KR970009042B1 - 1,4,10,13-테트라옥사-7,16-디아자씨클로옥타데칸 유도체와 상기 유도체를 함유한 약제학적 조성물 - Google Patents

1,4,10,13-테트라옥사-7,16-디아자씨클로옥타데칸 유도체와 상기 유도체를 함유한 약제학적 조성물 Download PDF

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Publication number: KR970009042B1
Authority: KR; South Korea
Prior art keywords: formula; compound; hydrogen; tetraoxa; iii
Prior art date: 1990-01-16
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.): Expired - Lifetime

Application number

KR1019910701044A

Other languages

English (en)

Korean (ko)

Other versions

KR920701184A (ko

Inventor

조제프 엠리

벨라 기요리

졸탄 고박스

에르뇌 브뤼쳐

라즐로 비. 스즈타니크

라즐로 바르가

외된 키랄리

벨라 칸야르

Original Assignee

기외르기 쾨텔레스;조제프 바르가

오르스자고스 "후레데릭 졸리옷-큐리" 수가르 바이오로기아이 수가레게스제귀기 쿠타토 인테제트

티보르 스자스즈;에르노 브뤼쳐

코수트 라조스 투도마니에기에템

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.)

1990-01-16

Filing date

1990-11-07

Publication date

1997-06-03

1990-11-07 Application filed by 기외르기 쾨텔레스;조제프 바르가, 오르스자고스 "후레데릭 졸리옷-큐리" 수가르 바이오로기아이 수가레게스제귀기 쿠타토 인테제트, 티보르 스자스즈;에르노 브뤼쳐, 코수트 라조스 투도마니에기에템 filed Critical 기외르기 쾨텔레스;조제프 바르가

1992-08-11 Publication of KR920701184A publication Critical patent/KR920701184A/ko

1997-06-03 Application granted granted Critical

1997-06-03 Publication of KR970009042B1 publication Critical patent/KR970009042B1/ko

