JP2008523075A5 - - Google Patents
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- Publication number
- JP2008523075A5 JP2008523075A5 JP2007545598A JP2007545598A JP2008523075A5 JP 2008523075 A5 JP2008523075 A5 JP 2008523075A5 JP 2007545598 A JP2007545598 A JP 2007545598A JP 2007545598 A JP2007545598 A JP 2007545598A JP 2008523075 A5 JP2008523075 A5 JP 2008523075A5
- Authority
- JP
- Japan
- Prior art keywords
- compound according
- piperazine
- fluoro
- biphenyl
- disorder
- 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.)
- Withdrawn
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- 150000001875 compounds Chemical class 0.000 claims 50
- 239000000203 mixture Substances 0.000 claims 14
- 229910052736 halogen Inorganic materials 0.000 claims 12
- 150000002367 halogens Chemical class 0.000 claims 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 8
- 208000035475 disorder Diseases 0.000 claims 8
- 238000000034 method Methods 0.000 claims 7
- 241001465754 Metazoa Species 0.000 claims 6
- 239000008194 pharmaceutical composition Substances 0.000 claims 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 6
- -1 2-trifluoromethylphenyl Chemical group 0.000 claims 5
- 210000003169 central nervous system Anatomy 0.000 claims 5
- 208000015114 central nervous system disease Diseases 0.000 claims 5
- 239000003814 drug Substances 0.000 claims 5
- 238000004519 manufacturing process Methods 0.000 claims 5
- 238000002560 therapeutic procedure Methods 0.000 claims 5
- 208000024827 Alzheimer disease Diseases 0.000 claims 4
- 241000124008 Mammalia Species 0.000 claims 4
- 208000012902 Nervous system disease Diseases 0.000 claims 4
- 208000008589 Obesity Diseases 0.000 claims 4
- 125000000217 alkyl group Chemical group 0.000 claims 4
- 235000020824 obesity Nutrition 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 239000012453 solvate Substances 0.000 claims 4
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 3
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 3
- 208000024172 Cardiovascular disease Diseases 0.000 claims 3
- 208000010228 Erectile Dysfunction Diseases 0.000 claims 3
- 208000018522 Gastrointestinal disease Diseases 0.000 claims 3
- 102100026383 Vasopressin-neurophysin 2-copeptin Human genes 0.000 claims 3
- 201000010064 diabetes insipidus Diseases 0.000 claims 3
- 201000001881 impotence Diseases 0.000 claims 3
- 201000002859 sleep apnea Diseases 0.000 claims 3
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims 2
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims 2
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 230000003542 behavioural effect Effects 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 125000002541 furyl group Chemical group 0.000 claims 2
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims 2
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims 2
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 125000001544 thienyl group Chemical group 0.000 claims 2
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 1
