NO972937L - Farmasöytiske piperazinforbindelser - Google Patents
Farmasöytiske piperazinforbindelserInfo
- Publication number
- NO972937L NO972937L NO972937A NO972937A NO972937L NO 972937 L NO972937 L NO 972937L NO 972937 A NO972937 A NO 972937A NO 972937 A NO972937 A NO 972937A NO 972937 L NO972937 L NO 972937L
- Authority
- NO
- Norway
- Prior art keywords
- phenyl
- ethyl
- dimethoxy
- tetrahydro
- piperazinylidene
- Prior art date
Links
- 150000004885 piperazines Chemical class 0.000 title claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 132
- 238000000034 method Methods 0.000 claims description 34
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 29
- 229910052739 hydrogen Inorganic materials 0.000 claims description 29
- 230000036457 multidrug resistance Effects 0.000 claims description 29
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 28
- 239000001257 hydrogen Substances 0.000 claims description 27
- XXUNIGZDNWWYED-UHFFFAOYSA-N 2-methylbenzamide Chemical compound CC1=CC=CC=C1C(N)=O XXUNIGZDNWWYED-UHFFFAOYSA-N 0.000 claims description 20
- 229910052736 halogen Inorganic materials 0.000 claims description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
- 150000002367 halogens Chemical class 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 17
- -1 methylenedioxy group Chemical group 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 15
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 13
- 239000003814 drug Substances 0.000 claims description 12
- 229940079593 drug Drugs 0.000 claims description 11
- 239000003960 organic solvent Substances 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 10
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 5
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 5
- 125000002541 furyl group Chemical group 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 125000004076 pyridyl group Chemical group 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- GAEOJCDYFMABJF-LPIHMFRFSA-N 2-[(2z,5z)-2-benzylidene-5-[[3-[[4-[2-(6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl)ethyl]phenyl]carbamoyl]phenyl]methylidene]-3,6-dioxopiperazin-1-yl]acetic acid Chemical compound C1C=2C=C(OC)C(OC)=CC=2CCN1CCC(C=C1)=CC=C1NC(=O)C(C=1)=CC=CC=1\C=C(C(N1CC(O)=O)=O)/NC(=O)\C1=C\C1=CC=CC=C1 GAEOJCDYFMABJF-LPIHMFRFSA-N 0.000 claims description 2
- VZHRVVBUCDKXIJ-LPIHMFRFSA-N 3-[(Z)-[(5Z)-5-[(2-chlorophenyl)methylidene]-4-methyl-3,6-dioxopiperazin-2-ylidene]methyl]-N-[4-[2-(6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl)ethyl]phenyl]benzamide Chemical compound COC1=CC2=C(CN(CCC3=CC=C(NC(=O)C4=CC(\C=C5/NC(=O)\C(=C\C6=C(Cl)C=CC=C6)N(C)C5=O)=CC=C4)C=C3)CC2)C=C1OC VZHRVVBUCDKXIJ-LPIHMFRFSA-N 0.000 claims description 2
