NL1027084C2

NL1027084C2 - Gesubstitueerde triazoolderivaten als oxytocine-antagonisten.

Gesubstitueerde triazoolderivaten als oxytocine-antagonisten. Download PDF

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Publication number: NL1027084C2
Authority: NL; Netherlands
Prior art keywords: triazol; methoxypyridin; methyl; fluoro; pyrazine
Prior art date: 2003-09-22

Application number

NL1027084A

Other languages

English (en)

Dutch (nl)

Other versions

NL1027084A1 (nl

Inventor

Alan Daniel Brown

David Ellis

Christopher Ronald Smith

Original Assignee

Pfizer

Priority date

2003-09-22

Filing date

2004-09-22

Publication date

2006-01-24

2003-09-22 Priority claimed from GB0322159A external-priority patent/GB0322159D0/en

2004-02-12 Priority claimed from GB0403150A external-priority patent/GB0403150D0/en

2004-07-05 Priority claimed from GB0415110A external-priority patent/GB0415110D0/en

2004-09-22 Application filed by Pfizer filed Critical Pfizer

2005-03-24 Publication of NL1027084A1 publication Critical patent/NL1027084A1/nl

2006-01-24 Application granted granted Critical

2006-01-24 Publication of NL1027084C2 publication Critical patent/NL1027084C2/nl

Links

239000003336 oxytocin antagonist Substances 0.000 title description 5
229940121361 oxytocin antagonists Drugs 0.000 title description 5
229940042055 systemic antimycotics triazole derivative Drugs 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 274
238000002360 preparation method Methods 0.000 claims description 274
-1 methoxy, ethoxy, 2-methoxyethoxy, dimethylamino, 1,2,3-triazol-2-yl Chemical group 0.000 claims description 188
238000000034 method Methods 0.000 claims description 107
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 55
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 48
KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 36
150000003839 salts Chemical class 0.000 claims description 35
125000003545 alkoxy group Chemical group 0.000 claims description 34
230000001568 sexual effect Effects 0.000 claims description 31
125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 26
239000003814 drug Substances 0.000 claims description 24
125000004093 cyano group Chemical group *C#N 0.000 claims description 23
229910052736 halogen Inorganic materials 0.000 claims description 23
150000002367 halogens Chemical class 0.000 claims description 23
XNOPRXBHLZRZKH-DSZYJQQASA-N oxytocin Chemical compound C([C@H]1C(=O)N[C@H](C(N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CSSC[C@H](N)C(=O)N1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC(C)C)C(=O)NCC(N)=O)=O)[C@@H](C)CC)C1=CC=C(O)C=C1 XNOPRXBHLZRZKH-DSZYJQQASA-N 0.000 claims description 23
101800000989 Oxytocin Proteins 0.000 claims description 22
XNOPRXBHLZRZKH-UHFFFAOYSA-N Oxytocin Natural products N1C(=O)C(N)CSSCC(C(=O)N2C(CCC2)C(=O)NC(CC(C)C)C(=O)NCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(CCC(N)=O)NC(=O)C(C(C)CC)NC(=O)C1CC1=CC=C(O)C=C1 XNOPRXBHLZRZKH-UHFFFAOYSA-N 0.000 claims description 22
229960001723 oxytocin Drugs 0.000 claims description 22
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 22
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 20
PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 20
