JPS6222986B2 - - Google Patents
Info
- Publication number
- JPS6222986B2 JPS6222986B2 JP52065252A JP6525277A JPS6222986B2 JP S6222986 B2 JPS6222986 B2 JP S6222986B2 JP 52065252 A JP52065252 A JP 52065252A JP 6525277 A JP6525277 A JP 6525277A JP S6222986 B2 JPS6222986 B2 JP S6222986B2
- Authority
- JP
- Japan
- Prior art keywords
- hydantoin
- formula
- carboxyhexyl
- 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
- 150000001875 compounds Chemical class 0.000 claims description 94
- 125000000217 alkyl group Chemical group 0.000 claims description 35
- 239000001257 hydrogen Substances 0.000 claims description 28
- 229910052739 hydrogen Inorganic materials 0.000 claims description 28
- 150000003839 salts Chemical class 0.000 claims description 17
- 150000002148 esters Chemical class 0.000 claims description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 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 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 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 description 2
- 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 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 description 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 description 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 description 2
- QQMADWFRXYPOPL-UHFFFAOYSA-N 1-(3-oxooctyl)imidazolidine-2,4-dione Chemical compound O=C(CCN1C(=O)NC(=O)C1)CCCCC QQMADWFRXYPOPL-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 125
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 77
- 239000000243 solution Substances 0.000 description 77
- -1 Lithium metals Chemical class 0.000 description 70
- 239000003921 oil Substances 0.000 description 56
- 239000000203 mixture Substances 0.000 description 51
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 49
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 45
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 44
- 238000002844 melting Methods 0.000 description 43
- 230000008018 melting Effects 0.000 description 43
- 229940091173 hydantoin Drugs 0.000 description 39
- 235000019441 ethanol Nutrition 0.000 description 35
- 238000000034 method Methods 0.000 description 34
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 description 33
- 238000006243 chemical reaction Methods 0.000 description 27
- CQMYCPZZIPXILQ-UHFFFAOYSA-N diethyl nonanedioate Chemical compound CCOC(=O)CCCCCCCC(=O)OCC CQMYCPZZIPXILQ-UHFFFAOYSA-N 0.000 description 23
- 239000002253 acid Substances 0.000 description 22
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 20
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 19
- 239000012230 colorless oil Substances 0.000 description 19
- 150000001469 hydantoins Chemical class 0.000 description 19
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
- 238000009835 boiling Methods 0.000 description 18
- 239000000284 extract Substances 0.000 description 18
- 238000003756 stirring Methods 0.000 description 18
- 239000002904 solvent Substances 0.000 description 16
- 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 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 229940125797 compound 12 Drugs 0.000 description 15
- 238000004519 manufacturing process Methods 0.000 description 15
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- VGUWZCUCNQXGBU-UHFFFAOYSA-N 3-[(4-methylpiperazin-1-yl)methyl]-5-nitro-1h-indole Chemical compound C1CN(C)CCN1CC1=CNC2=CC=C([N+]([O-])=O)C=C12 VGUWZCUCNQXGBU-UHFFFAOYSA-N 0.000 description 14
- 230000000694 effects Effects 0.000 description 14
- 239000000047 product Substances 0.000 description 14
- 238000002347 injection Methods 0.000 description 11
- 239000007924 injection Substances 0.000 description 11
- 241000124008 Mammalia Species 0.000 description 10
- 239000013078 crystal Substances 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 239000002585 base Substances 0.000 description 9
- 239000003814 drug Substances 0.000 description 9
- 238000009472 formulation Methods 0.000 description 9
- 239000005457 ice water Substances 0.000 description 9
- 239000000843 powder Substances 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
- 239000000543 intermediate Substances 0.000 description 8
- GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 description 8
- 229910052708 sodium Inorganic materials 0.000 description 8
- 239000011734 sodium Substances 0.000 description 8
