NO312460B1 - 6-fenylpyridyl-2-amin-derivater, anvendelse derav samt farmasöytisk sammensetning - Google Patents
6-fenylpyridyl-2-amin-derivater, anvendelse derav samt farmasöytisk sammensetning Download PDFInfo
- Publication number
- NO312460B1 NO312460B1 NO19984516A NO984516A NO312460B1 NO 312460 B1 NO312460 B1 NO 312460B1 NO 19984516 A NO19984516 A NO 19984516A NO 984516 A NO984516 A NO 984516A NO 312460 B1 NO312460 B1 NO 312460B1
- Authority
- NO
- Norway
- Prior art keywords
- phenyl
- ethyl
- nmr
- aza
- aminopyridin
- Prior art date
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- 239000008194 pharmaceutical composition Substances 0.000 title claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 84
- -1 methoxy, hydroxy Chemical group 0.000 claims description 61
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 29
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 24
- 150000003839 salts Chemical class 0.000 claims description 19
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims description 13
- 150000001412 amines Chemical class 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 241000124008 Mammalia Species 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 208000002193 Pain Diseases 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 7
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
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- FONQITKXUUBLDF-UHFFFAOYSA-N n-[2-[4-(6-aminopyridin-2-yl)phenyl]ethyl]-3-oxa-9-azabicyclo[3.3.1]nonan-7-amine Chemical compound NC1=CC=CC(C=2C=CC(CCNC3CC4COCC(N4)C3)=CC=2)=N1 FONQITKXUUBLDF-UHFFFAOYSA-N 0.000 claims description 6
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- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 4
- YGTFZZXTRLPAFA-UHFFFAOYSA-N 6-[4-[2-(8-azaspiro[4.5]decan-8-yl)ethyl]phenyl]pyridin-2-amine Chemical compound NC1=CC=CC(C=2C=CC(CCN3CCC4(CCCC4)CC3)=CC=2)=N1 YGTFZZXTRLPAFA-UHFFFAOYSA-N 0.000 claims description 4
- TWJHFSYMBVCUGP-UHFFFAOYSA-N 8-[2-[4-(6-aminopyridin-2-yl)phenyl]ethyl]-8-azabicyclo[3.2.1]octan-3-amine Chemical compound C1C(N)CC2CCC1N2CCC(C=C1)=CC=C1C1=CC=CC(N)=N1 TWJHFSYMBVCUGP-UHFFFAOYSA-N 0.000 claims description 4
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- 125000001424 substituent group Chemical group 0.000 claims description 4
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- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
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- NUBHUTJQYQCDCC-UHFFFAOYSA-N 3-[2-[4-(6-aminopyridin-2-yl)phenyl]ethyl]-n,n-dimethyl-3-azabicyclo[3.1.0]hexan-6-amine Chemical compound C1C2C(N(C)C)C2CN1CCC(C=C1)=CC=C1C1=CC=CC(N)=N1 NUBHUTJQYQCDCC-UHFFFAOYSA-N 0.000 claims description 2
- VJPTWOKAQQYAIG-UHFFFAOYSA-N 6-[4-[2-(1,3-dihydroisoindol-2-yl)ethyl]phenyl]pyridin-2-amine Chemical compound NC1=CC=CC(C=2C=CC(CCN3CC4=CC=CC=C4C3)=CC=2)=N1 VJPTWOKAQQYAIG-UHFFFAOYSA-N 0.000 claims description 2
- BTVALCJDZTZPBG-UHFFFAOYSA-N 6-[4-[2-(3,4-dihydro-1h-isoquinolin-2-yl)ethyl]phenyl]pyridin-2-amine Chemical compound NC1=CC=CC(C=2C=CC(CCN3CC4=CC=CC=C4CC3)=CC=2)=N1 BTVALCJDZTZPBG-UHFFFAOYSA-N 0.000 claims description 2
- YPJNBYZWWSYJPW-UHFFFAOYSA-N 6-[4-[2-(5-methyl-2,5-diazabicyclo[2.2.1]heptan-2-yl)ethyl]phenyl]pyridin-2-amine Chemical compound CN1CC2CC1CN2CCC(C=C1)=CC=C1C1=CC=CC(N)=N1 YPJNBYZWWSYJPW-UHFFFAOYSA-N 0.000 claims description 2
- CHHJCLLFBSIERA-UHFFFAOYSA-N 8-[2-[4-(6-aminopyridin-2-yl)phenyl]ethyl]-3-(2-phenylethyl)-1,3,8-triazaspiro[4.5]decane-2,4-dione Chemical compound NC1=CC=CC(C=2C=CC(CCN3CCC4(CC3)C(N(CCC=3C=CC=CC=3)C(=O)N4)=O)=CC=2)=N1 CHHJCLLFBSIERA-UHFFFAOYSA-N 0.000 claims description 2
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- QJZUKDFHGGYHMC-UHFFFAOYSA-N pyridine-3-carbaldehyde Chemical compound O=CC1=CC=CN=C1 QJZUKDFHGGYHMC-UHFFFAOYSA-N 0.000 description 1
