SK8052003A3 - 1,4-Disubstituted piperazine derivatives useful as uro-selective alpha1-adrenoceptor blockers - Google Patents

1,4-Disubstituted piperazine derivatives useful as uro-selective alpha1-adrenoceptor blockers Download PDF

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Publication number: SK8052003A3
Authority: SK; Slovakia
Prior art keywords: compound; propyl; dione; isoindole; piperazin
Prior art date: 2000-11-30

Application number

SK805-2003A

Other languages

English (en)

Slovak (sk)

Inventor

Nitya Anand

Sanjay Jain

Neelima Sinha

Anita Chugh

Laxminarayan G Hegde

Jang Bahadur Gupta

Original Assignee

Ranbaxy Lab Ltd

Priority date (The priority date 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 date listed.)

2000-11-30

Filing date

2001-11-29

Publication date

2003-12-02

2001-11-29 Application filed by Ranbaxy Lab Ltd filed Critical Ranbaxy Lab Ltd

2003-12-02 Publication of SK8052003A3 publication Critical patent/SK8052003A3/sk

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-1 1,4-Disubstituted piperazine Chemical class 0.000 title claims abstract 27
108020004102 alpha-1 Adrenergic Receptor Proteins 0.000 title claims abstract 4
102000015009 alpha1-adrenergic receptor activity proteins Human genes 0.000 title abstract 2
229940066771 systemic antihistamines piperazine derivative Drugs 0.000 title abstract 2
150000001875 compounds Chemical class 0.000 claims abstract 15
238000000034 method Methods 0.000 claims abstract 4
239000008194 pharmaceutical composition Substances 0.000 claims abstract 4
150000003839 salts Chemical class 0.000 claims abstract 4
125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 8
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 7
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 6
UZTZKICRSWXRFQ-UHFFFAOYSA-N 3a,4,5,6-tetrahydroisoindole-1,3-dione Chemical compound C1CCC2C(=O)NC(=O)C2=C1 UZTZKICRSWXRFQ-UHFFFAOYSA-N 0.000 claims 5
229910052736 halogen Inorganic materials 0.000 claims 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims 3
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 3
241000124008 Mammalia Species 0.000 claims 3
150000001204 N-oxides Chemical class 0.000 claims 3
150000001408 amides Chemical class 0.000 claims 3
125000005843 halogen group Chemical group 0.000 claims 3
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
239000002207 metabolite Substances 0.000 claims 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 3
239000000651 prodrug Substances 0.000 claims 3
229940002612 prodrug Drugs 0.000 claims 3
125000001424 substituent group Chemical group 0.000 claims 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 3
102000030619 alpha-1 Adrenergic Receptor Human genes 0.000 claims 2
239000005557 antagonist Substances 0.000 claims 2
206010020718 hyperplasia Diseases 0.000 claims 2
UAOUIVVJBYDFKD-XKCDOFEDSA-N (1R,9R,10S,11R,12R,15S,18S,21R)-10,11,21-trihydroxy-8,8-dimethyl-14-methylidene-4-(prop-2-enylamino)-20-oxa-5-thia-3-azahexacyclo[9.7.2.112,15.01,9.02,6.012,18]henicosa-2(6),3-dien-13-one Chemical compound C([C@@H]1[C@@H](O)[C@@]23C(C1=C)=O)C[C@H]2[C@]12C(N=C(NCC=C)S4)=C4CC(C)(C)[C@H]1[C@H](O)[C@]3(O)OC2 UAOUIVVJBYDFKD-XKCDOFEDSA-N 0.000 claims 1
AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 claims 1
GLGNXYJARSMNGJ-VKTIVEEGSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethyl-6-methoxy-2-oxo-4,5-dihydro-3h-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound CCN1C(=O)CCCC2=C(OC)C(NC=3N=C(C(=CN=3)Cl)N[C@H]3[C@H]([C@@]4([H])C[C@@]3(C=C4)[H])C(N)=O)=CC=C21 GLGNXYJARSMNGJ-VKTIVEEGSA-N 0.000 claims 1
SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 claims 1
GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 claims 1
WWTBZEKOSBFBEM-SPWPXUSOSA-N (2s)-2-[[2-benzyl-3-[hydroxy-[(1r)-2-phenyl-1-(phenylmethoxycarbonylamino)ethyl]phosphoryl]propanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound N([C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)O)C(=O)C(CP(O)(=O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1C=CC=CC=1)CC1=CC=CC=C1 WWTBZEKOSBFBEM-SPWPXUSOSA-N 0.000 claims 1
QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 claims 1
IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 claims 1
KQZLRWGGWXJPOS-NLFPWZOASA-N 1-[(1R)-1-(2,4-dichlorophenyl)ethyl]-6-[(4S,5R)-4-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-5-methylcyclohexen-1-yl]pyrazolo[3,4-b]pyrazine-3-carbonitrile Chemical compound ClC1=C(C=CC(=C1)Cl)[C@@H](C)N1N=C(C=2C1=NC(=CN=2)C1=CC[C@@H]([C@@H](C1)C)N1[C@@H](CCC1)CO)C#N KQZLRWGGWXJPOS-NLFPWZOASA-N 0.000 claims 1
WZZBNLYBHUDSHF-DHLKQENFSA-N 1-[(3s,4s)-4-[8-(2-chloro-4-pyrimidin-2-yloxyphenyl)-7-fluoro-2-methylimidazo[4,5-c]quinolin-1-yl]-3-fluoropiperidin-1-yl]-2-hydroxyethanone Chemical compound CC1=NC2=CN=C3C=C(F)C(C=4C(=CC(OC=5N=CC=CN=5)=CC=4)Cl)=CC3=C2N1[C@H]1CCN(C(=O)CO)C[C@@H]1F WZZBNLYBHUDSHF-DHLKQENFSA-N 0.000 claims 1
ONBQEOIKXPHGMB-VBSBHUPXSA-N 1-[2-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 ONBQEOIKXPHGMB-VBSBHUPXSA-N 0.000 claims 1
UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 claims 1
IKSMHIXAYFVXMX-UHFFFAOYSA-N 2-[3-[4-(2,4-dichlorophenyl)piperazin-1-yl]propyl]-3a,4,7,7a-tetrahydroisoindole-1,3-dione Chemical compound ClC1=CC(Cl)=CC=C1N1CCN(CCCN2C(C3CC=CCC3C2=O)=O)CC1 IKSMHIXAYFVXMX-UHFFFAOYSA-N 0.000 claims 1
AZUAWRJZUBMGEY-UHFFFAOYSA-N 2-[3-[4-(2,4-difluorophenyl)piperazin-1-yl]propyl]-3a,4,7,7a-tetrahydroisoindole-1,3-dione Chemical compound FC1=CC(F)=CC=C1N1CCN(CCCN2C(C3CC=CCC3C2=O)=O)CC1 AZUAWRJZUBMGEY-UHFFFAOYSA-N 0.000 claims 1
NHXWLJBNBXNNKA-UHFFFAOYSA-N 2-[3-[4-(2,4-dimethoxyphenyl)piperazin-1-yl]propyl]-3a,4,7,7a-tetrahydroisoindole-1,3-dione Chemical compound COC1=CC(OC)=CC=C1N1CCN(CCCN2C(C3CC=CCC3C2=O)=O)CC1 NHXWLJBNBXNNKA-UHFFFAOYSA-N 0.000 claims 1
RPFLJFRMWVKIAS-UHFFFAOYSA-N 2-[3-[4-(2,5-dimethoxyphenyl)piperazin-1-yl]propyl]-3a,4,7,7a-tetrahydroisoindole-1,3-dione Chemical compound COC1=CC=C(OC)C(N2CCN(CCCN3C(C4CC=CCC4C3=O)=O)CC2)=C1 RPFLJFRMWVKIAS-UHFFFAOYSA-N 0.000 claims 1
PCBHZULMXOWSKV-UHFFFAOYSA-N 2-[3-[4-(2,6-dimethylphenyl)piperazin-1-yl]propyl]-3a,4,7,7a-tetrahydroisoindole-1,3-dione Chemical compound CC1=CC=CC(C)=C1N1CCN(CCCN2C(C3CC=CCC3C2=O)=O)CC1 PCBHZULMXOWSKV-UHFFFAOYSA-N 0.000 claims 1
ZHQUZOHEZRAOBW-UHFFFAOYSA-N 2-[3-[4-(2-ethoxyphenyl)piperazin-1-yl]propyl]-3a,4,7,7a-tetrahydroisoindole-1,3-dione Chemical compound CCOC1=CC=CC=C1N1CCN(CCCN2C(C3CC=CCC3C2=O)=O)CC1 ZHQUZOHEZRAOBW-UHFFFAOYSA-N 0.000 claims 1
