CA1176261A - Hydantoin derivatives - Google Patents
Hydantoin derivativesInfo
- Publication number
- CA1176261A CA1176261A CA000280455A CA280455A CA1176261A CA 1176261 A CA1176261 A CA 1176261A CA 000280455 A CA000280455 A CA 000280455A CA 280455 A CA280455 A CA 280455A CA 1176261 A CA1176261 A CA 1176261A
- Authority
- CA
- Canada
- Prior art keywords
- hydroxy
- carbon atoms
- formula
- compound
- alkyl
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired
Links
- 150000001469 hydantoins Chemical class 0.000 title abstract description 26
- 229940053195 antiepileptics hydantoin derivative Drugs 0.000 title description 2
- -1 5-tetrazolyl Chemical group 0.000 claims abstract description 80
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 74
- 239000001257 hydrogen Substances 0.000 claims abstract description 64
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 64
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 62
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 42
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 37
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 30
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 30
- 150000003839 salts Chemical class 0.000 claims abstract description 24
- 125000005843 halogen group Chemical group 0.000 claims abstract description 22
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 22
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 21
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 20
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 18
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 18
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims abstract description 18
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 17
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims abstract description 16
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 16
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 16
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 13
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 10
- 125000004442 acylamino group Chemical group 0.000 claims abstract description 9
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 9
- 150000001602 bicycloalkyls Chemical group 0.000 claims abstract description 9
- 150000001721 carbon Chemical group 0.000 claims abstract description 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 6
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 5
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims abstract description 5
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims abstract 14
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims abstract 4
- 238000000034 method Methods 0.000 claims description 128
- 150000001875 compounds Chemical class 0.000 claims description 106
- 229940091173 hydantoin Drugs 0.000 claims description 71
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 68
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 claims description 56
- 239000000126 substance Substances 0.000 claims description 38
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 37
- 230000000875 corresponding effect Effects 0.000 claims description 30
- 238000006243 chemical reaction Methods 0.000 claims description 29
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 29
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 27
- 239000002253 acid Substances 0.000 claims description 26
- 150000002148 esters Chemical class 0.000 claims description 22
- 238000002360 preparation method Methods 0.000 claims description 18
- 239000002585 base Substances 0.000 claims description 14
- 239000002904 solvent Substances 0.000 claims description 14
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 9
- XLJMAIOERFSOGZ-UHFFFAOYSA-N cyanic acid Chemical compound OC#N XLJMAIOERFSOGZ-UHFFFAOYSA-N 0.000 claims description 8
- 239000012279 sodium borohydride Substances 0.000 claims description 8
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 8
- 150000001408 amides Chemical class 0.000 claims description 7
