CA2554090A1 - Derives de triazole inhibant l'activite antagoniste de la vasopressine - Google Patents

Info

Publication number

CA2554090A1

CA2554090A1 CA002554090A CA2554090A CA2554090A1 CA 2554090 A1 CA2554090 A1 CA 2554090A1 CA 002554090 A CA002554090 A CA 002554090A CA 2554090 A CA2554090 A CA 2554090A CA 2554090 A1 CA2554090 A1 CA 2554090A1

Authority

CA

Canada

Prior art keywords

triazol

methyl

bipyridinyl

tetrahydro

phenyl

Prior art date

2004-01-22

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.)

Abandoned

Links

• Espacenet
• Global Dossier
• CIPO
• Discuss

• KBZOIRJILGZLEJ-LGYYRGKSSA-N argipressin Chemical compound C([C@H]1C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CSSC[C@@H](C(N[C@@H](CC=2C=CC(O)=CC=2)C(=O)N1)=O)N)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCN=C(N)N)C(=O)NCC(N)=O)C1=CC=CC=C1 KBZOIRJILGZLEJ-LGYYRGKSSA-N 0.000 title description 15
• 229960003726 vasopressin Drugs 0.000 title description 6
• GXBMIBRIOWHPDT-UHFFFAOYSA-N Vasopressin Natural products N1C(=O)C(CC=2C=C(O)C=CC=2)NC(=O)C(N)CSSCC(C(=O)N2C(CCC2)C(=O)NC(CCCN=C(N)N)C(=O)NCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(CCC(N)=O)NC(=O)C1CC1=CC=CC=C1 GXBMIBRIOWHPDT-UHFFFAOYSA-N 0.000 title description 5
• 108010004977 Vasopressins Proteins 0.000 title description 5
• 102000002852 Vasopressins Human genes 0.000 title description 5
• 229940042055 systemic antimycotics triazole derivative Drugs 0.000 title description 4
• 230000003042 antagnostic effect Effects 0.000 title description 3
• 150000001875 compounds Chemical class 0.000 claims abstract description 182
• 206010013935 Dysmenorrhoea Diseases 0.000 claims abstract description 40
• -1 2-pyridinyl Chemical group 0.000 claims abstract description 32
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 21
• 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 11
• 208000019901 Anxiety disease Diseases 0.000 claims abstract description 10
• 201000001320 Atherosclerosis Diseases 0.000 claims abstract description 10
• 201000009273 Endometriosis Diseases 0.000 claims abstract description 9
• 206010002383 Angina Pectoris Diseases 0.000 claims abstract description 8
• 208000024172 Cardiovascular disease Diseases 0.000 claims abstract description 8
• 208000001362 Fetal Growth Retardation Diseases 0.000 claims abstract description 8
• 206010070531 Foetal growth restriction Diseases 0.000 claims abstract description 8
• 206010019280 Heart failures Diseases 0.000 claims abstract description 8
• 208000029422 Hypernatremia Diseases 0.000 claims abstract description 8
• 206010020772 Hypertension Diseases 0.000 claims abstract description 8
• 206010061218 Inflammation Diseases 0.000 claims abstract description 8
• 206010030113 Oedema Diseases 0.000 claims abstract description 8
• 208000003782 Raynaud disease Diseases 0.000 claims abstract description 8
• 208000012322 Raynaud phenomenon Diseases 0.000 claims abstract description 8
• 206010047700 Vomiting Diseases 0.000 claims abstract description 8
• 230000036506 anxiety Effects 0.000 claims abstract description 8
• 208000030941 fetal growth restriction Diseases 0.000 claims abstract description 8