FSWFXMVJHVJMTB-UHFFFAOYSA-N 2-[3-[4-(2-ethylphenyl)piperazin-1-yl]propyl]-3a,4,7,7a-tetrahydroisoindole-1,3-dione Chemical compound CCC1=CC=CC=C1N1CCN(CCCN2C(C3CC=CCC3C2=O)=O)CC1 FSWFXMVJHVJMTB-UHFFFAOYSA-N 0.000 claims 1
RFKMAUQMQSEPAM-UHFFFAOYSA-N 2-[3-[4-(2-hexoxyphenyl)piperazin-1-yl]propyl]-3a,4,7,7a-tetrahydroisoindole-1,3-dione Chemical compound CCCCCCOC1=CC=CC=C1N1CCN(CCCN2C(C3CC=CCC3C2=O)=O)CC1 RFKMAUQMQSEPAM-UHFFFAOYSA-N 0.000 claims 1
HQEJDUXSYIFXRT-UHFFFAOYSA-N 2-[3-[4-(2-methylphenyl)piperazin-1-yl]propyl]-3a,4,7,7a-tetrahydroisoindole-1,3-dione Chemical compound CC1=CC=CC=C1N1CCN(CCCN2C(C3CC=CCC3C2=O)=O)CC1 HQEJDUXSYIFXRT-UHFFFAOYSA-N 0.000 claims 1
JLANFRQMUIPFDD-UHFFFAOYSA-N 2-[3-[4-(2-propan-2-yloxyphenyl)piperazin-1-yl]propyl]-3a,4,7,7a-tetrahydroisoindole-1,3-dione Chemical compound CC(C)OC1=CC=CC=C1N1CCN(CCCN2C(C3CC=CCC3C2=O)=O)CC1 JLANFRQMUIPFDD-UHFFFAOYSA-N 0.000 claims 1
IMQZUGHDVLGWEU-UHFFFAOYSA-N 2-[3-[4-(2-propoxyphenyl)piperazin-1-yl]propyl]-3a,4,7,7a-tetrahydroisoindole-1,3-dione Chemical compound CCCOC1=CC=CC=C1N1CCN(CCCN2C(C3CC=CCC3C2=O)=O)CC1 IMQZUGHDVLGWEU-UHFFFAOYSA-N 0.000 claims 1
RVUHLVFRRYMVOQ-UHFFFAOYSA-N 2-[3-[4-(3,4-dimethylphenyl)piperazin-1-yl]propyl]-3a,4,7,7a-tetrahydroisoindole-1,3-dione Chemical compound C1=C(C)C(C)=CC=C1N1CCN(CCCN2C(C3CC=CCC3C2=O)=O)CC1 RVUHLVFRRYMVOQ-UHFFFAOYSA-N 0.000 claims 1
UAVXKOJYPGNVFE-UHFFFAOYSA-N 2-[3-[4-(3-chlorophenyl)piperazin-1-yl]propyl]-3a,4,7,7a-tetrahydroisoindole-1,3-dione Chemical compound ClC1=CC=CC(N2CCN(CCCN3C(C4CC=CCC4C3=O)=O)CC2)=C1 UAVXKOJYPGNVFE-UHFFFAOYSA-N 0.000 claims 1
WCGUNROULKMHMI-UHFFFAOYSA-N 2-[3-[4-(4-tert-butylphenyl)piperazin-1-yl]propyl]-3a,4,7,7a-tetrahydroisoindole-1,3-dione Chemical compound C1=CC(C(C)(C)C)=CC=C1N1CCN(CCCN2C(C3CC=CCC3C2=O)=O)CC1 WCGUNROULKMHMI-UHFFFAOYSA-N 0.000 claims 1
KGQYCVLFQOPZOX-UHFFFAOYSA-N 2-[3-[4-(5-chloro-2-methylphenyl)piperazin-1-yl]propyl]-3a,4,7,7a-tetrahydroisoindole-1,3-dione Chemical compound CC1=CC=C(Cl)C=C1N1CCN(CCCN2C(C3CC=CCC3C2=O)=O)CC1 KGQYCVLFQOPZOX-UHFFFAOYSA-N 0.000 claims 1
YSUIQYOGTINQIN-UZFYAQMZSA-N 2-amino-9-[(1S,6R,8R,9S,10R,15R,17R,18R)-8-(6-aminopurin-9-yl)-9,18-difluoro-3,12-dihydroxy-3,12-bis(sulfanylidene)-2,4,7,11,13,16-hexaoxa-3lambda5,12lambda5-diphosphatricyclo[13.2.1.06,10]octadecan-17-yl]-1H-purin-6-one Chemical compound NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(S)(=O)O[C@@H]4[C@@H](COP(S)(=O)O[C@@H]2[C@@H]3F)O[C@H]([C@H]4F)N2C=NC3=C2N=CN=C3N)C(=O)N1 YSUIQYOGTINQIN-UZFYAQMZSA-N 0.000 claims 1
TVTJUIAKQFIXCE-HUKYDQBMSA-N 2-amino-9-[(2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-ynyl-1H-purine-6,8-dione Chemical compound NC=1NC(C=2N(C(N(C=2N=1)[C@@H]1O[C@@H]([C@H]([C@H]1O)F)CO)=O)CC#C)=O TVTJUIAKQFIXCE-HUKYDQBMSA-N 0.000 claims 1
125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 1
QBWKPGNFQQJGFY-QLFBSQMISA-N 3-[(1r)-1-[(2r,6s)-2,6-dimethylmorpholin-4-yl]ethyl]-n-[6-methyl-3-(1h-pyrazol-4-yl)imidazo[1,2-a]pyrazin-8-yl]-1,2-thiazol-5-amine Chemical compound N1([C@H](C)C2=NSC(NC=3C4=NC=C(N4C=C(C)N=3)C3=CNN=C3)=C2)C[C@H](C)O[C@H](C)C1 QBWKPGNFQQJGFY-QLFBSQMISA-N 0.000 claims 1
