SK111499A3 - Process for the preparation of benzothiazolone compounds - Google Patents

Process for the preparation of benzothiazolone compounds Download PDF

Info

Publication number: SK111499A3
Authority: SK; Slovakia
Prior art keywords: formula; compound; prepared; process according; nhcoch
Prior art date: 1997-02-27

Application number

SK1114-99A

Other languages

English (en)

Slovak (sk)

Inventor

Christopher Goodwin

Original Assignee

Astra Pharma Prod

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.)

1997-02-27

Filing date

1998-02-17

Publication date

2000-05-16

1998-02-17 Application filed by Astra Pharma Prod filed Critical Astra Pharma Prod

2000-05-16 Publication of SK111499A3 publication Critical patent/SK111499A3/sk

Links

238000000034 method Methods 0.000 title claims abstract description 20
238000002360 preparation method Methods 0.000 title claims abstract description 7
BXQNSPXDWSNUKE-UHFFFAOYSA-N 1,3-benzothiazole 1-oxide Chemical class C1=CC=C2S(=O)C=NC2=C1 BXQNSPXDWSNUKE-UHFFFAOYSA-N 0.000 title description 3
150000001875 compounds Chemical class 0.000 claims abstract description 42
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 21
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 12
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 12
239000002904 solvent Substances 0.000 claims description 7
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 6
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 5
-1 2-aminobenzothiazole compound Chemical class 0.000 claims description 4
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 4
230000002140 halogenating effect Effects 0.000 claims description 4
BSQLQMLFTHJVKS-UHFFFAOYSA-N 2-chloro-1,3-benzothiazole Chemical compound C1=CC=C2SC(Cl)=NC2=C1 BSQLQMLFTHJVKS-UHFFFAOYSA-N 0.000 claims description 3
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 3
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 claims description 3
239000012346 acetyl chloride Substances 0.000 claims description 3
MMCPOSDMTGQNKG-UHFFFAOYSA-N anilinium chloride Chemical compound Cl.NC1=CC=CC=C1 MMCPOSDMTGQNKG-UHFFFAOYSA-N 0.000 claims description 3
CPEKAXYCDKETEN-UHFFFAOYSA-N benzoyl isothiocyanate Chemical compound S=C=NC(=O)C1=CC=CC=C1 CPEKAXYCDKETEN-UHFFFAOYSA-N 0.000 claims description 3
239000003153 chemical reaction reagent Substances 0.000 claims description 3
QXDAKFBVTWGQHQ-UHFFFAOYSA-N 2-nitroacetamide Chemical compound NC(=O)C[N+]([O-])=O QXDAKFBVTWGQHQ-UHFFFAOYSA-N 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
238000006396 nitration reaction Methods 0.000 claims description 2
239000007800 oxidant agent Substances 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
230000003301 hydrolyzing effect Effects 0.000 claims 1
239000000543 intermediate Substances 0.000 abstract description 2
239000000243 solution Substances 0.000 description 20
239000000203 mixture Substances 0.000 description 14
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
239000007787 solid Substances 0.000 description 11
238000003756 stirring Methods 0.000 description 10
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
239000011541 reaction mixture Substances 0.000 description 9
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
239000000047 product Substances 0.000 description 8
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 5
238000001914 filtration Methods 0.000 description 5
239000012299 nitrogen atmosphere Substances 0.000 description 5
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
229910000041 hydrogen chloride Inorganic materials 0.000 description 4
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
229910021592 Copper(II) chloride Inorganic materials 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
229960000583 acetic acid Drugs 0.000 description 3
238000001816 cooling Methods 0.000 description 3
238000004128 high performance liquid chromatography Methods 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
239000000843 powder Substances 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
UHGULLIUJBCTEF-UHFFFAOYSA-N 2-aminobenzothiazole Chemical compound C1=CC=C2SC(N)=NC2=C1 UHGULLIUJBCTEF-UHFFFAOYSA-N 0.000 description 2
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
LTPVSOCPYWDIFU-UHFFFAOYSA-N 4-methoxyphenylethylamine Chemical compound COC1=CC=C(CCN)C=C1 LTPVSOCPYWDIFU-UHFFFAOYSA-N 0.000 description 2
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 2
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
239000012362 glacial acetic acid Substances 0.000 description 2
229940098779 methanesulfonic acid Drugs 0.000 description 2
229910017604 nitric acid Inorganic materials 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
239000011734 sodium Substances 0.000 description 2
235000010288 sodium nitrite Nutrition 0.000 description 2
239000007858 starting material Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
NIPQZGSGGWQATG-UHFFFAOYSA-N 1$l^{4},2,3-benzothiadiazole 1-oxide Chemical class C1=CC=C2S(=O)N=NC2=C1 NIPQZGSGGWQATG-UHFFFAOYSA-N 0.000 description 1
JEYVGOXHPJRQET-UHFFFAOYSA-N 2-(1-oxo-1,3-benzothiazol-7-yl)ethanamine Chemical class NCCC1=CC=CC2=C1S(=O)C=N2 JEYVGOXHPJRQET-UHFFFAOYSA-N 0.000 description 1
VBHLGXLPPGNNIE-UHFFFAOYSA-N 4-(4-methoxyphenyl)butanamide Chemical compound COC1=CC=C(CCCC(N)=O)C=C1 VBHLGXLPPGNNIE-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 description 1
229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
239000002168 alkylating agent Substances 0.000 description 1
229940100198 alkylating agent Drugs 0.000 description 1
230000002152 alkylating effect Effects 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
SOIFLUNRINLCBN-UHFFFAOYSA-N ammonium thiocyanate Chemical compound [NH4+].[S-]C#N SOIFLUNRINLCBN-UHFFFAOYSA-N 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000002585 base Substances 0.000 description 1
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 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
239000003054 catalyst Substances 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
239000007789 gas Substances 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical group 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
239000005457 ice water Substances 0.000 description 1
DQMWMUMCNOJLSI-UHFFFAOYSA-N n-carbamothioylbenzamide Chemical compound NC(=S)NC(=O)C1=CC=CC=C1 DQMWMUMCNOJLSI-UHFFFAOYSA-N 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
239000007921 spray Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
230000002194 synthesizing effect Effects 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles 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 in position 2
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
- C07C233/17—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/18—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/34—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
- C07C233/35—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/36—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C335/04—Derivatives of thiourea
- C07C335/16—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C335/20—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C335/04—Derivatives of thiourea
- C07C335/24—Derivatives of thiourea containing any of the groups, X being a hetero atom, Y being any atom
- C07C335/26—Y being a hydrogen or a carbon atom, e.g. benzoylthioureas
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles 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 in position 2
- C07D277/82—Nitrogen atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Thiazole And Isothizaole Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