2010-11-07 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

239000008194 pharmaceutical composition Substances 0.000 title claims description 14
150000001875 compounds Chemical class 0.000 claims description 87
150000003839 salts Chemical class 0.000 claims description 36
229910052739 hydrogen Inorganic materials 0.000 claims description 29
239000001257 hydrogen Substances 0.000 claims description 20
125000000217 alkyl group Chemical group 0.000 claims description 16
-1 disodium Compound Chemical class 0.000 claims description 14
150000002431 hydrogen Chemical class 0.000 claims description 14
QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 claims description 13
150000001340 alkali metals Chemical class 0.000 claims description 10
150000001342 alkaline earth metals Chemical class 0.000 claims description 9
229910021645 metal ion Inorganic materials 0.000 claims description 9
239000000203 mixture Substances 0.000 claims description 9
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
239000004480 active ingredient Substances 0.000 claims description 7
229910001413 alkali metal ion Inorganic materials 0.000 claims description 7
229910052783 alkali metal Inorganic materials 0.000 claims description 6
229910001420 alkaline earth metal ion Inorganic materials 0.000 claims description 6
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 5
125000003342 alkenyl group Chemical group 0.000 claims description 5
PPQPEAAPRXUQES-UHFFFAOYSA-N calcium;2-[16-(dicarboxymethyl)-1,4,10,13-tetraoxa-7,16-diazacyclooctadec-7-yl]propanedioic acid Chemical compound [Ca].OC(=O)C(C(O)=O)N1CCOCCOCCN(C(C(O)=O)C(O)=O)CCOCCOCC1 PPQPEAAPRXUQES-UHFFFAOYSA-N 0.000 claims description 5
229910052736 halogen Inorganic materials 0.000 claims description 5
150000002367 halogens Chemical class 0.000 claims description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
229910001428 transition metal ion Inorganic materials 0.000 claims description 5
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical class [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 4
125000003545 alkoxy group Chemical group 0.000 claims description 4
125000003118 aryl group Chemical group 0.000 claims description 4
125000004093 cyano group Chemical group *C#N 0.000 claims description 4
239000008263 liquid aerosol Substances 0.000 claims description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
239000000843 powder Substances 0.000 claims description 4
229910001415 sodium ion Inorganic materials 0.000 claims description 4
239000003826 tablet Substances 0.000 claims description 4
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 3
HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 claims description 3
239000002775 capsule Substances 0.000 claims description 3
239000008298 dragée Substances 0.000 claims description 3
229910001416 lithium ion Inorganic materials 0.000 claims description 3
239000011734 sodium Substances 0.000 claims description 3
239000000829 suppository Substances 0.000 claims description 2
229940102223 injectable solution Drugs 0.000 claims 1
239000011505 plaster Substances 0.000 claims 1
JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 56
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241001465754 Metazoa Species 0.000 description 36
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
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239000000243 solution Substances 0.000 description 32
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210000001519 tissue Anatomy 0.000 description 28
239000000047 product Substances 0.000 description 26
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 24
238000012360 testing method Methods 0.000 description 24
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230000002285 radioactive effect Effects 0.000 description 21
IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 18
229910052712 strontium Inorganic materials 0.000 description 18
CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 18
230000000694 effects Effects 0.000 description 17
238000002360 preparation method Methods 0.000 description 16
238000006243 chemical reaction Methods 0.000 description 15
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
239000013067 intermediate product Substances 0.000 description 14
229910052757 nitrogen Inorganic materials 0.000 description 14
KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 14
239000011780 sodium chloride Substances 0.000 description 13
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238000000034 method Methods 0.000 description 10
238000001704 evaporation Methods 0.000 description 9
210000004072 lung Anatomy 0.000 description 9
NLMDJJTUQPXZFG-UHFFFAOYSA-N 1,4,10,13-tetraoxa-7,16-diazacyclooctadecane Chemical class C1COCCOCCNCCOCCOCCN1 NLMDJJTUQPXZFG-UHFFFAOYSA-N 0.000 description 8
230000008020 evaporation Effects 0.000 description 8
238000001228 spectrum Methods 0.000 description 8
VBZOUUJVGADJBK-UHFFFAOYSA-N 2-bromopropanedioic acid Chemical compound OC(=O)C(Br)C(O)=O VBZOUUJVGADJBK-UHFFFAOYSA-N 0.000 description 7
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 7
