CA1101870A - Derives de 1,2,4-triazolidine-3,5-dione - Google Patents

Derives de 1,2,4-triazolidine-3,5-dione

Info

Publication number: CA1101870A
Authority: CA; Canada
Prior art keywords: compound; formula; alkyl; phenyl; group
Prior art date: 1976-12-18
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

Application number

CA358,005A

Other languages

English (en)

Inventor

David R. Adams

Alexander C. Goudie

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Beecham Group PLC

Original Assignee

Beecham Group PLC

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1976-12-18

Filing date

1980-08-11

Publication date

1981-05-26

1977-10-19 Priority claimed from GB52956/76A external-priority patent/GB1598073A/en

1980-08-11 Application filed by Beecham Group PLC filed Critical Beecham Group PLC

1980-08-11 Priority to CA358,005A priority Critical patent/CA1101870A/fr

1981-05-26 Application granted granted Critical

1981-05-26 Publication of CA1101870A publication Critical patent/CA1101870A/fr

Status Expired legal-status Critical Current

Links

UDATXMIGEVPXTR-UHFFFAOYSA-N 1,2,4-triazolidine-3,5-dione Chemical class O=C1NNC(=O)N1 UDATXMIGEVPXTR-UHFFFAOYSA-N 0.000 title description 5
150000001875 compounds Chemical class 0.000 claims abstract description 120
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 59
239000001257 hydrogen Substances 0.000 claims abstract description 58
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 49
150000002431 hydrogen Chemical group 0.000 claims abstract description 24
-1 phenyl -C1-6 alkyl Chemical group 0.000 claims abstract description 20
150000003839 salts Chemical class 0.000 claims abstract description 19
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 17
229910052799 carbon Inorganic materials 0.000 claims abstract description 15
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 14
125000001624 naphthyl group Chemical group 0.000 claims abstract description 14
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 13
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 11
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 11
125000004185 ester group Chemical group 0.000 claims abstract description 9
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims abstract description 4
125000006621 (C3-C8) cycloalkyl-(C1-C6) alkyl group Chemical group 0.000 claims abstract description 3
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract 13
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract 7
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 6
125000006545 (C1-C9) alkyl group Chemical group 0.000 claims abstract 3
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 35
238000000034 method Methods 0.000 claims description 28
238000002360 preparation method Methods 0.000 claims description 23
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 22
239000002904 solvent Substances 0.000 claims description 9
239000002585 base Substances 0.000 claims description 6
125000005843 halogen group Chemical group 0.000 claims description 6
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 5
XJOOWWMZMXBLAO-UHFFFAOYSA-N 4-methyl-1,2,4-triazolidine-3,5-dione Chemical compound CN1C(=O)NNC1=O XJOOWWMZMXBLAO-UHFFFAOYSA-N 0.000 claims description 4
239000007818 Grignard reagent Substances 0.000 claims description 4
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 4
RWNJOXUVHRXHSD-UHFFFAOYSA-N hept-6-enoic acid Chemical compound OC(=O)CCCCC=C RWNJOXUVHRXHSD-UHFFFAOYSA-N 0.000 claims description 4
239000012312 sodium hydride Substances 0.000 claims description 4
229910000104 sodium hydride Inorganic materials 0.000 claims description 4
239000012038 nucleophile Substances 0.000 claims description 3
