DK200401246A - 3-(Nitrogen-substituerede)-phenyl-5beta-(aminomethyl)-oxazolidin-2-oner og farmaceutisk acceptable salte deraf samt anvendelse af disse forbindelser til fremstilling af et lægemiddel - Google Patents

3-(Nitrogen-substituerede)-phenyl-5beta-(aminomethyl)-oxazolidin-2-oner og farmaceutisk acceptable salte deraf samt anvendelse af disse forbindelser til fremstilling af et lægemiddel Download PDF

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Publication number: DK200401246A
Authority: DK; Denmark
Prior art keywords: alkyl; opt; substd; phenyl; so3h
Prior art date: 1988-09-15

Application number

DK200401246A

Other languages

English (en)

Inventor

Steven J Brickner

Original Assignee

Upjohn 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.)

1988-09-15

Filing date

2004-08-18

Publication date

2004-08-18

2004-08-18 Application filed by Upjohn Co filed Critical Upjohn Co

2004-08-18 Publication of DK200401246A publication Critical patent/DK200401246A/da

2005-08-01 Application granted granted Critical

2005-08-01 Publication of DK175940B1 publication Critical patent/DK175940B1/da

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VELIYQKFMHNDAW-UHFFFAOYSA-N 3-(2h-benzotriazol-4-yl)-1,3-oxazolidin-2-one Chemical compound O=C1OCCN1C1=CC=CC2=C1N=NN2 VELIYQKFMHNDAW-UHFFFAOYSA-N 0.000 title 1
239000003242 anti bacterial agent Substances 0.000 title 1
125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 title 1
125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 title 1
125000000217 alkyl group Chemical group 0.000 abstract description 29
-1 OEt Chemical group 0.000 abstract description 12
229910006069 SO3H Inorganic materials 0.000 abstract description 9
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract description 8
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract description 4
125000004076 pyridyl group Chemical group 0.000 abstract description 2
125000000719 pyrrolidinyl group Chemical group 0.000 abstract description 2
150000003839 salts Chemical class 0.000 abstract description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 8
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 abstract 5
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 abstract 4
125000000896 monocarboxylic acid group Chemical group 0.000 abstract 4
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 abstract 3
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 abstract 2
229910006074 SO2NH2 Inorganic materials 0.000 abstract 2
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 abstract 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 2
125000000753 cycloalkyl group Chemical group 0.000 abstract 2
125000001475 halogen functional group Chemical group 0.000 abstract 2
CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 abstract 2
125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 abstract 2
125000006217 methyl sulfide group Chemical group [H]C([H])([H])S* 0.000 abstract 2
WWUZIQQURGPMPG-KRWOKUGFSA-N sphingosine Chemical compound CCCCCCCCCCCCC\C=C\[C@@H](O)[C@@H](N)CO WWUZIQQURGPMPG-KRWOKUGFSA-N 0.000 abstract 2
IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 abstract 1
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 abstract 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 abstract 1
125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 abstract 1
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 abstract 1
101100240519 Caenorhabditis elegans nhr-13 gene Proteins 0.000 abstract 1
MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 abstract 1
150000001450 anions Chemical class 0.000 abstract 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 1
125000000466 oxiranyl group Chemical group 0.000 abstract 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 abstract 1
229920002554 vinyl polymer Polymers 0.000 abstract 1
150000001875 compounds Chemical class 0.000 description 7
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
125000004178 (C1-C4) alkyl group Chemical group 0.000 description 4
125000000623 heterocyclic group Chemical group 0.000 description 4
125000004433 nitrogen atom Chemical group N* 0.000 description 4
229920006395 saturated elastomer Polymers 0.000 description 3
125000006273 (C1-C3) alkyl group Chemical group 0.000 description 2
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
125000004400 (C1-C12) alkyl group Chemical group 0.000 description 1
125000006711 (C2-C12) alkynyl group Chemical group 0.000 description 1
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
239000003814 drug Substances 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
125000002541 furyl group Chemical group 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
208000015181 infectious disease Diseases 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen(.) Chemical class [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings 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
- C07D263/18—Oxygen atoms
- C07D263/20—Oxygen atoms attached in position 2
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/04—Immunostimulants
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond

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Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Immunology (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
General Chemical & Material Sciences (AREA)
Oncology (AREA)
Communicable Diseases (AREA)
Virology (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)

Description

PATENTKRAV·

1. 3- (Nitrogen-substitueret) -phenyl-5få- (amidomethyl) -ox.azolidin-2-oner, kendetegnet ved, at de har den almene formel LV

(LV) i hvilken (I) R1 er -H,

Ci-Ci2-alkyl, der eventuelt er substitueret med 1-3 Cl, C3-C12-cycloalkyl, C5-Ci2-alkenyl indeholdende én dobbeltbinding, -Φ, der eventuelt er substitueret med 1-3 -OH, -OCH3, -OC2H5, -N02, -F, -Cl, -Br, -COOH og -SO3H, -NiR;^) (Ri_2) -hvor R1_1 og R]__2 er ens eller forskellige og er -H eller C 4-C 2-alkyl, furanyl, tetrahydrofuranyl, 2-thiophen, pyrrolidinyl, pyridinyl, -0-R1_3, hvor Ri_3 er C1-C4-alkyl, -NH2, -NHR]_ _ 3, hvor Ri_3 er som ovenfor defineret, -NR1_3R1_4, hvor R1_4 er C1-C3-alkyl, og R]__3 er som ovenfor defineret, og hvor Rx_3 og R]__4 sammen med det tilknyttede nitrogenatom kan danne en mættet mono-nitrogen-C^-c7-heterocyclisk ring indeholdende -O-, -ch2-oh, -CH2-0R4_5, hvor Rx_5 er C1-C4-alkyl, eller -CO-R^g, hvor Tii-s er ^-04-alkyl eller -Φ, (II) to af R2, R3 og R4 er -H, og den anden af R2, R3 og R4 er -H, -F, -Cl, -Br, -I,

Ci-Cg-alkyl, -OH, -C0-0-R2_i, hvor R2-i er C1-C4-alkyl eller -Φ, -0-R2_i, hvor R2_i er som ovenfor defineret, -COOH, -COO~, -CHO, -CO-NR2_2R2_3, hvor R2_2 og R2_3 er ens eller forskellige og er -H, Ci-C3-alkyl, eller R2-2 °9 R2-3 han sammen med det tilknyttede nitrogenatom danne en mættet mono-nitro-gen-C3-Cg-heterocyclisk ring, der eventuelt indeholder -0-, -C=N, -C^CH, -N=C, -CHOH-CH3, -CO-CH3, -SH, -SO-CH3, -SO-Φ, -s-ch3, -Ξ-Φ, -so2-ch3, -so2-ø, -S03H, -so2-NH2, -N3, -no2, -NR2_4R2_5, hvor R2_4 og R2_5 er ens eller forskellige og er -H og Ci-C3-alkyl, -NH-CO-R2 _g, hvor R2-6 er Ci-C4-alkyl eller -Φ, -NH-C0-NH2, -CH=CH2, -ch2-ch=ch2, -CH=N-OH, -CH=N-OCH3, -ch3-c=n-oh, -ch3-c=n-och3 , -C*H-CH2-0*, hvor atomerne mærket med en stjerne {*) er bundet til hinanden til dannelse af en ring, (IIIA) hvor W3 og W2 tilsammen er -nr5-n=cr6- (XXXII) hvor R5 er -H,

Cl-C12 -a-lkyl, -οη2-φ, -CH2CH2-<i>, C3-C7-cycloalkyl, c2_C12-slkenyl indeholdende fra 1 til 3 dobbeltbindinger, C2-Ci2-alkynyl indeholdende 1 tredobbelt binding, -CHO, -CO-R5_1, hvor R5_i er (A) C]_-C6-alkyl, der eventuelt er substitueret med I -0-CH3, -COOH, -NH2, -SO3H eller 1-3 -Cl, (B) C3-C7-cycloalkyl, (C) 2-pyridinyl, 2-thiophen, 2-thiophenmethyl eller 2-pyrrol, (D) -Φ, der eventuelt er substitueret med 1-3 -F, -Cl, -Br, -I, C1-C6-alkyl, -OH, -C0-0-R5_2, hvor R5_2 er C]_-C4-alkyl eller -Φ, -0-R5_2i hvor R5_2 er som ovenfor defineret, -COOH, -CO-NRg_3R3_4, hvor R5_3 og R5_4 er ens eller forskellige og er -H, C3-C3-alkyl, eller R5_3 og R3_4 kan sammen med det tilknyttede nitrogenatom danne en mættet mononitrogen-C3-Cg-heterocyclisk ring, der eventuelt indeholder -O-, -C=N, -CHOH-CH3, -CO-CH3, -SH, -SO-CH3, -SO-Φ, -S-CH3, -S-Φ, -so2-ch3, -S02-<i>, -S03H, ~so2-nh2, -N3, -no2, hvor R5-5 og R^.g er ens eller forskellige og er -H og C^-C3-alkyl, -NH-C0-R5_7, hvor R5_7 er -C4-alkyl eller -Φ, -C0-0-R5_q, hvor Rg_g er C1-C4-alkyl eller -Φ, hver eventuelt substitueret med 1 eller 2 -F, -Cl, -Br, -I, C]_ -Cg-alkyl, -OH, -C0-0-R5_2; hvor R5.2 er som ovenfor defineret, -0 - Rg - 2 7 hvor Rg"2er som ovenfor defineret, -COOH, -CO-NRg _ 3R5-4, hvor R5-3 og Rg_4 er som ovenfor defineret, -CsN, -CHOH-CH3, -CO-CH3, -SH, -SO-CH3, -ΞΟ-Φ, -s-ch3, -S-Φ, -so2-ch3, -so2-Φ, -so3h, -so2-nh2, -n3, -no2, -NRg_5R5_g, hvor R5_5 og R5_g er som ovenfor defineret, -NH-CO-R5_7, hvor R5_7 er som ovenfor defineret, -CO-N (Rg_g) 2 1 hvor Rg-9 er -H eller Rg_g som ovenfor defineret, og hvor grupperne R5-9 sammen med det tilknyttede nitrogenatom kan danne en mættet mononitrogen-C3-C6--heterocyclisk ring, der eventuelt indeholder -O- eller -NH- , -CO-CH2-CN, -co-ch2-oh, -CO-CH2-O-Φ, hvor Φ eventuelt er substitueret med 1-3 -0-CH3, 1 -N02 og 1 -NH2, -CO-CH2-0-R5^1q, hvor R5-10 er ci_c6-alkyl, -Φ, der eventuelt er substitueret med 1-3 -0-CH3, 1 -N02 og -NH2, -C0-R5_11( hvor R5-11 er C4-Cg-alkyl, -Φ, der eventuelt er substitueret med 1-4 -F, 1-3 -Cl, 1 -OCH3, -OH, -NH2, -N02, -CO-CH3, -S02-CH3 og -S02-0H, -CO-CH(NH-CO-Rg_22)-R5-13 i hvor Rg_-]_3 er -H eller -CH3, og R5-12 er C]_-Cg-alkyl, -Φ, der eventuelt er substitueret med 1 eller 2 -OH, -OCH3, -N02, -NH2, -Cl, -F, -NH-CH3 og -N(CH3)2, -CO-CHNH2-R5_14, hvor R5_14 er -CH(CH3)2, -CH2-CH{CH3)2, -CHCH3-CH2-CH3, -CH2-OH, -CH(OH)-CH3, -οη2-φ, -ch2-ø-oh, -ch2-sh, -CH2-CH2-S-CH3, og -ch2-cooh, -so2-ch3, -S02-Φ, -so3h, og Rg er -Η og C4-C3-alkyl, (IIIB) hvor W4 og W2 tilsammen er -NR5-N=N-, (LIV) hvor R5 er som ovenfor defineret, samt farmaceutisk acceptable salte deraf. 2. Forbindelse ifølge krav 1, i hvilken og W2 tilsammen er -NRc;-N=CRg-. 3. Forbindelse ifølge krav 1, i hvilken W2 og W2 tilsammen er -NR5-N=N-. 4. Forbindelse ifølge ethvert af de foregående krav, i hvilken R2, R3 og R4 alle er H. 5. Forbindelse ifølge ethvert af de foregående krav, 1 hvilken R]_ er H, Cp-Cg-alkyl, C3-Cg-cycloalkyl, -OCH3 eller -CHC12, og Rs er valgt blandt -CH3, -CH2-CH=CH2, -CH2-C=CH, -CHO og -CO-R5_2, hvor Rg_2 er -CH3, -C2H5, -CH(CH3)2> -CHCI2, -CH2OH, -CH2-O-CH3, 2-thiophenyl eller cyclopentyl. 6. Forbindelse ifølge krav 2, der er 3 - [5 1 - (1-acetylindazolyl) -5IS- (acetamidomethyl) -oxazo-lidin-2-on, 3 -(51 -indazolyl)-5β- (acetamidomethyl)-oxazolidin- 2 -on, 3-[5'-(l-ethylindazolyl]-5S-(acetamidomethyl)-oxazo-lidin-2-on eller 3 - [ 5 1 - (1 - n - propyl i nda zolyl) ] - 5β- (acetamidomethyl) -oxazolidin-2-on. 7. Anvendelse af en forbindelse ifølge ethvert af de foregående krav til fremstilling af et lægemiddel til anvendelse ved behandling af infektion forårsaget af gram-positive eller anaerobe organismer. 8. Forbindelse ifølge ethvert af kravene 1-4, med undtagelse af, at R5 er H.

DK200401246A 1988-09-15 2004-08-18 3-(Nitrogensubstituerede)-phenyl-5beta-aminomethyloxazolidin-2-oner og farmaceutisk acceptable salte deraf samt anvendelse af disse forbindelser til fremstilling af et lægemiddel DK175940B1 (da)

Applications Claiming Priority (8)

Application Number	Priority Date	Filing Date	Title
US24498888A	1988-09-15	1988-09-15
US24498888		1988-09-15
US25385088A	1988-10-05	1988-10-05
US25385088		1988-10-05
US32494289A	1989-03-17	1989-03-17
US32494289		1989-03-17
DK45591		1991-03-13
DK199100455A DK175696B1 (da)	1988-09-15	1991-03-13	5'-Indolinyloxazolidin-2-oner med farmaceutisk acceptable salte deraf

Publications (2)

Publication Number	Publication Date
DK200401246A true DK200401246A (da)	2004-08-18
DK175940B1 DK175940B1 (da)	2005-08-01

Family

ID=27399816

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
DK199100455A DK175696B1 (da)	1988-09-15	1991-03-13	5'-Indolinyloxazolidin-2-oner med farmaceutisk acceptable salte deraf
DK200401246A DK175940B1 (da)	1988-09-15	2004-08-18	3-(Nitrogensubstituerede)-phenyl-5beta-aminomethyloxazolidin-2-oner og farmaceutisk acceptable salte deraf samt anvendelse af disse forbindelser til fremstilling af et lægemiddel

Family Applications Before (1)

Application Number	Title	Priority Date	Filing Date
DK199100455A DK175696B1 (da)	1988-09-15	1991-03-13	5'-Indolinyloxazolidin-2-oner med farmaceutisk acceptable salte deraf

Country Status (13)

Country	Link
EP (3)	EP0359418B1 (da)
JP (2)	JP2865211B2 (da)
KR (1)	KR0138262B1 (da)
AT (2)	ATE112773T1 (da)
AU (1)	AU617871B2 (da)
CA (1)	CA1335103C (da)
DE (2)	DE68929303T2 (da)
DK (2)	DK175696B1 (da)
ES (1)	ES2157934T3 (da)
GR (1)	GR3036491T3 (da)
LV (1)	LV12888B (da)
TW (1)	TW219936B (da)
WO (1)	WO1990002744A1 (da)

Families Citing this family (53)

* Cited by examiner, † Cited by third party
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KR100215627B1 (ko) *	1990-06-07	1999-08-16	레슬리 제인 에드워즈	치료용 헤테로사이클 화합물
DE69230563T2 (de) *	1991-08-14	2000-09-14	Procter & Gamble Pharmaceuticals, Inc.	Oxazolidinon-derivate mit antiarrhythmischer und antifibrillatorische wirkung
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AU666740B2 (en) *	1992-07-08	1996-02-22	Upjohn Company, The	5'-indolinyl oxazolidinones useful against (mycobacterium tuberculosis)
US5688792A (en) *	1994-08-16	1997-11-18	Pharmacia & Upjohn Company	Substituted oxazine and thiazine oxazolidinone antimicrobials
DE4425613A1 (de) *	1994-07-20	1996-01-25	Bayer Ag	5-gliedrige Heteroaryl-oxazolidinone
DE4425609A1 (de) *	1994-07-20	1996-01-25	Bayer Ag	Benzofuranyl- und Benzothienyloxazolidinone
DE4425612A1 (de) *	1994-07-20	1996-04-04	Bayer Ag	6-gliedrige stickstoffhaltige Heteroaryl-oxazolidinone
DE19514313A1 (de) *	1994-08-03	1996-02-08	Bayer Ag	Benzoxazolyl- und Benzothiazolyloxazolidinone
DK0788498T3 (da) *	1994-10-26	2001-11-05	Upjohn Co	Phenyloxazolidinoner med antimikrobiel virkning
BR9509673A (pt) *	1994-11-15	1997-09-30	Upjohn Co	Compostos e uso dos mesmos
CA2208603A1 (en) *	1995-02-03	1996-08-08	The Upjohn Company	Hetero-aromatic ring substituted phenyloxazolidinone antimicrobials
HRP960159A2 (en) *	1995-04-21	1997-08-31	Bayer Ag	Benzocyclopentane oxazolidinones containing heteroatoms
AU702752B2 (en) *	1995-05-11	1999-03-04	Pharmacia & Upjohn Company	Spirocyclic and bicyclic diazinyl and carbazinyl oxazolidinones
US5883093A (en) *	1995-09-12	1999-03-16	Pharmacia & Upjohn Company	Phenyloxazolidinone antimicrobials
ZA968661B (en) *	1995-11-17	1998-04-14	Upjohn Co	Oxazolidinone antibacterial agent with tricyclic substituents.
DE19601265A1 (de)	1996-01-16	1997-07-17	Bayer Ag	2-Oxo- und 2-Thio-1,2-dihydrochinolinyl-oxazolidinone
DE19601264A1 (de)	1996-01-16	1997-07-17	Bayer Ag	Pyrido-annellierte Thienyl- und Furanyl-Oxazolidinone
DE19601627A1 (de) *	1996-01-18	1997-07-24	Bayer Ag	Heteroatomhaltige Cyclopentanopyridyl-Oxazolidinone
GB9601666D0 (en) *	1996-01-27	1996-03-27	Zeneca Ltd	Chemical compounds
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1989
- 1989-08-22 AT AT89308506T patent/ATE112773T1/de not_active IP Right Cessation
- 1989-08-22 AU AU41957/89A patent/AU617871B2/en not_active Ceased
- 1989-08-22 EP EP89308506A patent/EP0359418B1/en not_active Expired - Lifetime
- 1989-08-22 EP EP89909990A patent/EP0434714A1/en active Pending
- 1989-08-22 WO PCT/US1989/003548 patent/WO1990002744A1/en not_active Ceased
- 1989-08-22 DE DE68929303T patent/DE68929303T2/de not_active Expired - Fee Related
- 1989-08-22 ES ES94102762T patent/ES2157934T3/es not_active Expired - Lifetime
- 1989-08-22 DE DE68918792T patent/DE68918792T2/de not_active Expired - Fee Related
- 1989-08-22 EP EP94102762A patent/EP0609905B1/en not_active Expired - Lifetime
- 1989-08-22 AT AT94102762T patent/ATE201870T1/de not_active IP Right Cessation
- 1989-08-22 JP JP1509255A patent/JP2865211B2/ja not_active Expired - Fee Related
- 1989-08-28 CA CA000609594A patent/CA1335103C/en not_active Expired - Fee Related
- 1989-08-29 TW TW078106662A patent/TW219936B/zh active
1990
- 1990-05-15 KR KR1019900701012A patent/KR0138262B1/ko not_active Expired - Fee Related
1991
- 1991-03-13 DK DK199100455A patent/DK175696B1/da not_active IP Right Cessation
1998
- 1998-07-07 JP JP19194998A patent/JP3188418B2/ja not_active Expired - Fee Related
2001
- 2001-08-31 GR GR20010401350T patent/GR3036491T3/el not_active IP Right Cessation
2002
- 2002-06-06 LV LVP-02-104A patent/LV12888B/en unknown
2004
- 2004-08-18 DK DK200401246A patent/DK175940B1/da not_active IP Right Cessation

Also Published As

Publication number	Publication date
EP0609905A1 (en)	1994-08-10
JPH1180139A (ja)	1999-03-26
HK1002234A1 (en)	1998-08-07
EP0359418B1 (en)	1994-10-12
LV12888B (en)	2002-12-20
ATE201870T1 (de)	2001-06-15
DK45591D0 (da)	1991-03-13
JP3188418B2 (ja)	2001-07-16
EP0434714A1 (en)	1991-07-03
ES2157934T3 (es)	2001-09-01
KR0138262B1 (ko)	1998-05-15
ATE112773T1 (de)	1994-10-15
TW219936B (da)	1994-02-01
DK45591A (da)	1991-03-13
EP0359418A1 (en)	1990-03-21
AU617871B2 (en)	1991-12-05
KR900701780A (ko)	1990-12-04
DK175696B1 (da)	2005-01-24
DE68929303T2 (de)	2002-05-02
DE68918792T2 (de)	1995-03-30
AU4195789A (en)	1990-04-02
DK175940B1 (da)	2005-08-01
WO1990002744A1 (en)	1990-03-22
GR3036491T3 (en)	2001-11-30
DE68918792D1 (de)	1994-11-17
JP2865211B2 (ja)	1999-03-08
EP0609905B1 (en)	2001-06-06
CA1335103C (en)	1995-04-04
DE68929303D1 (de)	2001-07-12
JPH04500665A (ja)	1992-02-06

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2007-03-26	PBP	Patent lapsed	Ref document number: DK

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