- NIBIUNYYIJEDNA-UHFFFAOYSA-N 1-(2-chloro-3-phenylphenyl)piperazine Chemical compound ClC1=C(N2CCNCC2)C=CC=C1C1=CC=CC=C1 NIBIUNYYIJEDNA-UHFFFAOYSA-N 0.000 claims 1
- XHUKTFFNIQQBCJ-UHFFFAOYSA-N 1-(2-fluoro-3-phenylphenyl)piperazine Chemical compound FC1=C(N2CCNCC2)C=CC=C1C1=CC=CC=C1 XHUKTFFNIQQBCJ-UHFFFAOYSA-N 0.000 claims 1
- XJKABXZTLBIDMP-UHFFFAOYSA-N 1-(2-fluoro-5-phenylphenyl)piperazine Chemical compound FC1=CC=C(C=2C=CC=CC=2)C=C1N1CCNCC1 XJKABXZTLBIDMP-UHFFFAOYSA-N 0.000 claims 1
- VIBNKGRWMCNKCV-UHFFFAOYSA-N 1-(2-fluoro-5-pyridin-3-ylphenyl)piperazine Chemical compound FC1=CC=C(C=2C=NC=CC=2)C=C1N1CCNCC1 VIBNKGRWMCNKCV-UHFFFAOYSA-N 0.000 claims 1
- IWCVFZOPGGYPEC-UHFFFAOYSA-N 1-(2-fluoro-5-thiophen-2-ylphenyl)piperazine Chemical compound FC1=CC=C(C=2SC=CC=2)C=C1N1CCNCC1 IWCVFZOPGGYPEC-UHFFFAOYSA-N 0.000 claims 1
- ILMZOYZNCZYFQP-UHFFFAOYSA-N 1-(2-fluoro-5-thiophen-3-ylphenyl)piperazine Chemical compound FC1=CC=C(C2=CSC=C2)C=C1N1CCNCC1 ILMZOYZNCZYFQP-UHFFFAOYSA-N 0.000 claims 1
- KXWSDVZLJFXPRF-UHFFFAOYSA-N 1-(3-fluoro-5-phenylphenyl)piperazine Chemical compound C=1C(F)=CC(N2CCNCC2)=CC=1C1=CC=CC=C1 KXWSDVZLJFXPRF-UHFFFAOYSA-N 0.000 claims 1
- BAJVCQQBZLAKTP-UHFFFAOYSA-N 1-(3-fluoro-5-thiophen-3-ylphenyl)piperazine Chemical compound C=1C(F)=CC(N2CCNCC2)=CC=1C=1C=CSC=1 BAJVCQQBZLAKTP-UHFFFAOYSA-N 0.000 claims 1
- BYCWTUDVLWJKCR-UHFFFAOYSA-N 1-(4-fluoro-3-phenylphenyl)piperazine Chemical compound FC1=CC=C(N2CCNCC2)C=C1C1=CC=CC=C1 BYCWTUDVLWJKCR-UHFFFAOYSA-N 0.000 claims 1
- PREZEXPFQHILJA-UHFFFAOYSA-N 1-(4-fluoro-3-pyridin-3-ylphenyl)piperazine Chemical compound FC1=CC=C(N2CCNCC2)C=C1C1=CC=CN=C1 PREZEXPFQHILJA-UHFFFAOYSA-N 0.000 claims 1
- WCPXBOXDTBVUED-UHFFFAOYSA-N 1-[2-fluoro-3-(2-fluorophenyl)phenyl]piperazine Chemical compound FC1=CC=CC=C1C1=CC=CC(N2CCNCC2)=C1F WCPXBOXDTBVUED-UHFFFAOYSA-N 0.000 claims 1
- BSSKACQVJGGTJJ-UHFFFAOYSA-N 1-[2-fluoro-3-(3-fluorophenyl)phenyl]piperazine Chemical compound FC1=CC=CC(C=2C(=C(N3CCNCC3)C=CC=2)F)=C1 BSSKACQVJGGTJJ-UHFFFAOYSA-N 0.000 claims 1
- BWEPWAYBIJPUNT-UHFFFAOYSA-N 1-[2-fluoro-3-(4-fluorophenyl)phenyl]piperazine Chemical compound C1=CC(F)=CC=C1C1=CC=CC(N2CCNCC2)=C1F BWEPWAYBIJPUNT-UHFFFAOYSA-N 0.000 claims 1
- KWLPQTRFPGIJAW-UHFFFAOYSA-N 1-[2-fluoro-5-(furan-3-yl)phenyl]piperazine Chemical compound FC1=CC=C(C2=COC=C2)C=C1N1CCNCC1 KWLPQTRFPGIJAW-UHFFFAOYSA-N 0.000 claims 1
- GQEPTNSSTADQFD-UHFFFAOYSA-N 1-[3-fluoro-5-(2-fluorophenyl)phenyl]piperazine Chemical compound C=1C(F)=CC(N2CCNCC2)=CC=1C1=CC=CC=C1F GQEPTNSSTADQFD-UHFFFAOYSA-N 0.000 claims 1
- GKFGCXPFEOHJFJ-UHFFFAOYSA-N 1-[3-fluoro-5-(2-methoxyphenyl)phenyl]piperazine Chemical compound COC1=CC=CC=C1C1=CC(F)=CC(N2CCNCC2)=C1 GKFGCXPFEOHJFJ-UHFFFAOYSA-N 0.000 claims 1
- FNMOODLZHLCWFQ-UHFFFAOYSA-N 1-[3-fluoro-5-(2-methylphenyl)phenyl]piperazine Chemical compound CC1=CC=CC=C1C1=CC(F)=CC(N2CCNCC2)=C1 FNMOODLZHLCWFQ-UHFFFAOYSA-N 0.000 claims 1
- OCWPCKCIYLGRFB-UHFFFAOYSA-N 1-[3-fluoro-5-(3-fluorophenyl)phenyl]piperazine Chemical compound FC1=CC=CC(C=2C=C(C=C(F)C=2)N2CCNCC2)=C1 OCWPCKCIYLGRFB-UHFFFAOYSA-N 0.000 claims 1