- 239000003638 chemical reducing agent Substances 0.000 claims description 7
- 150000002576 ketones Chemical class 0.000 claims description 7
- 238000010438 heat treatment Methods 0.000 claims description 5
- ICXMXDCVHKIDJF-UHFFFAOYSA-N 7-[3-(3-hydroxyoctyl)-2,5-dioxoimidazolidin-4-yl]heptanoic acid Chemical compound CCCCCC(O)CCN1C(CCCCCCC(O)=O)C(=O)NC1=O ICXMXDCVHKIDJF-UHFFFAOYSA-N 0.000 claims description 4
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 claims description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims description 4
- 150000004820 halides Chemical class 0.000 claims description 4
- 150000002825 nitriles Chemical group 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- ZIDQIOZJEJFMOH-UHFFFAOYSA-N 7-[3-(3-cyclohexyl-3-hydroxypropyl)-2,5-dioxoimidazolidin-4-yl]heptanoic acid Chemical compound C1CCCCC1C(O)CCN1C(CCCCCCC(O)=O)C(=O)NC1=O ZIDQIOZJEJFMOH-UHFFFAOYSA-N 0.000 claims description 3
- 150000008065 acid anhydrides Chemical class 0.000 claims description 3
- 150000001299 aldehydes Chemical class 0.000 claims description 3
- 125000001246 bromo group Chemical group Br* 0.000 claims description 3
- 239000004202 carbamide Substances 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 3
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 claims description 3
- 239000012948 isocyanate Substances 0.000 claims description 3
- CMUOJBJRZUHRMU-UHFFFAOYSA-N nitrourea Chemical compound NC(=O)N[N+]([O-])=O CMUOJBJRZUHRMU-UHFFFAOYSA-N 0.000 claims description 3
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical group [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 2
- 229910000102 alkali metal hydride Inorganic materials 0.000 claims description 2
- 150000008046 alkali metal hydrides Chemical class 0.000 claims description 2
- 150000004703 alkoxides Chemical class 0.000 claims description 2
- 229910000091 aluminium hydride Inorganic materials 0.000 claims description 2
- ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 claims description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 2
- 159000000000 sodium salts Chemical class 0.000 claims description 2
- 230000003301 hydrolyzing effect Effects 0.000 claims 10
- 238000007363 ring formation reaction Methods 0.000 claims 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 5
- 230000002152 alkylating effect Effects 0.000 claims 3
- CWNBYFYKHCQJOK-UHFFFAOYSA-N 7-[3-(3-cyclobutyl-3-hydroxypropyl)-2,5-dioxoimidazolidin-4-yl]heptanoic acid Chemical compound C1CCC1C(O)CCN1C(CCCCCCC(O)=O)C(=O)NC1=O CWNBYFYKHCQJOK-UHFFFAOYSA-N 0.000 claims 2
- AMAYXRDWNRWCBM-UHFFFAOYSA-N 7-[3-(3-cyclopentyl-3-hydroxypropyl)-2,5-dioxoimidazolidin-4-yl]heptanoic acid Chemical compound C1CCCC1C(O)CCN1C(CCCCCCC(O)=O)C(=O)NC1=O AMAYXRDWNRWCBM-UHFFFAOYSA-N 0.000 claims 2
- OBWREGPIKZZJLZ-UHFFFAOYSA-N 7-[3-(3-hydroxy-4,4-dimethyloctyl)-2,5-dioxoimidazolidin-4-yl]heptanoic acid Chemical compound CCCCC(C)(C)C(O)CCN1C(CCCCCCC(O)=O)C(=O)NC1=O OBWREGPIKZZJLZ-UHFFFAOYSA-N 0.000 claims 2
- KZAUFLQTAMVHIV-UHFFFAOYSA-N 7-[3-(3-hydroxynonyl)-2,5-dioxoimidazolidin-4-yl]heptanoic acid Chemical compound CCCCCCC(O)CCN1C(CCCCCCC(O)=O)C(=O)NC1=O KZAUFLQTAMVHIV-UHFFFAOYSA-N 0.000 claims 2
- 241000534944 Thia Species 0.000 claims 2
- 239000002168 alkylating agent Substances 0.000 claims 2
- 229940100198 alkylating agent Drugs 0.000 claims 2
- XLZWPJLGBYQJNH-UHFFFAOYSA-N ethyl 7-[3-(3-cyclohexyl-3-hydroxypropyl)-2,5-dioxoimidazolidin-4-yl]heptanoate Chemical compound O=C1NC(=O)C(CCCCCCC(=O)OCC)N1CCC(O)C1CCCCC1 XLZWPJLGBYQJNH-UHFFFAOYSA-N 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims 2
- MMKYCYXOGGDSNF-UHFFFAOYSA-N 7-[3-(3-hydroxy-4,4-dimethylpentyl)-2,5-dioxoimidazolidin-4-yl]heptanoic acid Chemical compound CC(C)(C)C(O)CCN1C(CCCCCCC(O)=O)C(=O)NC1=O MMKYCYXOGGDSNF-UHFFFAOYSA-N 0.000 claims 1
- 150000008044 alkali metal hydroxides Chemical group 0.000 claims 1
- 125000002008 alkyl bromide group Chemical group 0.000 claims 1
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 claims 1
