CA2554382A1

CA2554382A1 - Compounds useful in therapy

Compounds useful in therapy Download PDF

Info

Publication number: CA2554382A1
Authority: CA; Canada
Prior art keywords: dysmenorrhoea; methyl; dihydro; chloro; benzo
Prior art date: 2004-01-13
Legal status : Abandoned

Application number

CA002554382A

Other languages

English (en)

French (fr)

Inventor

Thomas Ryckmans

Current Assignee

Pfizer Corp SRL

Original Assignee

Individual

Priority date

2004-01-13

Filing date

2005-01-05

Publication date

2005-07-28

2005-01-05 Application filed by Individual filed Critical Individual

2005-07-28 Publication of CA2554382A1 publication Critical patent/CA2554382A1/en

Status Abandoned legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 163
238000002560 therapeutic procedure Methods 0.000 title description 3
206010013935 Dysmenorrhoea Diseases 0.000 claims abstract description 54
239000001257 hydrogen Substances 0.000 claims abstract description 16
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 16
208000024172 Cardiovascular disease Diseases 0.000 claims abstract description 14
206010061218 Inflammation Diseases 0.000 claims abstract description 14
206010047700 Vomiting Diseases 0.000 claims abstract description 14
230000004054 inflammatory process Effects 0.000 claims abstract description 14
208000019901 Anxiety disease Diseases 0.000 claims abstract description 12
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 12
201000001320 Atherosclerosis Diseases 0.000 claims abstract description 11
201000009273 Endometriosis Diseases 0.000 claims abstract description 11
206010002383 Angina Pectoris Diseases 0.000 claims abstract description 10
208000001362 Fetal Growth Retardation Diseases 0.000 claims abstract description 10
206010070531 Foetal growth restriction Diseases 0.000 claims abstract description 10
206010019280 Heart failures Diseases 0.000 claims abstract description 10
206010020772 Hypertension Diseases 0.000 claims abstract description 10
206010030113 Oedema Diseases 0.000 claims abstract description 10
206010033314 Ovulation pain Diseases 0.000 claims abstract description 10
208000003782 Raynaud disease Diseases 0.000 claims abstract description 10
208000012322 Raynaud phenomenon Diseases 0.000 claims abstract description 10
230000036506 anxiety Effects 0.000 claims abstract description 10
125000003118 aryl group Chemical group 0.000 claims abstract description 10
208000030941 fetal growth restriction Diseases 0.000 claims abstract description 10
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 10
201000003152 motion sickness Diseases 0.000 claims abstract description 10
230000002028 premature Effects 0.000 claims abstract description 10
206010036596 premature ejaculation Diseases 0.000 claims abstract description 10
206010039073 rheumatoid arthritis Diseases 0.000 claims abstract description 10
229910052736 halogen Inorganic materials 0.000 claims abstract description 8
150000002367 halogens Chemical class 0.000 claims abstract description 8
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 7
125000003545 alkoxy group Chemical group 0.000 claims abstract description 6
229910052727 yttrium Inorganic materials 0.000 claims abstract description 6
125000002947 alkylene group Chemical group 0.000 claims abstract description 5
101000582254 Homo sapiens Nuclear receptor corepressor 2 Proteins 0.000 claims abstract description 3
102100030569 Nuclear receptor corepressor 2 Human genes 0.000 claims abstract description 3
125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 3
125000001424 substituent group Chemical group 0.000 claims abstract description 3
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims abstract description 3
125000004209 (C1-C8) alkyl group Chemical group 0.000 claims abstract 15
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims abstract 9
RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims abstract 2
