OA12537A - 1,4-Disubstituted piperazine derivatives useful asuro-selective alpha 1-adrenoceptor blockers. - Google Patents

1,4-Disubstituted piperazine derivatives useful asuro-selective alpha 1-adrenoceptor blockers. Download PDF

Info

Publication number: OA12537A
Authority: OA; OAPI
Prior art keywords: compound; piperazin; dione; isoindole; propyl
Prior art date: 2000-11-30

Application number

OA1200300149A

Other languages

English (en)

Inventor

Nitya Anand

Anita Chugh

Jang Bahadur Gupta

Laxminarayan G Hegde

Sanjay Jain

Neelima Sinha

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

2006-06-05

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

2006-06-05 Publication of OA12537A publication Critical patent/OA12537A/en

Links

-1 1,4-Disubstituted piperazine Chemical class 0.000 title claims abstract description 19
108020004102 alpha-1 Adrenergic Receptor Proteins 0.000 title abstract description 3
229940066771 systemic antihistamines piperazine derivative Drugs 0.000 title abstract description 3
102000015009 alpha1-adrenergic receptor activity proteins Human genes 0.000 title abstract 2
150000001875 compounds Chemical class 0.000 claims abstract description 61
206010004446 Benign prostatic hyperplasia Diseases 0.000 claims abstract description 20
208000004403 Prostatic Hyperplasia Diseases 0.000 claims abstract description 19
150000003839 salts Chemical class 0.000 claims abstract description 7
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 6
125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 54
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 11
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
229940002612 prodrug Drugs 0.000 claims description 8
239000000651 prodrug Substances 0.000 claims description 8
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 description 7
150000001204 N-oxides Chemical class 0.000 claims description 7
125000003545 alkoxy group Chemical group 0.000 claims description 7
229910052736 halogen Inorganic materials 0.000 claims description 7
150000002367 halogens Chemical class 0.000 claims description 7
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
239000000203 mixture Substances 0.000 claims description 6
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 5
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 5
125000000217 alkyl group Chemical group 0.000 claims description 5
150000001408 amides Chemical class 0.000 claims description 5
125000000490 cinnamyl group Chemical group C(C=CC1=CC=CC=C1)* 0.000 claims description 5
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
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 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
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 2
238000004519 manufacturing process Methods 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
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
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
SGPGESCZOCHFCL-UHFFFAOYSA-N Tilisolol hydrochloride Chemical compound [Cl-].C1=CC=C2C(=O)N(C)C=C(OCC(O)C[NH2+]C(C)(C)C)C2=C1 SGPGESCZOCHFCL-UHFFFAOYSA-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
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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

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

OA1200300149A 2000-11-30 2001-11-29 1,4-Disubstituted piperazine derivatives useful asuro-selective alpha 1-adrenoceptor blockers. OA12537A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
IN1097DE2000		2000-11-30

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OA12537A true OA12537A (en)	2006-06-05

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Country Status (25)