241000700157 Rattus norvegicus Species 0.000 description 7
229960005069 calcium Drugs 0.000 description 7
239000011575 calcium Substances 0.000 description 7
230000008030 elimination Effects 0.000 description 7
238000003379 elimination reaction Methods 0.000 description 7
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230000017531 blood circulation Effects 0.000 description 6
210000000988 bone and bone Anatomy 0.000 description 6
229910052791 calcium Inorganic materials 0.000 description 6
238000002329 infrared spectrum Methods 0.000 description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
230000003247 decreasing effect Effects 0.000 description 5
IIYNNSHGLFMMRP-UHFFFAOYSA-L disodium;2-hydroxypropanedioate Chemical compound [Na+].[Na+].[O-]C(=O)C(O)C([O-])=O IIYNNSHGLFMMRP-UHFFFAOYSA-L 0.000 description 5
238000002474 experimental method Methods 0.000 description 5
230000014759 maintenance of location Effects 0.000 description 5
239000002244 precipitate Substances 0.000 description 5
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 4
239000002253 acid Substances 0.000 description 4
239000013543 active substance Substances 0.000 description 4
230000037396 body weight Effects 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
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231100000419 toxicity Toxicity 0.000 description 4
230000001988 toxicity Effects 0.000 description 4
229910052684 Cerium Inorganic materials 0.000 description 3
CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
241000699670 Mus sp. Species 0.000 description 3
239000012190 activator Substances 0.000 description 3
238000004458 analytical method Methods 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
239000002994 raw material Substances 0.000 description 3
JCPUKHWHNNFWDX-UHFFFAOYSA-N 2-(bromomethyl)propanedioic acid Chemical compound OC(=O)C(CBr)C(O)=O JCPUKHWHNNFWDX-UHFFFAOYSA-N 0.000 description 2
SSEXAOZOZMDLSJ-UHFFFAOYSA-N 2-benzyl-2-bromopropanedioic acid Chemical compound OC(=O)C(Br)(C(O)=O)CC1=CC=CC=C1 SSEXAOZOZMDLSJ-UHFFFAOYSA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
VTLYFUHAOXGGBS-UHFFFAOYSA-N Fe3+ Chemical compound [Fe+3] VTLYFUHAOXGGBS-UHFFFAOYSA-N 0.000 description 2
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
241000700159 Rattus Species 0.000 description 2
HEMHJVSKTPXQMS-DYCDLGHISA-M Sodium hydroxide-d Chemical compound [Na+].[2H][O-] HEMHJVSKTPXQMS-DYCDLGHISA-M 0.000 description 2
239000000654 additive Substances 0.000 description 2
230000000996 additive effect Effects 0.000 description 2
TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
239000002585 base Substances 0.000 description 2
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 2
239000000920 calcium hydroxide Substances 0.000 description 2
229910001861 calcium hydroxide Inorganic materials 0.000 description 2
159000000007 calcium salts Chemical class 0.000 description 2
238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 2
230000008859 change Effects 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
238000011109 contamination Methods 0.000 description 2
238000007796 conventional method Methods 0.000 description 2
150000004696 coordination complex Chemical class 0.000 description 2
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238000000151 deposition Methods 0.000 description 2
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150000002148 esters Chemical class 0.000 description 2
239000000469 ethanolic extract Substances 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
210000001723 extracellular space Anatomy 0.000 description 2
229910001447 ferric ion Inorganic materials 0.000 description 2
239000008103 glucose Substances 0.000 description 2
230000005802 health problem Effects 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
ROBFUDYVXSDBQM-UHFFFAOYSA-N hydroxymalonic acid Chemical compound OC(=O)C(O)C(O)=O ROBFUDYVXSDBQM-UHFFFAOYSA-N 0.000 description 2
238000002347 injection Methods 0.000 description 2
239000007924 injection Substances 0.000 description 2
229910003002 lithium salt Inorganic materials 0.000 description 2
159000000002 lithium salts Chemical class 0.000 description 2
210000004185 liver Anatomy 0.000 description 2
238000005259 measurement Methods 0.000 description 2
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150000002739 metals Chemical class 0.000 description 2
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206010033675 panniculitis Diseases 0.000 description 2
230000005855 radiation Effects 0.000 description 2
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210000004872 soft tissue Anatomy 0.000 description 2
230000006641 stabilisation Effects 0.000 description 2
238000011105 stabilization Methods 0.000 description 2
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210000004304 subcutaneous tissue Anatomy 0.000 description 2
MFAGQNNSWPCEKY-UHFFFAOYSA-J tetrasodium;2-[16-(dicarboxylatomethyl)-1,4,10,13-tetraoxa-7,16-diazacyclooctadec-7-yl]propanedioate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]C(=O)C(C([O-])=O)N1CCOCCOCCN(C(C([O-])=O)C([O-])=O)CCOCCOCC1 MFAGQNNSWPCEKY-UHFFFAOYSA-J 0.000 description 2