- 150000003857 carboxamides Chemical class 0.000 claims 1
- 150000001805 chlorine compounds Chemical group 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- FBGRKWRYTJJONG-UHFFFAOYSA-N diethyl 2-[carbamoyl-(3-cyclohexyl-3-hydroxypropyl)amino]nonanedioate Chemical compound CCOC(=O)CCCCCCC(C(=O)OCC)N(C(N)=O)CCC(O)C1CCCCC1 FBGRKWRYTJJONG-UHFFFAOYSA-N 0.000 claims 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 claims 1
- 229910001948 sodium oxide Inorganic materials 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 150000003180 prostaglandins Chemical class 0.000 abstract description 14
- 238000011282 treatment Methods 0.000 abstract description 11
- 229940094443 oxytocics prostaglandins Drugs 0.000 abstract description 7
- 230000004071 biological effect Effects 0.000 abstract description 5
- 239000003814 drug Substances 0.000 abstract description 4
- 208000007536 Thrombosis Diseases 0.000 abstract description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 110
- 239000000243 solution Substances 0.000 description 72
- 239000003921 oil Substances 0.000 description 67
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 45
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 37
- 239000000203 mixture Substances 0.000 description 37
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 35
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 18
- BDJRBEYXGGNYIS-UHFFFAOYSA-L azelaate(2-) Chemical compound [O-]C(=O)CCCCCCCC([O-])=O BDJRBEYXGGNYIS-UHFFFAOYSA-L 0.000 description 18
- 241000124008 Mammalia Species 0.000 description 16
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- 239000000284 extract Substances 0.000 description 12
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 11
- 229940125797 compound 12 Drugs 0.000 description 11
- 229910052708 sodium Inorganic materials 0.000 description 11
- 239000011734 sodium Substances 0.000 description 11
- 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 10
- 230000015572 biosynthetic process Effects 0.000 description 10
- 238000009472 formulation Methods 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 241000700159 Rattus Species 0.000 description 8
- 239000005457 ice water Substances 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- 231100000252 nontoxic Toxicity 0.000 description 8
- 230000003000 nontoxic effect Effects 0.000 description 8
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 7
- 230000002496 gastric effect Effects 0.000 description 7
- 239000012442 inert solvent Substances 0.000 description 7
- 239000000543 intermediate Substances 0.000 description 7
- 239000000377 silicon dioxide Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 6
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 150000001298 alcohols Chemical class 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 230000007062 hydrolysis Effects 0.000 description 6
- 238000006460 hydrolysis reaction Methods 0.000 description 6
- 238000001990 intravenous administration Methods 0.000 description 6
- 239000003208 petroleum Substances 0.000 description 6
- GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 description 6
- 238000011321 prophylaxis Methods 0.000 description 6
- 239000000376 reactant Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- 239000013078 crystal Substances 0.000 description 5
- 239000008187 granular material Substances 0.000 description 5
- 238000002347 injection Methods 0.000 description 5
- 239000007924 injection Substances 0.000 description 5
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate Chemical compound [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- 230000009467 reduction Effects 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- 239000003826 tablet Substances 0.000 description 5
- 239000008215 water for injection Substances 0.000 description 5
- 206010006482 Bronchospasm Diseases 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 208000025865 Ulcer Diseases 0.000 description 4
- 210000004369 blood Anatomy 0.000 description 4