KCBAMQOKOLXLOX-BSZYMOERSA-N CC1=C(SC=N1)C2=CC=C(C=C2)[C@H](C)NC(=O)[C@@H]3C[C@H](CN3C(=O)[C@H](C(C)(C)C)NC(=O)CCCCCCCCCCNCCCONC(=O)C4=C(C(=C(C=C4)F)F)NC5=C(C=C(C=C5)I)F)O Chemical compound CC1=C(SC=N1)C2=CC=C(C=C2)[C@H](C)NC(=O)[C@@H]3C[C@H](CN3C(=O)[C@H](C(C)(C)C)NC(=O)CCCCCCCCCCNCCCONC(=O)C4=C(C(=C(C=C4)F)F)NC5=C(C=C(C=C5)I)F)O KCBAMQOKOLXLOX-BSZYMOERSA-N 0.000 claims 1
229940126657 Compound 17 Drugs 0.000 claims 1
OPFJDXRVMFKJJO-ZHHKINOHSA-N N-{[3-(2-benzamido-4-methyl-1,3-thiazol-5-yl)-pyrazol-5-yl]carbonyl}-G-dR-G-dD-dD-dD-NH2 Chemical compound S1C(C=2NN=C(C=2)C(=O)NCC(=O)N[C@H](CCCN=C(N)N)C(=O)NCC(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(N)=O)=C(C)N=C1NC(=O)C1=CC=CC=C1 OPFJDXRVMFKJJO-ZHHKINOHSA-N 0.000 claims 1
LJOOWESTVASNOG-UFJKPHDISA-N [(1s,3r,4ar,7s,8s,8as)-3-hydroxy-8-[2-[(4r)-4-hydroxy-6-oxooxan-2-yl]ethyl]-7-methyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl] (2s)-2-methylbutanoate Chemical compound C([C@H]1[C@@H](C)C=C[C@H]2C[C@@H](O)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)CC1C[C@@H](O)CC(=O)O1 LJOOWESTVASNOG-UFJKPHDISA-N 0.000 claims 1
LNUFLCYMSVYYNW-ZPJMAFJPSA-N [(2r,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[[(3s,5s,8r,9s,10s,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-disulfo Chemical compound O([C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1C[C@@H]2CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@H](C)CCCC(C)C)[C@H]1O[C@H](COS(O)(=O)=O)[C@@H](OS(O)(=O)=O)[C@H](OS(O)(=O)=O)[C@H]1OS(O)(=O)=O LNUFLCYMSVYYNW-ZPJMAFJPSA-N 0.000 claims 1
125000000217 alkyl group Chemical group 0.000 claims 1
XRWSZZJLZRKHHD-WVWIJVSJSA-N asunaprevir Chemical compound O=C([C@@H]1C[C@H](CN1C(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)(C)C)OC1=NC=C(C2=CC=C(Cl)C=C21)OC)N[C@]1(C(=O)NS(=O)(=O)C2CC2)C[C@H]1C=C XRWSZZJLZRKHHD-WVWIJVSJSA-N 0.000 claims 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
229940125773 compound 10 Drugs 0.000 claims 1
229940125797 compound 12 Drugs 0.000 claims 1
229940126543 compound 14 Drugs 0.000 claims 1
229940125758 compound 15 Drugs 0.000 claims 1
229940126142 compound 16 Drugs 0.000 claims 1
229940125810 compound 20 Drugs 0.000 claims 1
229940126086 compound 21 Drugs 0.000 claims 1
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229940125833 compound 23 Drugs 0.000 claims 1
229940125961 compound 24 Drugs 0.000 claims 1
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229940125851 compound 27 Drugs 0.000 claims 1
229940127204 compound 29 Drugs 0.000 claims 1
229940125877 compound 31 Drugs 0.000 claims 1
239000003937 drug carrier Substances 0.000 claims 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 claims 1
150000002367 halogens Chemical class 0.000 claims 1
125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 claims 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 claims 1
150000004885 piperazines Chemical class 0.000 claims 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
206010004446 Benign prostatic hyperplasia Diseases 0.000 abstract 3
208000004403 Prostatic Hyperplasia Diseases 0.000 abstract 3
208000024891 symptom Diseases 0.000 abstract 2
239000002253 acid Substances 0.000 abstract 1
230000003042 antagnostic effect Effects 0.000 abstract 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1

