CA2562371A1 - Derives de diarylamine utilises comme bloquants des canaux calciques - Google Patents
Derives de diarylamine utilises comme bloquants des canaux calciques Download PDFInfo
- Publication number
- CA2562371A1 CA2562371A1 CA002562371A CA2562371A CA2562371A1 CA 2562371 A1 CA2562371 A1 CA 2562371A1 CA 002562371 A CA002562371 A CA 002562371A CA 2562371 A CA2562371 A CA 2562371A CA 2562371 A1 CA2562371 A1 CA 2562371A1
- Authority
- CA
- Canada
- Prior art keywords
- phenyl
- piperazin
- methyl
- acetamide
- diphenyl
- 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.)
- Abandoned
Links
- 229940127291 Calcium channel antagonist Drugs 0.000 title description 6
- 239000000480 calcium channel blocker Substances 0.000 title description 3
- 125000005266 diarylamine group Chemical group 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 114
- 102000003922 Calcium Channels Human genes 0.000 claims abstract description 38
- 108090000312 Calcium Channels Proteins 0.000 claims abstract description 38
- 230000000694 effects Effects 0.000 claims abstract description 36
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 34
- 125000001424 substituent group Chemical group 0.000 claims abstract description 34
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 32
- 125000003118 aryl group Chemical group 0.000 claims abstract description 32
- 208000002193 Pain Diseases 0.000 claims abstract description 26
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 19
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 13
- 150000003839 salts Chemical class 0.000 claims abstract description 10
- 208000000094 Chronic Pain Diseases 0.000 claims abstract description 9
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000002837 carbocyclic group Chemical group 0.000 claims abstract description 7
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 5
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 5
- 230000001404 mediated effect Effects 0.000 claims abstract description 5
- 125000004103 aminoalkyl group Chemical group 0.000 claims abstract description 3
- 125000002947 alkylene group Chemical group 0.000 claims abstract 2
- 238000000034 method Methods 0.000 claims description 22
- -1 GF3 Chemical group 0.000 claims description 19
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 17
- 239000003814 drug Substances 0.000 claims description 14
- 208000004296 neuralgia Diseases 0.000 claims description 13
- 208000021722 neuropathic pain Diseases 0.000 claims description 13
- 125000003342 alkenyl group Chemical group 0.000 claims description 12
- 125000000304 alkynyl group Chemical group 0.000 claims description 12
- 229940079593 drug Drugs 0.000 claims description 12
- 238000011282 treatment Methods 0.000 claims description 12
- 208000019901 Anxiety disease Diseases 0.000 claims description 9
- 230000036506 anxiety Effects 0.000 claims description 9
- 230000001537 neural effect Effects 0.000 claims description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 8
- 208000035475 disorder Diseases 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 208000019695 Migraine disease Diseases 0.000 claims description 7
