CA1204741A - 8-substituted 7-phenyl-1,2,4-triazolo (2,3-c) pyrimidines 5-amines and amides - Google Patents
8-substituted 7-phenyl-1,2,4-triazolo (2,3-c) pyrimidines 5-amines and amidesInfo
- Publication number
- CA1204741A CA1204741A CA000456918A CA456918A CA1204741A CA 1204741 A CA1204741 A CA 1204741A CA 000456918 A CA000456918 A CA 000456918A CA 456918 A CA456918 A CA 456918A CA 1204741 A CA1204741 A CA 1204741A
- Authority
- CA
- Canada
- Prior art keywords
- compound
- prepared
- carbon atoms
- triazolo
- inclusive
- 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
- -1 8-substituted 7-phenyl-1,2,4-triazolo (2,3-c) pyrimidines Chemical class 0.000 title claims description 32
- 150000001408 amides Chemical class 0.000 title abstract description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 136
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 41
- 239000001257 hydrogen Substances 0.000 claims abstract description 40
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 37
- 125000001589 carboacyl group Chemical group 0.000 claims abstract description 12
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 12
- 125000005041 acyloxyalkyl group Chemical group 0.000 claims abstract description 11
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims abstract description 8
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 5
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 5
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 4
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 4
- 150000002367 halogens Chemical group 0.000 claims abstract description 4
- 150000002431 hydrogen Chemical group 0.000 claims abstract 11
- 238000000034 method Methods 0.000 claims description 101
- 230000008569 process Effects 0.000 claims description 84
- 125000004432 carbon atom Chemical group C* 0.000 claims description 68
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 22
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical group CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 15
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 6
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 6
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 6
- FVLAYJRLBLHIPV-UHFFFAOYSA-N pyrimidin-5-amine Chemical compound NC1=CN=CN=C1 FVLAYJRLBLHIPV-UHFFFAOYSA-N 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims description 4
- ACSYCXURMTTXAX-UHFFFAOYSA-N 2-(5-acetamido-7-phenyl-[1,2,4]triazolo[1,5-c]pyrimidin-8-yl)ethyl acetate Chemical compound CC(=O)OCCC=1C2=NC=NN2C(NC(=O)C)=NC=1C1=CC=CC=C1 ACSYCXURMTTXAX-UHFFFAOYSA-N 0.000 claims description 3
- XQISXHSYSWFKSE-UHFFFAOYSA-N 2-(5-acetamido-7-phenyl-[1,2,4]triazolo[1,5-c]pyrimidin-8-yl)ethyl octanoate Chemical compound N1=C(NC(C)=O)N2N=CN=C2C(CCOC(=O)CCCCCCC)=C1C1=CC=CC=C1 XQISXHSYSWFKSE-UHFFFAOYSA-N 0.000 claims description 3
- JOCHIKNGJVVXBL-UHFFFAOYSA-N 2-(5-amino-7-phenyl-[1,2,4]triazolo[1,5-c]pyrimidin-8-yl)ethanol Chemical compound OCCC=1C2=NC=NN2C(N)=NC=1C1=CC=CC=C1 JOCHIKNGJVVXBL-UHFFFAOYSA-N 0.000 claims description 3
- TYNREYPHWZKOLX-UHFFFAOYSA-N 2-(5-amino-7-phenyl-[1,2,4]triazolo[1,5-c]pyrimidin-8-yl)ethyl acetate Chemical compound N1=C(N)N2N=CN=C2C(CCOC(=O)C)=C1C1=CC=CC=C1 TYNREYPHWZKOLX-UHFFFAOYSA-N 0.000 claims description 3
- AOGVRHWEFXJJTA-UHFFFAOYSA-N 2-(5-amino-7-phenyl-[1,2,4]triazolo[1,5-c]pyrimidin-8-yl)ethyl adamantane-1-carboxylate Chemical compound C1C(C2)CC(C3)CC2CC13C(=O)OCCC=1C2=NC=NN2C(N)=NC=1C1=CC=CC=C1 AOGVRHWEFXJJTA-UHFFFAOYSA-N 0.000 claims description 3
- VYLXMOSZQPQNGZ-UHFFFAOYSA-N 4-[2-(5-amino-7-phenyl-[1,2,4]triazolo[1,5-c]pyrimidin-8-yl)ethoxy]-4-oxobutanoic acid Chemical compound OC(=O)CCC(=O)OCCC=1C2=NC=NN2C(N)=NC=1C1=CC=CC=C1 VYLXMOSZQPQNGZ-UHFFFAOYSA-N 0.000 claims description 3