Classifications

- 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
- C07D401/06—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 carbon chain containing only aliphatic carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/08—Drugs for disorders of the urinary system of the prostate
- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Engineering & Computer Science (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Urology & Nephrology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Indole Compounds (AREA)

SK805-2003A 2000-11-30 2001-11-29 1,4-Disubstituted piperazine derivatives useful as uro-selective alpha1-adrenoceptor blockers SK8052003A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
IN1097DE2000		2000-11-30
PCT/IB2001/002261 WO2002044151A1 (en)	2000-11-30	2001-11-29	1,4-disubstituted piperazine derivatives useful as uro-selective $g(a)1-adrenoceptor blockers

Publications (1)

Publication Number	Publication Date
SK8052003A3 true SK8052003A3 (en)	2003-12-02

Family

ID=11097130

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK805-2003A SK8052003A3 (en)	2000-11-30	2001-11-29	1,4-Disubstituted piperazine derivatives useful as uro-selective alpha1-adrenoceptor blockers

Country Status (25)

Country	Link
US (1)	US6914064B2 (cs)
EP (1)	EP1339682A1 (cs)
JP (1)	JP2004514711A (cs)
KR (1)	KR20030068164A (cs)
CN (1)	CN1230423C (cs)
AP (1)	AP2003002810A0 (cs)
AR (1)	AR035930A1 (cs)
AU (2)	AU2231502A (cs)
BG (1)	BG107943A (cs)
BR (1)	BR0115865A (cs)
CA (1)	CA2430343A1 (cs)
CZ (1)	CZ20031698A3 (cs)
DO (1)	DOP2001000296A (cs)
EA (1)	EA006941B1 (cs)
EE (1)	EE200300250A (cs)
HU (1)	HUP0400545A3 (cs)
MA (1)	MA26064A1 (cs)
MX (1)	MXPA03004850A (cs)
NZ (1)	NZ526226A (cs)
OA (1)	OA12537A (cs)
PA (1)	PA8534001A1 (cs)
PL (1)	PL362210A1 (cs)
SK (1)	SK8052003A3 (cs)
WO (1)	WO2002044151A1 (cs)
ZA (1)	ZA200304242B (cs)