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

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AU2002253429A1 (en) *	2002-04-08	2003-10-20	Ranbaxy Laboratories Limited	ALPHA, OMEGA-DICARBOXIMIDE DERIVATIVES AS USEFUL URO-SELECTIVE Alpha1Alpha 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 (fr) *	2004-03-22	2007-01-31	Ranbaxy Laboratories, Ltd.	Therapie combinee destinee a reduire les symptomes des voies urinaires
WO2005113498A1 (fr) *	2004-05-19	2005-12-01	Ranbaxy Laboratories Limited	Antagonistes du recepteur adrenergique
US20090312344A1 (en) *	2004-05-31	2009-12-17	Mohammad Salman	Arylpiperazine derivatives as adrenergic receptor antagonists
WO2006018815A1 (fr) *	2004-08-16	2006-02-23	Ranbaxy Laboratories Limited	Derives de piperazine utilises comme antagonistes de recepteurs adrenergiques
WO2006051374A2 (fr) *	2004-11-11	2006-05-18	Ranbaxy Laboratories Limited	Antagonistes des recepteurs adrenergiques
WO2006051399A1 (fr) *	2004-11-11	2006-05-18	Ranbaxy Laboratories Limited	Derives de piperazine utiles en tant qu'antagonistes des recepteurs adrenergiques
WO2006092710A1 (fr) *	2005-03-02	2006-09-08	Ranbaxy Laboratories Limited	Metabolites de la 2-{3-[4-(2-isopropoxyphenyl)piperazin-1-yl]-propyl}-3a,4,7,7a-tetrahydro-1h-isoindole-1,3-(2h)-dione
WO2006117760A1 (fr) *	2005-05-03	2006-11-09	Ranbaxy Laboratories Limited	Antagonistes de recepteurs adrenergiques
WO2007029156A2 (fr) *	2005-09-05	2007-03-15	Ranbaxy Laboratories Limited	Derives d'isoindoledione comme antagonistes de recepteurs adrenergiques
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2001
- 2001-11-29 KR KR10-2003-7007305A patent/KR20030068164A/ko not_active Withdrawn
- 2001-11-29 AP APAP/P/2003/002810A patent/AP2003002810A0/en unknown
- 2001-11-29 CN CNB018220460A patent/CN1230423C/zh not_active Expired - Fee Related
- 2001-11-29 HU HU0400545A patent/HUP0400545A3/hu unknown
- 2001-11-29 EP EP01998540A patent/EP1339682A1/fr not_active Withdrawn
- 2001-11-29 AU AU2231502A patent/AU2231502A/xx active Pending
- 2001-11-29 PA PA20018534001A patent/PA8534001A1/es unknown
- 2001-11-29 WO PCT/IB2001/002261 patent/WO2002044151A1/fr not_active Ceased
- 2001-11-29 CZ CZ20031698A patent/CZ20031698A3/cs unknown
- 2001-11-29 AU AU2002222315A patent/AU2002222315B2/en not_active Ceased
- 2001-11-29 BR BR0115865-1A patent/BR0115865A/pt not_active IP Right Cessation
- 2001-11-29 MX MXPA03004850A patent/MXPA03004850A/es unknown
- 2001-11-29 SK SK805-2003A patent/SK8052003A3/sk not_active Application Discontinuation
- 2001-11-29 EA EA200300620A patent/EA006941B1/ru not_active IP Right Cessation
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- 2001-11-29 PL PL01362210A patent/PL362210A1/xx not_active Application Discontinuation
- 2001-11-29 JP JP2002546521A patent/JP2004514711A/ja not_active Withdrawn
- 2001-11-29 CA CA002430343A patent/CA2430343A1/fr not_active Abandoned
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- 2001-11-30 US US09/998,115 patent/US6914064B2/en not_active Expired - Fee Related
2003
- 2003-05-30 MA MA27188A patent/MA26064A1/fr unknown
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Also Published As

Publication number	Publication date
SK8052003A3 (en)	2003-12-02
KR20030068164A (ko)	2003-08-19
EA006941B1 (ru)	2006-06-30
CN1230423C (zh)	2005-12-07
BR0115865A (pt)	2003-12-23
ZA200304242B (en)	2004-03-02
AU2231502A (en)	2002-06-11
PL362210A1 (en)	2004-10-18
EE200300250A (et)	2003-10-15
AU2002222315B2 (en)	2007-06-21
AR035930A1 (es)	2004-07-28
MA26064A1 (fr)	2004-04-01
US6914064B2 (en)	2005-07-05
AP2003002810A0 (en)	2003-06-30
US20020156085A1 (en)	2002-10-24
JP2004514711A (ja)	2004-05-20
HUP0400545A3 (en)	2007-05-02
HUP0400545A2 (hu)	2004-07-28
BG107943A (bg)	2004-08-31
WO2002044151A1 (fr)	2002-06-06
DOP2001000296A (es)	2003-03-15
MXPA03004850A (es)	2004-01-26
CN1486300A (zh)	2004-03-31
EA200300620A1 (ru)	2003-12-25
CZ20031698A3 (cs)	2003-11-12
CA2430343A1 (fr)	2002-06-06
NZ526226A (en)	2004-05-28
EP1339682A1 (fr)	2003-09-03
PA8534001A1 (es)	2002-12-11

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OA12537A (en)	2006-06-05	1,4-Disubstituted piperazine derivatives useful asuro-selective alpha 1-adrenoceptor blockers.
AU2002222315A1 (en)	2002-08-15	1,4-disubstituted piperazine derivatives useful as uro-selective alpha1-adrenoceptor blockers
HU189886B (en)	1986-08-28	Process for preparing /2-oxo-1,2,3,5-tetrahydro-imidazo/2,1-b/quinazolinyl/-oxy-alkane-carboxylic acid amides and pharmaceutical compositions containing such compounds
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MXPA04009821A (es)	2004-12-13	Derivados de carboximida como utiles bloqueadores del adrenoceptor alfa-1a uro-selectivos.
JP3987113B2 (ja)	2007-10-03	抗高血圧活性を有する新規キナゾリン―４―アミノ―２―（ピペリジン―１―イル―４―置換）誘導体並びにその製造法および医薬用途
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CS202071B2 (cs)	1980-12-31	Způsob přípravy 2-(4-substituovaných piperazin-1-yl)-4-amino-6,7- -dimethoxychinazolinů
ZA200101971B (en)	2002-03-11	N-substituted azabicycloheptane derivatives, production and use thereof.