- GFGUUOSZHKSJJX-UHFFFAOYSA-N 1-[3-fluoro-5-(3-methoxyphenyl)phenyl]piperazine Chemical compound COC1=CC=CC(C=2C=C(C=C(F)C=2)N2CCNCC2)=C1 GFGUUOSZHKSJJX-UHFFFAOYSA-N 0.000 claims 1
- DYOIGVKJAQUVDE-UHFFFAOYSA-N 1-[3-fluoro-5-(3-methylphenyl)phenyl]piperazine Chemical compound CC1=CC=CC(C=2C=C(C=C(F)C=2)N2CCNCC2)=C1 DYOIGVKJAQUVDE-UHFFFAOYSA-N 0.000 claims 1
- CHFFBFUBUFLWRB-UHFFFAOYSA-N 1-[3-fluoro-5-(4-fluorophenyl)phenyl]piperazine Chemical compound C1=CC(F)=CC=C1C1=CC(F)=CC(N2CCNCC2)=C1 CHFFBFUBUFLWRB-UHFFFAOYSA-N 0.000 claims 1
- KXKGTIQGCJAZDP-UHFFFAOYSA-N 1-[3-fluoro-5-(4-methoxyphenyl)phenyl]piperazine Chemical compound C1=CC(OC)=CC=C1C1=CC(F)=CC(N2CCNCC2)=C1 KXKGTIQGCJAZDP-UHFFFAOYSA-N 0.000 claims 1
- CMHHBGFMVJIZBR-UHFFFAOYSA-N 1-[3-fluoro-5-(4-methylphenyl)phenyl]piperazine Chemical compound C1=CC(C)=CC=C1C1=CC(F)=CC(N2CCNCC2)=C1 CMHHBGFMVJIZBR-UHFFFAOYSA-N 0.000 claims 1
- QSBYGGVQWDBABH-UHFFFAOYSA-N 1-[3-fluoro-5-(furan-3-yl)phenyl]piperazine Chemical compound C=1C(F)=CC(N2CCNCC2)=CC=1C=1C=COC=1 QSBYGGVQWDBABH-UHFFFAOYSA-N 0.000 claims 1
- MLRGZCCYGYPALE-UHFFFAOYSA-N 1-[3-fluoro-5-[2-(trifluoromethyl)phenyl]phenyl]piperazine Chemical compound C=1C(F)=CC(N2CCNCC2)=CC=1C1=CC=CC=C1C(F)(F)F MLRGZCCYGYPALE-UHFFFAOYSA-N 0.000 claims 1
- IPVYYMCMEUTLEA-UHFFFAOYSA-N 1-[3-fluoro-5-[3-(trifluoromethyl)phenyl]phenyl]piperazine Chemical compound C=1C(F)=CC(N2CCNCC2)=CC=1C1=CC=CC(C(F)(F)F)=C1 IPVYYMCMEUTLEA-UHFFFAOYSA-N 0.000 claims 1
- IZQKHNYWZIXMJL-UHFFFAOYSA-N 1-[3-fluoro-5-[4-(trifluoromethyl)phenyl]phenyl]piperazine Chemical compound C=1C(F)=CC(N2CCNCC2)=CC=1C1=CC=C(C(F)(F)F)C=C1 IZQKHNYWZIXMJL-UHFFFAOYSA-N 0.000 claims 1
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims 1
- 208000007848 Alcoholism Diseases 0.000 claims 1
- 208000000103 Anorexia Nervosa Diseases 0.000 claims 1
- 208000019901 Anxiety disease Diseases 0.000 claims 1
- 208000020925 Bipolar disease Diseases 0.000 claims 1
- 208000032841 Bulimia Diseases 0.000 claims 1
- 206010006550 Bulimia nervosa Diseases 0.000 claims 1
- 206010008874 Chronic Fatigue Syndrome Diseases 0.000 claims 1
- 206010012289 Dementia Diseases 0.000 claims 1
- 206010019233 Headaches Diseases 0.000 claims 1
- 208000019695 Migraine disease Diseases 0.000 claims 1
- 208000027626 Neurocognitive disease Diseases 0.000 claims 1
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims 1
- 208000002193 Pain Diseases 0.000 claims 1
- 206010036618 Premenstrual syndrome Diseases 0.000 claims 1
- 208000028017 Psychotic disease Diseases 0.000 claims 1
- 201000001880 Sexual dysfunction Diseases 0.000 claims 1
- 206010041250 Social phobia Diseases 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 claims 1
- 125000004423 acyloxy group Chemical group 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 125000005431 alkyl carboxamide group Chemical group 0.000 claims 1
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims 1
- 125000005422 alkyl sulfonamido group Chemical group 0.000 claims 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 1