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WO2003084928A1 (en) *	2002-04-08	2003-10-16	Ranbaxy Laboratories Limited	Alpha, omega-dicarboximide derivatives as useful uro-selective α1α adrenoceptor blockers
AU2003278403A1 (en) *	2003-10-15	2005-05-05	Ranbaxy Laboratories Limited	1-alkylpiperazinyl-pyrrolidin-2, 5-dione derivatives as adrenergic receptor antagonist
EP1746998A1 (en) *	2004-03-22	2007-01-31	Ranbaxy Laboratories, Ltd.	Combination therapy for lower urinary tract symptoms
WO2005113498A1 (en) *	2004-05-19	2005-12-01	Ranbaxy Laboratories Limited	Adrenergic receptor antagonists
WO2005118537A2 (en) *	2004-05-31	2005-12-15	Ranbaxy Laboratories Limited	Arylpiperazine derivatives as adrenergic receptor antagonists
WO2006018815A1 (en) *	2004-08-16	2006-02-23	Ranbaxy Laboratories Limited	Piperazine derivatives as adrenergic receptor antagonists
WO2006051374A2 (en) *	2004-11-11	2006-05-18	Ranbaxy Laboratories Limited	Arylpiperazines useful as adrenergic receptor antagonists
WO2006051399A1 (en) *	2004-11-11	2006-05-18	Ranbaxy Laboratories Limited	Piperazine derivatives useful as adrenergic receptor antagonists
WO2006092710A1 (en) *	2005-03-02	2006-09-08	Ranbaxy Laboratories Limited	Metabolites of 2-{3-[4-(2-isopropoxyphenyl) piperazin-1-yl]-propyl}-3a,4,7,7a-tetrahydro-1h-isoindole-1,3-(2h)-dione
WO2006117760A1 (en) *	2005-05-03	2006-11-09	Ranbaxy Laboratories Limited	Adrenergic receptor antagonists
WO2007029156A2 (en) *	2005-09-05	2007-03-15	Ranbaxy Laboratories Limited	Isoindoledione derivatives as adrenergic receptor antagonists
WO2007039809A1 (en) *	2005-10-05	2007-04-12	Ranbaxy Laboratories Limited	Metabolites of 2- {3-[4-(5-fluoro-2-isopropoxy-phenyl)-piperazin-1-yl]-propyl} -5,6-dihydroxy-hexahydro-isoindole-1,3-dione
JP5701213B2 (ja)	2008-10-10	2015-04-15	インスティチュートオブファーマコロジーアンドトキシコロジーアカデミーオブミリタリーメディカルサイエンシズピー．エル．エー．チャイナ	新規なドーパミンｄ３受容体リガンド、その調製及び使用
US9227944B2 (en)	2008-10-10	2016-01-05	Institute Of Pharmacology And Toxicology Academy Of Military Science P.L.A. China	Dopamine D3 receptor ligands and preparation and medical uses of the same
SG176553A1 (en)	2009-05-05	2012-01-30	Muthiah Manoharan	Lipid compositions

