SK169397A3 - Aminophenyl ketone derivatives and preparation method thereof - Google Patents

Aminophenyl ketone derivatives and preparation method thereof Download PDF

Info

Publication number: SK169397A3
Authority: SK; Slovakia
Prior art keywords: atoms; carbon; group; alkyl; compound
Prior art date: 1996-12-20

Application number

SK1693-97A

Other languages

English (en)

Slovak (sk)

Inventor

David A Cortes

Kenneth A M Kremer

Original Assignee

American Cyanamid Co

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.)

1996-12-20

Filing date

1997-12-09

Publication date

1998-09-09

1997-12-09 Application filed by American Cyanamid Co filed Critical American Cyanamid Co

1998-09-09 Publication of SK169397A3 publication Critical patent/SK169397A3/sk

Links

238000002360 preparation method Methods 0.000 title claims abstract description 18
GSEZYWGNEACOIW-UHFFFAOYSA-N bis(2-aminophenyl)methanone Chemical class NC1=CC=CC=C1C(=O)C1=CC=CC=C1N GSEZYWGNEACOIW-UHFFFAOYSA-N 0.000 title abstract description 3
238000000034 method Methods 0.000 claims abstract description 18
125000004432 carbon atom Chemical group C* 0.000 claims description 45
150000001875 compounds Chemical class 0.000 claims description 45
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 29
125000005843 halogen group Chemical group 0.000 claims description 29
229910052799 carbon Inorganic materials 0.000 claims description 25
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 24
125000000217 alkyl group Chemical group 0.000 claims description 21
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 15
125000004414 alkyl thio group Chemical group 0.000 claims description 15
125000004429 atom Chemical group 0.000 claims description 12
-1 tetrahydro-2-oxo-3-furoyl Chemical group 0.000 claims description 12
125000003545 alkoxy group Chemical group 0.000 claims description 11
239000002253 acid Substances 0.000 claims description 10
125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 9
239000003960 organic solvent Substances 0.000 claims description 9
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
229910052736 halogen Inorganic materials 0.000 claims description 8
150000002367 halogens Chemical class 0.000 claims description 8
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 7
239000000460 chlorine Chemical group 0.000 claims description 7
125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 6
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 6
239000000203 mixture Substances 0.000 claims description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
229910052801 chlorine Inorganic materials 0.000 claims description 4
229910052757 nitrogen Inorganic materials 0.000 claims description 4
HMOJKUDFFLOQTN-UHFFFAOYSA-N (2-aminophenyl)-cyclopropylmethanone Chemical compound NC1=CC=CC=C1C(=O)C1CC1 HMOJKUDFFLOQTN-UHFFFAOYSA-N 0.000 claims description 3
125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 3
125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 3
RVDLHGSZWAELAU-UHFFFAOYSA-N 5-tert-butylthiophene-2-carbonyl chloride Chemical compound CC(C)(C)C1=CC=C(C(Cl)=O)S1 RVDLHGSZWAELAU-UHFFFAOYSA-N 0.000 claims description 3
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 3
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
BIPUHAHGLJKIPK-UHFFFAOYSA-N dicyclopropylmethanone Chemical compound C1CC1C(=O)C1CC1 BIPUHAHGLJKIPK-UHFFFAOYSA-N 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 3
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
229910052794 bromium Chemical group 0.000 claims description 2
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
125000001309 chloro group Chemical group Cl* 0.000 claims description 2
WRJWRGBVPUUDLA-UHFFFAOYSA-N chlorosulfonyl isocyanate Chemical compound ClS(=O)(=O)N=C=O WRJWRGBVPUUDLA-UHFFFAOYSA-N 0.000 claims description 2
238000002425 crystallisation Methods 0.000 claims description 2
230000008025 crystallization Effects 0.000 claims description 2
125000004093 cyano group Chemical group *C#N 0.000 claims description 2
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 2
125000000623 heterocyclic group Chemical group 0.000 claims description 2
230000007062 hydrolysis Effects 0.000 claims description 2
238000006460 hydrolysis reaction Methods 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
229910052760 oxygen Inorganic materials 0.000 claims description 2
239000001301 oxygen Substances 0.000 claims description 2
239000002904 solvent Substances 0.000 claims description 2
125000004434 sulfur atom Chemical group 0.000 claims description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
125000003282 alkyl amino group Chemical group 0.000 claims 2
125000004663 dialkyl amino group Chemical group 0.000 claims 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
238000006704 dehydrohalogenation reaction Methods 0.000 claims 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
125000003944 tolyl group Chemical group 0.000 claims 1
230000002363 herbicidal effect Effects 0.000 abstract description 9
OJXASOYYODXRPT-UHFFFAOYSA-N sulfamoylurea Chemical class NC(=O)NS(N)(=O)=O OJXASOYYODXRPT-UHFFFAOYSA-N 0.000 abstract description 7