239000003960 organic solvent Substances 0.000 claims description 3
ZFAIFXGDBTYQOH-UHFFFAOYSA-N 4-methyl-1-(3-oxooctyl)-1,2,4-triazolidine-3,5-dione Chemical compound CCCCCC(=O)CCN1NC(=O)N(C)C1=O ZFAIFXGDBTYQOH-UHFFFAOYSA-N 0.000 claims description 2
239000003638 chemical reducing agent Substances 0.000 claims description 2
HKKXVKUPDRNFHM-UHFFFAOYSA-N methyl 7-(4-methyl-3,5-dioxo-1,2,4-triazolidin-1-yl)hept-5-enoate Chemical compound COC(=O)CCCC=CCN1NC(=O)N(C)C1=O HKKXVKUPDRNFHM-UHFFFAOYSA-N 0.000 claims description 2
239000012279 sodium borohydride Substances 0.000 claims description 2
229910000033 sodium borohydride Inorganic materials 0.000 claims description 2
239000000126 substance Substances 0.000 claims 4
VUMQONVBEUKGPJ-UHFFFAOYSA-N 1-(3-hydroxyoctyl)-4-methyl-1,2,4-triazolidine-3,5-dione Chemical compound CCCCCC(O)CCN1NC(=O)N(C)C1=O VUMQONVBEUKGPJ-UHFFFAOYSA-N 0.000 claims 2
KJBZIQQVKCDJIA-UHFFFAOYSA-N 4-methyl-1-(3-oxononyl)-1,2,4-triazolidine-3,5-dione Chemical compound CN1C(N(NC1=O)CCC(CCCCCC)=O)=O KJBZIQQVKCDJIA-UHFFFAOYSA-N 0.000 claims 2
KKNDTZFBTQUCMB-UHFFFAOYSA-N methyl 7-(4-methyl-3,5-dioxo-1,2,4-triazolidin-1-yl)heptanoate Chemical compound COC(=O)CCCCCCN1NC(=O)N(C)C1=O KKNDTZFBTQUCMB-UHFFFAOYSA-N 0.000 claims 2
XRYKNRLGZZNWEE-UHFFFAOYSA-N 4-methyl-1,2,4-triazole-3,5-dione Chemical compound CN1C(=O)N=NC1=O XRYKNRLGZZNWEE-UHFFFAOYSA-N 0.000 claims 1
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 1
239000003054 catalyst Substances 0.000 claims 1
HILCQVNWWOARMT-UHFFFAOYSA-N non-1-en-3-one Chemical compound CCCCCCC(=O)C=C HILCQVNWWOARMT-UHFFFAOYSA-N 0.000 claims 1
150000001721 carbon Chemical group 0.000 abstract description 6
229910052736 halogen Inorganic materials 0.000 abstract description 5
150000002367 halogens Chemical class 0.000 abstract description 5
230000000144 pharmacologic effect Effects 0.000 abstract description 4
125000004356 hydroxy functional group Chemical group O* 0.000 abstract 3
125000000217 alkyl group Chemical group 0.000 description 60
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 55
239000000460 chlorine Substances 0.000 description 47
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 39
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 36
239000000243 solution Substances 0.000 description 34
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
239000000203 mixture Substances 0.000 description 28
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
101150041968 CDC13 gene Proteins 0.000 description 23
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 23
238000004949 mass spectrometry Methods 0.000 description 23
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
229910001868 water Inorganic materials 0.000 description 18
238000006243 chemical reaction Methods 0.000 description 16
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
239000000706 filtrate Substances 0.000 description 14
229940093499 ethyl acetate Drugs 0.000 description 13
235000019439 ethyl acetate Nutrition 0.000 description 13
238000010992 reflux Methods 0.000 description 12
239000011369 resultant mixture Substances 0.000 description 12
230000000694 effects Effects 0.000 description 11
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 11
239000000284 extract Substances 0.000 description 11
239000011541 reaction mixture Substances 0.000 description 11
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 9
239000003921 oil Substances 0.000 description 9
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 9
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
125000003545 alkoxy group Chemical group 0.000 description 8
238000007792 addition Methods 0.000 description 7
239000000741 silica gel Substances 0.000 description 7
229910002027 silica gel Inorganic materials 0.000 description 7