• 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 8
• 230000004054 inflammatory process Effects 0.000 claims abstract description 8
• 201000003152 motion sickness Diseases 0.000 claims abstract description 8
• 230000002028 premature Effects 0.000 claims abstract description 8
• 206010036596 premature ejaculation Diseases 0.000 claims abstract description 8
• 206010039073 rheumatoid arthritis Diseases 0.000 claims abstract description 8
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 5
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract description 5
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 3
• 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims abstract description 3
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims abstract 3
• 125000006413 ring segment Chemical group 0.000 claims abstract 2
• 238000002360 preparation method Methods 0.000 claims description 42
• 238000000034 method Methods 0.000 claims description 26
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 17
• 239000003814 drug Substances 0.000 claims description 17
• 208000035475 disorder Diseases 0.000 claims description 13
• 239000005557 antagonist Substances 0.000 claims description 8
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 7
• 239000000825 pharmaceutical preparation Substances 0.000 claims description 7
• 229940127557 pharmaceutical product Drugs 0.000 claims description 6
• 229940123333 Phosphodiesterase 5 inhibitor Drugs 0.000 claims description 5
• 239000003085 diluting agent Substances 0.000 claims description 5
• 239000008194 pharmaceutical composition Substances 0.000 claims description 5
• 239000002590 phosphodiesterase V inhibitor Substances 0.000 claims description 5
• 125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 claims description 4
• 229940124638 COX inhibitor Drugs 0.000 claims description 4
• ODKSFYDXXFIFQN-BYPYZUCNSA-N L-arginine Chemical compound OC(=O)[C@@H](N)CCCN=C(N)N ODKSFYDXXFIFQN-BYPYZUCNSA-N 0.000 claims description 4
• 239000003539 oral contraceptive agent Substances 0.000 claims description 4
• MKNTTXSUSCMFON-UHFFFAOYSA-N 2-[4-[4-(2-ethylphenyl)-5-methyl-1,2,4-triazol-3-yl]piperidin-1-yl]pyrimidine Chemical compound CCC1=CC=CC=C1N1C(C2CCN(CC2)C=2N=CC=CN=2)=NN=C1C MKNTTXSUSCMFON-UHFFFAOYSA-N 0.000 claims description 3
• SHOIYGMIUFNMSQ-UHFFFAOYSA-N 2-[4-[4-(4-methoxy-2-methylphenyl)-5-methyl-1,2,4-triazol-3-yl]piperidin-1-yl]pyridine Chemical group CC1=CC(OC)=CC=C1N1C(C2CCN(CC2)C=2N=CC=CC=2)=NN=C1C SHOIYGMIUFNMSQ-UHFFFAOYSA-N 0.000 claims description 3
• 229930064664 L-arginine Natural products 0.000 claims description 3
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• 239000002840 nitric oxide donor Substances 0.000 claims description 3
• 229940127234 oral contraceptive Drugs 0.000 claims description 3
• HVGGDNWEFQHDDM-UHFFFAOYSA-N 2-[4-(5-methyl-4-phenyl-1,2,4-triazol-3-yl)piperidin-1-yl]pyridine Chemical group C=1C=CC=CC=1N1C(C)=NN=C1C(CC1)CCN1C1=CC=CC=N1 HVGGDNWEFQHDDM-UHFFFAOYSA-N 0.000 claims description 2
• KSQHIDGSPGZHQT-UHFFFAOYSA-N 2-[4-[4-(2,4-dimethylphenyl)-5-methyl-1,2,4-triazol-3-yl]piperidin-1-yl]pyridine Chemical group C=1C=C(C)C=C(C)C=1N1C(C)=NN=C1C(CC1)CCN1C1=CC=CC=N1 KSQHIDGSPGZHQT-UHFFFAOYSA-N 0.000 claims description 2