- VSWPXILDBNFXIB-YWQXDYITSA-N 3-[(z)-[(5z)-5-(cyclohexylmethylidene)-4-methyl-3,6-dioxopiperazin-2-ylidene]methyl]-n-[4-[2-(6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl)ethyl]phenyl]benzamide Chemical compound C1C=2C=C(OC)C(OC)=CC=2CCN1CCC(C=C1)=CC=C1NC(=O)C(C=1)=CC=CC=1\C=C(C(N1C)=O)/NC(=O)\C1=C\C1CCCCC1 VSWPXILDBNFXIB-YWQXDYITSA-N 0.000 claims description 2
- AFSLGMUGRASLRI-LPIHMFRFSA-N 3-[(z)-[(5z)-5-[(3-chlorophenyl)methylidene]-4-methyl-3,6-dioxopiperazin-2-ylidene]methyl]-n-[4-[2-(6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl)ethyl]phenyl]benzamide Chemical compound C1C=2C=C(OC)C(OC)=CC=2CCN1CCC(C=C1)=CC=C1NC(=O)C(C=1)=CC=CC=1\C=C(C(N1C)=O)/NC(=O)\C1=C\C1=CC=CC(Cl)=C1 AFSLGMUGRASLRI-LPIHMFRFSA-N 0.000 claims description 2
- LULGGPSIFKBXMT-CKPXSJKLSA-N 3-[(z)-[(5z)-5-benzylidene-4-(cyclopropylmethyl)-3,6-dioxopiperazin-2-ylidene]methyl]-n-[4-[2-(6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl)ethyl]phenyl]benzamide Chemical compound C1C=2C=C(OC)C(OC)=CC=2CCN1CCC(C=C1)=CC=C1NC(=O)C(C=1)=CC=CC=1\C=C(C(N1CC2CC2)=O)/NC(=O)\C1=C\C1=CC=CC=C1 LULGGPSIFKBXMT-CKPXSJKLSA-N 0.000 claims description 2
- LNDHBVSESSZAIU-HSZPEWSQSA-N 3-[(z)-[(5z)-5-benzylidene-4-ethyl-3,6-dioxopiperazin-2-ylidene]methyl]-n-[4-[2-(6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl)ethyl]phenyl]benzamide Chemical compound CCN1C(=O)\C(=C\C=2C=C(C=CC=2)C(=O)NC=2C=CC(CCN3CC4=CC(OC)=C(OC)C=C4CC3)=CC=2)NC(=O)\C1=C\C1=CC=CC=C1 LNDHBVSESSZAIU-HSZPEWSQSA-N 0.000 claims description 2
- JWMWQAUZAUFNIN-QASZCPKBSA-N 4-[(z)-[(5z)-4-benzyl-5-benzylidene-3,6-dioxopiperazin-2-ylidene]methyl]-n-[4-[2-(6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl)ethyl]phenyl]benzamide Chemical compound C1C=2C=C(OC)C(OC)=CC=2CCN1CCC(C=C1)=CC=C1NC(=O)C(C=C1)=CC=C1\C=C(C(N1CC=2C=CC=CC=2)=O)/NC(=O)\C1=C\C1=CC=CC=C1 JWMWQAUZAUFNIN-QASZCPKBSA-N 0.000 claims description 2
- AZDVUUMYSDAHFB-YWQXDYITSA-N 4-[(z)-[(5z)-5-(cyclohexylmethylidene)-4-methyl-3,6-dioxopiperazin-2-ylidene]methyl]-n-[4-[2-(6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl)ethyl]phenyl]benzamide Chemical compound C1C=2C=C(OC)C(OC)=CC=2CCN1CCC(C=C1)=CC=C1NC(=O)C(C=C1)=CC=C1\C=C(C(N1C)=O)/NC(=O)\C1=C\C1CCCCC1 AZDVUUMYSDAHFB-YWQXDYITSA-N 0.000 claims description 2
- HHGLBCGKPGBNMG-LPIHMFRFSA-N 4-[(z)-[(5z)-5-[(3-chlorophenyl)methylidene]-4-methyl-3,6-dioxopiperazin-2-ylidene]methyl]-n-[4-[2-(6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl)ethyl]phenyl]benzamide Chemical compound C1C=2C=C(OC)C(OC)=CC=2CCN1CCC(C=C1)=CC=C1NC(=O)C(C=C1)=CC=C1\C=C(C(N1C)=O)/NC(=O)\C1=C\C1=CC=CC(Cl)=C1 HHGLBCGKPGBNMG-LPIHMFRFSA-N 0.000 claims description 2
- IBVIZIOPXPHKOB-LPIHMFRFSA-N 4-[(z)-[(5z)-5-[(4-chlorophenyl)methylidene]-4-methyl-3,6-dioxopiperazin-2-ylidene]methyl]-n-[4-[2-(6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl)ethyl]phenyl]benzamide Chemical compound C1C=2C=C(OC)C(OC)=CC=2CCN1CCC(C=C1)=CC=C1NC(=O)C(C=C1)=CC=C1\C=C(C(N1C)=O)/NC(=O)\C1=C\C1=CC=C(Cl)C=C1 IBVIZIOPXPHKOB-LPIHMFRFSA-N 0.000 claims description 2