239000000203 mixture Substances 0.000 claims description 58
-1 1-[4-(8-Chloro-5-methyl-5,6-dihydro-4H-2,3,5,10b-tetraaza-benzo[e] azulen-7-yl)-piperidin-1-yl]-2-o-tolyl-ethanone Chemical compound 0.000 claims description 38
238000009472 formulation Methods 0.000 claims description 35
238000002360 preparation method Methods 0.000 claims description 34
239000003814 drug Substances 0.000 claims description 16
125000001588 azulen-1-yl group Chemical group [H]C1=C([H])C2=C([H])C([H])=C([H])C([H])=C([H])C2=C1* 0.000 claims description 11
239000005557 antagonist Substances 0.000 claims description 8
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239000000825 pharmaceutical preparation Substances 0.000 claims description 7
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239000008194 pharmaceutical composition Substances 0.000 claims description 5
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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
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239000002840 nitric oxide donor Substances 0.000 claims description 3
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OCIOIOFHZYPZMC-UHFFFAOYSA-N 1-[4-(8-chloro-5-methyl-4,6-dihydro-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-1-yl)piperidin-1-yl]butan-1-one Chemical compound C1CN(C(=O)CCC)CCC1C1=NN=C2N1C1=CC=C(Cl)C=C1CN(C)C2 OCIOIOFHZYPZMC-UHFFFAOYSA-N 0.000 claims description 2
101150085511 PEDS1 gene Proteins 0.000 claims description 2
102100037592 Plasmanylethanolamine desaturase Human genes 0.000 claims description 2
HMOVLAJSVILELK-UHFFFAOYSA-N [4-(8-chloro-5-methyl-4,6-dihydro-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-1-yl)piperidin-1-yl]-(1h-indol-3-yl)methanone Chemical compound N12C3=CC=C(Cl)C=C3CN(C)CC2=NN=C1C1CCN(C(=O)C=2C3=CC=CC=C3NC=2)CC1 HMOVLAJSVILELK-UHFFFAOYSA-N 0.000 claims description 2
NBNGJKUNWJBONP-UHFFFAOYSA-N [4-(8-chloro-5-methyl-4,6-dihydro-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-1-yl)piperidin-1-yl]-(3-fluorophenyl)methanone Chemical compound N12C3=CC=C(Cl)C=C3CN(C)CC2=NN=C1C(CC1)CCN1C(=O)C1=CC=CC(F)=C1 NBNGJKUNWJBONP-UHFFFAOYSA-N 0.000 claims description 2
KGIPOTCNKIWDSY-UHFFFAOYSA-N [4-(8-chloro-5-methyl-4,6-dihydro-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-1-yl)piperidin-1-yl]-(3-methoxyphenyl)methanone Chemical compound COC1=CC=CC(C(=O)N2CCC(CC2)C=2N3C4=CC=C(Cl)C=C4CN(C)CC3=NN=2)=C1 KGIPOTCNKIWDSY-UHFFFAOYSA-N 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
125000003386 piperidinyl group Chemical group 0.000 claims description 2
229920003199 poly(diethylsiloxane) Polymers 0.000 claims description 2
DMEKQAADBPOJEO-UHFFFAOYSA-N [4-(8-chloro-5-methyl-4,6-dihydro-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-1-yl)piperidin-1-yl]-(1-methylcyclohexyl)methanone Chemical compound N12C3=CC=C(Cl)C=C3CN(C)CC2=NN=C1C(CC1)CCN1C(=O)C1(C)CCCCC1 DMEKQAADBPOJEO-UHFFFAOYSA-N 0.000 claims 1
LUNAHEGNSDARJA-UHFFFAOYSA-N [4-(8-chloro-5-methyl-4,6-dihydro-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-1-yl)piperidin-1-yl]-(1h-indol-2-yl)methanone Chemical compound N12C3=CC=C(Cl)C=C3CN(C)CC2=NN=C1C1CCN(C(=O)C=2NC3=CC=CC=C3C=2)CC1 LUNAHEGNSDARJA-UHFFFAOYSA-N 0.000 claims 1
QZGGATRCENWZPA-UHFFFAOYSA-N [4-(8-chloro-5-methyl-4,6-dihydro-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-1-yl)piperidin-1-yl]-(1h-indol-6-yl)methanone Chemical compound N12C3=CC=C(Cl)C=C3CN(C)CC2=NN=C1C1CCN(C(=O)C=2C=C3NC=CC3=CC=2)CC1 QZGGATRCENWZPA-UHFFFAOYSA-N 0.000 claims 1
125000000217 alkyl group Chemical group 0.000 abstract description 12
208000029422 Hypernatremia Diseases 0.000 abstract description 6
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150000003839 salts Chemical class 0.000 description 26
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210000004027 cell Anatomy 0.000 description 17
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 16
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