- 125000004414 alkyl thio group Chemical group 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 208000025748 atypical depressive disease Diseases 0.000 claims 1
- 125000005392 carboxamide group Chemical class NC(=O)* 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 125000004663 dialkyl amino group Chemical group 0.000 claims 1
- 208000010643 digestive system disease Diseases 0.000 claims 1
- 206010013663 drug dependence Diseases 0.000 claims 1
- 206010015037 epilepsy Diseases 0.000 claims 1
- 230000037406 food intake Effects 0.000 claims 1
- 235000012631 food intake Nutrition 0.000 claims 1
- 208000018685 gastrointestinal system disease Diseases 0.000 claims 1
- 125000004438 haloalkoxy group Chemical group 0.000 claims 1
- 125000001188 haloalkyl group Chemical group 0.000 claims 1
- 125000004440 haloalkylsulfinyl group Chemical group 0.000 claims 1
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims 1
- 125000004995 haloalkylthio group Chemical group 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 230000001939 inductive effect Effects 0.000 claims 1
- 201000009941 intracranial hypertension Diseases 0.000 claims 1
- 206010027175 memory impairment Diseases 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 206010027599 migraine Diseases 0.000 claims 1
- 208000029766 myalgic encephalomeyelitis/chronic fatigue syndrome Diseases 0.000 claims 1
- 208000022821 personality disease Diseases 0.000 claims 1
- 201000000484 premenstrual tension Diseases 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 208000020016 psychiatric disease Diseases 0.000 claims 1
- 230000036186 satiety Effects 0.000 claims 1
- 235000019627 satiety Nutrition 0.000 claims 1
- 201000000980 schizophrenia Diseases 0.000 claims 1
- 231100000872 sexual dysfunction Toxicity 0.000 claims 1
- 208000019116 sleep disease Diseases 0.000 claims 1
- 208000020685 sleep-wake disease Diseases 0.000 claims 1
- 208000011117 substance-related disease Diseases 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 125000003396 thiol group Chemical class [H]S* 0.000 claims 1
- 230000004584 weight gain Effects 0.000 claims 1
- 235000019786 weight gain Nutrition 0.000 claims 1
- 0 *c1c(*)c([Al])c(*)c(N2CCN(*)CC2)c1* Chemical compound *c1c(*)c([Al])c(*)c(N2CCN(*)CC2)c1* 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US63578504P | 2004-12-13 | 2004-12-13 | |
| PCT/US2005/044293 WO2006065600A2 (en) | 2004-12-13 | 2005-12-09 | N-biaryl and n-arylheteroaryl piperazine derivatives as modulators of the 5ht2c receptor useful for the treatment of disorders related thereto |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2008523075A JP2008523075A (ja) | 2008-07-03 |
| JP2008523075A5 true JP2008523075A5 (enExample) | 2009-01-22 |
Family
ID=36129730
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007545598A Withdrawn JP2008523075A (ja) | 2004-12-13 | 2005-12-09 | ５ｈｔ２ｃレセプター関連障害の処置に有用な５ｈｔ２ｃレセプターのモジュレーターとしてのｎ−ビアリールピペラジン誘導体およびｎ−アリールヘテロアリールピペラジン誘導体 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US20080119477A1 (enExample) |
| EP (1) | EP1828156A2 (enExample) |
| JP (1) | JP2008523075A (enExample) |