- IMNHZHFEHWIUPQ-HSZPEWSQSA-N 4-[(z)-[(5z)-5-benzylidene-4-ethyl-3,6-dioxopiperazin-2-ylidene]methyl]-n-[4-[2-(6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl)ethyl]phenyl]benzamide Chemical compound CCN1C(=O)\C(=C\C=2C=CC(=CC=2)C(=O)NC=2C=CC(CCN3CC4=CC(OC)=C(OC)C=C4CC3)=CC=2)NC(=O)\C1=C\C1=CC=CC=C1 IMNHZHFEHWIUPQ-HSZPEWSQSA-N 0.000 claims description 2
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 2
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 2
- GJPZEJYOLLPGKQ-PXDBBHOGSA-N N-[4-[2-(6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl)ethyl]phenyl]-3-[(Z)-[(5Z)-4-methyl-5-(naphthalen-1-ylmethylidene)-3,6-dioxopiperazin-2-ylidene]methyl]benzamide Chemical compound c1c(OC)c(OC)cc(C2)c1CCN2CCc1ccc(NC(=O)c2cccc(c2)\C=c/2c(=O)n(C)c(/c([nH]\2)=O)=C\c2cccc3c2cccc3)cc1 GJPZEJYOLLPGKQ-PXDBBHOGSA-N 0.000 claims description 2
- YNVWWCFEGXMQMQ-VANQDGIVSA-N [2-[(z)-[(5z)-5-[[3-[[4-[2-(6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl)ethyl]phenyl]carbamoyl]phenyl]methylidene]-1-methyl-3,6-dioxopiperazin-2-ylidene]methyl]phenyl] acetate Chemical compound C1C=2C=C(OC)C(OC)=CC=2CCN1CCC(C=C1)=CC=C1NC(=O)C(C=1)=CC=CC=1\C=C(C(N1C)=O)/NC(=O)\C1=C\C1=CC=CC=C1OC(C)=O YNVWWCFEGXMQMQ-VANQDGIVSA-N 0.000 claims description 2
- NEMWFLYOMMLWMD-XEMPJQOTSA-N [3-[(z)-[(5z)-5-[[3-[[4-[2-(6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl)ethyl]phenyl]carbamoyl]phenyl]methylidene]-1-methyl-3,6-dioxopiperazin-2-ylidene]methyl]phenyl] acetate Chemical compound C1C=2C=C(OC)C(OC)=CC=2CCN1CCC(C=C1)=CC=C1NC(=O)C(C=1)=CC=CC=1\C=C(C(N1C)=O)/NC(=O)\C1=C\C1=CC=CC(OC(C)=O)=C1 NEMWFLYOMMLWMD-XEMPJQOTSA-N 0.000 claims description 2
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- UTHDNQZLEUCHCA-JTTISPGVSA-N ethyl 2-[(2z,5z)-2-benzylidene-5-[[3-[[4-[2-(6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl)ethyl]phenyl]carbamoyl]phenyl]methylidene]-3,6-dioxopiperazin-1-yl]acetate Chemical compound CCOC(=O)CN1C(=O)\C(=C\C=2C=C(C=CC=2)C(=O)NC=2C=CC(CCN3CC4=CC(OC)=C(OC)C=C4CC3)=CC=2)NC(=O)\C1=C\C1=CC=CC=C1 UTHDNQZLEUCHCA-JTTISPGVSA-N 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- WZXXNTKUPAIPGW-VANQDGIVSA-N methyl 2-[(2z,5z)-2-benzylidene-5-[[3-[[4-[2-(6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl)ethyl]phenyl]carbamoyl]phenyl]methylidene]-3,6-dioxopiperazin-1-yl]acetate Chemical compound COC(=O)CN1C(=O)\C(=C\C=2C=C(C=CC=2)C(=O)NC=2C=CC(CCN3CC4=CC(OC)=C(OC)C=C4CC3)=CC=2)NC(=O)\C1=C\C1=CC=CC=C1 WZXXNTKUPAIPGW-VANQDGIVSA-N 0.000 claims description 2
- WLFJHNWIUYKMRL-VFHXEFSMSA-N n-[2-(6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl)ethyl]-3-[(z)-[(5z)-4-methyl-3,6-dioxo-5-(3-phenylpropylidene)piperazin-2-ylidene]methyl]benzamide Chemical compound C1C=2C=C(OC)C(OC)=CC=2CCN1CCNC(=O)C(C=1)=CC=CC=1\C=C(C(N1C)=O)/NC(=O)\C1=C\CCC1=CC=CC=C1 WLFJHNWIUYKMRL-VFHXEFSMSA-N 0.000 claims description 2