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
CHWNDULWKHVOBS-UHFFFAOYSA-N 1,2-diazacyclooctadecane Chemical compound C1CCCCCCCCNNCCCCCCC1 CHWNDULWKHVOBS-UHFFFAOYSA-N 0.000 description 1
HEMRLQBWVAFPBH-UHFFFAOYSA-N 1-oxa-4,13-diazacyclooctadecane Chemical compound C1CCCCNCCOCCCCCNCCC1 HEMRLQBWVAFPBH-UHFFFAOYSA-N 0.000 description 1
PNDPGZBMCMUPRI-HVTJNCQCSA-N 10043-66-0 Chemical compound [131I][131I] PNDPGZBMCMUPRI-HVTJNCQCSA-N 0.000 description 1
238000005160 1H NMR spectroscopy Methods 0.000 description 1
BSWWXRFVMJHFBN-UHFFFAOYSA-N 2,4,6-tribromophenol Chemical compound OC1=C(Br)C=C(Br)C=C1Br BSWWXRFVMJHFBN-UHFFFAOYSA-N 0.000 description 1
KPMAGKCNQVAMKJ-UHFFFAOYSA-N 2-(2-bromoethyl)propanedioic acid Chemical compound OC(=O)C(C(O)=O)CCBr KPMAGKCNQVAMKJ-UHFFFAOYSA-N 0.000 description 1
QJRGVSUIFZYBQK-UHFFFAOYSA-N 2-[16-(dicarboxymethyl)-1,4,10,13-tetraoxa-7,16-diazacyclooctadec-7-yl]propanedioic acid;magnesium Chemical compound [Mg].OC(=O)C(C(O)=O)N1CCOCCOCCN(C(C(O)=O)C(O)=O)CCOCCOCC1 QJRGVSUIFZYBQK-UHFFFAOYSA-N 0.000 description 1
WBXFLFGMNUTPEK-UHFFFAOYSA-N 2-bromo-3-methoxy-3-oxopropanoic acid Chemical compound COC(=O)C(Br)C(O)=O WBXFLFGMNUTPEK-UHFFFAOYSA-N 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
GXZMZBDZHXMNJB-UHFFFAOYSA-L C(CC(=O)[O-])(=O)OO.[Na+].[Na+].OOC(CC(=O)[O-])=O Chemical compound C(CC(=O)[O-])(=O)OO.[Na+].[Na+].OOC(CC(=O)[O-])=O GXZMZBDZHXMNJB-UHFFFAOYSA-L 0.000 description 1
BHXNCWUSSNATLV-UHFFFAOYSA-I CCC(C(O)=O)(C(O)=O)N(CCOCCOCC1)CCOCCOCCN1C(C(O)=O)C(O)=O.[Na+].[Na+].[Na+].[Na+].[Na+].[Br-].[Br-].[Br-].[Br-].[Br-] Chemical compound CCC(C(O)=O)(C(O)=O)N(CCOCCOCC1)CCOCCOCCN1C(C(O)=O)C(O)=O.[Na+].[Na+].[Na+].[Na+].[Na+].[Br-].[Br-].[Br-].[Br-].[Br-] BHXNCWUSSNATLV-UHFFFAOYSA-I 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
JLVVSXFLKOJNIY-UHFFFAOYSA-N Magnesium ion Chemical compound [Mg+2] JLVVSXFLKOJNIY-UHFFFAOYSA-N 0.000 description 1
QPCDCPDFJACHGM-UHFFFAOYSA-N N,N-bis{2-[bis(carboxymethyl)amino]ethyl}glycine Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(=O)O)CCN(CC(O)=O)CC(O)=O QPCDCPDFJACHGM-UHFFFAOYSA-N 0.000 description 1
NPYPAHLBTDXSSS-UHFFFAOYSA-N Potassium ion Chemical compound [K+] NPYPAHLBTDXSSS-UHFFFAOYSA-N 0.000 description 1
FKNQFGJONOIPTF-UHFFFAOYSA-N Sodium cation Chemical compound [Na+] FKNQFGJONOIPTF-UHFFFAOYSA-N 0.000 description 1
CIOAGBVUUVVLOB-NJFSPNSNSA-N Strontium-90 Chemical compound [90Sr] CIOAGBVUUVVLOB-NJFSPNSNSA-N 0.000 description 1
241000282898 Sus scrofa Species 0.000 description 1
101100489892 Sus scrofa ABCG2 gene Proteins 0.000 description 1
PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 description 1
210000000683 abdominal cavity Anatomy 0.000 description 1
229910000272 alkali metal oxide Inorganic materials 0.000 description 1
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
210000001124 body fluid Anatomy 0.000 description 1
239000010839 body fluid Substances 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
150000001669 calcium Chemical class 0.000 description 1
229910001622 calcium bromide Inorganic materials 0.000 description 1
239000001110 calcium chloride Substances 0.000 description 1
229960002713 calcium chloride Drugs 0.000 description 1
229910001628 calcium chloride Inorganic materials 0.000 description 1
LLSDKQJKOVVTOJ-UHFFFAOYSA-L calcium chloride dihydrate Chemical compound O.O.[Cl-].[Cl-].[Ca+2] LLSDKQJKOVVTOJ-UHFFFAOYSA-L 0.000 description 1
229940052299 calcium chloride dihydrate Drugs 0.000 description 1
WGEFECGEFUFIQW-UHFFFAOYSA-L calcium dibromide Chemical compound [Ca+2].[Br-].[Br-] WGEFECGEFUFIQW-UHFFFAOYSA-L 0.000 description 1
229910001424 calcium ion Inorganic materials 0.000 description 1
XCETYVGOGDDIMM-UHFFFAOYSA-L calcium;2-hydroxypropanedioate Chemical group [Ca+2].[O-]C(=O)C(O)C([O-])=O XCETYVGOGDDIMM-UHFFFAOYSA-L 0.000 description 1
125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 1
239000000969 carrier Substances 0.000 description 1
210000004027 cell Anatomy 0.000 description 1
GWXLDORMOJMVQZ-UHFFFAOYSA-N cerium Chemical compound [Ce] GWXLDORMOJMVQZ-UHFFFAOYSA-N 0.000 description 1
GWXLDORMOJMVQZ-OUBTZVSYSA-N cerium-141 Chemical compound [141Ce] GWXLDORMOJMVQZ-OUBTZVSYSA-N 0.000 description 1
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TVFDJXOCXUVLDH-OUBTZVSYSA-N cesium-134 Chemical compound [134Cs] TVFDJXOCXUVLDH-OUBTZVSYSA-N 0.000 description 1
TVFDJXOCXUVLDH-RNFDNDRNSA-N cesium-137 Chemical compound [137Cs] TVFDJXOCXUVLDH-RNFDNDRNSA-N 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
230000009918 complex formation Effects 0.000 description 1
239000000356 contaminant Substances 0.000 description 1
239000012050 conventional carrier Substances 0.000 description 1
230000002596 correlated effect Effects 0.000 description 1
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238000012217 deletion Methods 0.000 description 1
230000037430 deletion Effects 0.000 description 1
230000008021 deposition Effects 0.000 description 1
150000001991 dicarboxylic acids Chemical class 0.000 description 1