- 206010015037 epilepsy Diseases 0.000 claims description 7
- 206010027599 migraine Diseases 0.000 claims description 7
- 206010019196 Head injury Diseases 0.000 claims description 6
- 206010028980 Neoplasm Diseases 0.000 claims description 6
- 208000005298 acute pain Diseases 0.000 claims description 6
- 201000011510 cancer Diseases 0.000 claims description 6
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 6
- 208000007848 Alcoholism Diseases 0.000 claims description 5
- JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 claims description 5
- 108010081348 HRT1 protein Hairy Proteins 0.000 claims description 5
- 102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 claims description 5
- 206010020853 Hypertonic bladder Diseases 0.000 claims description 5
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 5
- 125000000520 N-substituted aminocarbonyl group Chemical group [*]NC(=O)* 0.000 claims description 5
- 208000009722 Overactive Urinary Bladder Diseases 0.000 claims description 5
- 208000006011 Stroke Diseases 0.000 claims description 5
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 5
- 206010009887 colitis Diseases 0.000 claims description 5
- 206010012601 diabetes mellitus Diseases 0.000 claims description 5
- 206010013663 drug dependence Diseases 0.000 claims description 5
- 208000002551 irritable bowel syndrome Diseases 0.000 claims description 5
- 208000020629 overactive bladder Diseases 0.000 claims description 5
- 208000019116 sleep disease Diseases 0.000 claims description 5
- 208000011117 substance-related disease Diseases 0.000 claims description 5
- 206010065390 Inflammatory pain Diseases 0.000 claims description 4
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 3
- 201000001880 Sexual dysfunction Diseases 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 230000003412 degenerative effect Effects 0.000 claims description 3
- 230000002526 effect on cardiovascular system Effects 0.000 claims description 3
- HDCXQTPVTAIPNZ-UHFFFAOYSA-N n-({[4-(aminosulfonyl)phenyl]amino}carbonyl)-4-methylbenzenesulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)NC1=CC=C(S(N)(=O)=O)C=C1 HDCXQTPVTAIPNZ-UHFFFAOYSA-N 0.000 claims description 3
- 201000000980 schizophrenia Diseases 0.000 claims description 3
- 231100000872 sexual dysfunction Toxicity 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 125000003386 piperidinyl group Chemical group 0.000 claims description 2
- 125000001475 halogen functional group Chemical group 0.000 claims 4
- FMJSSIYEDJFGBC-UHFFFAOYSA-N 1-[4-[(2,3-dichlorophenyl)-phenylmethyl]piperazin-1-yl]-2-(n-phenylanilino)ethanone Chemical compound ClC1=CC=CC(C(N2CCN(CC2)C(=O)CN(C=2C=CC=CC=2)C=2C=CC=CC=2)C=2C=CC=CC=2)=C1Cl FMJSSIYEDJFGBC-UHFFFAOYSA-N 0.000 claims 3
- DPOJHTYMAOYZKG-UHFFFAOYSA-N 1-(4-benzhydrylpiperazin-1-yl)-2-(n-phenylanilino)ethanone Chemical compound C1CN(C(C=2C=CC=CC=2)C=2C=CC=CC=2)CCN1C(=O)CN(C=1C=CC=CC=1)C1=CC=CC=C1 DPOJHTYMAOYZKG-UHFFFAOYSA-N 0.000 claims 2