- NIHYIHSLXCXAFX-KRFZJYALSA-N n-[2-(6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl)ethyl]-4-[(z)-[(5z)-4-methyl-3,6-dioxo-5-(3-phenylpropylidene)piperazin-2-ylidene]methyl]benzamide Chemical compound C1C=2C=C(OC)C(OC)=CC=2CCN1CCNC(=O)C(C=C1)=CC=C1\C=C(C(N1C)=O)/NC(=O)\C1=C\CCC1=CC=CC=C1 NIHYIHSLXCXAFX-KRFZJYALSA-N 0.000 claims description 2
- VLGMBRZXBCWLPY-BEORVMNHSA-N n-[4-[2-(6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl)ethyl]phenyl]-3-[(z)-[(5z)-4-methyl-3,6-dioxo-5-(thiophen-2-ylmethylidene)piperazin-2-ylidene]methyl]benzamide Chemical compound C1C=2C=C(OC)C(OC)=CC=2CCN1CCC(C=C1)=CC=C1NC(=O)C(C=1)=CC=CC=1\C=C(C(N1C)=O)/NC(=O)\C1=C\C1=CC=CS1 VLGMBRZXBCWLPY-BEORVMNHSA-N 0.000 claims description 2
- JVLZNBZOCPFCJN-HEZNUULDSA-N n-[4-[2-(6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl)ethyl]phenyl]-3-[(z)-[(5z)-4-methyl-3,6-dioxo-5-(thiophen-3-ylmethylidene)piperazin-2-ylidene]methyl]benzamide Chemical compound C1C=2C=C(OC)C(OC)=CC=2CCN1CCC(C=C1)=CC=C1NC(=O)C(C=1)=CC=CC=1\C=C(C(N1C)=O)/NC(=O)\C1=C\C=1C=CSC=1 JVLZNBZOCPFCJN-HEZNUULDSA-N 0.000 claims description 2
- DHHYWFVEXOEYQF-PPUHNOCVSA-N n-[4-[2-(6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl)ethyl]phenyl]-3-[(z)-[(5z)-4-methyl-3,6-dioxo-5-[[(4s)-4-prop-1-en-2-ylcyclohexen-1-yl]methylidene]piperazin-2-ylidene]methyl]benzamide Chemical compound C1C=2C=C(OC)C(OC)=CC=2CCN1CCC(C=C1)=CC=C1NC(=O)C(C=1)=CC=CC=1\C=C(C(N1C)=O)/NC(=O)\C1=C\C1=CC[C@@H](C(C)=C)CC1 DHHYWFVEXOEYQF-PPUHNOCVSA-N 0.000 claims description 2
- LLHJNNKUEFHGMG-GCEMHJBXSA-N n-[4-[2-(6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl)ethyl]phenyl]-3-[(z)-[(5z)-4-methyl-3,6-dioxo-5-pentylidenepiperazin-2-ylidene]methyl]benzamide Chemical compound N1C(=O)C(=C/CCCC)/N(C)C(=O)\C1=C\C1=CC=CC(C(=O)NC=2C=CC(CCN3CC4=CC(OC)=C(OC)C=C4CC3)=CC=2)=C1 LLHJNNKUEFHGMG-GCEMHJBXSA-N 0.000 claims description 2
- QEGNZHVGNUUXJD-UXNCMSBCSA-N n-[4-[2-(6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl)ethyl]phenyl]-3-[(z)-[(5z)-4-methyl-5-(2-methylpropylidene)-3,6-dioxopiperazin-2-ylidene]methyl]benzamide Chemical compound C1C=2C=C(OC)C(OC)=CC=2CCN1CCC(C=C1)=CC=C1NC(=O)C(C=1)=CC=CC=1\C=C1/NC(=O)\C(=C\C(C)C)N(C)C1=O QEGNZHVGNUUXJD-UXNCMSBCSA-N 0.000 claims description 2
- UMVDXPFNYQMLDY-PXDBBHOGSA-N n-[4-[2-(6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl)ethyl]phenyl]-3-[(z)-[(5z)-4-methyl-5-(naphthalen-2-ylmethylidene)-3,6-dioxopiperazin-2-ylidene]methyl]benzamide Chemical compound C1=CC=CC2=CC(/C=C3/C(=O)N\C(C(N3C)=O)=C/C=3C=CC=C(C=3)C(=O)NC3=CC=C(C=C3)CCN3CCC=4C=C(C(=CC=4C3)OC)OC)=CC=C21 UMVDXPFNYQMLDY-PXDBBHOGSA-N 0.000 claims description 2