210000002249 digestive system Anatomy 0.000 description 1
229910001873 dinitrogen Inorganic materials 0.000 description 1
QDXAUAYSNLIWOM-UHFFFAOYSA-L dipotassium;2-(1,4,10,13-tetraoxa-7,16-diazacyclooctadec-7-yl)propanedioate Chemical compound [K+].[K+].[O-]C(=O)C(C([O-])=O)N1CCOCCOCCNCCOCCOCC1 QDXAUAYSNLIWOM-UHFFFAOYSA-L 0.000 description 1
AINVBOAFYIASFL-UHFFFAOYSA-L disodium 2-methyl-2-(1,4,10,13-tetraoxa-7,16-diazacyclooctadec-7-yl)propanedioate Chemical compound [Na+].[Na+].C(=O)([O-])C(C)(C(=O)[O-])N1CCOCCOCCNCCOCCOCC1 AINVBOAFYIASFL-UHFFFAOYSA-L 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
210000000981 epithelium Anatomy 0.000 description 1
239000012259 ether extract Substances 0.000 description 1
238000004880 explosion Methods 0.000 description 1
229960002089 ferrous chloride Drugs 0.000 description 1
229910001448 ferrous ion Inorganic materials 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
230000000977 initiatory effect Effects 0.000 description 1
238000007912 intraperitoneal administration Methods 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
NMCUIPGRVMDVDB-UHFFFAOYSA-L iron dichloride Chemical compound Cl[Fe]Cl NMCUIPGRVMDVDB-UHFFFAOYSA-L 0.000 description 1
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
231100000225 lethality Toxicity 0.000 description 1
239000007791 liquid phase Substances 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
210000004324 lymphatic system Anatomy 0.000 description 1
150000002678 macrocyclic compounds Chemical class 0.000 description 1
229940050906 magnesium chloride hexahydrate Drugs 0.000 description 1
DHRRIBDTHFBPNG-UHFFFAOYSA-L magnesium dichloride hexahydrate Chemical compound O.O.O.O.O.O.[Mg+2].[Cl-].[Cl-] DHRRIBDTHFBPNG-UHFFFAOYSA-L 0.000 description 1
229910001425 magnesium ion Inorganic materials 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
229910001510 metal chloride Inorganic materials 0.000 description 1
229910001507 metal halide Inorganic materials 0.000 description 1
150000005309 metal halides Chemical class 0.000 description 1
210000003205 muscle Anatomy 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
230000005298 paramagnetic effect Effects 0.000 description 1
230000037361 pathway Effects 0.000 description 1
ZQZYIBGFRCIVLF-UHFFFAOYSA-I pentasodium pentabromide Chemical compound [Br-].[Na+].[Na+].[Na+].[Na+].[Na+].[Br-].[Br-].[Br-].[Br-] ZQZYIBGFRCIVLF-UHFFFAOYSA-I 0.000 description 1
229960003330 pentetic acid Drugs 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
125000003884 phenylalkyl group Chemical group 0.000 description 1
239000011148 porous material Substances 0.000 description 1
229910001414 potassium ion Inorganic materials 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
230000029058 respiratory gaseous exchange Effects 0.000 description 1
238000012552 review Methods 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
PRWXGRGLHYDWPS-UHFFFAOYSA-L sodium malonate Chemical compound [Na+].[Na+].[O-]C(=O)CC([O-])=O PRWXGRGLHYDWPS-UHFFFAOYSA-L 0.000 description 1
239000011343 solid material Substances 0.000 description 1
239000012265 solid product Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
150000003437 strontium Chemical class 0.000 description 1
CIOAGBVUUVVLOB-OUBTZVSYSA-N strontium-89 Chemical compound [89Sr] CIOAGBVUUVVLOB-OUBTZVSYSA-N 0.000 description 1
229940006509 strontium-89 Drugs 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
239000000725 suspension Substances 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
UYNAZBZWALOHCZ-UHFFFAOYSA-J tetralithium;2-[16-(dicarboxylatomethyl)-1,4,10,13-tetraoxa-7,16-diazacyclooctadec-7-yl]propanedioate Chemical class [Li+].[Li+].[Li+].[Li+].[O-]C(=O)C(C([O-])=O)N1CCOCCOCCN(C(C([O-])=O)C([O-])=O)CCOCCOCC1 UYNAZBZWALOHCZ-UHFFFAOYSA-J 0.000 description 1
QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
ILOFQXCSDHFUJP-UHFFFAOYSA-J tetrapotassium;2-[16-(dicarboxylatomethyl)-1,4,10,13-tetraoxa-7,16-diazacyclooctadec-7-yl]propanedioate Chemical compound [K+].[K+].[K+].[K+].[O-]C(=O)C(C([O-])=O)N1CCOCCOCCN(C(C([O-])=O)C([O-])=O)CCOCCOCC1 ILOFQXCSDHFUJP-UHFFFAOYSA-J 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
210000003437 trachea Anatomy 0.000 description 1
HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1
235000005074 zinc chloride Nutrition 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D273/00—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00
- C07D273/08—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00 having two nitrogen atoms and more than one oxygen atom
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D273/00—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
- A61P39/02—Antidotes
- 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)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
Veterinary Medicine (AREA)
General Health & Medical Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Toxicology (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Epidemiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Medicinal Preparation (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

