessation
- 1991-11-20 NZ NZ240677A patent/NZ240677A/en unknown
- 1991-11-21 ES ES91119889T patent/ES2084756T3/es not_active Expired - Lifetime
- 1991-11-21 FI FI915484A patent/FI915484A/fi not_active Application Discontinuation
- 1991-11-21 ZA ZA919205A patent/ZA919205B/xx unknown
- 1991-11-21 RU SU915010111A patent/RU2028292C1/ru active
- 1991-11-21 IE IE404891A patent/IE74248B1/en not_active IP Right Cessation
- 1991-11-21 HU HU913644A patent/HU213676B/hu not_active IP Right Cessation
- 1991-11-21 JP JP3305990A patent/JPH04275273A/ja active Pending
- 1991-11-21 EP EP91119889A patent/EP0487095B1/de not_active Expired - Lifetime
- 1991-11-21 PT PT99571A patent/PT99571B/pt not_active IP Right Cessation
- 1991-11-21 AT AT91119889T patent/ATE134619T1/de not_active IP Right Cessation
- 1991-11-21 NO NO914567A patent/NO175634C/no unknown
- 1991-11-21 DK DK91119889.3T patent/DK0487095T3/da active
- 1991-11-21 DE DE59107462T patent/DE59107462D1/de not_active Expired - Fee Related
- 1991-11-21 KR KR1019910020776A patent/KR920009799A/ko active IP Right Grant
- 1991-11-21 CA CA002055950A patent/CA2055950A1/en not_active Abandoned
-
1996
- 1996-04-29 GR GR960401163T patent/GR3019783T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NZ240677A (en) | 1994-12-22 |
| EP0487095A1 (de) | 1992-05-27 |
| ATE134619T1 (de) | 1996-03-15 |
| NO175634C (no) | 1994-11-09 |
| ZA919205B (en) | 1993-05-21 |
| EP0487095B1 (de) | 1996-02-28 |
| FI915484A (fi) | 1992-05-23 |
| IL100097A0 (en) | 1992-08-18 |
| JPH04275273A (ja) | 1992-09-30 |
| PT99571B (pt) | 1999-04-30 |
| DE4037112A1 (de) | 1992-05-27 |
| AU8796491A (en) | 1992-05-28 |
| CA2055950A1 (en) | 1992-05-23 |
| HU913644D0 (en) | 1992-02-28 |
| NO914567D0 (no) | 1991-11-21 |
| IE74248B1 (en) | 1997-07-16 |
| RU2028292C1 (ru) | 1995-02-09 |
| DE59107462D1 (de) | 1996-04-04 |
| GR3019783T3 (en) | 1996-07-31 |
| IL100097A (en) | 1995-07-31 |
| HU213676B (en) | 1997-09-29 |
| NO914567L (no) | 1992-05-25 |
| HUT60472A (en) | 1992-09-28 |
| IE914048A1 (en) | 1992-06-03 |
| ES2084756T3 (es) | 1996-05-16 |
| KR920009799A (ko) | 1992-06-25 |
| DK0487095T3 (da) | 1996-06-24 |
| FI915484A0 (fi) | 1991-11-21 |
| PT99571A (pt) | 1992-10-30 |
| AU640063B2 (en) | 1993-08-12 |
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