- SKXLCHNDFHOMRI-UHFFFAOYSA-N 1-[4-[(1-methylpiperidin-3-yl)methyl]piperazin-1-yl]-2-(n-phenylanilino)ethanone Chemical compound C1N(C)CCCC1CN1CCN(C(=O)CN(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 SKXLCHNDFHOMRI-UHFFFAOYSA-N 0.000 claims 2
- SZXAWCKROBFQPN-UHFFFAOYSA-N 1-[4-[(2,4-dichlorophenyl)-phenylmethyl]piperazin-1-yl]-2-(n-phenylanilino)ethanone Chemical compound ClC1=CC(Cl)=CC=C1C(C=1C=CC=CC=1)N1CCN(C(=O)CN(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 SZXAWCKROBFQPN-UHFFFAOYSA-N 0.000 claims 2
- DKVOGZPCCPBBPU-UHFFFAOYSA-N 1-[4-[(2,4-dimethylphenyl)-phenylmethyl]piperazin-1-yl]-2-(n-phenylanilino)ethanone Chemical compound CC1=CC(C)=CC=C1C(C=1C=CC=CC=1)N1CCN(C(=O)CN(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 DKVOGZPCCPBBPU-UHFFFAOYSA-N 0.000 claims 2
- APFIMMRBLUEEJX-UHFFFAOYSA-N 1-[4-[(2-chlorophenyl)-phenylmethyl]piperazin-1-yl]-2-(n-phenylanilino)ethanone Chemical compound ClC1=CC=CC=C1C(C=1C=CC=CC=1)N1CCN(C(=O)CN(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 APFIMMRBLUEEJX-UHFFFAOYSA-N 0.000 claims 2
- YZBMBXSAQFTDCP-UHFFFAOYSA-N 1-[4-[(3-chlorophenyl)-phenylmethyl]piperazin-1-yl]-2-(n-phenylanilino)ethanone Chemical compound ClC1=CC=CC(C(N2CCN(CC2)C(=O)CN(C=2C=CC=CC=2)C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 YZBMBXSAQFTDCP-UHFFFAOYSA-N 0.000 claims 2
- RLEMIIBGFDBVBD-UHFFFAOYSA-N 1-[4-[(4-chlorophenyl)-phenylmethyl]piperazin-1-yl]-2-(n-phenylanilino)ethanone Chemical compound C1=CC(Cl)=CC=C1C(C=1C=CC=CC=1)N1CCN(C(=O)CN(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RLEMIIBGFDBVBD-UHFFFAOYSA-N 0.000 claims 2
- QXNYWQVYZYCACA-UHFFFAOYSA-N 2-(4-benzhydrylpiperazin-1-yl)-n,n-diphenylacetamide Chemical compound C=1C=CC=CC=1N(C=1C=CC=CC=1)C(=O)CN(CC1)CCN1C(C=1C=CC=CC=1)C1=CC=CC=C1 QXNYWQVYZYCACA-UHFFFAOYSA-N 0.000 claims 2
- KRGYCIIPAAXAKA-UHFFFAOYSA-N 2-[4-[(1-methylpiperidin-4-yl)methyl]piperazin-1-yl]-n,n-diphenylacetamide Chemical compound C1CN(C)CCC1CN1CCN(CC(=O)N(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 KRGYCIIPAAXAKA-UHFFFAOYSA-N 0.000 claims 2
- NIMFDABOPDBIHU-UHFFFAOYSA-N 2-[4-[(2,3-dichlorophenyl)-phenylmethyl]piperazin-1-yl]-n,n-diphenylacetamide Chemical compound ClC1=CC=CC(C(N2CCN(CC(=O)N(C=3C=CC=CC=3)C=3C=CC=CC=3)CC2)C=2C=CC=CC=2)=C1Cl NIMFDABOPDBIHU-UHFFFAOYSA-N 0.000 claims 2
- GGKXNHJATNHIDB-UHFFFAOYSA-N 2-[4-[(2,4-dichlorophenyl)-phenylmethyl]piperazin-1-yl]-n,n-diphenylacetamide Chemical compound ClC1=CC(Cl)=CC=C1C(C=1C=CC=CC=1)N1CCN(CC(=O)N(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GGKXNHJATNHIDB-UHFFFAOYSA-N 0.000 claims 2
- RWSPYBHNSGQITH-UHFFFAOYSA-N 2-[4-[(2,4-dimethylphenyl)-phenylmethyl]piperazin-1-yl]-n,n-diphenylacetamide Chemical compound CC1=CC(C)=CC=C1C(C=1C=CC=CC=1)N1CCN(CC(=O)N(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWSPYBHNSGQITH-UHFFFAOYSA-N 0.000 claims 2
- ROOQZCIZDJRFFY-UHFFFAOYSA-N 2-[4-[(2-chlorophenyl)-phenylmethyl]piperazin-1-yl]-n,n-diphenylacetamide Chemical compound ClC1=CC=CC=C1C(C=1C=CC=CC=1)N1CCN(CC(=O)N(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 ROOQZCIZDJRFFY-UHFFFAOYSA-N 0.000 claims 2
- NTCNYPJNYIBPSC-UHFFFAOYSA-N 2-[4-[(3-chlorophenyl)-phenylmethyl]piperazin-1-yl]-n,n-diphenylacetamide Chemical compound ClC1=CC=CC(C(N2CCN(CC(=O)N(C=3C=CC=CC=3)C=3C=CC=CC=3)CC2)C=2C=CC=CC=2)=C1 NTCNYPJNYIBPSC-UHFFFAOYSA-N 0.000 claims 2