KR1019910701044A 1990-01-16 1990-11-07 1,4,10,13-테트라옥사-7,16-디아자씨클로옥타데칸 유도체와 상기 유도체를 함유한 약제학적 조성물 Expired - Lifetime KR970009042B1 (ko)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
HU90145A HU210667B (hu)	1990-01-16	1990-01-16	Eljárás N,N'-bisz(dikarboxi-metil)-1,4,10,13-tetraoxa-7,16-diaza-ciklooktadekán-származékok sói és komplexei és a vegyületeket tartalmazó gyógyászati készítmények előállítására
HU145/90		1990-01-16
PCT/HU1990/000070 WO1991010655A1 (en)	1990-01-16	1990-11-07	1,4,10,13-tetraoxa-7,16-diazacyclooctadecane derivatives, pharmaceutical compositions containing them and their use for the removal of toxic metal ions and radioactive isotopes from the living organism

Publications (2)

Publication Number	Publication Date
KR920701184A KR920701184A (ko)	1992-08-11
KR970009042B1 true KR970009042B1 (ko)	1997-06-03

Family

ID=10948158

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
KR1019910701044A Expired - Lifetime KR970009042B1 (ko)	1990-01-16	1990-11-07	1,4,10,13-테트라옥사-7,16-디아자씨클로옥타데칸 유도체와 상기 유도체를 함유한 약제학적 조성물

Country Status (10)