| CN (1) | CN101084205A (enExample) |
| AU (1) | AU2005316825A1 (enExample) |
| CA (1) | CA2588595A1 (enExample) |
| WO (1) | WO2006065600A2 (enExample) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006124865A2 (en) * | 2005-05-19 | 2006-11-23 | Vertex Pharmaceuticals Incorporated | Biaryls derivatives useful as modulators of ion channels |
| EP1904491A2 (en) | 2005-05-31 | 2008-04-02 | Vertex Pharmaceuticals Incorporated | Heterocycles useful as modulators of ion channels |
| JP5528699B2 (ja) | 2006-05-16 | 2014-06-25 | 武田薬品工業株式会社 | 縮合複素環化合物およびその用途 |
| JP5520051B2 (ja) | 2007-11-15 | 2014-06-11 | 武田薬品工業株式会社 | 縮合ピリジン誘導体およびその用途 |
| MX2010009110A (es) * | 2008-02-19 | 2010-11-30 | Adolor Corp | Beloxepina, sus enantiomeros, y analogos de la misma para el tratamiento de dolor. |
| WO2011071136A1 (ja) | 2009-12-11 | 2011-06-16 | アステラス製薬株式会社 | 線維筋痛症治療剤 |
| AU2011212930B2 (en) | 2010-02-04 | 2016-02-11 | The Board Of Trustees Of The University Of Illinois | Highly selective 5-HT(2C) receptor agonists having antagonist activity at the 5-HT(2B) receptor |
| US20130267500A1 (en) | 2010-09-01 | 2013-10-10 | Arena Pharmaceuticals, Inc. | 5-ht2c receptor agonists in the treatment of disorders ameliorated by reduction of norepinephrine level |
| WO2015066344A1 (en) | 2013-11-01 | 2015-05-07 | Arena Pharmaceuticals, Inc. | 5-ht2c receptor agonists and compositions and methods of use |
| PL3250549T3 (pl) | 2015-01-29 | 2021-12-13 | The Board Of Trustees Of The University Of Illinois | Cyklopropylometanoaminy jako selektywni agoniści receptora 5-HT(2C) |
| WO2019131902A1 (ja) | 2017-12-27 | 2019-07-04 | 武田薬品工業株式会社 | 腹圧性尿失禁および便失禁の治療薬 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA7546B (en) * | 1974-01-21 | 1976-08-25 | Parke Davis & Co | New antibacterial amide compounds and methods for their production |
| CA2144669A1 (en) * | 1994-03-29 | 1995-09-30 | Kozo Akasaka | Biphenyl derivatives |
| TR200101239T2 (tr) * | 1998-11-03 | 2001-11-21 | Basf Aktiengesellschaft | İkameli-2-fenilbenzimidazoller, üretimleri ve kullanımları |
| DE19939516A1 (de) * | 1999-08-20 | 2001-02-22 | Boehringer Ingelheim Pharma | Substituierte Piperazinderivate, ihre Herstellung und ihre Verwendung als Arzneimittel |
| DE19939745A1 (de) * | 1999-08-21 | 2001-02-22 | Boehringer Ingelheim Pharma | Substituierte Piperazinderivate, ihre Herstellung und ihre Verwendung als Arzneimittel |
| ATE461932T1 (de) * | 2004-04-21 | 2010-04-15 | Schering Corp | Pyrazoloä4,3-eü-1,2,4-triazoloä1,5-cüpyrimidine als antagonisten des adenosin-a2a-rezeptors |
-
2005
- 2005-12-09 WO PCT/US2005/044293 patent/WO2006065600A2/en not_active Ceased
- 2005-12-09 AU AU2005316825A patent/AU2005316825A1/en not_active Abandoned
- 2005-12-09 JP JP2007545598A patent/JP2008523075A/ja not_active Withdrawn
- 2005-12-09 US US11/792,894 patent/US20080119477A1/en not_active Abandoned
- 2005-12-09 EP EP05853255A patent/EP1828156A2/en not_active Withdrawn
- 2005-12-09 CN CNA2005800424116A patent/CN101084205A/zh active Pending
- 2005-12-09 CA CA002588595A patent/CA2588595A1/en not_active Abandoned