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JPS57197265A (en) *	1981-05-29	1982-12-03	Eisai Co Ltd	Carboxylic acid imide derivative, its preparation and medicament containing the same
JPS5936661A (ja) *	1982-08-26	1984-02-28	Eisai Co Ltd	カルボン酸イミド誘導体およびその製造方法ならびにそれを含有する医薬
JPS5976059A (ja) *	1982-10-21	1984-04-28	Sumitomo Chem Co Ltd	環状イミド誘導体及びその酸付加塩
JPS5995267A (ja) *	1982-11-25	1984-06-01	Eisai Co Ltd	カルボン酸イミド誘導体およびその製造方法
AT387773B (de) *	1983-09-12	1989-03-10	Bristol Myers Co	Verfahren zur herstellung von 1-heteroaryl-4-((2,5-pyrrolidindion-1-yl)aklyl) iperazin-derivaten
US4524206A (en) *	1983-09-12	1985-06-18	Mead Johnson & Company	1-Heteroaryl-4-(2,5-pyrrolidinedion-1-yl)alkyl)piperazine derivatives
JPS60204784A (ja)	1984-03-29	1985-10-16	Eisai Co Ltd	カルボン酸イミド誘導体
JP2918899B2 (ja)	1989-03-09	1999-07-12	住友製薬株式会社	環状イミド誘導体の製造方法
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ATE201016T1 (de) *	1995-06-09	2001-05-15	Hoffmann La Roche	Pyrimidindion-, pyrimidintrion-, triazindion- derivate als alpha-1-adrenergische rezeptorantagonisten
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2001
- 2001-11-29 EP EP01998540A patent/EP1339682A1/en not_active Withdrawn
- 2001-11-29 OA OA1200300149A patent/OA12537A/en unknown
- 2001-11-29 SK SK805-2003A patent/SK8052003A3/sk not_active Application Discontinuation
- 2001-11-29 BR BR0115865-1A patent/BR0115865A/pt not_active IP Right Cessation
- 2001-11-29 CZ CZ20031698A patent/CZ20031698A3/cs unknown
- 2001-11-29 MX MXPA03004850A patent/MXPA03004850A/es unknown
- 2001-11-29 AU AU2231502A patent/AU2231502A/xx active Pending
- 2001-11-29 KR KR10-2003-7007305A patent/KR20030068164A/ko not_active Withdrawn
- 2001-11-29 CA CA002430343A patent/CA2430343A1/en not_active Abandoned
- 2001-11-29 AU AU2002222315A patent/AU2002222315B2/en not_active Ceased
- 2001-11-29 EA EA200300620A patent/EA006941B1/ru not_active IP Right Cessation
- 2001-11-29 CN CNB018220460A patent/CN1230423C/zh not_active Expired - Fee Related
- 2001-11-29 PA PA20018534001A patent/PA8534001A1/es unknown
- 2001-11-29 HU HU0400545A patent/HUP0400545A3/hu unknown
- 2001-11-29 JP JP2002546521A patent/JP2004514711A/ja not_active Withdrawn
- 2001-11-29 PL PL01362210A patent/PL362210A1/xx not_active Application Discontinuation
- 2001-11-29 EE EEP200300250A patent/EE200300250A/xx unknown
- 2001-11-29 NZ NZ526226A patent/NZ526226A/en unknown
- 2001-11-29 WO PCT/IB2001/002261 patent/WO2002044151A1/en not_active Ceased
- 2001-11-29 AP APAP/P/2003/002810A patent/AP2003002810A0/en unknown
- 2001-11-30 DO DO2001000296A patent/DOP2001000296A/es unknown
- 2001-11-30 US US09/998,115 patent/US6914064B2/en not_active Expired - Fee Related
- 2001-11-30 AR ARP010105588A patent/AR035930A1/es not_active Application Discontinuation
2003
- 2003-05-30 ZA ZA200304242A patent/ZA200304242B/en unknown
- 2003-05-30 MA MA27188A patent/MA26064A1/fr unknown
- 2003-06-25 BG BG107943A patent/BG107943A/bg unknown

Also Published As

Publication number	Publication date
PL362210A1 (en)	2004-10-18
AU2002222315B2 (en)	2007-06-21
NZ526226A (en)	2004-05-28
PA8534001A1 (es)	2002-12-11
EP1339682A1 (en)	2003-09-03
CZ20031698A3 (cs)	2003-11-12
DOP2001000296A (es)	2003-03-15
BR0115865A (pt)	2003-12-23
ZA200304242B (en)	2004-03-02
AP2003002810A0 (en)	2003-06-30
EE200300250A (et)	2003-10-15
MXPA03004850A (es)	2004-01-26
US6914064B2 (en)	2005-07-05
JP2004514711A (ja)	2004-05-20
HUP0400545A3 (en)	2007-05-02
CA2430343A1 (en)	2002-06-06
WO2002044151A1 (en)	2002-06-06
US20020156085A1 (en)	2002-10-24
EA200300620A1 (ru)	2003-12-25
KR20030068164A (ko)	2003-08-19
MA26064A1 (fr)	2004-04-01
AR035930A1 (es)	2004-07-28
CN1486300A (zh)	2004-03-31
EA006941B1 (ru)	2006-06-30
CN1230423C (zh)	2005-12-07
AU2231502A (en)	2002-06-11
BG107943A (bg)	2004-08-31
HUP0400545A2 (hu)	2004-07-28
OA12537A (en)	2006-06-05