- VQVILPCHXGJQTD-RFKWEDMZSA-N n-[4-[2-(6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl)ethyl]phenyl]-3-[(z)-[(5z)-4-methyl-5-[(1-methylindol-3-yl)methylidene]-3,6-dioxopiperazin-2-ylidene]methyl]benzamide Chemical compound C1=CC=C2C(/C=C3/C(=O)N\C(C(N3C)=O)=C/C=3C=CC=C(C=3)C(=O)NC3=CC=C(C=C3)CCN3CCC=4C=C(C(=CC=4C3)OC)OC)=CN(C)C2=C1 VQVILPCHXGJQTD-RFKWEDMZSA-N 0.000 claims description 2
- FXAUBFKBIZUBOO-PCNBCNDESA-N n-[4-[2-(6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl)ethyl]phenyl]-3-[(z)-[(5z)-4-methyl-5-[(1-methylpyrrol-3-yl)methylidene]-3,6-dioxopiperazin-2-ylidene]methyl]benzamide Chemical compound C1C=2C=C(OC)C(OC)=CC=2CCN1CCC(C=C1)=CC=C1NC(=O)C(C=1)=CC=CC=1\C=C(C(N1C)=O)/NC(=O)\C1=C\C=1C=CN(C)C=1 FXAUBFKBIZUBOO-PCNBCNDESA-N 0.000 claims description 2
- LWCNHERLJGRQMD-XREVHHEISA-N n-[4-[2-(6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl)ethyl]phenyl]-3-[(z)-[(5z)-5-(3,3-dimethylbutylidene)-4-methyl-3,6-dioxopiperazin-2-ylidene]methyl]benzamide Chemical compound C1C=2C=C(OC)C(OC)=CC=2CCN1CCC(C=C1)=CC=C1NC(=O)C(C=1)=CC=CC=1\C=C1/NC(=O)\C(=C\CC(C)(C)C)N(C)C1=O LWCNHERLJGRQMD-XREVHHEISA-N 0.000 claims description 2
- DJNAGHXXJTWJHR-BEORVMNHSA-N n-[4-[2-(6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl)ethyl]phenyl]-3-[(z)-[(5z)-5-(furan-2-ylmethylidene)-4-methyl-3,6-dioxopiperazin-2-ylidene]methyl]benzamide Chemical compound C1C=2C=C(OC)C(OC)=CC=2CCN1CCC(C=C1)=CC=C1NC(=O)C(C=1)=CC=CC=1\C=C(C(N1C)=O)/NC(=O)\C1=C\C1=CC=CO1 DJNAGHXXJTWJHR-BEORVMNHSA-N 0.000 claims description 2
- IIEKSEMMAMJSLP-HEZNUULDSA-N n-[4-[2-(6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl)ethyl]phenyl]-3-[(z)-[(5z)-5-(furan-3-ylmethylidene)-4-methyl-3,6-dioxopiperazin-2-ylidene]methyl]benzamide Chemical compound C1C=2C=C(OC)C(OC)=CC=2CCN1CCC(C=C1)=CC=C1NC(=O)C(C=1)=CC=CC=1\C=C(C(N1C)=O)/NC(=O)\C1=C\C=1C=COC=1 IIEKSEMMAMJSLP-HEZNUULDSA-N 0.000 claims description 2
- PBIASUOLHHQIHG-VANQDGIVSA-N n-[4-[2-(6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl)ethyl]phenyl]-3-[(z)-[(5z)-5-[(3-methoxyphenyl)methylidene]-4-methyl-3,6-dioxopiperazin-2-ylidene]methyl]benzamide Chemical compound COC1=CC=CC(\C=C/2C(NC(=C\C=3C=C(C=CC=3)C(=O)NC=3C=CC(CCN4CC5=CC(OC)=C(OC)C=C5CC4)=CC=3)/C(=O)N\2C)=O)=C1 PBIASUOLHHQIHG-VANQDGIVSA-N 0.000 claims description 2
- QQDGGFKWPHSTIN-PCNBCNDESA-N n-[4-[2-(6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl)ethyl]phenyl]-4-[(z)-[(5z)-4-methyl-3,6-dioxo-5-(pyridin-3-ylmethylidene)piperazin-2-ylidene]methyl]benzamide Chemical compound C1C=2C=C(OC)C(OC)=CC=2CCN1CCC(C=C1)=CC=C1NC(=O)C(C=C1)=CC=C1\C=C(C(N1C)=O)/NC(=O)\C1=C\C1=CC=CN=C1 QQDGGFKWPHSTIN-PCNBCNDESA-N 0.000 claims description 2
