BG64280B1 - М...'од за пол"-аван... на 3-изопропил-1н-2,1,3-б...нзо'иадиазин-4(3н)-он-2,2-диок'ид - Google Patents

М...'од за пол"-аван... на 3-изопропил-1н-2,1,3-б...нзо'иадиазин-4(3н)-он-2,2-диок'ид Download PDF

Info

Publication number: BG64280B1
Authority: BG; Bulgaria
Prior art keywords: dichloroethane; mol; solution; formula; sulfur trioxide
Prior art date: 1997-08-19

Application number

BG104121A

Other languages

Bulgarian (bg)

English (en)

Other versions

BG104121A (en

Inventor

Hans R. Merkle

Otto Woerz

Erich Fretschner

Hanspeter Hansen

Albrecht Mueller

Kurt Benz

Original Assignee

Basf Aktiengesellschaft

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.)

1997-08-19

Filing date

2000-02-03

Publication date

2004-08-31

2000-02-03 Application filed by Basf Aktiengesellschaft filed Critical Basf Aktiengesellschaft

2000-09-29 Publication of BG104121A publication Critical patent/BG104121A/xx

2004-08-31 Publication of BG64280B1 publication Critical patent/BG64280B1/bg

Links

238000000034 method Methods 0.000 title claims abstract description 26
238000002360 preparation method Methods 0.000 title claims abstract description 8
AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 claims abstract description 61
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims abstract description 31
150000003839 salts Chemical class 0.000 claims abstract description 17
150000001875 compounds Chemical class 0.000 claims abstract description 15
150000007530 organic bases Chemical class 0.000 claims abstract description 13
XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 claims abstract description 9
BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 claims description 49
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 45
238000010992 reflux Methods 0.000 claims description 19
238000006243 chemical reaction Methods 0.000 claims description 17
OTTDACPMYLDVTL-UHFFFAOYSA-N ethyl quinoline-3-carboxylate Chemical compound C1=CC=CC2=CC(C(=O)OCC)=CN=C21 OTTDACPMYLDVTL-UHFFFAOYSA-N 0.000 claims description 15
239000002904 solvent Substances 0.000 claims description 13
ZOMSMJKLGFBRBS-UHFFFAOYSA-N bentazone Chemical compound C1=CC=C2NS(=O)(=O)N(C(C)C)C(=O)C2=C1 ZOMSMJKLGFBRBS-UHFFFAOYSA-N 0.000 claims description 9
KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 claims description 8
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 5
-1 aromatic organic base Chemical class 0.000 claims description 4
150000003222 pyridines Chemical class 0.000 claims description 3
150000008282 halocarbons Chemical class 0.000 claims 1
125000001741 organic sulfur group Chemical group 0.000 claims 1
XUWVIABDWDTJRZ-UHFFFAOYSA-N propan-2-ylazanide Chemical compound CC(C)[NH-] XUWVIABDWDTJRZ-UHFFFAOYSA-N 0.000 abstract description 3
238000009835 boiling Methods 0.000 abstract description 2
239000002253 acid Substances 0.000 abstract 1
230000004941 influx Effects 0.000 abstract 1
239000000243 solution Substances 0.000 description 38
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 36
239000012074 organic phase Substances 0.000 description 21
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 14
239000000203 mixture Substances 0.000 description 14
239000011541 reaction mixture Substances 0.000 description 13
239000008346 aqueous phase Substances 0.000 description 12
239000000047 product Substances 0.000 description 9
239000012442 inert solvent Substances 0.000 description 8
239000012071 phase Substances 0.000 description 7
238000003756 stirring Methods 0.000 description 7
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
239000003960 organic solvent Substances 0.000 description 5
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 4
238000004821 distillation Methods 0.000 description 4
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 4
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
230000007062 hydrolysis Effects 0.000 description 3
238000006460 hydrolysis reaction Methods 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical class NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 3
PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 2