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 20
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 20
238000011282 treatment Methods 0.000 claims description 20
239000012453 solvate Substances 0.000 claims description 19
125000001424 substituent group Chemical group 0.000 claims description 19
208000035475 disorder Diseases 0.000 claims description 16
125000000217 alkyl group Chemical group 0.000 claims description 15
125000000623 heterocyclic group Chemical group 0.000 claims description 15
239000000460 chlorine Substances 0.000 claims description 14
229910052720 vanadium Inorganic materials 0.000 claims description 14
230000008602 contraction Effects 0.000 claims description 13
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
229910052727 yttrium Inorganic materials 0.000 claims description 13
208000006262 Psychological Sexual Dysfunctions Diseases 0.000 claims description 12
201000001880 Sexual dysfunction Diseases 0.000 claims description 12
125000005842 heteroatom Chemical group 0.000 claims description 12
229910052721 tungsten Inorganic materials 0.000 claims description 12
229910052757 nitrogen Inorganic materials 0.000 claims description 11
231100000872 sexual dysfunction Toxicity 0.000 claims description 11
229910052717 sulfur Inorganic materials 0.000 claims description 9
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 8
208000019454 Feeding and Eating disease Diseases 0.000 claims description 8
150000001204 N-oxides Chemical class 0.000 claims description 8
229910052760 oxygen Inorganic materials 0.000 claims description 8
MFRYLRNQOQUDDZ-UHFFFAOYSA-N 5-(2,3-dimethylphenyl)-2-[4-(6-methoxypyridin-3-yl)-5-(pyrrolidin-1-ylmethyl)-1,2,4-triazol-3-yl]pyridine Chemical compound C1=NC(OC)=CC=C1N1C(C=2N=CC(=CC=2)C=2C(=C(C)C=CC=2)C)=NN=C1CN1CCCC1 MFRYLRNQOQUDDZ-UHFFFAOYSA-N 0.000 claims description 7
239000003085 diluting agent Substances 0.000 claims description 7
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JTBHLQXMGZKKRH-UHFFFAOYSA-N 2-(4-fluoro-2-methylphenyl)-5-[4-(6-methoxypyridin-3-yl)-5-methyl-1,2,4-triazol-3-yl]pyrazine Chemical compound C1=NC(OC)=CC=C1N1C(C=2N=CC(=NC=2)C=2C(=CC(F)=CC=2)C)=NN=C1C JTBHLQXMGZKKRH-UHFFFAOYSA-N 0.000 claims description 5
UWVQTFRVRSCGAZ-UHFFFAOYSA-N 2-(5-fluoro-2-methoxyphenyl)-5-[5-(methoxymethyl)-4-(6-methoxypyridin-3-yl)-1,2,4-triazol-3-yl]pyridine Chemical compound C=1C=C(OC)N=CC=1N1C(COC)=NN=C1C(C=N1)=CC=C1C1=CC(F)=CC=C1OC UWVQTFRVRSCGAZ-UHFFFAOYSA-N 0.000 claims description 5
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
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208000007222 Physiological Sexual Dysfunction Diseases 0.000 claims description 5
125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 5
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229910052731 fluorine Inorganic materials 0.000 claims description 5
125000004076 pyridyl group Chemical group 0.000 claims description 5
125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 4
QHESCAMHVWJIJA-UHFFFAOYSA-N 2-(2,3-dimethylphenyl)-5-[4-(6-methoxypyridin-3-yl)-5-methyl-1,2,4-triazol-3-yl]pyrazine Chemical compound C1=NC(OC)=CC=C1N1C(C=2N=CC(=NC=2)C=2C(=C(C)C=CC=2)C)=NN=C1C QHESCAMHVWJIJA-UHFFFAOYSA-N 0.000 claims description 4