- SKQQDBRSZKPGTM-UHFFFAOYSA-N 8-(2-ethoxyethyl)-7-(4-methoxyphenyl)-[1,2,4]triazolo[1,5-c]pyrimidin-5-amine Chemical compound N1=C(N)N2N=CN=C2C(CCOCC)=C1C1=CC=C(OC)C=C1 SKQQDBRSZKPGTM-UHFFFAOYSA-N 0.000 claims description 3
- IGOGUNGSMYVAFW-UHFFFAOYSA-N 8-(2-ethoxyethyl)-n-methyl-7-phenyl-[1,2,4]triazolo[1,5-c]pyrimidin-5-amine Chemical compound N1=C(NC)N2N=CN=C2C(CCOCC)=C1C1=CC=CC=C1 IGOGUNGSMYVAFW-UHFFFAOYSA-N 0.000 claims description 3
- DDMUQNDWZSKEJW-UHFFFAOYSA-N 8-(2-ethylsulfanylethyl)-7-phenyl-[1,2,4]triazolo[1,5-c]pyrimidin-5-amine Chemical compound N1=C(N)N2N=CN=C2C(CCSCC)=C1C1=CC=CC=C1 DDMUQNDWZSKEJW-UHFFFAOYSA-N 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical group IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 3
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 claims description 3
- JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 claims description 2
- CEOCVKWBUWKBKA-UHFFFAOYSA-N 2,4-dichlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)C=C1Cl CEOCVKWBUWKBKA-UHFFFAOYSA-N 0.000 claims description 2
- PQSVZWKBXMQOLR-UHFFFAOYSA-N 2-(5-acetamido-7-phenyl-[1,2,4]triazolo[1,5-c]pyrimidin-8-yl)ethyl adamantane-1-carboxylate Chemical compound C1C(C2)CC(C3)CC2CC13C(=O)OCCC=1C2=NC=NN2C(NC(=O)C)=NC=1C1=CC=CC=C1 PQSVZWKBXMQOLR-UHFFFAOYSA-N 0.000 claims description 2
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 claims description 2
- SGOOCKQLBFNGAZ-UHFFFAOYSA-N 2-[5-(methylamino)-7-phenyl-[1,2,4]triazolo[1,5-c]pyrimidin-8-yl]ethanol Chemical compound OCCC=1C2=NC=NN2C(NC)=NC=1C1=CC=CC=C1 SGOOCKQLBFNGAZ-UHFFFAOYSA-N 0.000 claims description 2
- BNZVWRPSZKVOLA-UHFFFAOYSA-N 2-[5-amino-7-(4-chlorophenyl)-[1,2,4]triazolo[1,5-c]pyrimidin-8-yl]ethanol Chemical compound OCCC=1C2=NC=NN2C(N)=NC=1C1=CC=C(Cl)C=C1 BNZVWRPSZKVOLA-UHFFFAOYSA-N 0.000 claims description 2
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 2
- WZVAZINAGJIZIX-UHFFFAOYSA-N 7-(4-chlorophenyl)-8-(2-ethoxyethyl)-[1,2,4]triazolo[1,5-c]pyrimidin-5-amine Chemical compound N1=C(N)N2N=CN=C2C(CCOCC)=C1C1=CC=C(Cl)C=C1 WZVAZINAGJIZIX-UHFFFAOYSA-N 0.000 claims description 2
- FYORLVJJWGBXHA-UHFFFAOYSA-N 8-(2-methoxyethyl)-n-methyl-7-phenyl-[1,2,4]triazolo[1,5-c]pyrimidin-5-amine Chemical compound COCCC=1C2=NC=NN2C(NC)=NC=1C1=CC=CC=C1 FYORLVJJWGBXHA-UHFFFAOYSA-N 0.000 claims description 2
- MIBQYWIOHFTKHD-UHFFFAOYSA-N adamantane-1-carbonyl chloride Chemical compound C1C(C2)CC3CC2CC1(C(=O)Cl)C3 MIBQYWIOHFTKHD-UHFFFAOYSA-N 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- REEZZSHJLXOIHL-UHFFFAOYSA-N octanoyl chloride Chemical compound CCCCCCCC(Cl)=O REEZZSHJLXOIHL-UHFFFAOYSA-N 0.000 claims description 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims description 2
- 229940014800 succinic anhydride Drugs 0.000 claims description 2
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 claims description 2
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 claims description 2
- 235000013350 formula milk Nutrition 0.000 claims 22
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 6
- 230000010933 acylation Effects 0.000 claims 6
- 238000005917 acylation reaction Methods 0.000 claims 6
- 230000000875 corresponding effect Effects 0.000 claims 6
- 239000003085 diluting agent Substances 0.000 claims 4
- 239000002904 solvent Substances 0.000 claims 4
- UKQNQPXNBOHMKJ-UHFFFAOYSA-N 2-(5-acetamido-7-phenyl-[1,2,4]triazolo[1,5-c]pyrimidin-8-yl)ethyl 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)OCCC=1C2=NC=NN2C(NC(=O)C)=NC=1C1=CC=CC=C1 UKQNQPXNBOHMKJ-UHFFFAOYSA-N 0.000 claims 2
- LWSUXUYDOLVEAO-UHFFFAOYSA-N 2-(5-acetamido-7-phenyl-[1,2,4]triazolo[1,5-c]pyrimidin-8-yl)ethyl 2,4-dichlorobenzoate Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(=O)OCCC=1C2=NC=NN2C(NC(=O)C)=NC=1C1=CC=CC=C1 LWSUXUYDOLVEAO-UHFFFAOYSA-N 0.000 claims 2