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 2
FKNQCJSGGFJEIZ-UHFFFAOYSA-N 4-methylpyridine Chemical compound CC1=CC=NC=C1 FKNQCJSGGFJEIZ-UHFFFAOYSA-N 0.000 description 2
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
235000011114 ammonium hydroxide Nutrition 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 2
238000000605 extraction Methods 0.000 description 2
230000003993 interaction Effects 0.000 description 2
238000005191 phase separation Methods 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
239000012716 precipitator Substances 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
159000000000 sodium salts Chemical class 0.000 description 2
239000000126 substance Substances 0.000 description 2
UWHSPZZUAYSGTB-UHFFFAOYSA-N 1,1,3,3-tetraethylurea Chemical compound CCN(CC)C(=O)N(CC)CC UWHSPZZUAYSGTB-UHFFFAOYSA-N 0.000 description 1
AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 description 1
KNKRKFALVUDBJE-UHFFFAOYSA-N 1,2-dichloropropane Chemical compound CC(Cl)CCl KNKRKFALVUDBJE-UHFFFAOYSA-N 0.000 description 1
DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical class CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
GMCRNNWINPJXJN-UHFFFAOYSA-N 1h-2,1,3-benzothiadiazine Chemical compound C1=CC=C2NSN=CC2=C1 GMCRNNWINPJXJN-UHFFFAOYSA-N 0.000 description 1
PXBFMLJZNCDSMP-UHFFFAOYSA-N 2-Aminobenzamide Chemical class NC(=O)C1=CC=CC=C1N PXBFMLJZNCDSMP-UHFFFAOYSA-N 0.000 description 1
WMITWVBNOFXTJE-UHFFFAOYSA-N 2-aminobenzoic acid;propan-2-amine Chemical compound CC(C)N.NC1=CC=CC=C1C(O)=O WMITWVBNOFXTJE-UHFFFAOYSA-N 0.000 description 1
ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 description 1
JVQIKJMSUIMUDI-UHFFFAOYSA-N 3-pyrroline Chemical compound C1NCC=C1 JVQIKJMSUIMUDI-UHFFFAOYSA-N 0.000 description 1
HVCNXQOWACZAFN-UHFFFAOYSA-N 4-ethylmorpholine Chemical compound CCN1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-N 0.000 description 1
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
DJEQZVQFEPKLOY-UHFFFAOYSA-N N,N-dimethylbutylamine Chemical compound CCCCN(C)C DJEQZVQFEPKLOY-UHFFFAOYSA-N 0.000 description 1
SVYKKECYCPFKGB-UHFFFAOYSA-N N,N-dimethylcyclohexylamine Chemical compound CN(C)C1CCCCC1 SVYKKECYCPFKGB-UHFFFAOYSA-N 0.000 description 1
BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
239000003849 aromatic solvent Substances 0.000 description 1
229950005499 carbon tetrachloride Drugs 0.000 description 1
238000001816 cooling Methods 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 1
HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 1
238000009472 formulation Methods 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
239000007788 liquid Substances 0.000 description 1
ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
239000001095 magnesium carbonate Substances 0.000 description 1
229910000021 magnesium carbonate Inorganic materials 0.000 description 1
VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
239000000347 magnesium hydroxide Substances 0.000 description 1
229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
DAZXVJBJRMWXJP-UHFFFAOYSA-N n,n-dimethylethylamine Chemical compound CCN(C)C DAZXVJBJRMWXJP-UHFFFAOYSA-N 0.000 description 1
ZUHZZVMEUAUWHY-UHFFFAOYSA-N n,n-dimethylpropan-1-amine Chemical compound CCCN(C)C ZUHZZVMEUAUWHY-UHFFFAOYSA-N 0.000 description 1
PPHQUIPUBYPZLD-UHFFFAOYSA-N n-ethyl-n-methylaniline Chemical compound CCN(C)C1=CC=CC=C1 PPHQUIPUBYPZLD-UHFFFAOYSA-N 0.000 description 1
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000011814 protection agent Substances 0.000 description 1
239000000376 reactant Substances 0.000 description 1
239000013557 residual solvent Substances 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
229910052711 selenium Inorganic materials 0.000 description 1
239000011669 selenium Substances 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/15—Six-membered rings
- C07D285/16—Thiadiazines; Hydrogenated thiadiazines

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Plural Heterocyclic Compounds (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Pyridine Compounds (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)