- HPEWOOFNLLPKBJ-HEZNUULDSA-N n-[4-[2-(6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl)ethyl]phenyl]-4-[(z)-[(5z)-4-methyl-3,6-dioxo-5-(thiophen-3-ylmethylidene)piperazin-2-ylidene]methyl]benzamide Chemical compound C1C=2C=C(OC)C(OC)=CC=2CCN1CCC(C=C1)=CC=C1NC(=O)C(C=C1)=CC=C1\C=C(C(N1C)=O)/NC(=O)\C1=C\C=1C=CSC=1 HPEWOOFNLLPKBJ-HEZNUULDSA-N 0.000 claims description 2
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- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002790 naphthalenes Chemical group 0.000 description 1
- 229920001206 natural gum Polymers 0.000 description 1
- 229940085033 nolvadex Drugs 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229960001592 paclitaxel Drugs 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 229960003171 plicamycin Drugs 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 229940068965 polysorbates Drugs 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000015424 sodium Nutrition 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229920003109 sodium starch glycolate Polymers 0.000 description 1
- 239000008109 sodium starch glycolate Substances 0.000 description 1
- 229940079832 sodium starch glycolate Drugs 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 239000007940 sugar coated tablet Substances 0.000 description 1
- 238000009495 sugar coating Methods 0.000 description 1
- 231100000338 sulforhodamine B assay Toxicity 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229960001603 tamoxifen Drugs 0.000 description 1
- RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000003053 toxin Substances 0.000 description 1
- 231100000765 toxin Toxicity 0.000 description 1
- 108700012359 toxins Proteins 0.000 description 1
- 238000001890 transfection Methods 0.000 description 1
- 229960003048 vinblastine Drugs 0.000 description 1
- JXLYSJRDGCGARV-XQKSVPLYSA-N vincaleukoblastine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 JXLYSJRDGCGARV-XQKSVPLYSA-N 0.000 description 1
- OGWKCGZFUXNPDA-XQKSVPLYSA-N vincristine Chemical compound C([N@]1C[C@@H](C[C@]2(C(=O)OC)C=3C(=CC4=C([C@]56[C@H]([C@@]([C@H](OC(C)=O)[C@]7(CC)C=CCN([C@H]67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)C[C@@](C1)(O)CC)CC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-XQKSVPLYSA-N 0.000 description 1
- 229960004528 vincristine Drugs 0.000 description 1
- OGWKCGZFUXNPDA-UHFFFAOYSA-N vincristine Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(OC(C)=O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
- C07D217/04—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9426224.3A GB9426224D0 (en) | 1994-12-23 | 1994-12-23 | Pharmaceutical compounds |
| PCT/GB1995/003027 WO1996020190A1 (en) | 1994-12-23 | 1995-12-22 | Piperazine 2,5 dione derivatives as modulators of multi-drug resistance |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO972937D0 NO972937D0 (no) | 1997-06-23 |
| NO972937L true NO972937L (no) | 1997-06-23 |
Family
ID=10766589