Country	Link
EP (1)	EP0463123A1 (hu)
JP (1)	JPH04505626A (hu)
KR (1)	KR970009042B1 (hu)
AU (1)	AU645507B2 (hu)
CA (1)	CA2048627A1 (hu)
HU (2)	HU210667B (hu)
IN (1)	IN171733B (hu)
RU (1)	RU2060256C1 (hu)
UA (1)	UA35547C2 (hu)
WO (1)	WO1991010655A1 (hu)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPH06505795A (ja) *	1990-09-27	1994-06-30	リサーチ・コーポレイション・テクノロジーズ	キレート化剤
IL117302A (en) *	1995-03-07	2005-03-20	Univ Hawaii	Cryptophycin derivatives, methods for the production thereof and pharmaceutical compositions containing the same
HUP1100731A2 (en) *	2011-12-30	2013-06-28	Stratoxer S Kft	Complex forming compounds
EA201201241A1 (ru) *	2012-06-19	2013-12-30	Елена Владимировна ОРЛОВА	БИОБЕЗОПАСНЫЙ НАНОКОМПОЗИТНЫЙ ПОЛИМЕРНЫЙ СОРБЕНТ ДЛЯ СЕЛЕКТИВНОГО СВЯЗЫВАНИЯ ИЗОТОПОВ Sr И Cs ИЗ ЖИДКИХ СРЕД И СЫРЬЕВАЯ СМЕСЬ ДЛЯ ЕГО ИЗГОТОВЛЕНИЯ

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4190462A (en) *	1978-07-04	1980-02-26	Shell Oil Company	Dissolving barium sulfate scale with aqueous solutions of salts of carboxymethyl monocyclic macrocyclic polyamines
US4597903A (en) *	1984-08-21	1986-07-01	University Of Maryland	Process for the direct preparation of N,N-disubstituted derivatives for 4,13-diaza-18-crown-6
JPS61263964A (ja) *	1985-05-17	1986-11-21	Terumo Corp	新規クラウン（チオ）エ−テルおよびその製造方法

1990
- 1990-01-16 HU HU90145A patent/HU210667B/hu not_active IP Right Cessation
- 1990-01-16 HU HU9502769A patent/HUT73493A/hu unknown
- 1990-11-07 WO PCT/HU1990/000070 patent/WO1991010655A1/en not_active Application Discontinuation
- 1990-11-07 UA UA5001786A patent/UA35547C2/uk unknown
- 1990-11-07 JP JP2515439A patent/JPH04505626A/ja active Pending
- 1990-11-07 RU SU905001786A patent/RU2060256C1/ru active
- 1990-11-07 KR KR1019910701044A patent/KR970009042B1/ko not_active Expired - Lifetime
- 1990-11-07 AU AU67116/90A patent/AU645507B2/en not_active Ceased
- 1990-11-07 CA CA002048627A patent/CA2048627A1/en not_active Abandoned
- 1990-11-07 EP EP90916523A patent/EP0463123A1/en not_active Withdrawn
- 1990-11-22 IN IN943/MAS/90A patent/IN171733B/en unknown

Also Published As

Publication number	Publication date
KR920701184A (ko)	1992-08-11
WO1991010655A1 (en)	1991-07-25
RU2060256C1 (ru)	1996-05-20
UA35547C2 (uk)	2001-04-16
AU6711690A (en)	1991-08-05
HU900145D0 (en)	1990-03-28
AU645507B2 (en)	1994-01-20
EP0463123A1 (en)	1992-01-02
HUT73493A (en)	1996-08-28
IN171733B (hu)	1992-12-26
CA2048627A1 (en)	1991-07-17
JPH04505626A (ja)	1992-10-01
HU210667B (hu)	1998-03-30
HU9502769D0 (en)	1995-11-28