BG104121A 1997-08-19 2000-02-03 М...'од за пол"-аван... на 3-изопропил-1н-2,1,3-б...нзо'иадиазин-4(3н)-он-2,2-диок'ид BG64280B1 (bg)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE19735682A DE19735682A1 (de)	1997-08-19	1997-08-19	Verfahren zur Herstellung von 3-Isopropyl-1H-2,1,3-benzothiadiazin-4(3H)-on-2,2-dioxid
PCT/EP1998/004664 WO1999009019A1 (de)	1997-08-19	1998-07-25	Verfahren zur herstellung von 3-isopropyl-1h-2, 1,3-benzothiadiazin-4 (3h)-on-2,2-dioxid

Publications (2)

Publication Number	Publication Date
BG104121A BG104121A (en)	2000-09-29
BG64280B1 true BG64280B1 (bg)	2004-08-31

Family

ID=7839256

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
BG104121A BG64280B1 (bg)	1997-08-19	2000-02-03	М...'од за пол"-аван... на 3-изопропил-1н-2,1,3-б...нзо'иадиазин-4(3н)-он-2,2-диок'ид

Country Status (29)

Country	Link
US (1)	US6252069B1 (cs)
EP (1)	EP1005462B1 (cs)
JP (1)	JP4376452B2 (cs)
KR (1)	KR100546521B1 (cs)
CN (1)	CN1117740C (cs)
AR (1)	AR015421A1 (cs)
AT (1)	ATE346846T1 (cs)
AU (1)	AU748904B2 (cs)
BG (1)	BG64280B1 (cs)
BR (1)	BR9811306A (cs)
CA (1)	CA2301194C (cs)
CY (1)	CY1106345T1 (cs)
CZ (1)	CZ289520B6 (cs)
DE (2)	DE19735682A1 (cs)
DK (1)	DK1005462T3 (cs)
EA (1)	EA002121B1 (cs)
ES (1)	ES2278418T3 (cs)
HU (1)	HU225668B1 (cs)
IL (2)	IL134247A0 (cs)
NO (1)	NO314305B1 (cs)
NZ (1)	NZ502659A (cs)
PL (1)	PL195320B1 (cs)
PT (1)	PT1005462E (cs)
SK (1)	SK282808B6 (cs)
TR (1)	TR200000424T2 (cs)
TW (1)	TW472050B (cs)
UA (1)	UA55480C2 (cs)
WO (1)	WO1999009019A1 (cs)
ZA (1)	ZA987411B (cs)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
ATE446294T1 (de)	2005-11-15	2009-11-15	Array Biopharma Inc	N4-phenyl-chinazolin-4-aminderivate und verwandte verbindungen als inhibitoren der erbb-typ-i- rezeptortyrosinkinase zur behandlung hyperproliferativer krankheiten
CN101830866B (zh) *	2010-02-03	2011-09-28	江苏省农用激素工程技术研究中心有限公司	灭草松的制备方法
CN102924405B (zh) *	2012-11-21	2016-01-20	合肥星宇化学有限责任公司	一种灭草松水剂的制备方法

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2710382C2 (de) *	1977-03-10	1983-12-22	Basf Ag, 6700 Ludwigshafen	Verfahren zur Herstellung von 2,1,3-Benzothiadiazin-4-on-2,2-dioxid-derivaten
CN1063688A (zh) *	1991-01-28	1992-08-19	南开大学	苯达松除草剂的合成方法