• FIJWBLYILZAKRG-UHFFFAOYSA-N 2-[4-[4-(4-chloro-2-methylphenyl)-5-(triazol-2-ylmethyl)-1,2,4-triazol-3-yl]piperidin-1-yl]pyridine Chemical group CC1=CC(Cl)=CC=C1N1C(C2CCN(CC2)C=2N=CC=CC=2)=NN=C1CN1N=CC=N1 FIJWBLYILZAKRG-UHFFFAOYSA-N 0.000 claims description 2
• FAMKWLXFIXGFSV-UHFFFAOYSA-N 2-[4-[4-(4-chlorophenyl)-5-(triazol-2-ylmethyl)-1,2,4-triazol-3-yl]piperidin-1-yl]pyridine Chemical group C1=CC(Cl)=CC=C1N1C(C2CCN(CC2)C=2N=CC=CC=2)=NN=C1CN1N=CC=N1 FAMKWLXFIXGFSV-UHFFFAOYSA-N 0.000 claims description 2
• LBFJBVVULXJRNT-UHFFFAOYSA-N 2-[4-[4-(4-chlorophenyl)-5-methyl-1,2,4-triazol-3-yl]piperidin-1-yl]pyridine Chemical group C=1C=C(Cl)C=CC=1N1C(C)=NN=C1C(CC1)CCN1C1=CC=CC=N1 LBFJBVVULXJRNT-UHFFFAOYSA-N 0.000 claims description 2
• FGHNXCRYGGXBCK-UHFFFAOYSA-N 2-[4-[4-(4-methoxyphenyl)-5-(triazol-2-ylmethyl)-1,2,4-triazol-3-yl]piperidin-1-yl]pyridine Chemical group C1=CC(OC)=CC=C1N1C(C2CCN(CC2)C=2N=CC=CC=2)=NN=C1CN1N=CC=N1 FGHNXCRYGGXBCK-UHFFFAOYSA-N 0.000 claims description 2
• KAEOYJPYGWYJDV-UHFFFAOYSA-N 2-[4-[4-(4-methoxyphenyl)-5-methyl-1,2,4-triazol-3-yl]piperidin-1-yl]pyridine Chemical group C1=CC(OC)=CC=C1N1C(C2CCN(CC2)C=2N=CC=CC=2)=NN=C1C KAEOYJPYGWYJDV-UHFFFAOYSA-N 0.000 claims description 2
• NXSHMIUOYWQJIS-UHFFFAOYSA-N 2-[4-[4-phenyl-5-(piperidin-1-ylmethyl)-1,2,4-triazol-3-yl]piperidin-1-yl]pyridine Chemical group N=1N=C(C2CCN(CC2)C=2N=CC=CC=2)N(C=2C=CC=CC=2)C=1CN1CCCCC1 NXSHMIUOYWQJIS-UHFFFAOYSA-N 0.000 claims description 2
• DLFYJSHXTMOPFS-UHFFFAOYSA-N 2-[4-[4-phenyl-5-(triazol-2-ylmethyl)-1,2,4-triazol-3-yl]piperidin-1-yl]pyridine Chemical group N1=CC=NN1CC(N1C=2C=CC=CC=2)=NN=C1C(CC1)CCN1C1=CC=CC=N1 DLFYJSHXTMOPFS-UHFFFAOYSA-N 0.000 claims description 2
• WKPUTGWASCNKOY-UHFFFAOYSA-N 2-[4-[5-methyl-4-(2-methylphenyl)-1,2,4-triazol-3-yl]piperidin-1-yl]pyridine Chemical group C=1C=CC=C(C)C=1N1C(C)=NN=C1C(CC1)CCN1C1=CC=CC=N1 WKPUTGWASCNKOY-UHFFFAOYSA-N 0.000 claims description 2
• SEXVTVLAOYMVCU-UHFFFAOYSA-N 2-[4-[5-methyl-4-(4-methylphenyl)-1,2,4-triazol-3-yl]piperidin-1-yl]pyridine Chemical group C=1C=C(C)C=CC=1N1C(C)=NN=C1C(CC1)CCN1C1=CC=CC=N1 SEXVTVLAOYMVCU-UHFFFAOYSA-N 0.000 claims description 2
• FLMSMEHRRWOEDD-UHFFFAOYSA-N 4-[[4-(4-chloro-2-methylphenyl)-5-(1-pyridin-2-ylpiperidin-4-yl)-1,2,4-triazol-3-yl]methyl]morpholine Chemical group CC1=CC(Cl)=CC=C1N1C(C2CCN(CC2)C=2N=CC=CC=2)=NN=C1CN1CCOCC1 FLMSMEHRRWOEDD-UHFFFAOYSA-N 0.000 claims description 2
• 238000004519 manufacturing process Methods 0.000 claims description 2
• FIVNCACRPXNZDP-UHFFFAOYSA-N 2-[4-[4-(4-chloro-2-methylphenyl)-5-methyl-1,2,4-triazol-3-yl]piperidin-1-yl]pyridine Chemical group C=1C=C(Cl)C=C(C)C=1N1C(C)=NN=C1C(CC1)CCN1C1=CC=CC=N1 FIVNCACRPXNZDP-UHFFFAOYSA-N 0.000 claims 1
• GXABPYWLPRHDEO-UHFFFAOYSA-N 2-[4-[5-methyl-4-(2-propan-2-ylphenyl)-1,2,4-triazol-3-yl]piperidin-1-yl]pyrimidine;4-[[4-phenyl-5-(1-pyridin-2-ylpiperidin-4-yl)-1,2,4-triazol-3-yl]methyl]morpholine Chemical group CC(C)C1=CC=CC=C1N1C(C2CCN(CC2)C=2N=CC=CN=2)=NN=C1C.N=1N=C(C2CCN(CC2)C=2N=CC=CC=2)N(C=2C=CC=CC=2)C=1CN1CCOCC1 GXABPYWLPRHDEO-UHFFFAOYSA-N 0.000 claims 1
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