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 7
- 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 7
- 239000003153 chemical reaction reagent Substances 0.000 description 7
- 239000012442 inert solvent Substances 0.000 description 7
- 238000000746 purification Methods 0.000 description 7
- 239000000377 silicon dioxide Substances 0.000 description 7
- 229910000033 sodium borohydride Inorganic materials 0.000 description 7
- 239000012279 sodium borohydride Substances 0.000 description 7
- 239000000126 substance 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
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 241000700159 Rattus Species 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
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 239000003638 chemical reducing agent Substances 0.000 description 6
- 239000012259 ether extract Substances 0.000 description 6
- 238000004128 high performance liquid chromatography Methods 0.000 description 6
- 229930195733 hydrocarbon Natural products 0.000 description 6
- 230000007062 hydrolysis Effects 0.000 description 6
- 238000006460 hydrolysis reaction Methods 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
- 239000008213 purified water Substances 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 239000003826 tablet Substances 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- 150000001298 alcohols Chemical class 0.000 description 5
- 229910052783 alkali metal Inorganic materials 0.000 description 5
- 150000001721 carbon Chemical group 0.000 description 5
- 238000004440 column chromatography Methods 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 229940079593 drug Drugs 0.000 description 5
- 239000008187 granular material Substances 0.000 description 5
- 150000002430 hydrocarbons Chemical class 0.000 description 5
- 231100000252 nontoxic Toxicity 0.000 description 5
- 230000003000 nontoxic effect Effects 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- 230000003042 antagnostic effect Effects 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 210000004369 blood Anatomy 0.000 description 4
- 239000008280 blood Substances 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 229940125782 compound 2 Drugs 0.000 description 4
- VZNFKFKDZBVGNF-UHFFFAOYSA-N diethyl 2-(3-hydroxyoctylamino)nonanedioate Chemical compound CCCCCC(O)CCNC(C(=O)OCC)CCCCCCC(=O)OCC VZNFKFKDZBVGNF-UHFFFAOYSA-N 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
- 125000004494 ethyl ester group Chemical group 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 150000002431 hydrogen Chemical class 0.000 description 4
- 150000002576 ketones Chemical class 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 230000009467 reduction Effects 0.000 description 4
- 238000007363 ring formation reaction Methods 0.000 description 4
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 208000024891 symptom Diseases 0.000 description 4
- 150000003536 tetrazoles Chemical class 0.000 description 4
- SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 3
- RAIXQSNYRUTLRE-UHFFFAOYSA-N 1-octylimidazolidine-2,4-dione Chemical compound CCCCCCCCN1CC(=O)NC1=O RAIXQSNYRUTLRE-UHFFFAOYSA-N 0.000 description 3
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 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
- 206010006482 Bronchospasm Diseases 0.000 description 3
- 208000031226 Hyperlipidaemia Diseases 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
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 229920002472 Starch Polymers 0.000 description 3
- 208000007536 Thrombosis Diseases 0.000 description 3
- 239000004015 abortifacient agent Substances 0.000 description 3
- 231100000641 abortifacient agent Toxicity 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 238000004220 aggregation Methods 0.000 description 3
- 230000002776 aggregation Effects 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 230000002744 anti-aggregatory effect Effects 0.000 description 3
- 230000004071 biological effect Effects 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000036772 blood pressure Effects 0.000 description 3
- 230000007885 bronchoconstriction Effects 0.000 description 3
- 150000001768 cations Chemical class 0.000 description 3