- CEXBUHRJNQKOBZ-UHFFFAOYSA-N 2-[4-[(4-chlorophenyl)-phenylmethyl]piperazin-1-yl]-n,n-diphenylacetamide Chemical compound C1=CC(Cl)=CC=C1C(C=1C=CC=CC=1)N1CCN(CC(=O)N(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 CEXBUHRJNQKOBZ-UHFFFAOYSA-N 0.000 claims 2
- NYYPRPLNQDSXRP-UHFFFAOYSA-N 2-[4-[3-(dimethylamino)propyl]piperazin-1-yl]-n,n-diphenylacetamide Chemical compound C1CN(CCCN(C)C)CCN1CC(=O)N(C=1C=CC=CC=1)C1=CC=CC=C1 NYYPRPLNQDSXRP-UHFFFAOYSA-N 0.000 claims 2
- OSFNXHBALFELHH-UHFFFAOYSA-N 4-benzhydryl-1-[2-(n-phenylanilino)acetyl]piperazine-2-carboxylic acid Chemical compound OC(=O)C1CN(C(C=2C=CC=CC=2)C=2C=CC=CC=2)CCN1C(=O)CN(C=1C=CC=CC=1)C1=CC=CC=C1 OSFNXHBALFELHH-UHFFFAOYSA-N 0.000 claims 2
- PVVPSVNUJPFQPW-UHFFFAOYSA-N 1-[4-[(1-methylpiperidin-4-yl)methyl]piperazin-1-yl]-2-(n-phenylanilino)ethanone Chemical compound C1CN(C)CCC1CN1CCN(C(=O)CN(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 PVVPSVNUJPFQPW-UHFFFAOYSA-N 0.000 claims 1
- FARJWOMDJXMQPH-UHFFFAOYSA-N 1-[4-[(4-methoxyphenyl)-[4-(trifluoromethyl)phenyl]methyl]piperazin-1-yl]-2-(n-phenylanilino)ethanone Chemical compound C1=CC(OC)=CC=C1C(C=1C=CC(=CC=1)C(F)(F)F)N1CCN(C(=O)CN(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 FARJWOMDJXMQPH-UHFFFAOYSA-N 0.000 claims 1
- QSXIVAXDDHAOEH-UHFFFAOYSA-N 1-[4-[(4-tert-butylphenyl)-phenylmethyl]piperazin-1-yl]-2-(n-phenylanilino)ethanone Chemical compound C1=CC(C(C)(C)C)=CC=C1C(C=1C=CC=CC=1)N1CCN(C(=O)CN(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 QSXIVAXDDHAOEH-UHFFFAOYSA-N 0.000 claims 1
- PKXBXCYVGWVZFJ-UHFFFAOYSA-N 1-[4-[1,3-benzodioxol-5-yl(phenyl)methyl]piperazin-1-yl]-2-(n-phenylanilino)ethanone Chemical compound C1CN(C(C=2C=CC=CC=2)C=2C=C3OCOC3=CC=2)CCN1C(=O)CN(C=1C=CC=CC=1)C1=CC=CC=C1 PKXBXCYVGWVZFJ-UHFFFAOYSA-N 0.000 claims 1
- SDZZVKZLVNXMAA-UHFFFAOYSA-N 1-benzhydryl-4-[2-(n-phenylanilino)acetyl]piperazine-2,5-dione Chemical compound C1C(=O)N(C(C=2C=CC=CC=2)C=2C=CC=CC=2)CC(=O)N1C(=O)CN(C=1C=CC=CC=1)C1=CC=CC=C1 SDZZVKZLVNXMAA-UHFFFAOYSA-N 0.000 claims 1
- LBRMOKAVQPUHFR-UHFFFAOYSA-N 2-(4-benzhydryl-2,3-dioxopiperazin-1-yl)-n,n-diphenylacetamide Chemical compound C=1C=CC=CC=1N(C=1C=CC=CC=1)C(=O)CN(C(C1=O)=O)CCN1C(C=1C=CC=CC=1)C1=CC=CC=C1 LBRMOKAVQPUHFR-UHFFFAOYSA-N 0.000 claims 1
- OBXOTGZFQOWABC-UHFFFAOYSA-N 2-(4-benzhydryl-2,5-dioxopiperazin-1-yl)-n,n-diphenylacetamide Chemical compound C=1C=CC=CC=1N(C=1C=CC=CC=1)C(=O)CN(C(C1)=O)CC(=O)N1C(C=1C=CC=CC=1)C1=CC=CC=C1 OBXOTGZFQOWABC-UHFFFAOYSA-N 0.000 claims 1
- UPYRYNWGOSUWQK-UHFFFAOYSA-N 2-(n-phenylanilino)-1-[4-(pyridin-2-ylmethyl)piperazin-1-yl]ethanone Chemical compound C1CN(CC=2N=CC=CC=2)CCN1C(=O)CN(C=1C=CC=CC=1)C1=CC=CC=C1 UPYRYNWGOSUWQK-UHFFFAOYSA-N 0.000 claims 1
- ZDJCGICDLDTLBE-UHFFFAOYSA-N 2-(n-phenylanilino)-1-[4-(pyridin-3-ylmethyl)piperazin-1-yl]ethanone Chemical compound C1CN(CC=2C=NC=CC=2)CCN1C(=O)CN(C=1C=CC=CC=1)C1=CC=CC=C1 ZDJCGICDLDTLBE-UHFFFAOYSA-N 0.000 claims 1