- QMGKDYWYKFLVQX-UHFFFAOYSA-N 2-(5-amino-7-phenyl-[1,2,4]triazolo[1,5-c]pyrimidin-8-yl)ethyl 2,2-dimethylpropanoate Chemical compound N1=C(N)N2N=CN=C2C(CCOC(=O)C(C)(C)C)=C1C1=CC=CC=C1 QMGKDYWYKFLVQX-UHFFFAOYSA-N 0.000 claims 2
- XWGSGCHTEKJVDA-UHFFFAOYSA-N 2-(5-amino-7-phenyl-[1,2,4]triazolo[1,5-c]pyrimidin-8-yl)ethyl octanoate Chemical compound N1=C(N)N2N=CN=C2C(CCOC(=O)CCCCCCC)=C1C1=CC=CC=C1 XWGSGCHTEKJVDA-UHFFFAOYSA-N 0.000 claims 2
- AXGZWJJNQUVMNG-UHFFFAOYSA-N 8-(2-bromoethyl)-7-phenyl-[1,2,4]triazolo[1,5-c]pyrimidin-5-amine Chemical compound BrCCC=1C2=NC=NN2C(N)=NC=1C1=CC=CC=C1 AXGZWJJNQUVMNG-UHFFFAOYSA-N 0.000 claims 2
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims 2
- 150000008065 acid anhydrides Chemical class 0.000 claims 2
- 150000001266 acyl halides Chemical class 0.000 claims 2
- 150000001351 alkyl iodides Chemical class 0.000 claims 2
- 230000002152 alkylating effect Effects 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 125000005999 2-bromoethyl group Chemical group 0.000 claims 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 1
- DBPKMSBWOKAKLA-UHFFFAOYSA-N 4-chloropyrimidine Chemical compound ClC1=CC=NC=N1 DBPKMSBWOKAKLA-UHFFFAOYSA-N 0.000 claims 1
- 238000005804 alkylation reaction Methods 0.000 claims 1
- XZBIXDPGRMLSTC-UHFFFAOYSA-N formohydrazide Chemical compound NNC=O XZBIXDPGRMLSTC-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 239000002934 diuretic Substances 0.000 abstract description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- 238000004458 analytical method Methods 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 238000004440 column chromatography Methods 0.000 description 6
- 229940030606 diuretics Drugs 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- 210000005239 tubule Anatomy 0.000 description 5
- 210000002700 urine Anatomy 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 230000001882 diuretic effect Effects 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- OZSPQIXKOVJJGE-UHFFFAOYSA-N 8-(2-ethoxyethyl)-7-phenyl-[1,2,4]triazolo[1,5-c]pyrimidin-5-amine Chemical compound N1=C(N)N2N=CN=C2C(CCOCC)=C1C1=CC=CC=C1 OZSPQIXKOVJJGE-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
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- 239000003451 thiazide diuretic agent Substances 0.000 description 3
- 206010003445 Ascites Diseases 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
- JZUFKLXOESDKRF-UHFFFAOYSA-N Chlorothiazide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NCNS2(=O)=O JZUFKLXOESDKRF-UHFFFAOYSA-N 0.000 description 2
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- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 2
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- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 2
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- 206010016654 Fibrosis Diseases 0.000 description 1
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- 241000124008 Mammalia Species 0.000 description 1
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- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 206010070863 Toxicity to various agents Diseases 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 description 1
- TVWHNULVHGKJHS-UHFFFAOYSA-N Uric acid Natural products N1C(=O)NC(=O)C2NC(=O)NC21 TVWHNULVHGKJHS-UHFFFAOYSA-N 0.000 description 1
- 102100026383 Vasopressin-neurophysin 2-copeptin Human genes 0.000 description 1
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- 239000008346 aqueous phase Substances 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 238000004166 bioassay Methods 0.000 description 1
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- 238000007796 conventional method Methods 0.000 description 1
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- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 201000010064 diabetes insipidus Diseases 0.000 description 1