- 229940126543 compound 14 Drugs 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- LMVIQDQFGKIILS-UHFFFAOYSA-N diethyl 2-(octylamino)nonanedioate Chemical compound CCCCCCCCNC(C(=O)OCC)CCCCCCC(=O)OCC LMVIQDQFGKIILS-UHFFFAOYSA-N 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 239000002552 dosage form Substances 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 238000001990 intravenous administration Methods 0.000 description 3
- 239000012948 isocyanate Substances 0.000 description 3
- 239000008101 lactose Substances 0.000 description 3
- 235000019359 magnesium stearate Nutrition 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 239000012528 membrane Substances 0.000 description 3
- 235000010755 mineral Nutrition 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- 238000000465 moulding Methods 0.000 description 3
- 150000002825 nitriles Chemical class 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 3
- 210000004623 platelet-rich plasma Anatomy 0.000 description 3
- 239000011148 porous material Substances 0.000 description 3
- 150000003180 prostaglandins Chemical class 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000008107 starch Substances 0.000 description 3
- 235000019698 starch Nutrition 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 210000002784 stomach Anatomy 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 238000004809 thin layer chromatography Methods 0.000 description 3
- 231100000816 toxic dose Toxicity 0.000 description 3
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 2
- UZFMOKQJFYMBGY-UHFFFAOYSA-N 4-hydroxy-TEMPO Chemical compound CC1(C)CC(O)CC(C)(C)N1[O] UZFMOKQJFYMBGY-UHFFFAOYSA-N 0.000 description 2
- QMKZSSRYCAZEFT-UHFFFAOYSA-N 5-octylimidazolidine-2,4-dione Chemical compound CCCCCCCCC1NC(=O)NC1=O QMKZSSRYCAZEFT-UHFFFAOYSA-N 0.000 description 2
- NYJNESBEEDOJQB-UHFFFAOYSA-N 7-(5-octyl-2,4-dioxoimidazolidin-1-yl)heptanoic acid Chemical compound CCCCCCCCC1N(CCCCCCC(O)=O)C(=O)NC1=O NYJNESBEEDOJQB-UHFFFAOYSA-N 0.000 description 2
- 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 2
- WODBPAHYQHBSAP-NTCAYCPXSA-N 7-[(5e)-5-(3-hydroxyoctylidene)-2,4-dioxoimidazolidin-1-yl]heptanoic acid Chemical compound CCCCCC(O)C\C=C1\N(CCCCCCC(O)=O)C(=O)NC1=O WODBPAHYQHBSAP-NTCAYCPXSA-N 0.000 description 2
- WMFMAAVGKGMXMB-UHFFFAOYSA-N 7-[2,5-dioxo-3-(3-oxooctyl)imidazolidin-4-yl]heptanoic acid Chemical compound CCCCCC(=O)CCN1C(CCCCCCC(O)=O)C(=O)NC1=O WMFMAAVGKGMXMB-UHFFFAOYSA-N 0.000 description 2
- LONCVEMSOKBZHZ-UHFFFAOYSA-N 7-[3-[3-(oxan-2-yloxy)octyl]-2,5-dioxoimidazolidin-4-yl]heptanoic acid Chemical compound C1CCCOC1OC(CCCCC)CCN1C(CCCCCCC(O)=O)C(=O)NC1=O LONCVEMSOKBZHZ-UHFFFAOYSA-N 0.000 description 2
- 244000215068 Acacia senegal Species 0.000 description 2
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- VHPHLYYCMCIEMQ-UHFFFAOYSA-N ethyl 7-(3-octyl-2,5-dioxoimidazolidin-4-yl)heptanoate Chemical compound CCCCCCCCN1C(CCCCCCC(=O)OCC)C(=O)NC1=O VHPHLYYCMCIEMQ-UHFFFAOYSA-N 0.000 description 1
- VPNHTVSHQQOKHB-UHFFFAOYSA-N ethyl 7-[(1,1-dibutoxy-3-ethoxy-3-oxopropan-2-yl)amino]heptanoate;hydrobromide Chemical compound Br.CCCCOC(OCCCC)C(C(=O)OCC)NCCCCCCC(=O)OCC VPNHTVSHQQOKHB-UHFFFAOYSA-N 0.000 description 1
- JWKLFXRLBZAPRK-UHFFFAOYSA-N ethyl 7-[1-methyl-2,5-dioxo-3-(3-oxooctyl)imidazolidin-4-yl]heptanoate Chemical compound CCCCCC(=O)CCN1C(CCCCCCC(=O)OCC)C(=O)N(C)C1=O JWKLFXRLBZAPRK-UHFFFAOYSA-N 0.000 description 1
- SGCSAWOTNMPCGD-UHFFFAOYSA-N ethyl 7-[2,5-dioxo-3-(3-oxooctyl)imidazolidin-4-yl]heptanoate Chemical compound CCCCCC(=O)CCN1C(CCCCCCC(=O)OCC)C(=O)NC1=O SGCSAWOTNMPCGD-UHFFFAOYSA-N 0.000 description 1
- GFSKDNLWYHCQGB-UHFFFAOYSA-N ethyl 7-[2,5-dioxo-3-(5-phenylpentyl)imidazolidin-4-yl]heptanoate Chemical compound O=C1NC(=O)C(CCCCCCC(=O)OCC)N1CCCCCC1=CC=CC=C1 GFSKDNLWYHCQGB-UHFFFAOYSA-N 0.000 description 1
- XCITXJMUTZPPHL-UHFFFAOYSA-N ethyl 7-[3-[3-(oxan-2-yloxy)octyl]-2,5-dioxoimidazolidin-4-yl]heptanoate Chemical compound C1CCCOC1OC(CCCCC)CCN1C(CCCCCCC(=O)OCC)C(=O)NC1=O XCITXJMUTZPPHL-UHFFFAOYSA-N 0.000 description 1
- VKRLCNBNMMXEPM-UHFFFAOYSA-N ethyl 7-[5-(dibutoxymethyl)-2,4-dioxoimidazolidin-1-yl]heptanoate Chemical compound CCCCOC(OCCCC)C1N(CCCCCCC(=O)OCC)C(=O)NC1=O VKRLCNBNMMXEPM-UHFFFAOYSA-N 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 210000001105 femoral artery Anatomy 0.000 description 1