- USCUPPLJGUYXHP-UHFFFAOYSA-N 2-(n-phenylanilino)-1-[4-[(1-phenylpiperidin-4-yl)methyl]piperazin-1-yl]ethanone Chemical compound C1CN(CC2CCN(CC2)C=2C=CC=CC=2)CCN1C(=O)CN(C=1C=CC=CC=1)C1=CC=CC=C1 USCUPPLJGUYXHP-UHFFFAOYSA-N 0.000 claims 1
- XZKMPNBFUZUQSW-UHFFFAOYSA-N 2-(n-phenylanilino)-1-[4-[phenyl(pyridin-2-yl)methyl]piperazin-1-yl]ethanone Chemical compound C1CN(C(C=2C=CC=CC=2)C=2N=CC=CC=2)CCN1C(=O)CN(C=1C=CC=CC=1)C1=CC=CC=C1 XZKMPNBFUZUQSW-UHFFFAOYSA-N 0.000 claims 1
- PNXILTVTJVNILC-UHFFFAOYSA-N 2-(n-phenylanilino)-1-[4-[phenyl(pyridin-3-yl)methyl]piperazin-1-yl]ethanone Chemical compound C1CN(C(C=2C=CC=CC=2)C=2C=NC=CC=2)CCN1C(=O)CN(C=1C=CC=CC=1)C1=CC=CC=C1 PNXILTVTJVNILC-UHFFFAOYSA-N 0.000 claims 1
- JXYATHVXQYVBJO-UHFFFAOYSA-N 2-[(1-benzhydrylpiperidin-4-yl)-methylamino]-n,n-diphenylacetamide Chemical compound C1CN(C(C=2C=CC=CC=2)C=2C=CC=CC=2)CCC1N(C)CC(=O)N(C=1C=CC=CC=1)C1=CC=CC=C1 JXYATHVXQYVBJO-UHFFFAOYSA-N 0.000 claims 1
- LRKALVWAAPNJRN-UHFFFAOYSA-N 2-[4-[(1-methylpiperidin-3-yl)methyl]piperazin-1-yl]-n,n-diphenylacetamide Chemical compound C1N(C)CCCC1CN1CCN(CC(=O)N(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 LRKALVWAAPNJRN-UHFFFAOYSA-N 0.000 claims 1
- INSJYMBFPUNNMW-UHFFFAOYSA-N 2-[4-[(1-methylpiperidin-4-yl)methyl]piperazin-1-yl]-2-oxo-n,n-diphenylacetamide Chemical compound C1CN(C)CCC1CN1CCN(C(=O)C(=O)N(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 INSJYMBFPUNNMW-UHFFFAOYSA-N 0.000 claims 1
- KVHLLKTXBXVGEW-UHFFFAOYSA-N 2-[4-[(4-methoxyphenyl)-[4-(trifluoromethyl)phenyl]methyl]piperazin-1-yl]-n,n-diphenylacetamide Chemical compound C1=CC(OC)=CC=C1C(C=1C=CC(=CC=1)C(F)(F)F)N1CCN(CC(=O)N(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 KVHLLKTXBXVGEW-UHFFFAOYSA-N 0.000 claims 1
- UDSQWVDNIUDBJB-UHFFFAOYSA-N 2-[4-[(4-methoxyphenyl)-phenylmethyl]piperazin-1-yl]-n,n-diphenylacetamide Chemical compound C1=CC(OC)=CC=C1C(C=1C=CC=CC=1)N1CCN(CC(=O)N(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 UDSQWVDNIUDBJB-UHFFFAOYSA-N 0.000 claims 1
- LDQDTCVWNQAJHI-UHFFFAOYSA-N 2-[4-[(4-tert-butylphenyl)-phenylmethyl]piperazin-1-yl]-n,n-diphenylacetamide Chemical compound C1=CC(C(C)(C)C)=CC=C1C(C=1C=CC=CC=1)N1CCN(CC(=O)N(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 LDQDTCVWNQAJHI-UHFFFAOYSA-N 0.000 claims 1
- QLWOJJRGGXBYKN-UHFFFAOYSA-N 2-[4-[1,3-benzodioxol-5-yl(phenyl)methyl]piperazin-1-yl]-n,n-diphenylacetamide Chemical compound C=1C=CC=CC=1N(C=1C=CC=CC=1)C(=O)CN(CC1)CCN1C(C=1C=C2OCOC2=CC=1)C1=CC=CC=C1 QLWOJJRGGXBYKN-UHFFFAOYSA-N 0.000 claims 1
- OVFVLNJXORDHRZ-UHFFFAOYSA-N 2-oxo-n,n-diphenyl-2-[4-[(1-phenylpiperidin-4-yl)methyl]piperazin-1-yl]acetamide Chemical compound C1CN(CC2CCN(CC2)C=2C=CC=CC=2)CCN1C(=O)C(=O)N(C=1C=CC=CC=1)C1=CC=CC=C1 OVFVLNJXORDHRZ-UHFFFAOYSA-N 0.000 claims 1
- PLTFXOUUDYHREG-UHFFFAOYSA-N 4-benzhydryl-1-[2-oxo-2-(n-phenylanilino)ethyl]piperazine-2-carboxylic acid Chemical compound OC(=O)C1CN(C(C=2C=CC=CC=2)C=2C=CC=CC=2)CCN1CC(=O)N(C=1C=CC=CC=1)C1=CC=CC=C1 PLTFXOUUDYHREG-UHFFFAOYSA-N 0.000 claims 1
- NXUWQYSOBUBOBU-UHFFFAOYSA-N ClC1=CC=C(C=C1)C(N1CCN(CC1)C(C(=O)N(C1=CC=CC=C1)C1=CC=CC=C1)=O)C1CCN(CC1)C Chemical compound ClC1=CC=C(C=C1)C(N1CCN(CC1)C(C(=O)N(C1=CC=CC=C1)C1=CC=CC=C1)=O)C1CCN(CC1)C NXUWQYSOBUBOBU-UHFFFAOYSA-N 0.000 claims 1