- BGUWFUQJCDRPTL-UHFFFAOYSA-N pyridine-4-carbaldehyde Chemical compound O=CC1=CC=NC=C1 BGUWFUQJCDRPTL-UHFFFAOYSA-N 0.000 description 1
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- 125000003107 substituted aryl group Chemical group 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
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- NUZXPHIQZUYMOR-UHFFFAOYSA-N tert-butyl 3,5-dimethylpiperazine-1-carboxylate Chemical compound CC1CN(C(=O)OC(C)(C)C)CC(C)N1 NUZXPHIQZUYMOR-UHFFFAOYSA-N 0.000 description 1
- ZVRIIQQTFKQUQE-UHFFFAOYSA-N tert-butyl n-(2,6-dimethylpiperidin-4-yl)carbamate Chemical compound CC1CC(NC(=O)OC(C)(C)C)CC(C)N1 ZVRIIQQTFKQUQE-UHFFFAOYSA-N 0.000 description 1
- PJGMDHUHBZCJMI-UHFFFAOYSA-N tert-butyl n-(3-oxa-9-azabicyclo[3.3.1]nonan-7-yl)carbamate Chemical compound C1OCC2CC(NC(=O)OC(C)(C)C)CC1N2 PJGMDHUHBZCJMI-UHFFFAOYSA-N 0.000 description 1
- WUOQXNWMYLFAHT-UHFFFAOYSA-N tert-butyl n-piperidin-3-ylcarbamate Chemical compound CC(C)(C)OC(=O)NC1CCCNC1 WUOQXNWMYLFAHT-UHFFFAOYSA-N 0.000 description 1
- CKXZPVPIDOJLLM-UHFFFAOYSA-N tert-butyl n-piperidin-4-ylcarbamate Chemical compound CC(C)(C)OC(=O)NC1CCNCC1 CKXZPVPIDOJLLM-UHFFFAOYSA-N 0.000 description 1
- DQQJBEAXSOOCPG-UHFFFAOYSA-N tert-butyl n-pyrrolidin-3-ylcarbamate Chemical compound CC(C)(C)OC(=O)NC1CCNC1 DQQJBEAXSOOCPG-UHFFFAOYSA-N 0.000 description 1
- CWXPZXBSDSIRCS-UHFFFAOYSA-N tert-butyl piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCNCC1 CWXPZXBSDSIRCS-UHFFFAOYSA-N 0.000 description 1
- RQCNHUCCQJMSRG-UHFFFAOYSA-N tert-butyl piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCCCC1 RQCNHUCCQJMSRG-UHFFFAOYSA-N 0.000 description 1
- JBGVNDWTUGVGOO-UHFFFAOYSA-N tert-butylcarbamic acid;2,6-dimethylpiperidin-4-amine Chemical compound CC(C)(C)NC(O)=O.CC1CC(N)CC(C)N1 JBGVNDWTUGVGOO-UHFFFAOYSA-N 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 238000006478 transmetalation reaction Methods 0.000 description 1
- JBWKIWSBJXDJDT-UHFFFAOYSA-N triphenylmethyl chloride Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 JBWKIWSBJXDJDT-UHFFFAOYSA-N 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
Classifications
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- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/73—Unsubstituted amino or imino radicals
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- 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
- C07D401/10—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 aromatic rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- 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
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- 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
- C07D405/02—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 two hetero rings
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- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
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- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
- C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
- C07D451/04—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof with hetero atoms directly attached in position 3 of the 8-azabicyclo [3.2.1] octane or in position 7 of the 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/10—Spiro-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/08—Bridged systems
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Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US1434396P | 1996-03-29 | 1996-03-29 | |
PCT/IB1997/000132 WO1997036871A1 (en) | 1996-03-29 | 1997-02-17 | 6-phenylpyridyl-2-amine derivatives |
Publications (3)
Publication Number | Publication Date |
---|---|
NO984516L NO984516L (no) | 1998-09-28 |
NO984516D0 NO984516D0 (no) | 1998-09-28 |
NO312460B1 true NO312460B1 (no) | 2002-05-13 |
Family
ID=21764907
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO19984516A NO312460B1 (no) | 1996-03-29 | 1998-09-28 | 6-fenylpyridyl-2-amin-derivater, anvendelse derav samt farmasöytisk sammensetning |