1997
- 1997-08-19 DE DE19735682A patent/DE19735682A1/de not_active Withdrawn
1998
- 1998-07-25 DK DK98942624T patent/DK1005462T3/da active
- 1998-07-25 BR BR9811306-2A patent/BR9811306A/pt not_active Application Discontinuation
- 1998-07-25 WO PCT/EP1998/004664 patent/WO1999009019A1/de not_active Ceased
- 1998-07-25 UA UA2000031557A patent/UA55480C2/uk unknown
- 1998-07-25 CN CN98808270A patent/CN1117740C/zh not_active Expired - Lifetime
- 1998-07-25 EP EP98942624A patent/EP1005462B1/de not_active Expired - Lifetime
- 1998-07-25 TR TR2000/00424T patent/TR200000424T2/xx unknown
- 1998-07-25 CZ CZ2000558A patent/CZ289520B6/cs not_active IP Right Cessation
- 1998-07-25 HU HU0004710A patent/HU225668B1/hu not_active IP Right Cessation
- 1998-07-25 IL IL13424798A patent/IL134247A0/xx active IP Right Grant
- 1998-07-25 DE DE59813831T patent/DE59813831D1/de not_active Expired - Lifetime
- 1998-07-25 US US09/485,768 patent/US6252069B1/en not_active Expired - Lifetime
- 1998-07-25 CA CA002301194A patent/CA2301194C/en not_active Expired - Lifetime
- 1998-07-25 JP JP2000509702A patent/JP4376452B2/ja not_active Expired - Lifetime
- 1998-07-25 SK SK151-2000A patent/SK282808B6/sk not_active IP Right Cessation
- 1998-07-25 NZ NZ502659A patent/NZ502659A/xx not_active IP Right Cessation
- 1998-07-25 PL PL98338800A patent/PL195320B1/pl unknown
- 1998-07-25 ES ES98942624T patent/ES2278418T3/es not_active Expired - Lifetime
- 1998-07-25 AT AT98942624T patent/ATE346846T1/de active
- 1998-07-25 KR KR1020007001646A patent/KR100546521B1/ko not_active Expired - Lifetime
- 1998-07-25 PT PT98942624T patent/PT1005462E/pt unknown
- 1998-07-25 AU AU90691/98A patent/AU748904B2/en not_active Expired
- 1998-07-25 EA EA200000227A patent/EA002121B1/ru not_active IP Right Cessation
- 1998-08-18 ZA ZA9807411A patent/ZA987411B/xx unknown
- 1998-08-19 TW TW087113673A patent/TW472050B/zh not_active IP Right Cessation
- 1998-08-19 AR ARP980104096A patent/AR015421A1/es active IP Right Grant
2000
- 2000-01-27 IL IL134247A patent/IL134247A/en not_active IP Right Cessation
- 2000-02-03 BG BG104121A patent/BG64280B1/bg unknown
- 2000-02-17 NO NO20000787A patent/NO314305B1/no not_active IP Right Cessation
2007
- 2007-02-27 CY CY20071100277T patent/CY1106345T1/el unknown

Also Published As

Publication number	Publication date
TW472050B (en)	2002-01-11
UA55480C2 (uk)	2003-04-15
BR9811306A (pt)	2000-08-29
CZ289520B6 (cs)	2002-02-13
CN1117740C (zh)	2003-08-13
AR015421A1 (es)	2001-05-02
CY1106345T1 (el)	2011-10-12
KR20010023032A (ko)	2001-03-26
ATE346846T1 (de)	2006-12-15
PL338800A1 (en)	2000-11-20
HUP0004710A3 (en)	2002-01-28
BG104121A (en)	2000-09-29
ZA987411B (en)	2000-02-18
NZ502659A (en)	2003-06-30
HU225668B1 (en)	2007-05-29
KR100546521B1 (ko)	2006-01-26
DK1005462T3 (da)	2007-03-26
AU748904B2 (en)	2002-06-13
JP4376452B2 (ja)	2009-12-02
EP1005462B1 (de)	2006-11-29
CN1267287A (zh)	2000-09-20
NO20000787L (no)	2000-02-17
WO1999009019A1 (de)	1999-02-25
EA200000227A1 (ru)	2000-10-30
IL134247A (en)	2006-12-31
HUP0004710A2 (hu)	2001-05-28
US6252069B1 (en)	2001-06-26
IL134247A0 (en)	2001-04-30
SK1512000A3 (en)	2000-07-11
CA2301194A1 (en)	1999-02-25
TR200000424T2 (tr)	2000-07-21
ES2278418T3 (es)	2007-08-01
PT1005462E (pt)	2007-01-31
EP1005462A1 (de)	2000-06-07
PL195320B1 (pl)	2007-08-31
CZ2000558A3 (cs)	2000-05-17
NO20000787D0 (no)	2000-02-17
DE59813831D1 (de)	2007-01-11
NO314305B1 (no)	2003-03-03
EA002121B1 (ru)	2001-12-24
JP2001515073A (ja)	2001-09-18
DE19735682A1 (de)	1999-02-25
AU9069198A (en)	1999-03-08
SK282808B6 (sk)	2002-12-03
CA2301194C (en)	2007-05-15

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