- AOYMTRHODPHBBQ-UHFFFAOYSA-N ethyl 4-benzhydryl-1-[2-oxo-2-(n-phenylanilino)ethyl]piperazine-2-carboxylate Chemical compound CCOC(=O)C1CN(C(C=2C=CC=CC=2)C=2C=CC=CC=2)CCN1CC(=O)N(C=1C=CC=CC=1)C1=CC=CC=C1 AOYMTRHODPHBBQ-UHFFFAOYSA-N 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- WXXLGOMQNIVFQX-UHFFFAOYSA-N n,n-diphenyl-2-[4-[phenyl(pyridin-2-yl)methyl]piperazin-1-yl]acetamide Chemical compound C=1C=CC=CC=1N(C=1C=CC=CC=1)C(=O)CN(CC1)CCN1C(C=1N=CC=CC=1)C1=CC=CC=C1 WXXLGOMQNIVFQX-UHFFFAOYSA-N 0.000 claims 1
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Classifications
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- C07D—HETEROCYCLIC COMPOUNDS
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- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
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- C07D211/58—Nitrogen atoms attached in position 4
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- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
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- C07D295/15—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
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Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US10/821,584 US20040259866A1 (en) | 1998-06-30 | 2004-04-09 | Calcium channel blockers comprising two benzhydril moieties |
US10/821,584 | 2004-04-09 | ||
US10/928,564 US20050227999A1 (en) | 2004-04-09 | 2004-08-27 | Diarylamine derivatives as calcium channel blockers |
US10/928,564 | 2004-08-27 | ||
PCT/CA2005/000544 WO2005097779A1 (fr) | 2004-04-09 | 2005-04-08 | Derives de diarylamine utilises comme bloquants des canaux calciques |
Publications (1)
Publication Number | Publication Date |
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CA2562371A1 true CA2562371A1 (fr) | 2005-10-20 |
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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CA002562371A Abandoned CA2562371A1 (fr) | 2004-04-09 | 2005-04-08 | Derives de diarylamine utilises comme bloquants des canaux calciques |
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EP (1) | EP1745042A4 (fr) |
JP (1) | JP2007532492A (fr) |
KR (1) | KR20070044803A (fr) |
AU (1) | AU2005231872A1 (fr) |
BR (1) | BRPI0509715A (fr) |
CA (1) | CA2562371A1 (fr) |
WO (1) | WO2005097779A1 (fr) |
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TW200630337A (en) | 2004-10-14 | 2006-09-01 | Euro Celtique Sa | Piperidinyl compounds and the use thereof |
EP1976823A1 (fr) * | 2005-12-16 | 2008-10-08 | Neuropharma, S.A. | Dérivés de dibenzène en tant que bloqueurs des canaux calciques |
EP1798220A1 (fr) | 2005-12-16 | 2007-06-20 | Neuropharma S.A. | Derivés de dibenzène comme inhibiteurs des canaux calciques |
WO2007110449A1 (fr) | 2006-03-29 | 2007-10-04 | Euro-Celtique S.A. | Composés de benzènesulfonamide et utilisation de ceux-ci |
WO2007118854A1 (fr) | 2006-04-13 | 2007-10-25 | Euro-Celtique S.A. | Composés à base de benzènesulfonamide et leur utilisation |
US8791264B2 (en) | 2006-04-13 | 2014-07-29 | Purdue Pharma L.P. | Benzenesulfonamide compounds and their use as blockers of calcium channels |