- 239000008280 blood Substances 0.000 description 4
- 230000036772 blood pressure Effects 0.000 description 4
- 230000007885 bronchoconstriction Effects 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- IWPQQEFLLHFOCF-UHFFFAOYSA-N ethyl 2-[(7-ethoxy-7-oxoheptyl)amino]decanoate Chemical compound CCCCCCCCC(C(=O)OCC)NCCCCCCC(=O)OCC IWPQQEFLLHFOCF-UHFFFAOYSA-N 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 150000002430 hydrocarbons Chemical class 0.000 description 4
- 150000002500 ions Chemical class 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
- 230000003278 mimic effect Effects 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 230000000144 pharmacologic effect Effects 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 230000002829 reductive effect Effects 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 3
- QAHBEAJDPRONLZ-NTCAYCPXSA-N 7-[(5e)-2,4-dioxo-5-(3-oxooctylidene)imidazolidin-1-yl]heptanoic acid Chemical compound CCCCCC(=O)C\C=C1\N(CCCCCCC(O)=O)C(=O)NC1=O QAHBEAJDPRONLZ-NTCAYCPXSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 3
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 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
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- 229960001138 acetylsalicylic acid Drugs 0.000 description 3
- 230000002776 aggregation Effects 0.000 description 3
- 238000004220 aggregation Methods 0.000 description 3
- 229940125782 compound 2 Drugs 0.000 description 3
- IQFVPQOLBLOTPF-HKXUKFGYSA-L congo red Chemical compound [Na+].[Na+].C1=CC=CC2=C(N)C(/N=N/C3=CC=C(C=C3)C3=CC=C(C=C3)/N=N/C3=C(C4=CC=CC=C4C(=C3)S([O-])(=O)=O)N)=CC(S([O-])(=O)=O)=C21 IQFVPQOLBLOTPF-HKXUKFGYSA-L 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 230000027119 gastric acid secretion Effects 0.000 description 3
- 229960001340 histamine Drugs 0.000 description 3
- 230000001939 inductive effect Effects 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or 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 to ring carbon atoms
- C07D309/10—Oxygen atoms
- C07D309/12—Oxygen atoms only hydrogen atoms and one oxygen atom directly attached to ring carbon atoms, e.g. tetrahydropyranyl ethers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or 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 to ring carbon atoms
- C07D233/72—Two oxygen atoms, e.g. hydantoin
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or 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 to ring carbon atoms
- C07D233/72—Two oxygen atoms, e.g. hydantoin
- C07D233/76—Two oxygen atoms, e.g. hydantoin with substituted hydrocarbon radicals attached to the third ring carbon atom
- C07D233/78—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or 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 to ring carbon atoms
- C07D233/86—Oxygen and sulfur atoms, e.g. thiohydantoin
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB22877/76 | 1976-06-03 | ||
| GB2287776 | 1976-06-03 | ||
| GB50340/76 | 1976-12-02 | ||
| GB5034076 | 1976-12-02 | ||
| GB12145/77 | 1977-03-23 | ||
| GB1214577 | 1977-03-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1176261A true CA1176261A (en) | 1984-10-16 |
Family
ID=27256793
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000280455A Expired CA1176261A (en) | 1976-06-03 | 1977-06-02 | Hydantoin derivatives |
Country Status (12)
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1602188A (en) * | 1977-12-01 | 1981-11-11 | Wellcome Found | Hydantoin derivatives |
| DK391678A (da) * | 1977-09-05 | 1979-03-06 | Wellcome Found | Nitrogen-heterocycliske forbindelser fremgangsmaade til deres fremstilling samt deres anvendelse |
| AU531493B2 (en) * | 1977-12-01 | 1983-08-25 | The Wellcome Foundation Limited | Thiohydantion derivatives |
| DE2963795D1 (en) * | 1978-01-23 | 1982-11-11 | Beecham Group Plc | Hydantoins and thiohydantoins, method for their preparation and pharmaceutical compositions containing them |