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO972937A NO972937L (no) | 1994-12-23 | 1997-06-23 | Farmasöytiske piperazinforbindelser |
Country Status (19)
| Country | Link |
|---|---|
| EP (1) | EP0799222A1 (fi) |
| JP (1) | JPH10511384A (fi) |
| CN (1) | CN1175253A (fi) |
| AU (1) | AU698828B2 (fi) |
| BG (1) | BG101602A (fi) |
| BR (1) | BR9510410A (fi) |
| CA (1) | CA2207500A1 (fi) |
| CZ (1) | CZ190097A3 (fi) |
| FI (1) | FI972660A (fi) |
| GB (1) | GB9426224D0 (fi) |
| HU (1) | HUT77943A (fi) |
| IL (1) | IL116525A0 (fi) |
| NO (1) | NO972937L (fi) |
| NZ (1) | NZ297847A (fi) |
| PL (1) | PL320916A1 (fi) |
| SK (1) | SK83697A3 (fi) |
| TW (1) | TW358094B (fi) |
| WO (1) | WO1996020190A1 (fi) |
| ZA (1) | ZA9510909B (fi) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA979329B (en) * | 1996-10-18 | 1999-04-19 | Xenova Ltd | Pharmaceutical compounds |
| GB9717576D0 (en) * | 1997-08-19 | 1997-10-22 | Xenova Ltd | Pharmaceutical compounds |
| GB9708805D0 (en) | 1997-05-01 | 1997-06-25 | Smithkline Beecham Plc | Compounds |
| GB9810876D0 (en) | 1998-05-20 | 1998-07-22 | Smithkline Beecham Plc | Compounds |
| WO2000021951A1 (en) | 1998-10-08 | 2000-04-20 | Smithkline Beecham Plc | Tetrahydrobenzazepine derivatives useful as modulators of dopamine d3 receptors (antipsychotic agents) |
| EP1264831A4 (en) * | 2000-01-18 | 2005-11-23 | Nereus Pharmaceuticals Inc | Cell division inhibitors and a method for fixing the same |
| US6693099B2 (en) | 2000-10-17 | 2004-02-17 | The Procter & Gamble Company | Substituted piperazine compounds optionally containing a quinolyl moiety for treating multidrug resistance |
| EP1529044B1 (en) | 2002-08-02 | 2007-10-03 | Nereus Pharmaceuticals, Inc. | Dehydrophenylahistins and analogs thereof and the synthesis of dehydrophenylahistins and analogs thereof |
| US7935704B2 (en) | 2003-08-01 | 2011-05-03 | Nereus Pharmaceuticals, Inc. | Dehydrophenylahistins and analogs thereof and the synthesis of dehydrophenylahistins and analogs thereof |
| US7919497B2 (en) | 2002-08-02 | 2011-04-05 | Nereus Pharmaceuticals, Inc. | Analogs of dehydrophenylahistins and their therapeutic use |
| US8129527B2 (en) | 2006-11-03 | 2012-03-06 | Nereus Pharmacuticals, Inc. | Analogs of dehydrophenylahistins and their therapeutic use |
| CN103396372B (zh) * | 2013-08-09 | 2015-05-20 | 中国科学院南海海洋研究所 | 一类2,5-二酮哌嗪衍生物及其制备方法和在制备抗海洋污损生物防除剂中的应用 |
| US10076518B2 (en) | 2015-03-06 | 2018-09-18 | Beyondspring Pharmaceuticals, Inc. | Method of treating a brain tumor |
| CA2978567A1 (en) | 2015-03-06 | 2016-09-15 | Beyondspring Pharmaceuticals, Inc. | Method of treating cancer associated with a ras mutation using plinabulin |
| EP3334726B1 (en) | 2015-07-13 | 2022-03-16 | Beyondspring Pharmaceuticals, Inc. | Plinabulin compositions |
| US10912748B2 (en) | 2016-02-08 | 2021-02-09 | Beyondspring Pharmaceuticals, Inc. | Compositions containing tucaresol or its analogs |