239000000543 intermediate Substances 0.000 abstract description 6
238000004519 manufacturing process Methods 0.000 abstract description 6
239000004009 herbicide Substances 0.000 abstract description 5
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract description 2
239000004202 carbamide Substances 0.000 abstract description 2
239000000047 product Substances 0.000 description 13
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
238000005481 NMR spectroscopy Methods 0.000 description 6
238000004458 analytical method Methods 0.000 description 6
239000000243 solution Substances 0.000 description 6
239000002585 base Substances 0.000 description 4
239000000725 suspension Substances 0.000 description 4
239000012044 organic layer Substances 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
239000000284 extract Substances 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
238000001914 filtration Methods 0.000 description 2
229910052500 inorganic mineral Inorganic materials 0.000 description 2
239000011707 mineral Substances 0.000 description 2
238000005191 phase separation Methods 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
239000008096 xylene Substances 0.000 description 2
125000004455 (C1-C3) alkylthio group Chemical group 0.000 description 1
125000004765 (C1-C4) haloalkyl group Chemical group 0.000 description 1
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
SUYDUAIIHIGTOF-UHFFFAOYSA-N 1-(2-aminophenyl)-4-chlorobutan-1-one;hydrochloride Chemical compound Cl.NC1=CC=CC=C1C(=O)CCCCl SUYDUAIIHIGTOF-UHFFFAOYSA-N 0.000 description 1
SBUNONZKFNLXPY-UHFFFAOYSA-N 1-(2-aminophenyl)-4-hydroxybutan-1-one Chemical compound NC1=CC=CC=C1C(=O)CCCO SBUNONZKFNLXPY-UHFFFAOYSA-N 0.000 description 1
OGILDNZHSOSLPI-UHFFFAOYSA-N 2-cyclopropylethenone Chemical compound O=C=CC1CC1 OGILDNZHSOSLPI-UHFFFAOYSA-N 0.000 description 1
BWWHTIHDQBHTHP-UHFFFAOYSA-N 2-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=CC=C1C(Cl)=O BWWHTIHDQBHTHP-UHFFFAOYSA-N 0.000 description 1
OMQHDIHZSDEIFH-UHFFFAOYSA-N 3-Acetyldihydro-2(3H)-furanone Chemical compound CC(=O)C1CCOC1=O OMQHDIHZSDEIFH-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
VQKLUVMQJGUSRT-UHFFFAOYSA-N Cl.C(CCC)N(CCCC=C)CCCC Chemical compound Cl.C(CCC)N(CCCC=C)CCCC VQKLUVMQJGUSRT-UHFFFAOYSA-N 0.000 description 1
229940126062 Compound A Drugs 0.000 description 1
NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
150000004703 alkoxides Chemical class 0.000 description 1
125000004448 alkyl carbonyl group Chemical group 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical class C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
150000008366 benzophenones Chemical class 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
230000002051 biphasic effect Effects 0.000 description 1
239000012455 biphasic mixture Substances 0.000 description 1
235000013339 cereals Nutrition 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
125000006255 cyclopropyl carbonyl group Chemical group [H]C1([H])C([H])([H])C1([H])C(*)=O 0.000 description 1
238000010586 diagram Methods 0.000 description 1
150000001983 dialkylethers Chemical class 0.000 description 1
239000002360 explosive Substances 0.000 description 1
238000000605 extraction Methods 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
239000010410 layer Substances 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
CRGZYKWWYNQGEC-UHFFFAOYSA-N magnesium;methanolate Chemical compound [Mg+2].[O-]C.[O-]C CRGZYKWWYNQGEC-UHFFFAOYSA-N 0.000 description 1
238000004949 mass spectrometry Methods 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
UOYJQYCQZFTBFW-UHFFFAOYSA-N n-[2-(cyclopropanecarbonyl)phenyl]-4-methylbenzenesulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC1=CC=CC=C1C(=O)C1CC1 UOYJQYCQZFTBFW-UHFFFAOYSA-N 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000012071 phase Substances 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
238000010992 reflux Methods 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D307/32—Oxygen atoms
- C07D307/33—Oxygen atoms in position 2, the oxygen atom being in its keto or unsubstituted enol form
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C307/00—Amides of sulfuric acids, i.e. compounds having singly-bound oxygen atoms of sulfate groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C307/04—Diamides of sulfuric acids
- C07C307/10—Diamides of sulfuric acids having nitrogen atoms of the sulfamide groups bound to carbon atoms of six-membered aromatic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
- C07C303/04—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof by substitution of hydrogen atoms by sulfo or halosulfonyl groups
- C07C303/08—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof by substitution of hydrogen atoms by sulfo or halosulfonyl groups by reaction with halogenosulfonic acids
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
- C07C311/21—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Plural Heterocyclic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