Country Status (44)
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AU744313B2 (en) * | 1997-02-10 | 2002-02-21 | Pfizer Products Inc. | 2-amino-6-(2-substituted-4-phenoxy)-substituted-pyridines |
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DE69923448T2 (de) * | 1998-06-03 | 2005-12-29 | Pfizer Products Inc., Groton | 2-aminopyridine mit kondensierten ringsubstituenten als stickstoff-oxid-synthase inhibitoren |
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DE19845830A1 (de) * | 1998-09-24 | 2000-03-30 | Schering Ag | Aminoalkyl-3,4-dihydrochinolin-Derivate und ihre Verwendung in Arzneimitteln |
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CN1077886C (zh) * | 1993-10-21 | 2002-01-16 | G·D·瑟尔公司 | 用作一氧化一氮合酶抑制剂的脒基衍生物 |
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DE69728138T2 (de) * | 1996-03-29 | 2004-09-16 | Pfizer Inc. | 6-phenylpyridinderivate |
HN1997000027A (es) * | 1996-12-06 | 1997-06-05 | Pfizer Prod Inc | Derivados de 6-fenil piridil - 2 amina |
-
1997
- 1997-02-17 DE DE69728138T patent/DE69728138T2/de not_active Expired - Fee Related
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- 1997-02-17 KR KR1019980707773A patent/KR100313641B1/ko not_active IP Right Cessation
- 1997-02-17 CZ CZ19982614A patent/CZ291647B6/cs not_active IP Right Cessation
- 1997-02-17 CN CNA2004100058259A patent/CN1546470A/zh active Pending
- 1997-02-17 HU HU9902455A patent/HUP9902455A3/hu unknown
- 1997-02-17 UA UA98084618A patent/UA49006C2/uk unknown
- 1997-02-17 EA EA199800772A patent/EA002270B1/ru not_active IP Right Cessation
- 1997-02-17 PT PT97901748T patent/PT891332E/pt unknown
- 1997-02-17 AU AU15548/97A patent/AU729129B2/en not_active Ceased
- 1997-02-17 DK DK97901748T patent/DK0891332T3/da active
- 1997-02-17 SI SI9730630T patent/SI0891332T1/xx unknown
- 1997-02-17 ES ES97901748T patent/ES2214604T3/es not_active Expired - Lifetime
- 1997-02-17 SK SK1139-98A patent/SK113998A3/sk unknown
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- 1997-02-17 BR BR9708386A patent/BR9708386A/pt not_active Application Discontinuation
- 1997-02-17 EP EP20040003268 patent/EP1471055A1/en not_active Ceased
- 1997-02-17 CN CNB971935262A patent/CN1168719C/zh not_active Expired - Fee Related
- 1997-02-17 WO PCT/IB1997/000132 patent/WO1997036871A1/en active IP Right Grant
- 1997-02-17 NZ NZ500927A patent/NZ500927A/en unknown
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- 1997-03-13 US US08/816,235 patent/US6235747B1/en not_active Expired - Fee Related
- 1997-03-13 PE PE1997000192A patent/PE55098A1/es not_active Application Discontinuation
- 1997-03-19 GT GT199700033A patent/GT199700033A/es unknown
- 1997-03-20 CO CO97015141A patent/CO4650042A1/es unknown
- 1997-03-25 AR ARP970101201A patent/AR006391A1/es not_active Application Discontinuation
- 1997-03-26 DZ DZ970044A patent/DZ2197A1/fr active
- 1997-03-26 UY UY24503A patent/UY24503A1/es not_active IP Right Cessation
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- 1997-03-26 TN TNTNSN97055A patent/TNSN97055A1/fr unknown
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- 1997-03-27 AP APAP/P/1997/000954A patent/AP677A/en active
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- 1997-03-28 MY MYPI97001365A patent/MY118283A/en unknown
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- 1998-08-13 IS IS4823A patent/IS4823A/is unknown
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- 1998-09-28 NO NO19984516A patent/NO312460B1/no not_active IP Right Cessation
- 1998-10-27 BG BG102872A patent/BG64310B1/bg unknown
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1999
- 1999-09-02 HK HK99103798A patent/HK1018780A1/xx not_active IP Right Cessation
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2001
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