239000003981 vehicle Substances 0.000 description 7
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
238000004458 analytical method Methods 0.000 description 6
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 6
239000000543 intermediate Substances 0.000 description 6
239000011734 sodium Substances 0.000 description 6
239000012267 brine Substances 0.000 description 5
230000008020 evaporation Effects 0.000 description 5
238000001704 evaporation Methods 0.000 description 5
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
239000000725 suspension Substances 0.000 description 5
238000011282 treatment Methods 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
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 4
101150059476 SLC44A3 gene Proteins 0.000 description 4
125000003118 aryl group Chemical group 0.000 description 4
239000012298 atmosphere Substances 0.000 description 4
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
WFPZPJSADLPSON-UHFFFAOYSA-N dinitrogen tetroxide Inorganic materials [O-][N+](=O)[N+]([O-])=O WFPZPJSADLPSON-UHFFFAOYSA-N 0.000 description 4
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
208000035475 disorder Diseases 0.000 description 4
239000007788 liquid Substances 0.000 description 4
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
229910000029 sodium carbonate Inorganic materials 0.000 description 4
238000003756 stirring Methods 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
229910014033 C-OH Inorganic materials 0.000 description 3
229910014570 C—OH Inorganic materials 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
239000002253 acid Substances 0.000 description 3
239000003513 alkali Substances 0.000 description 3
238000005886 esterification reaction Methods 0.000 description 3
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 3
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
229940094443 oxytocics prostaglandins Drugs 0.000 description 3
238000012856 packing Methods 0.000 description 3
239000008194 pharmaceutical composition Substances 0.000 description 3
235000009518 sodium iodide Nutrition 0.000 description 3
239000007787 solid Substances 0.000 description 3
239000003826 tablet Substances 0.000 description 3
WRFWAYDBNCOWRA-UHFFFAOYSA-N 3,4-dichloro-1-(6-iodo-4-oxo-2-thiophen-2-ylquinazolin-3-yl)pyrrole-2,5-dione Chemical compound O=C1C(Cl)=C(Cl)C(=O)N1N1C(=O)C2=CC(I)=CC=C2N=C1C1=CC=CS1 WRFWAYDBNCOWRA-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
239000007832 Na2SO4 Substances 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
229940022663 acetate Drugs 0.000 description 2
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
239000012346 acetyl chloride Substances 0.000 description 2
238000004220 aggregation Methods 0.000 description 2
230000002776 aggregation Effects 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
125000004429 atom Chemical group 0.000 description 2
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 2
125000001246 bromo group Chemical group Br* 0.000 description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
239000002775 capsule Substances 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
238000007796 conventional method Methods 0.000 description 2
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
239000006185 dispersion Substances 0.000 description 2
150000002148 esters Chemical group 0.000 description 2
239000011737 fluorine Substances 0.000 description 2
229910052731 fluorine Inorganic materials 0.000 description 2
150000002500 ions Chemical class 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
HSZCZNFXUDYRKD-UHFFFAOYSA-M lithium iodide Chemical compound [Li+].[I-] HSZCZNFXUDYRKD-UHFFFAOYSA-M 0.000 description 2
MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 2