SK1693-97A 1996-12-20 1997-12-09 Aminophenyl ketone derivatives and preparation method thereof SK169397A3 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US77131896A	1996-12-20	1996-12-20

Publications (1)

Publication Number	Publication Date
SK169397A3 true SK169397A3 (en)	1998-09-09

Family

ID=25091429

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK1693-97A SK169397A3 (en)	1996-12-20	1997-12-09	Aminophenyl ketone derivatives and preparation method thereof

Country Status (28)

Country	Link
EP (1)	EP0849262B1 (pt)
JP (1)	JP3958851B2 (pt)
KR (1)	KR100555052B1 (pt)
CN (1)	CN1100755C (pt)
AR (1)	AR011771A1 (pt)
AT (1)	ATE207066T1 (pt)
AU (1)	AU721862B2 (pt)
BG (1)	BG63390B1 (pt)
BR (1)	BR9706365A (pt)
CA (1)	CA2225206C (pt)
CO (1)	CO5021225A1 (pt)
CZ (1)	CZ393797A3 (pt)
DE (1)	DE69707408T2 (pt)
EG (1)	EG21392A (pt)
ES (1)	ES2166052T3 (pt)
HR (1)	HRP970613B1 (pt)
HU (1)	HU219612B (pt)
IL (1)	IL122672A (pt)
NO (1)	NO309934B1 (pt)
NZ (1)	NZ329428A (pt)
PL (1)	PL190620B1 (pt)
RU (1)	RU2201418C2 (pt)
SG (1)	SG64466A1 (pt)
SK (1)	SK169397A3 (pt)
TR (1)	TR199701597A2 (pt)
UA (1)	UA43896C2 (pt)
YU (1)	YU48897A (pt)
ZA (1)	ZA9711397B (pt)

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0184122B1 (en) *	1984-12-03	1991-07-17	Ppg Industries, Inc.	Sulfamoyl urea derivatives
US4559081A (en) *	1984-12-03	1985-12-17	Ppg Industries, Inc.	Sulfamoyl urea derivatives
US5009699A (en) *	1990-06-22	1991-04-23	American Cyanamid Company	1-{[O-(cyclopropylcarbonyl)phenyl]sulfamoyl}-3-(4,6-dimethoxy-2-pyrimidinyl)urea herbicidal composition and use
DE4337847A1 (de) *	1993-11-05	1995-05-11	Bayer Ag	Substituierte Phenylaminosulfonylharnstoffe
CZ289916B6 (cs) *	1993-11-30	2002-04-17	American Cyanamid Company	Způsob výroby o-aminofenylketonů
DE4414476A1 (de) *	1994-04-26	1995-11-02	Bayer Ag	Substituierte Cyclopropylcarbonyl-phenylaminosulfonyl-harnstoffe
DE4414840A1 (de) *	1994-04-28	1995-11-02	Bayer Ag	Substituierte Phenylaminosulfonylharnstoffe