- 230000006864 diuretic response Effects 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
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- 238000000921 elemental analysis Methods 0.000 description 1
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- 206010015037 epilepsy Diseases 0.000 description 1
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethyl mercaptane Natural products CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000003889 eye drop Substances 0.000 description 1
- 229940012356 eye drops Drugs 0.000 description 1
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- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 230000024924 glomerular filtration Effects 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 210000002216 heart Anatomy 0.000 description 1
- 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 1
- 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 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 230000009610 hypersensitivity Effects 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- 206010027599 migraine Diseases 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229960002748 norepinephrine Drugs 0.000 description 1
- SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 230000036581 peripheral resistance Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 230000012495 positive regulation of renal sodium excretion Effects 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 208000007645 potassium deficiency Diseases 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000035935 pregnancy Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000001325 propanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005767 propoxymethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])[#8]C([H])([H])* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- LJXQPZWIHJMPQQ-UHFFFAOYSA-N pyrimidin-2-amine Chemical compound NC1=NC=CC=N1 LJXQPZWIHJMPQQ-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000010183 spectrum analysis Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000007619 statistical method Methods 0.000 description 1
- 238000012066 statistical methodology Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
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- 230000032258 transport Effects 0.000 description 1
- 230000010245 tubular reabsorption Effects 0.000 description 1
- 230000010248 tubular secretion Effects 0.000 description 1
- 229940116269 uric acid Drugs 0.000 description 1
- 230000002485 urinary effect Effects 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- 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
- A61P7/10—Antioedematous agents; Diuretics
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Diabetes (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Hematology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US506,157 | 1983-06-20 | ||
| US06/506,157 US4483987A (en) | 1983-06-20 | 1983-06-20 | 8-Substituted 7-phenyl-1,2,4-triazolo[2,3-c]pyrimidines-5-amines and amides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1204741A true CA1204741A (en) | 1986-05-20 |
Family
ID=24013440
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000456918A Expired CA1204741A (en) | 1983-06-20 | 1984-06-19 | 8-substituted 7-phenyl-1,2,4-triazolo (2,3-c) pyrimidines 5-amines and amides |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4483987A (enExample) |
| EP (1) | EP0129247A1 (enExample) |
| JP (1) | JPS6013792A (enExample) |
| AU (1) | AU566670B2 (enExample) |
| CA (1) | CA1204741A (enExample) |
| ES (1) | ES8506714A1 (enExample) |
| ZA (1) | ZA844669B (enExample) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3130633A1 (de) * | 1981-08-01 | 1983-02-17 | Basf Ag, 6700 Ludwigshafen | 7-amino-azolo(1,5-a)pyrimidine und diese enthaltende fungizide |