239000002480 mineral oil Substances 0.000 description 2
235000010446 mineral oil Nutrition 0.000 description 2
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
230000007935 neutral effect Effects 0.000 description 2
229910052760 oxygen Inorganic materials 0.000 description 2
125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
239000000843 powder Substances 0.000 description 2
239000003755 preservative agent Substances 0.000 description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
150000003180 prostaglandins Chemical class 0.000 description 2
239000002002 slurry Substances 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
238000002560 therapeutic procedure Methods 0.000 description 2
125000005490 tosylate group Chemical group 0.000 description 2
ASGMFNBUXDJWJJ-JLCFBVMHSA-N (1R,3R)-3-[[3-bromo-1-[4-(5-methyl-1,3,4-thiadiazol-2-yl)phenyl]pyrazolo[3,4-d]pyrimidin-6-yl]amino]-N,1-dimethylcyclopentane-1-carboxamide Chemical compound BrC1=NN(C2=NC(=NC=C21)N[C@H]1C[C@@](CC1)(C(=O)NC)C)C1=CC=C(C=C1)C=1SC(=NN=1)C ASGMFNBUXDJWJJ-JLCFBVMHSA-N 0.000 description 1
IUSARDYWEPUTPN-OZBXUNDUSA-N (2r)-n-[(2s,3r)-4-[[(4s)-6-(2,2-dimethylpropyl)spiro[3,4-dihydropyrano[2,3-b]pyridine-2,1'-cyclobutane]-4-yl]amino]-3-hydroxy-1-[3-(1,3-thiazol-2-yl)phenyl]butan-2-yl]-2-methoxypropanamide Chemical compound C([C@H](NC(=O)[C@@H](C)OC)[C@H](O)CN[C@@H]1C2=CC(CC(C)(C)C)=CN=C2OC2(CCC2)C1)C(C=1)=CC=CC=1C1=NC=CS1 IUSARDYWEPUTPN-OZBXUNDUSA-N 0.000 description 1
YJLIKUSWRSEPSM-WGQQHEPDSA-N (2r,3r,4s,5r)-2-[6-amino-8-[(4-phenylphenyl)methylamino]purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1CNC1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O YJLIKUSWRSEPSM-WGQQHEPDSA-N 0.000 description 1
NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
WWTBZEKOSBFBEM-SPWPXUSOSA-N (2s)-2-[[2-benzyl-3-[hydroxy-[(1r)-2-phenyl-1-(phenylmethoxycarbonylamino)ethyl]phosphoryl]propanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound N([C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)O)C(=O)C(CP(O)(=O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1C=CC=CC=1)CC1=CC=CC=C1 WWTBZEKOSBFBEM-SPWPXUSOSA-N 0.000 description 1
UDQTXCHQKHIQMH-KYGLGHNPSA-N (3ar,5s,6s,7r,7ar)-5-(difluoromethyl)-2-(ethylamino)-5,6,7,7a-tetrahydro-3ah-pyrano[3,2-d][1,3]thiazole-6,7-diol Chemical compound S1C(NCC)=N[C@H]2[C@@H]1O[C@H](C(F)F)[C@@H](O)[C@@H]2O UDQTXCHQKHIQMH-KYGLGHNPSA-N 0.000 description 1
HUWSZNZAROKDRZ-RRLWZMAJSA-N (3r,4r)-3-azaniumyl-5-[[(2s,3r)-1-[(2s)-2,3-dicarboxypyrrolidin-1-yl]-3-methyl-1-oxopentan-2-yl]amino]-5-oxo-4-sulfanylpentane-1-sulfonate Chemical compound OS(=O)(=O)CC[C@@H](N)[C@@H](S)C(=O)N[C@@H]([C@H](C)CC)C(=O)N1CCC(C(O)=O)[C@H]1C(O)=O HUWSZNZAROKDRZ-RRLWZMAJSA-N 0.000 description 1
OMBVEVHRIQULKW-DNQXCXABSA-M (3r,5r)-7-[3-(4-fluorophenyl)-8-oxo-7-phenyl-1-propan-2-yl-5,6-dihydro-4h-pyrrolo[2,3-c]azepin-2-yl]-3,5-dihydroxyheptanoate Chemical compound O=C1C=2N(C(C)C)C(CC[C@@H](O)C[C@@H](O)CC([O-])=O)=C(C=3C=CC(F)=CC=3)C=2CCCN1C1=CC=CC=C1 OMBVEVHRIQULKW-DNQXCXABSA-M 0.000 description 1
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WZZBNLYBHUDSHF-DHLKQENFSA-N 1-[(3s,4s)-4-[8-(2-chloro-4-pyrimidin-2-yloxyphenyl)-7-fluoro-2-methylimidazo[4,5-c]quinolin-1-yl]-3-fluoropiperidin-1-yl]-2-hydroxyethanone Chemical compound CC1=NC2=CN=C3C=C(F)C(C=4C(=CC(OC=5N=CC=CN=5)=CC=4)Cl)=CC3=C2N1[C@H]1CCN(C(=O)CO)C[C@@H]1F WZZBNLYBHUDSHF-DHLKQENFSA-N 0.000 description 1
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Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA358,005A 1976-12-18 1980-08-11 Derives de 1,2,4-triazolidine-3,5-dione Expired CA1101870A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA358,005A CA1101870A (fr)	1976-12-18	1980-08-11	Derives de 1,2,4-triazolidine-3,5-dione