1997
- 1997-11-14 HR HR970613A patent/HRP970613B1/xx not_active IP Right Cessation
- 1997-12-05 CZ CZ973937A patent/CZ393797A3/cs unknown
- 1997-12-09 SK SK1693-97A patent/SK169397A3/sk unknown
- 1997-12-11 TR TR97/01597A patent/TR199701597A2/xx unknown
- 1997-12-11 BG BG102110A patent/BG63390B1/bg unknown
- 1997-12-15 AT AT97310120T patent/ATE207066T1/de not_active IP Right Cessation
- 1997-12-15 ES ES97310120T patent/ES2166052T3/es not_active Expired - Lifetime
- 1997-12-15 EP EP97310120A patent/EP0849262B1/en not_active Expired - Lifetime
- 1997-12-15 DE DE69707408T patent/DE69707408T2/de not_active Expired - Lifetime
- 1997-12-16 JP JP36342597A patent/JP3958851B2/ja not_active Expired - Fee Related
- 1997-12-17 BR BR9706365A patent/BR9706365A/pt not_active Application Discontinuation
- 1997-12-18 CA CA002225206A patent/CA2225206C/en not_active Expired - Fee Related
- 1997-12-18 AU AU48459/97A patent/AU721862B2/en not_active Ceased
- 1997-12-18 CO CO97073946A patent/CO5021225A1/es unknown
- 1997-12-18 UA UA97126152A patent/UA43896C2/uk unknown
- 1997-12-18 EG EG135297A patent/EG21392A/xx active
- 1997-12-18 IL IL12267297A patent/IL122672A/xx not_active IP Right Cessation
- 1997-12-18 ZA ZA9711397A patent/ZA9711397B/xx unknown
- 1997-12-18 YU YU48897A patent/YU48897A/sr unknown
- 1997-12-18 NZ NZ329428A patent/NZ329428A/en unknown
- 1997-12-18 SG SG1997004560A patent/SG64466A1/en unknown
- 1997-12-19 NO NO975983A patent/NO309934B1/no not_active IP Right Cessation
- 1997-12-19 RU RU97122130/04A patent/RU2201418C2/ru not_active IP Right Cessation
- 1997-12-19 PL PL97323892A patent/PL190620B1/pl not_active IP Right Cessation
- 1997-12-19 KR KR1019970070780A patent/KR100555052B1/ko not_active Expired - Fee Related
- 1997-12-19 AR ARP970106066A patent/AR011771A1/es active IP Right Grant
- 1997-12-19 HU HU9702511A patent/HU219612B/hu not_active IP Right Cessation
- 1997-12-19 CN CN97108762A patent/CN1100755C/zh not_active Expired - Fee Related

Also Published As

Publication number	Publication date
RU2201418C2 (ru)	2003-03-27
CA2225206A1 (en)	1998-06-20
HRP970613B1 (en)	2002-06-30
CO5021225A1 (es)	2001-03-27
UA43896C2 (uk)	2002-01-15
BG63390B1 (bg)	2001-12-29
YU48897A (en)	1999-11-22
NO309934B1 (no)	2001-04-23
KR100555052B1 (ko)	2006-06-29
CA2225206C (en)	2008-03-18
NZ329428A (en)	1999-10-28
SG64466A1 (en)	1999-04-27
TR199701597A2 (xx)	1998-07-21
EP0849262B1 (en)	2001-10-17
PL190620B1 (pl)	2005-12-30
JP3958851B2 (ja)	2007-08-15
AR011771A1 (es)	2000-09-13
PL323892A1 (en)	1998-06-22
BG102110A (en)	1998-11-30
ATE207066T1 (de)	2001-11-15
NO975983D0 (no)	1997-12-19
HRP970613A2 (en)	1998-10-31
IL122672A0 (en)	1998-08-16
ZA9711397B (en)	1999-06-18
IL122672A (en)	2001-08-26
CZ393797A3 (cs)	1998-07-15
AU721862B2 (en)	2000-07-13
DE69707408D1 (de)	2001-11-22
HUP9702511A1 (hu)	1998-11-30
HU9702511D0 (en)	1998-03-02
NO975983L (no)	1998-06-22
KR19980064371A (ko)	1998-10-07
DE69707408T2 (de)	2002-07-04
EP0849262A1 (en)	1998-06-24
HK1012504A1 (en)	1999-08-06
HU219612B (hu)	2001-05-28
CN1185430A (zh)	1998-06-24
EG21392A (en)	2001-10-31
MX9710069A (es)	1998-10-31
AU4845997A (en)	1998-06-25
BR9706365A (pt)	1999-05-18
JPH10226676A (ja)	1998-08-25
CN1100755C (zh)	2003-02-05
ES2166052T3 (es)	2002-04-01

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