YHKZSUNEWODEEO-UHFFFAOYSA-N 4-[5-[4-(6-methoxypyridin-3-yl)-5-methyl-1,2,4-triazol-3-yl]pyrazin-2-yl]-3-methylbenzonitrile Chemical compound C1=NC(OC)=CC=C1N1C(C=2N=CC(=NC=2)C=2C(=CC(=CC=2)C#N)C)=NN=C1C YHKZSUNEWODEEO-UHFFFAOYSA-N 0.000 claims description 4
AUIGHINKBLJVFJ-UHFFFAOYSA-N 4-[6-[5-(methoxymethyl)-4-(6-methoxypyridin-3-yl)-1,2,4-triazol-3-yl]pyridin-3-yl]-3-methylbenzonitrile Chemical compound C=1C=C(OC)N=CC=1N1C(COC)=NN=C1C(N=C1)=CC=C1C1=CC=C(C#N)C=C1C AUIGHINKBLJVFJ-UHFFFAOYSA-N 0.000 claims description 4
WWCKNCVBSIWKGU-UHFFFAOYSA-N 5-(2,3-dimethylphenyl)-2-[5-(methoxymethyl)-4-(6-methoxypyridin-3-yl)-1,2,4-triazol-3-yl]pyridine Chemical compound C=1C=C(OC)N=CC=1N1C(COC)=NN=C1C(N=C1)=CC=C1C1=CC=CC(C)=C1C WWCKNCVBSIWKGU-UHFFFAOYSA-N 0.000 claims description 4
208000027559 Appetite disease Diseases 0.000 claims description 4
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125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 3
PFIGDGJSZCKKLC-UHFFFAOYSA-N 2-(2,3-dimethylphenyl)-5-[5-(methoxymethyl)-4-(6-methoxypyridin-3-yl)-1,2,4-triazol-3-yl]pyrazine Chemical compound C=1C=C(OC)N=CC=1N1C(COC)=NN=C1C(N=C1)=CN=C1C1=CC=CC(C)=C1C PFIGDGJSZCKKLC-UHFFFAOYSA-N 0.000 claims description 3
ZSIWQFWQNSLVMF-UHFFFAOYSA-N 2-(2,3-dimethylphenyl)-5-[5-(methoxymethyl)-4-(6-methoxypyridin-3-yl)-1,2,4-triazol-3-yl]pyridine Chemical compound C=1C=C(OC)N=CC=1N1C(COC)=NN=C1C(C=N1)=CC=C1C1=CC=CC(C)=C1C ZSIWQFWQNSLVMF-UHFFFAOYSA-N 0.000 claims description 3
WIGMUHOLXOUURZ-UHFFFAOYSA-N 2-(2-fluoro-5-methoxyphenyl)-5-[4-(6-methoxypyridin-3-yl)-5-methyl-1,2,4-triazol-3-yl]pyrazine Chemical compound COC1=CC=C(F)C(C=2N=CC(=NC=2)C=2N(C(C)=NN=2)C=2C=NC(OC)=CC=2)=C1 WIGMUHOLXOUURZ-UHFFFAOYSA-N 0.000 claims description 3
HWPDYNZUAISOPP-UHFFFAOYSA-N 2-(3-fluoro-2-methoxyphenyl)-5-[4-(6-methoxypyridin-3-yl)-5-methyl-1,2,4-triazol-3-yl]pyrazine Chemical compound C1=NC(OC)=CC=C1N1C(C=2N=CC(=NC=2)C=2C(=C(F)C=CC=2)OC)=NN=C1C HWPDYNZUAISOPP-UHFFFAOYSA-N 0.000 claims description 3
OFTJGQHJFQERAX-UHFFFAOYSA-N 2-(4-fluoro-2-methylphenyl)-5-[5-(methoxymethyl)-4-(6-methoxypyridin-3-yl)-1,2,4-triazol-3-yl]pyridine Chemical compound C=1C=C(OC)N=CC=1N1C(COC)=NN=C1C(C=N1)=CC=C1C1=CC=C(F)C=C1C OFTJGQHJFQERAX-UHFFFAOYSA-N 0.000 claims description 3
YROLZLACGLYWCR-UHFFFAOYSA-N 4-[5-[5-(methoxymethyl)-4-(6-methoxypyridin-3-yl)-1,2,4-triazol-3-yl]pyrazin-2-yl]-3-methylbenzonitrile Chemical compound C=1C=C(OC)N=CC=1N1C(COC)=NN=C1C(N=C1)=CN=C1C1=CC=C(C#N)C=C1C YROLZLACGLYWCR-UHFFFAOYSA-N 0.000 claims description 3
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125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
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UAFXQKAEBVQYOV-UHFFFAOYSA-N 2-(2,3-dimethylphenyl)-5-[5-(2-methoxyethoxymethyl)-4-(6-methoxypyridin-3-yl)-1,2,4-triazol-3-yl]pyridine Chemical compound C=1C=C(OC)N=CC=1N1C(COCCOC)=NN=C1C(C=N1)=CC=C1C1=CC=CC(C)=C1C UAFXQKAEBVQYOV-UHFFFAOYSA-N 0.000 claims description 2
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125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 2
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102100031951 Oxytocin-neurophysin 1 Human genes 0.000 claims 2
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