Publication	Publication Date	Title
EP0357150B1 (en)	1993-12-08	Pharmaceutical compositions
US5624901A (en)	1997-04-29	3-hydroxy-2(1H)-pyridinone chelating agents
US5885548A (en)	1999-03-23	Multiply substituted DTPA derivatives and their metal complexes, and their metal complexes, pharmaceutical agents that contain these complexes, their use in diagnosis and therapy, as well as process for the production of pharmaceutical agents
JP2877844B2 (ja)	1999-04-05	５員‐又は６員‐環を有する巨大環状ポリアザ‐化合物、その製法及びこれを含有するｎｍｒ‐、ｘ線‐、放射線‐診断用及び放射能‐及び照射線‐治療用薬剤及びこの薬剤の製法
US4355043A (en)	1982-10-19	Novel derivatives of 3-aminopropanesulfonic acid having a reinforced activity on membrane
CA1253803A (en)	1989-05-09	Buccal and nasal compositions containing iron complexes of 3-hydroxy-4-pyrones
US5104865A (en)	1992-04-14	Iron complexes of hydroxypyridones useful for treating iron overload
HU201301B (en)	1990-10-28	Process for production of izocyanides substituated by ether and diagnostical composition containing them and diagnostical products
HK7091A (en)	1991-02-01	Pharmaceutical compositions containing 1-hydroxypyrid-2-one derivatives
JP2953670B2 (ja)	1999-09-27	複素環式キレート化剤
KR19980701674A (ko)	1998-06-25	비스무트 화합물
EP0840727B1 (en)	2004-05-06	3-hydroxy-2(1h)-pyridinone chelating agents
IE921760A1 (en)	1992-12-02	Gallium compounds
KR970009042B1 (ko)	1997-06-03	1,4,10,13-테트라옥사-7,16-디아자씨클로옥타데칸 유도체와 상기 유도체를 함유한 약제학적 조성물
EP0186252A2 (en)	1986-07-02	Use of thiophene compounds for the manufacture of a medicament against tumours
JPS588044A (ja)	1983-01-18	１１−デオキソグリチルレチン酸水素マレ−ト及びそれを有効成分とする医薬
JPS61158922A (ja)	1986-07-18	フイブリンからの不溶性フイブリンの形成阻止剤
US5440031A (en)	1995-08-08	1,4,10,13-tetraoxa-7,16-diazacyclooctadecane derivatives, pharmaceutical compositions containing them and their use for the removal of toxic metal ions and radioactive isotopes from living organism
JPS606355B2 (ja)	1985-02-18	新規アミノ安息香酸誘導体、その製法及び医薬組成物
US5288718A (en)	1994-02-22	Method for decorporating radioactive isotope from living organism
JPH05505624A (ja)	1993-08-19	ラジオグラフィ造影剤として有用なヘキサデンテートリガンド類
EP0003897B1 (en)	1983-05-25	Phosphinegold(i)salts, process for their preparation and compositions containing them
JPS5940400B2 (ja)	1984-09-29	新規ｄ−アロ−ス誘導体及びこれを有効成分とする抗腫瘍剤
HU211923A9 (hu)	1996-01-29	1,4,10,13-Tetraoxa-7,16-diaza-ciklooktadekán-származékok, a vegyületeket tartalmazó gyógyászati készítmények és alkalmazásuk toxikus fémionok és radioaktív izotópok élő szervezetből történő eltávolítására Az átmeneti oltalom az 1-7. igénypontokra vonatkozik.
JP2004509924A (ja)	2004-04-02	Ｍｒｉ画像増強組成物

Legal Events

Date	Code	Title	Description
1991-09-04	PA0109	Patent application	Patent event code: PA01091R01D Comment text: Patent Application Patent event date: 19910904
1992-08-11	PG1501	Laying open of application
1992-10-13	A201	Request for examination
1992-10-13	PA0201	Request for examination	Patent event code: PA02012R01D Patent event date: 19921013 Comment text: Request for Examination of Application Patent event code: PA02011R01I Patent event date: 19910904 Comment text: Patent Application
1995-09-21	E902	Notification of reason for refusal
1995-09-21	PE0902	Notice of grounds for rejection	Comment text: Notification of reason for refusal Patent event date: 19950921 Patent event code: PE09021S01D
1996-03-21	E601	Decision to refuse application
1996-03-21	PE0601	Decision on rejection of patent	Patent event date: 19960321 Comment text: Decision to Refuse Application Patent event code: PE06012S01D Patent event date: 19950921 Comment text: Notification of reason for refusal Patent event code: PE06011S01I
1996-04-24	J2X1	Appeal (before the patent court)	Free format text: APPEAL AGAINST DECISION TO DECLINE REFUSAL
1996-04-24	PJ2001	Appeal	Appeal kind category: Appeal against decision to decline refusal Decision date: 19970331 Appeal identifier: 1996201000836 Request date: 19960424
1997-05-02	G160	Decision to publish patent application
1997-06-03	PG1605	Publication of application before grant of patent	Comment text: Decision on Publication of Application Patent event code: PG16051S01I Patent event date: 19970502
1997-08-26	E701	Decision to grant or registration of patent right
1997-08-26	PE0701	Decision of registration	Patent event code: PE07011S01D Comment text: Decision to Grant Registration Patent event date: 19970826
1998-05-26	NORF	Unpaid initial registration fee
1998-05-26	PC1904	Unpaid initial registration fee