Legal Events

Date	Code	Title	Description
2010-12-07	FC9A	Refused patent application

Publication	Publication Date	Title
MY114679A (en)	2002-12-31	Aroyl-piperidine derivatives
CY1111075T1 (el)	2015-06-11	Φαρμακευτικες συνθεσεις που περιεχουν τα παραγωγα της 3-αμινο-αζετιδινης, τα νεα παραγωγα τους και η προετοιμασια τους
PL346345A1 (en)	2002-02-11	Heterocyclic compounds and methods to treat cardiac failure and other disorders
PT91580A (pt)	1990-03-08	Processo para a preparacao de compostos de nicotinamida n-substituida antidepressivos
YU43001A (sh)	2004-09-03	Supstituisani biciklični derivati korisni kao sredstva protiv kancera
NO982907L (no)	1998-06-22	Tyrosinderivater som <alfa>-v-integrininhibitorer
HRP20030636B1 (en)	2012-05-31	Phthalayinone-piperidino-derivatives as pde4 inhibitors
ATE252575T1 (de)	2003-11-15	Indole und 2,3-dihydroindolderivate, ihre herstellung und verwendung
HRP20040429B1 (hr)	2007-10-31	Derivati sulfonamida, njihova priprema i upotrebakao lijekova
MEP24208A (en)	2010-06-10	Derivatives of dioxane-2-alkyl carbamates, preparation method thereof and application of same in therapeutics
NZ526226A (en)	2004-05-28	1,4-disubstituted piperazine derivatives useful as uro-selective alpha1-adrenoceptor blockers
MEP37508A (en)	2011-02-10	Process for the preparation of mesylates of piperazine derivatives
FR2798126B1 (fr)	2001-10-19	Heteroaryloxypropanolamines, procede pour leur preparation et compositions pharmaceutiques les contenant
ATE172454T1 (de)	1998-11-15	Pyridazinon derivate mit pharmazeutischer wirkung
MEP12108A (en)	2010-06-10	Novel branched substituted amino derivatives of 3-amino-1-phenyl-1h[1,2,4]triazol, methods for producing them and pharmaceutical compositions containing them
EA200400469A1 (ru)	2004-08-26	Замещенные производные алкиламинопиридазинона, способ их получения и содержащие их фармацевтические композиции
HRP20020470B1 (hr)	2009-04-30	POSTUPAK PRIREĐIVANJA {2-[4-(α-FENIL-p-KLORBENZIL)-PIPERAZIN-1-IL]ETOKSI} OCTENE KISELINE I NOVIH INTERMEDIJERA
EA200300691A1 (ru)	2003-12-25	Производные 2,3-бензодиазепина и фармацевтические композиции, содержащие эти производные в качестве активного ингредиента
EP1431293A4 (en)	2004-12-22	WATER-SOLUBLE PHENYLPYRIDAZINE DERIVATIVES AND MEDICINAL PRODUCTS CONTAINING THEM
TR200001621A2 (tr)	2001-07-23	Yeni arilpiperazinilalkil-3(2H)-Piridaziononlar
RU98107001A (ru)	2000-01-27	Новые производные нафтилпиперазина
TH67158A (th)	2005-02-07	อนุพันธ์ 1, 4-ไดซับสติติวเต็ด ไพเพอราซินส์ สำหรับใช้เป็นตัวขัดขวางที่เฉพาะต่อตัวรับ อัลฟา1-อาคริโนเซบเตอร์ของอวัยวะปัสสาวะ
DK0588850T3 (da)	1996-01-08	N-hydroxyureaderivater, som inhiberer lipoxygenase
HRP20080129T3 (en)	2008-04-30	Indol-2-one derivatives for the treatment of central nervous disorders, gastrointestinal disorders and cardiovascular disorders
NO20064058L (no)	2006-09-08	Fremgangsmate for fremstilling av 1,5-d ifenylpyrazolkarboksylsyrederlvat