GB0700893D0 (en) | 2007-01-17 | 2007-02-21 | King S College London | Male contraceptive |
WO2008124118A1 (fr) | 2007-04-09 | 2008-10-16 | Purdue Pharma L.P. | Composés benzènesulfonylés et leur utilisation |
US8765736B2 (en) | 2007-09-28 | 2014-07-01 | Purdue Pharma L.P. | Benzenesulfonamide compounds and the use thereof |
WO2013110134A1 (fr) * | 2012-01-25 | 2013-08-01 | Spinifex Pharmaceuticals Pty Ltd | Composés hétérocycliques et leurs procédés d'utilisation |
Family Cites Families (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4411904A (en) * | 1981-05-29 | 1983-10-25 | Warner-Lambert Company | Diphenylpropanamines, compositions thereof and use thereof |
ES2010104A6 (es) * | 1989-01-26 | 1989-10-16 | Gema Sa | Procedimiento de preparacion de ureas asimetricas y utilizacion de las mismas. |
TW205034B (fr) * | 1990-09-13 | 1993-05-01 | Pola Kasei Kogyo Kk | |
ES2156934T3 (es) * | 1993-12-08 | 2001-08-01 | Alcon Lab Inc | Compuestos que presentan una potente actividad de antagonistas del calcio y de antioxidantes y su utilizacion como agentes citoprotectores. |
JP3064425B2 (ja) * | 1995-09-15 | 2000-07-12 | ノイロサーチ アクティーゼルスカブ | カルシウムチャンネル・ブロッカーとしてのピペリジン化合物 |
GB9526560D0 (en) * | 1995-12-27 | 1996-02-28 | Bayer Ag | Use of 2-Amino-Heterocycles |
IT1293804B1 (it) * | 1997-08-01 | 1999-03-10 | Recordati Chem Pharm | Diarilalchilpiperazine attive sulle basse vie urinarie |
US6951862B2 (en) * | 1998-06-30 | 2005-10-04 | Neuromed Technologies, Inc. | Calcium channel blockers comprising two benzhydril moieties |
US6011035A (en) * | 1998-06-30 | 2000-01-04 | Neuromed Technologies Inc. | Calcium channel blockers |
US7186726B2 (en) * | 1998-06-30 | 2007-03-06 | Neuromed Pharmaceuticals Ltd. | Preferentially substituted calcium channel blockers |
US6387897B1 (en) * | 1998-06-30 | 2002-05-14 | Neuromed Technologies, Inc. | Preferentially substituted calcium channel blockers |
PL212089B1 (pl) * | 2002-03-13 | 2012-08-31 | Janssen Pharmaceutica Nv | Związki heterocykliczne jako inhibitory deacetylazy histonowej, kompozycja farmaceutyczna je zawierająca, ich zastosowanie, sposób wytwarzania, sposób wykrywania lub identyfikacji HDAC oraz kompozycja |
-
2005
- 2005-04-08 WO PCT/CA2005/000544 patent/WO2005097779A1/fr active Application Filing
- 2005-04-08 BR BRPI0509715-0A patent/BRPI0509715A/pt not_active IP Right Cessation
- 2005-04-08 AU AU2005231872A patent/AU2005231872A1/en not_active Abandoned
- 2005-04-08 KR KR1020067023525A patent/KR20070044803A/ko not_active Application Discontinuation
- 2005-04-08 JP JP2007506628A patent/JP2007532492A/ja active Pending
- 2005-04-08 CA CA002562371A patent/CA2562371A1/fr not_active Abandoned
- 2005-04-08 EP EP05734348A patent/EP1745042A4/fr not_active Withdrawn
Also Published As
Publication number | Publication date |
---|---|
WO2005097779A1 (fr) | 2005-10-20 |
EP1745042A4 (fr) | 2010-07-14 |
JP2007532492A (ja) | 2007-11-15 |
KR20070044803A (ko) | 2007-04-30 |
EP1745042A1 (fr) | 2007-01-24 |
AU2005231872A1 (en) | 2005-10-20 |
BRPI0509715A (pt) | 2007-09-18 |
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