| US4562192A (en) * | 1984-02-03 | 1985-12-31 | G. D. Searle & Co. | 6-Substituted-5-phenyltetrazolo[1,5-a][1,2,4]triazole[1,5-c]pyrimidines, and pharmaceutical compositions containing them |
| JPS62107954A (ja) * | 1985-11-05 | 1987-05-19 | Tomiji Saito | 可塑性研磨材料 |
| EP0244948A3 (en) * | 1986-04-30 | 1989-03-15 | Schering Agrochemicals Limited | Triazolopyrimidine herbicides |
| JPH07115284B2 (ja) * | 1986-07-18 | 1995-12-13 | 株式会社東芝 | 非球面部材のみがき装置 |
| US5338743A (en) * | 1988-06-06 | 1994-08-16 | Fujisawa Pharmaceutical Co., Ltd. | New use of the adenosine antagonist |
| US4866063A (en) * | 1988-12-22 | 1989-09-12 | G. D. Searle & Co. | Diol metabolites of 7-phenyl-1,2,4-triazolo[2,3-c]pyrimidines-5-amines |
| FR2687676B1 (fr) * | 1992-02-24 | 1994-07-08 | Union Pharma Scient Appl | Nouveaux derives de polyazaindenes antagonistes des recepteurs a l'angiotensine ii; leurs procedes de preparation, compositions pharmaceutiques les contenant. |
| CA2284737C (en) * | 1997-03-24 | 2007-03-13 | Kyowa Hakko Kogyo Co., Ltd. | [1,2,4]triazolo[1,5-c]pyrimidine derivatives |
| WO2000017201A1 (en) | 1998-09-22 | 2000-03-30 | Kyowa Hakko Kogyo Co., Ltd. | [1,2,4]TRIAZOLO[1,5-c]PYRIMIDINE DERIVATIVES |
| JP2001302667A (ja) * | 2000-04-28 | 2001-10-31 | Bayer Ag | イミダゾピリミジン誘導体およびトリアゾロピリミジン誘導体 |
| US6998148B1 (en) | 2001-03-28 | 2006-02-14 | Shipley Company, L.L.C. | Porous materials |
| MXPA04004534A (es) * | 2001-11-16 | 2004-08-11 | Childrens Medical Center | Aumento de la funcion de un organo. |
| AU2003272886A1 (en) * | 2002-09-24 | 2004-04-19 | Kyowa Hakko Kogyo Co., Ltd. | (1,2,4)-TRIAZOLO(1,5-c)PYRIMIDINE DERIVATIVE |
| WO2020106560A1 (en) * | 2018-11-20 | 2020-05-28 | Merck Sharp & Dohme Corp. | Substituted amino triazolopyrimidine and amino triazolopyrazine adenosine receptor antagonists, pharmaceutical compositions and their use |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3053844A (en) * | 1959-04-13 | 1962-09-11 | Ici Ltd | Mono-acyl derivatives of s-triazolo [2, 3-c] pyrimidines |
| US3046276A (en) * | 1959-06-15 | 1962-07-24 | Ici Ltd | S-triazolo-[2, 3-c] pyrimidine derivatives |
| US4205169A (en) * | 1979-04-09 | 1980-05-27 | G. D. Searle & Co. | N-[4-Azido-5-(2-ethoxyethyl)-6-phenyl-2-pyrimidinyl]acetamide and congeners |
| US4405780A (en) * | 1979-08-08 | 1983-09-20 | G. D. Searle & Co. | 8-Substituted 7-phenyl-1,2,4,-triazolo[4,3-c]/[2,3-c]pyrimidines-5-amines and amides |
| AU531507B2 (en) * | 1979-08-08 | 1983-08-25 | G.D. Searle & Co. | 8-substituted 7-phenyl-1,2,4-triazolo(4,3-c) pyrimidines -5-amines and amides |
| US4269980A (en) * | 1979-12-17 | 1981-05-26 | American Cyanamid Company | (Substituted-phenyl)-1,2,4-triazolo[4,3-c]pyrimidines and (substituted-phenyl)-1,2,4-triazolo[1,5-c]pyrimidines |
-
1983
- 1983-06-20 US US06/506,157 patent/US4483987A/en not_active Expired - Fee Related
-
1984
- 1984-06-19 ES ES533537A patent/ES8506714A1/es not_active Expired
- 1984-06-19 EP EP84107022A patent/EP0129247A1/en not_active Withdrawn
- 1984-06-19 CA CA000456918A patent/CA1204741A/en not_active Expired
- 1984-06-19 AU AU29494/84A patent/AU566670B2/en not_active Ceased
- 1984-06-20 ZA ZA844669A patent/ZA844669B/xx unknown
- 1984-06-20 JP JP59127266A patent/JPS6013792A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| ES533537A0 (es) | 1985-08-01 |
| ES8506714A1 (es) | 1985-08-01 |
| AU2949484A (en) | 1985-01-03 |
| AU566670B2 (en) | 1987-10-29 |
| ZA844669B (en) | 1985-08-28 |
| JPH0471074B2 (enExample) | 1992-11-12 |
| JPS6013792A (ja) | 1985-01-24 |
| EP0129247A1 (en) | 1984-12-27 |
| US4483987A (en) | 1984-11-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry | ||
| MKEX | Expiry |
Effective date: 20040619 |