- 230000001605 fetal effect Effects 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 238000006170 formylation reaction Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 230000027119 gastric acid secretion Effects 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 150000004820 halides Chemical group 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 230000035876 healing Effects 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 150000003840 hydrochlorides 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
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 150000002440 hydroxy compounds Chemical class 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 230000001631 hypertensive effect Effects 0.000 description 1
- CUILPNURFADTPE-UHFFFAOYSA-N hypobromous acid Chemical class BrO CUILPNURFADTPE-UHFFFAOYSA-N 0.000 description 1
- 150000002463 imidates Chemical class 0.000 description 1
- 150000002464 imidothioesters Chemical class 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000000411 inducer Substances 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000004715 keto acids Chemical class 0.000 description 1
- 201000006370 kidney failure Diseases 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 208000007903 liver failure Diseases 0.000 description 1
- 231100000835 liver failure Toxicity 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 230000003211 malignant effect Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- MJGFBOZCAJSGQW-UHFFFAOYSA-N mercury sodium Chemical compound [Na].[Hg] MJGFBOZCAJSGQW-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000010446 mirabilite Substances 0.000 description 1
- 239000007932 molded tablet Substances 0.000 description 1
- 210000002464 muscle smooth vascular Anatomy 0.000 description 1
- 208000010125 myocardial infarction Diseases 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
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000009935 nitrosation Effects 0.000 description 1
- 238000007034 nitrosation reaction Methods 0.000 description 1
- CMUOJBJRZUHRMU-UHFFFAOYSA-N nitrourea Chemical compound NC(=O)N[N+]([O-])=O CMUOJBJRZUHRMU-UHFFFAOYSA-N 0.000 description 1
- GQPLMRYTRLFLPF-UHFFFAOYSA-N nitrous oxide Inorganic materials [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 1
- 239000007764 o/w emulsion Substances 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 235000010603 pastilles Nutrition 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- UCUUFSAXZMGPGH-UHFFFAOYSA-N penta-1,4-dien-3-one Chemical class C=CC(=O)C=C UCUUFSAXZMGPGH-UHFFFAOYSA-N 0.000 description 1
- ANRIQLNBZQLTFV-DZUOILHNSA-N pentagastrin Chemical compound C([C@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CC=1[C]2C=CC=CC2=NC=1)NC(=O)CCNC(=O)OC(C)(C)C)CCSC)C(N)=O)C1=CC=CC=C1 ANRIQLNBZQLTFV-DZUOILHNSA-N 0.000 description 1
- 229960000444 pentagastrin Drugs 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 125000004346 phenylpentyl group Chemical group C1(=CC=CC=C1)CCCCC* 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 239000000106 platelet aggregation inhibitor Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000006041 probiotic Substances 0.000 description 1
- 235000018291 probiotics Nutrition 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- FKRCODPIKNYEAC-UHFFFAOYSA-N propionic acid ethyl ester Natural products CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000000541 pulsatile effect Effects 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 210000000664 rectum Anatomy 0.000 description 1
- 230000033904 relaxation of vascular smooth muscle Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 208000015891 sexual disease Diseases 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229910001923 silver oxide Inorganic materials 0.000 description 1
- 229910001023 sodium amalgam Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- RSIJVJUOQBWMIM-UHFFFAOYSA-L sodium sulfate decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].[O-]S([O-])(=O)=O RSIJVJUOQBWMIM-UHFFFAOYSA-L 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 239000006190 sub-lingual tablet Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- WMOVHXAZOJBABW-UHFFFAOYSA-N tert-butyl acetate Chemical compound CC(=O)OC(C)(C)C WMOVHXAZOJBABW-UHFFFAOYSA-N 0.000 description 1
- 125000004187 tetrahydropyran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical class 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 230000001256 tonic effect Effects 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 230000000304 vasodilatating effect Effects 0.000 description 1