Applications Claiming Priority (6)

Application Number	Priority Date	Filing Date	Title
GB5295676		1976-12-18
GB52956/76		1976-12-18
GB43407/77		1977-10-19
GB52956/76A GB1598073A (en)	1976-12-18	1977-10-19	8,10,12-triazaprostaglandins
CA293,240A CA1097660A (fr)	1976-12-18	1977-12-16	Traduction non-disponible
CA358,005A CA1101870A (fr)	1976-12-18	1980-08-11	Derives de 1,2,4-triazolidine-3,5-dione

Publications (1)

Publication Number	Publication Date
CA1101870A true CA1101870A (fr)	1981-05-26

Family

ID=27426045

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA358,005A Expired CA1101870A (fr)	1976-12-18	1980-08-11	Derives de 1,2,4-triazolidine-3,5-dione

Country Status (1)

Country	Link
CA (1)	CA1101870A (fr)

1980
- 1980-08-11 CA CA358,005A patent/CA1101870A/fr not_active Expired

Legal Events

Date	Code	Title	Description
1998-05-26	MKEX	Expiry

Publication	Publication Date	Title
SU1416058A3 (ru)	1988-08-07	Способ получени азоловых соединений или их кислотно-аддитивных солей,их простых или сложных эфиров
EP0054974A1 (fr)	1982-06-30	Dérivés de l'imidazolylpropanole et leurs sels d'addition avec un acide, procédé de préparation et leur utilisation
CA1245666A (fr)	1988-11-29	Derives de substitution de diazolylalcoyl-carbinols; preparation et utilisation comme antimycosiques
EP0117578A2 (fr)	1984-09-05	Dérivés d'alcool substitués par azole
KR830002451B1 (ko)	1983-10-26	이미다졸릴 비닐 에테르의 제조방법
CA1287059C (fr)	1991-07-30	Derives ditriazole presentant une activite antifongique
CA1340507C (fr)	1999-04-20	Derives de substitution azoliques de cycloalcanol, methode pour les preprer et leur emploi comme fongicides en agriculture et en horticulture
CA1101870A (fr)	1981-05-26	Derives de 1,2,4-triazolidine-3,5-dione
HK32389A (en)	1989-04-28	Triazole antifungal agents
IE840652L (en)	1984-09-16	Triazoles
EP0007180B1 (fr)	1983-03-30	Dérivés de triazole analogues de prostaglandine, procédés pour leur préparation et composition pharmaceutique les contenant
CA1097660A (fr)	1981-03-17	Traduction non-disponible
US4341789A (en)	1982-07-27	Cycloaliphatic prostaglandin analogues
US4152445A (en)	1979-05-01	1-(3-Hydroxyalk-1-yl)-5-(carboxyalkyl)hydantoin derivatives
US4136190A (en)	1979-01-23	4,4-dimethyl-3,5-pyrrolidinediones
CA1127641A (fr)	1982-07-13	Diamides cycliques
US4064259A (en)	1977-12-20	Thiazole cardiovascular agents
US4201864A (en)	1980-05-06	Oxy-alkylamino acids and esters
CA1203243A (fr)	1986-04-15	Compose d'imidazolylpropanol ayant des proprietes optiques et utilisation
EP0127848A2 (fr)	1984-12-12	Dérivés d'acide 5-thiaalkanoique à activité antihypercholestérolémique
US4177283A (en)	1979-12-04	Aromatic prostaglandin analogues
US4187312A (en)	1980-02-05	3-Hydroxy-4,4-dimethyl-5-pyrrolidone derivatives
DE3717846C2 (de)	1996-04-04	Carbacyclinderivate, Verfahren zu deren Herstellung und diese enthaltende Arzneimittel
US5095028A (en)	1992-03-10	2-(4-chlorobenzyl)-1-(1H-imidazole-1-ylmethyl)-1-cyclohexanol and cycloheptanol
GB1598662A (en)	1981-09-23	10,12-diazoprostaglandins