| JP7025416B2 (ja) | 2016-06-06 | 2022-02-24 | ビヨンドスプリング ファーマシューティカルズ，インコーポレイテッド | 好中球減少症を低減させるための組成物および方法 |
| US11633393B2 (en) | 2017-01-06 | 2023-04-25 | Beyondspring Pharmaceuticals, Inc. | Tubulin binding compounds and therapeutic use thereof |
| WO2018144764A1 (en) | 2017-02-01 | 2018-08-09 | Beyondspring Pharmaceuticals, Inc. | Method of reducing neutropenia |
| WO2019147615A1 (en) | 2018-01-24 | 2019-08-01 | Beyondspring Pharmaceuticals, Inc. | Composition and method for reducing thrombocytopenia via the administration of plinabulin |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2718830B2 (ja) * | 1992-07-10 | 1998-02-25 | ラボラトワール、グラクソ、ソシエテ、アノニム | アニリド誘導体 |
| GB9217331D0 (en) * | 1992-08-14 | 1992-09-30 | Xenova Ltd | Pharmaceutical compounds |
-
1994
- 1994-12-23 GB GBGB9426224.3A patent/GB9426224D0/en active Pending
-
1995
- 1995-12-21 ZA ZA9510909A patent/ZA9510909B/xx unknown
- 1995-12-22 CA CA002207500A patent/CA2207500A1/en not_active Abandoned
- 1995-12-22 BR BR9510410-0A patent/BR9510410A/pt not_active Application Discontinuation
- 1995-12-22 NZ NZ297847A patent/NZ297847A/en unknown
- 1995-12-22 JP JP8520301A patent/JPH10511384A/ja active Pending
- 1995-12-22 PL PL95320916A patent/PL320916A1/xx unknown
- 1995-12-22 EP EP95941797A patent/EP0799222A1/en not_active Withdrawn
- 1995-12-22 HU HU9800398A patent/HUT77943A/hu unknown
- 1995-12-22 AU AU43100/96A patent/AU698828B2/en not_active Ceased
- 1995-12-22 WO PCT/GB1995/003027 patent/WO1996020190A1/en not_active Application Discontinuation
- 1995-12-22 CZ CZ971900A patent/CZ190097A3/cs unknown
- 1995-12-22 IL IL11652595A patent/IL116525A0/xx unknown
- 1995-12-22 CN CN95197672A patent/CN1175253A/zh active Pending
- 1995-12-22 SK SK836-97A patent/SK83697A3/sk unknown
- 1995-12-23 TW TW084113836A patent/TW358094B/zh active
-
1997
- 1997-06-11 BG BG101602A patent/BG101602A/xx unknown
- 1997-06-19 FI FI972660A patent/FI972660A/fi unknown
- 1997-06-23 NO NO972937A patent/NO972937L/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NO972937D0 (no) | 1997-06-23 |
| TW358094B (en) | 1999-05-11 |
| NZ297847A (en) | 1999-04-29 |
| PL320916A1 (en) | 1997-11-10 |
| BG101602A (en) | 1998-02-27 |
| WO1996020190A1 (en) | 1996-07-04 |
| SK83697A3 (en) | 1998-05-06 |
| BR9510410A (pt) | 1999-09-08 |
| HUT77943A (hu) | 1998-12-28 |
| AU698828B2 (en) | 1998-11-05 |
| CZ190097A3 (cs) | 1998-01-14 |
| CA2207500A1 (en) | 1996-07-04 |
| IL116525A0 (en) | 1996-03-31 |
| ZA9510909B (en) | 1996-08-30 |
| FI972660A (fi) | 1997-08-22 |
| AU4310096A (en) | 1996-07-19 |
| GB9426224D0 (en) | 1995-02-22 |
| CN1175253A (zh) | 1998-03-04 |
| EP0799222A1 (en) | 1997-10-08 |
| FI972660A0 (fi) | 1997-06-19 |
| JPH10511384A (ja) | 1998-11-04 |
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