SK1114-99A 1997-02-27 1998-02-17 Process for the preparation of benzothiazolone compounds SK111499A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
SE9700706A SE9700706D0 (sv)	1997-02-27	1997-02-27	Process for the preparation of benzothiazoline compounds
PCT/SE1998/000274 WO1998038180A1 (en)	1997-02-27	1998-02-17	Process for the preparation of benzothiazolone compounds

Publications (1)

Publication Number	Publication Date
SK111499A3 true SK111499A3 (en)	2000-05-16

Family

ID=20405955

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK1114-99A SK111499A3 (en)	1997-02-27	1998-02-17	Process for the preparation of benzothiazolone compounds

Country Status (20)

Country	Link
US (6)	US6087508A (id)
EP (1)	EP0970064A1 (id)
JP (1)	JP2001513770A (id)
KR (1)	KR20000075720A (id)
CN (1)	CN1083447C (id)
AU (1)	AU724616B2 (id)
BR (1)	BR9807785A (id)
CA (1)	CA2280010A1 (id)
EE (1)	EE9900373A (id)
HU (1)	HUP0000766A3 (id)
ID (1)	ID22430A (id)
IL (1)	IL131121A0 (id)
IS (1)	IS5162A (id)
NO (1)	NO994131D0 (id)
NZ (1)	NZ336877A (id)
PL (1)	PL334901A1 (id)
SE (1)	SE9700706D0 (id)
SK (1)	SK111499A3 (id)
TR (1)	TR199902057T2 (id)
WO (1)	WO1998038180A1 (id)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US7158870B2 (en) *	2002-01-24	2007-01-02	Ford Global Technologies, Llc	Post collision restraints control module
TW200738658A (en)	2005-08-09	2007-10-16	Astrazeneca Ab	Novel compounds
TW200745067A (en)	2006-03-14	2007-12-16	Astrazeneca Ab	Novel compounds
US7270805B1 (en) *	2006-03-30	2007-09-18	Conopco, Inc.	Skin lightening agents, compositions and methods
TW200833670A (en)	2006-12-20	2008-08-16	Astrazeneca Ab	Novel compounds 569
GB0702458D0 (en)	2007-02-08	2007-03-21	Astrazeneca Ab	Salts 668
JP2011524896A (ja)	2008-06-18	2011-09-08	アストラゼネカ・アクチエボラーグ	呼吸器障害の処置用のベータ２−アドレナリン受容体アゴニストとして作用するベンズオキサジノン誘導体

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3832365A (en) *	1972-03-14	1974-08-27	Hoffmann La Roche	Quinone intermediates for synthesis of 6-hydroxydopamine
CH592644A5 (id) *	1975-01-22	1977-10-31	Lonza Ag
DE2631163B2 (de) *	1976-07-10	1978-06-29	Basf Ag, 6700 Ludwigshafen	Verfahren zur Herstellung von 2-Iminobenzothiazolen
DE3231885A1 (de) *	1982-08-27	1984-03-01	Hoechst Ag, 6230 Frankfurt	Verfahren zur herstellung halogensubstituierter 2-aminobenzthiazole
DE3507824A1 (de) *	1985-03-06	1986-09-11	Bayer Ag, 5090 Leverkusen	Verfahren zur herstellung von substituierten styrolen
DE3522941A1 (de) *	1985-06-27	1987-01-08	Hoechst Ag	Verfahren zur herstellung von 2-aminobenzthiazolen
EP0529600B1 (de) *	1991-08-30	1996-11-06	Hoechst Aktiengesellschaft	Verfahren zur Herstellung von 2-Aminobenzthiazolen
JPH0558998A (ja) *	1991-09-06	1993-03-09	Taisho Pharmaceut Co Ltd	カルバゾール誘導体
DE4313930A1 (de) *	1993-04-28	1994-11-03	Hoechst Ag	Verfahren zur Herstellung von 2(3H)-Benzothiazolen

1997
- 1997-02-27 SE SE9700706A patent/SE9700706D0/xx unknown
1998
- 1998-02-17 SK SK1114-99A patent/SK111499A3/sk unknown
- 1998-02-17 US US09/029,831 patent/US6087508A/en not_active Expired - Fee Related
- 1998-02-17 JP JP53756798A patent/JP2001513770A/ja active Pending
- 1998-02-17 BR BR9807785-6A patent/BR9807785A/pt not_active IP Right Cessation
- 1998-02-17 CA CA002280010A patent/CA2280010A1/en not_active Abandoned
- 1998-02-17 HU HU0000766A patent/HUP0000766A3/hu unknown
- 1998-02-17 PL PL98334901A patent/PL334901A1/xx unknown
- 1998-02-17 CN CN98802761A patent/CN1083447C/zh not_active Expired - Fee Related
- 1998-02-17 NZ NZ336877A patent/NZ336877A/en unknown
- 1998-02-17 IL IL13112198A patent/IL131121A0/xx unknown
- 1998-02-17 KR KR1019997007789A patent/KR20000075720A/ko not_active Withdrawn
- 1998-02-17 ID IDW990871A patent/ID22430A/id unknown
- 1998-02-17 EE EEP199900373A patent/EE9900373A/xx unknown
- 1998-02-17 AU AU66407/98A patent/AU724616B2/en not_active Ceased
- 1998-02-17 TR TR1999/02057T patent/TR199902057T2/xx unknown
- 1998-02-17 WO PCT/SE1998/000274 patent/WO1998038180A1/en not_active Ceased
- 1998-02-17 EP EP98908361A patent/EP0970064A1/en not_active Withdrawn
1999
- 1999-08-23 IS IS5162A patent/IS5162A/is unknown
- 1999-08-26 NO NO994131A patent/NO994131D0/no not_active Application Discontinuation
- 1999-10-01 US US09/410,066 patent/US6194614B1/en not_active Expired - Fee Related
- 1999-10-01 US US09/411,162 patent/US6147219A/en not_active Expired - Fee Related
- 1999-10-01 US US09/410,069 patent/US6114578A/en not_active Expired - Fee Related
- 1999-10-01 US US09/410,042 patent/US6124468A/en not_active Expired - Fee Related
- 1999-10-01 US US09/410,067 patent/US6118024A/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
PL334901A1 (en)	2000-03-27
IL131121A0 (en)	2001-01-28
US6124468A (en)	2000-09-26
EP0970064A1 (en)	2000-01-12
KR20000075720A (ko)	2000-12-26
HUP0000766A3 (en)	2001-12-28
ID22430A (id)	1999-10-14
IS5162A (is)	1999-08-23
CA2280010A1 (en)	1998-09-03
US6114578A (en)	2000-09-05
WO1998038180A1 (en)	1998-09-03
NO994131L (no)	1999-08-26
NZ336877A (en)	2001-07-27
US6194614B1 (en)	2001-02-27
US6147219A (en)	2000-11-14
AU6640798A (en)	1998-09-18
SE9700706D0 (sv)	1997-02-27
NO994131D0 (no)	1999-08-26
JP2001513770A (ja)	2001-09-04
BR9807785A (pt)	2000-02-22
US6118024A (en)	2000-09-12
HUP0000766A2 (hu)	2000-10-28
AU724616B2 (en)	2000-09-28
US6087508A (en)	2000-07-11
CN1248252A (zh)	2000-03-22
TR199902057T2 (xx)	2000-02-21
CN1083447C (zh)	2002-04-24
EE9900373A (et)	2000-04-17

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