- 230000024883 vasodilation Effects 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000007762 w/o emulsion Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
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 (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2287776 | 1976-06-03 | ||
| GB5034076 | 1976-12-02 | ||
| GB1214577 | 1977-03-23 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS52151168A JPS52151168A (en) | 1977-12-15 |
| JPS6222986B2 true JPS6222986B2 (pt) | 1987-05-20 |
Family
ID=27256793
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP6525277A Granted JPS52151168A (en) | 1976-06-03 | 1977-06-02 | Heterocyclic compound |
Country Status (12)
| Country | Link |
|---|---|
| JP (1) | JPS52151168A (pt) |
| CA (1) | CA1176261A (pt) |
| CH (3) | CH645631A5 (pt) |
| DE (1) | DE2724948A1 (pt) |
| DK (1) | DK244577A (pt) |
| ES (5) | ES459412A1 (pt) |
| FI (1) | FI71930C (pt) |
| FR (1) | FR2362839A1 (pt) |
| HU (1) | HU183046B (pt) |
| NL (1) | NL7706064A (pt) |
| NZ (1) | NZ184281A (pt) |
| SE (2) | SE446336B (pt) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
Families Citing this family (16)
| 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 |
| JPS5492962A (en) * | 1977-12-01 | 1979-07-23 | Wellcome Found | Thiohydantoin compound |
| 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 |
| EP0006352A1 (en) * | 1978-06-15 | 1980-01-09 | Beecham Group Plc | Hydantoins and thiohydantoins, process for their preparation and pharmaceutical compositions containing them |
| AU4778279A (en) * | 1978-06-15 | 1979-12-20 | Beecham Group Limited | Prostaglandin analogues |
| AU4806979A (en) * | 1978-06-15 | 1979-12-20 | Beecham Group Limited | 1,2,4 triazole derivatives |
| IL57504A0 (en) * | 1978-06-15 | 1979-10-31 | Beecham Group Ltd | Prostagandin analogues,their preparation and pharmaceutical compositions containing |
| IL59065A0 (en) * | 1979-01-18 | 1980-05-30 | Beecham Group Ltd | Hydantoin derivatives,their preparation pharmaceutical compositons containing them |
| JPS55151569A (en) * | 1979-05-09 | 1980-11-26 | Wellcome Found | Optically active heterocyclic compounds* their synthesis and medical blend containing them |
| US4684735A (en) * | 1985-07-01 | 1987-08-04 | Stauffer Chemical Company | Promotion of raney nickel hydrogenation catalyst |
| KR20050044606A (ko) | 2001-11-30 | 2005-05-12 | 일라이 릴리 앤드 캄파니 | 퍼옥시솜 증식제에 의해 활성화된 수용체 아고니스트 |
| CA2528179C (en) * | 2003-06-06 | 2013-10-22 | 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 JP JP6525277A patent/JPS52151168A/ja active Granted
- 1977-06-02 FR FR7716849A patent/FR2362839A1/fr active Granted
- 1977-06-02 SE SE7706428A patent/SE446336B/xx unknown
- 1977-06-02 ES ES459412A patent/ES459412A1/es not_active Expired
- 1977-06-02 DE DE19772724948 patent/DE2724948A1/de not_active Ceased
- 1977-06-02 NL NL7706064A patent/NL7706064A/xx not_active Application Discontinuation
- 1977-06-02 NZ NZ184281A patent/NZ184281A/xx unknown
- 1977-06-02 DK DK244577A patent/DK244577A/da not_active Application Discontinuation
- 1977-06-02 CA CA000280455A patent/CA1176261A/en not_active Expired
- 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 FI FI771763A patent/FI71930C/fi not_active IP Right Cessation
-
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/ES489883A0/es active Granted
-
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
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
Also Published As
| Publication number | Publication date |
|---|---|
| ES8103057A1 (es) | 1981-02-16 |
| SE7706428L (sv) | 1977-12-04 |
| DK244577A (da) | 1977-12-04 |
| CA1176261A (en) | 1984-10-16 |
| JPS52151168A (en) | 1977-12-15 |
| NL7706064A (nl) | 1977-12-06 |
| ES482010A1 (es) | 1980-08-16 |
| ES459412A1 (es) | 1978-11-01 |
| NZ184281A (en) | 1980-04-28 |
| ES470428A1 (es) | 1979-09-01 |
| FI71930B (fi) | 1986-11-28 |
| SE8203161L (sv) | 1982-05-19 |
| FI71930C (fi) | 1987-03-09 |
| DE2724948A1 (de) | 1977-12-15 |
| FR2362839A1 (fr) | 1978-03-24 |
| FI771763A (fi) | 1977-12-04 |
| ES478156A1 (es) | 1979-11-01 |
| FR2362839B1 (pt) | 1980-02-01 |
| CH645631A5 (en) | 1984-10-15 |
| ES489883A0 (es) | 1981-02-16 |
| SE446336B (sv) | 1986-09-01 |
| HU183046B (en) | 1984-04-28 |
| CH646426A5 (en) | 1984-11-30 |
| CH647511A5 (en) | 1985-01-31 |
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