| EP0004723A1 (en) * | 1978-03-30 | 1979-10-17 | Beecham Group Plc | Deoxyhydantoins, processes for their preparation and pharmaceutical compositions containing them |
| GB1599740A (en) * | 1978-05-31 | 1981-10-07 | Wellcome Found | Hydantoin derivatives |
| AU4806979A (en) * | 1978-06-15 | 1979-12-20 | Beecham Group Limited | 1,2,4 triazole derivatives |
| EP0006352A1 (en) * | 1978-06-15 | 1980-01-09 | Beecham Group Plc | Hydantoins and thiohydantoins, process for their preparation and pharmaceutical compositions containing them |
| IL57504A0 (en) * | 1978-06-15 | 1979-10-31 | Beecham Group Ltd | Prostagandin analogues,their preparation and pharmaceutical compositions containing |
| AU4778279A (en) * | 1978-06-15 | 1979-12-20 | Beecham Group Limited | Prostaglandin analogues |
| IL59065A0 (en) * | 1979-01-18 | 1980-05-30 | Beecham Group Ltd | Hydantoin derivatives,their preparation pharmaceutical compositons containing them |
| EP0019223A1 (en) * | 1979-05-09 | 1980-11-26 | The Wellcome Foundation Limited | Optically active hydantoin derivatives, their synthesis, pharmaceutical formulations containing them, and intermediates |
| US4684735A (en) * | 1985-07-01 | 1987-08-04 | Stauffer Chemical Company | Promotion of raney nickel hydrogenation catalyst |
| JP3022878U (ja) * | 1995-08-18 | 1996-04-02 | 有限会社春江加工 | ミニディスク用ケース |
| PL370515A1 (en) | 2001-11-30 | 2005-05-30 | Eli Lilly And Company | Peroxisome proliferator activated receptor agonists |
| EP1631355B1 (en) * | 2003-06-06 | 2014-08-13 | Allergan, Inc. | Piperidinyl prostaglandin e analogs |
| US7179820B2 (en) * | 2003-06-06 | 2007-02-20 | Allergan, Inc. | Piperidinyl prostaglandin E analogs |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1524818A (en) * | 1974-11-29 | 1978-09-13 | Beecham Group Ltd | 12-azaprostaglandins |
-
1977
- 1977-06-02 CA CA000280455A patent/CA1176261A/en not_active Expired
- 1977-06-02 DE DE19772724948 patent/DE2724948A1/de not_active Ceased
- 1977-06-02 FR FR7716849A patent/FR2362839A1/fr active Granted
- 1977-06-02 ES ES459412A patent/ES459412A1/es not_active Expired
- 1977-06-02 NZ NZ184281A patent/NZ184281A/xx unknown
- 1977-06-02 SE SE7706428A patent/SE446336B/xx unknown
- 1977-06-02 DK DK244577A patent/DK244577A/da not_active Application Discontinuation
- 1977-06-02 HU HU77WE560A patent/HU183046B/hu unknown
- 1977-06-02 CH CH679677A patent/CH645631A5/de not_active IP Right Cessation
- 1977-06-02 NL NL7706064A patent/NL7706064A/xx not_active Application Discontinuation
- 1977-06-02 FI FI771763A patent/FI71930C/fi not_active IP Right Cessation
- 1977-06-02 JP JP6525277A patent/JPS52151168A/ja active Granted
-
1978
- 1978-06-01 ES ES470428A patent/ES470428A1/es not_active Expired
-
1979
- 1979-02-28 ES ES478156A patent/ES478156A1/es not_active Expired
- 1979-06-28 ES ES482010A patent/ES482010A1/es not_active Expired
-
1980
- 1980-03-25 ES ES489883A patent/ES8103057A1/es not_active Expired
-
1982
- 1982-05-19 SE SE8203161A patent/SE8203161L/sv not_active Application Discontinuation
-
1984
- 1984-02-07 CH CH576/84A patent/CH647511A5/de not_active IP Right Cessation
- 1984-02-07 CH CH57784A patent/CH646426A5/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CH646426A5 (en) | 1984-11-30 |
| ES482010A1 (es) | 1980-08-16 |
| JPS6222986B2 (enrdf_load_stackoverflow) | 1987-05-20 |
| HU183046B (en) | 1984-04-28 |
| DK244577A (da) | 1977-12-04 |
| SE8203161L (sv) | 1982-05-19 |
| ES459412A1 (es) | 1978-11-01 |
| FI71930B (fi) | 1986-11-28 |
| ES470428A1 (es) | 1979-09-01 |
| CH647511A5 (en) | 1985-01-31 |
| NL7706064A (nl) | 1977-12-06 |
| SE7706428L (sv) | 1977-12-04 |
| SE446336B (sv) | 1986-09-01 |
| FR2362839A1 (fr) | 1978-03-24 |
| CH645631A5 (en) | 1984-10-15 |
| ES489883A0 (es) | 1981-02-16 |
| ES8103057A1 (es) | 1981-02-16 |
| DE2724948A1 (de) | 1977-12-15 |
| ES478156A1 (es) | 1979-11-01 |
| JPS52151168A (en) | 1977-12-15 |
| FI771763A7 (fi) | 1977-12-04 |
| FI71930C (fi) | 1987-03-09 |
| NZ184281A (en) | 1980-04-28 |
| FR2362839B1 (enrdf_load_stackoverflow) | 1980-02-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |