BG64529B1 - Заместени бета - дикетони и тяхното използване - Google Patents

Заместени бета - дикетони и тяхното използване Download PDF

Info

Publication number: BG64529B1
Authority: BG; Bulgaria
Prior art keywords: compound; pentanedione; halogen; methylene; methylsulfonyl
Prior art date: 1998-07-01

Application number

BG105080A

Other languages

Bulgarian (bg)

English (en)

Other versions

BG105080A (en

Inventor

Paeivi Aho

Reijo Backstroem

Anita Koponen

Inge-Britt Linden

Timo Lotta

Kari Loennberg

Aino Pippuri

Pentti Pohto

Original Assignee

Orion Corporation

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.)

1998-07-01

Filing date

2000-12-21

Publication date

2005-06-30

2000-12-21 Application filed by Orion Corporation filed Critical Orion Corporation

2001-09-28 Publication of BG105080A publication Critical patent/BG105080A/xx

2005-06-30 Publication of BG64529B1 publication Critical patent/BG64529B1/bg

Links

150000001875 compounds Chemical class 0.000 claims abstract description 44
208000006673 asthma Diseases 0.000 claims abstract description 21
229910052736 halogen Inorganic materials 0.000 claims abstract description 17
150000002367 halogens Chemical class 0.000 claims abstract description 17
238000011282 treatment Methods 0.000 claims abstract description 14
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 13
239000001257 hydrogen Substances 0.000 claims abstract description 13
201000010099 disease Diseases 0.000 claims abstract description 10
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 10
230000002265 prevention Effects 0.000 claims abstract description 7
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 6
208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims abstract description 5
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 4
239000000203 mixture Substances 0.000 claims description 26
GUBGYTABKSRVRQ-QKKXKWKRSA-N lactose group Chemical group OC1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@@H](O)[C@H](O2)CO)[C@H](O1)CO GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 claims description 11
239000008101 lactose Substances 0.000 claims description 10
125000001424 substituent group Chemical group 0.000 claims description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
239000003814 drug Substances 0.000 claims description 7
238000009472 formulation Methods 0.000 claims description 6
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 5
239000002245 particle Substances 0.000 claims description 5
ZUIYTTCOLRKEHO-UHFFFAOYSA-N 3-[(3-chloro-4-methylsulfonylphenyl)methylidene]pentane-2,4-dione Chemical compound CC(=O)C(C(C)=O)=CC1=CC=C(S(C)(=O)=O)C(Cl)=C1 ZUIYTTCOLRKEHO-UHFFFAOYSA-N 0.000 claims description 4
CAWYWWPWSAMGBV-UHFFFAOYSA-N 3-[(4-methylsulfonylphenyl)methylidene]pentane-2,4-dione Chemical compound CC(=O)C(C(C)=O)=CC1=CC=C(S(C)(=O)=O)C=C1 CAWYWWPWSAMGBV-UHFFFAOYSA-N 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
LITPXWODWSLZIB-UHFFFAOYSA-N 3-[(3,5-dichloro-4-methylsulfonylphenyl)methylidene]pentane-2,4-dione Chemical compound CC(=O)C(C(C)=O)=CC1=CC(Cl)=C(S(C)(=O)=O)C(Cl)=C1 LITPXWODWSLZIB-UHFFFAOYSA-N 0.000 claims description 3
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
229910052794 bromium Inorganic materials 0.000 claims description 3
229910052731 fluorine Inorganic materials 0.000 claims description 3
239000011737 fluorine Substances 0.000 claims description 3
QNVKHNRVDKUYQR-UHFFFAOYSA-N 3-[(4-chloro-3-methylsulfonylphenyl)methylidene]pentane-2,4-dione Chemical compound CC(=O)C(C(C)=O)=CC1=CC=C(Cl)C(S(C)(=O)=O)=C1 QNVKHNRVDKUYQR-UHFFFAOYSA-N 0.000 claims description 2
VQVXLUIYQIQWLH-UHFFFAOYSA-N 3-bromo-4-methylsulfonylbenzaldehyde Chemical compound CS(=O)(=O)C1=CC=C(C=O)C=C1Br VQVXLUIYQIQWLH-UHFFFAOYSA-N 0.000 claims description 2
ATFKDQOGYYWXIY-UHFFFAOYSA-N 3-fluoro-4-methylsulfonylbenzaldehyde Chemical compound CS(=O)(=O)C1=CC=C(C=O)C=C1F ATFKDQOGYYWXIY-UHFFFAOYSA-N 0.000 claims description 2
206010038687 Respiratory distress Diseases 0.000 claims description 2
230000001154 acute effect Effects 0.000 claims description 2
125000001246 bromo group Chemical group Br* 0.000 claims description 2
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229940126214 compound 3 Drugs 0.000 claims 5
MSLCOWHBLCTBOW-UHFFFAOYSA-N hex-5-ene-2,4-dione Chemical compound CC(=O)CC(=O)C=C MSLCOWHBLCTBOW-UHFFFAOYSA-N 0.000 claims 3
210000000056 organ Anatomy 0.000 claims 1
230000000241 respiratory effect Effects 0.000 claims 1
125000002345 steroid group Chemical group 0.000 claims 1
150000003431 steroids Chemical class 0.000 abstract description 6
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208000013616 Respiratory Distress Syndrome Diseases 0.000 abstract 2
201000000028 adult respiratory distress syndrome Diseases 0.000 abstract 2
JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical group COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 abstract 1
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YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
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235000015497 potassium bicarbonate Nutrition 0.000 description 6
229910000028 potassium bicarbonate Inorganic materials 0.000 description 6
239000011736 potassium bicarbonate Substances 0.000 description 6
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229910052938 sodium sulfate Inorganic materials 0.000 description 6
235000011152 sodium sulphate Nutrition 0.000 description 6
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 5
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IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
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FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
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210000002345 respiratory system Anatomy 0.000 description 4
CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 4
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PSVPUHBSBYJSMQ-UHFFFAOYSA-N 4-methylsulfonylbenzaldehyde Chemical compound CS(=O)(=O)C1=CC=C(C=O)C=C1 PSVPUHBSBYJSMQ-UHFFFAOYSA-N 0.000 description 3
241000700199 Cavia porcellus Species 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
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229960001334 corticosteroids Drugs 0.000 description 3
229940079593 drug Drugs 0.000 description 3
235000017557 sodium bicarbonate Nutrition 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical class [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 3
DFMBOVYGRYKHBQ-UHFFFAOYSA-N (4-chloro-3-methylsulfonylphenyl)methanol Chemical compound CS(=O)(=O)C1=CC(CO)=CC=C1Cl DFMBOVYGRYKHBQ-UHFFFAOYSA-N 0.000 description 2
QPCTVMOFLWABON-UHFFFAOYSA-N 2-(2,6-dichloro-4-ethoxycarbonylphenyl)sulfonylacetic acid Chemical compound CCOC(=O)C1=CC(Cl)=C(S(=O)(=O)CC(O)=O)C(Cl)=C1 QPCTVMOFLWABON-UHFFFAOYSA-N 0.000 description 2
MTLLWRVBRPGQBC-UHFFFAOYSA-N 2-(2-chloro-5-methoxycarbonylphenyl)sulfonylacetic acid Chemical compound COC(=O)C1=CC=C(Cl)C(S(=O)(=O)CC(O)=O)=C1 MTLLWRVBRPGQBC-UHFFFAOYSA-N 0.000 description 2
XHZGTAJSUWDJOE-UHFFFAOYSA-N 3-[(3-fluoro-4-methylsulfonylphenyl)methylidene]pentane-2,4-dione Chemical compound CC(=O)C(C(C)=O)=CC1=CC=C(S(C)(=O)=O)C(F)=C1 XHZGTAJSUWDJOE-UHFFFAOYSA-N 0.000 description 2
PRXIEGNPKOEMKI-UHFFFAOYSA-N 4-chloro-3-methylsulfonylbenzaldehyde Chemical compound CS(=O)(=O)C1=CC(C=O)=CC=C1Cl PRXIEGNPKOEMKI-UHFFFAOYSA-N 0.000 description 2
VOVIALXJUBGFJZ-KWVAZRHASA-N Budesonide Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1C[C@H]3OC(CCC)O[C@@]3(C(=O)CO)[C@@]1(C)C[C@@H]2O VOVIALXJUBGFJZ-KWVAZRHASA-N 0.000 description 2
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NLPRXDKTULOVCK-UHFFFAOYSA-N methyl 4-chloro-3-methylsulfonylbenzoate Chemical compound COC(=O)C1=CC=C(Cl)C(S(C)(=O)=O)=C1 NLPRXDKTULOVCK-UHFFFAOYSA-N 0.000 description 2
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230000005764 inhibitory process Effects 0.000 description 1
239000002085 irritant Substances 0.000 description 1
231100000021 irritant Toxicity 0.000 description 1
OWFXIOWLTKNBAP-UHFFFAOYSA-N isoamyl nitrite Chemical compound CC(C)CCON=O OWFXIOWLTKNBAP-UHFFFAOYSA-N 0.000 description 1
238000011866 long-term treatment Methods 0.000 description 1
230000000527 lymphocytic effect Effects 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
229960000485 methotrexate Drugs 0.000 description 1
LOCJPOYKBUUVKU-UHFFFAOYSA-N methyl 3-amino-4-chlorobenzoate Chemical compound COC(=O)C1=CC=C(Cl)C(N)=C1 LOCJPOYKBUUVKU-UHFFFAOYSA-N 0.000 description 1
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
239000002547 new drug Substances 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
230000037361 pathway Effects 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
230000002685 pulmonary effect Effects 0.000 description 1
238000007873 sieving Methods 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
230000000087 stabilizing effect Effects 0.000 description 1
125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
230000001629 suppression Effects 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
230000009885 systemic effect Effects 0.000 description 1
229940037128 systemic glucocorticoids Drugs 0.000 description 1
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 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
210000003462 vein Anatomy 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/24—Sulfones; Sulfoxides having sulfone or sulfoxide groups and doubly-bound oxygen atoms bound to the same carbon skeleton
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/02—Nasal agents, e.g. decongestants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics

Landscapes

Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Pulmonology (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Otolaryngology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Steroid Compounds (AREA)
Paper (AREA)
Electrophonic Musical Instruments (AREA)
Stringed Musical Instruments (AREA)
Detergent Compositions (AREA)
Materials For Medical Uses (AREA)
Tents Or Canopies (AREA)

BG105080A 1998-07-01 2000-12-21 Заместени бета - дикетони и тяхното използване BG64529B1 (bg)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FI981521A FI981521A0 (fi)	1998-07-01	1998-07-01	Substituoidut beta-diketonit ja niiden käyttö
US09/346,397 US6201027B1 (en)	1998-07-01	1999-07-01	Substituted β diketones and their use

Publications (2)

Publication Number	Publication Date
BG105080A BG105080A (en)	2001-09-28
BG64529B1 true BG64529B1 (bg)	2005-06-30

Family

ID=26160612

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
BG105080A BG64529B1 (bg)	1998-07-01	2000-12-21	Заместени бета - дикетони и тяхното използване

Country Status (28)

Country	Link
US (1)	US6201027B1 (de)
EP (1)	EP1091933B1 (de)
JP (1)	JP2002519407A (de)
CN (1)	CN1258526C (de)
AT (1)	ATE255088T1 (de)
AU (1)	AU745338B2 (de)
BG (1)	BG64529B1 (de)
BR (1)	BR9911626A (de)
CA (1)	CA2336300A1 (de)
CZ (1)	CZ296378B6 (de)
DE (1)	DE69913145T2 (de)
DK (1)	DK1091933T3 (de)
EA (1)	EA002693B1 (de)
EE (1)	EE200000789A (de)
ES (1)	ES2212590T3 (de)
FI (1)	FI981521A0 (de)
HR (1)	HRP20000911B1 (de)
HU (1)	HUP0103006A3 (de)
IL (1)	IL139963A0 (de)
IS (1)	IS2037B (de)
NO (1)	NO20006665L (de)
PL (1)	PL195216B1 (de)
PT (1)	PT1091933E (de)
SI (1)	SI1091933T1 (de)
SK (1)	SK284934B6 (de)
TR (1)	TR200003773T2 (de)
WO (1)	WO2000001667A1 (de)
ZA (1)	ZA200006961B (de)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AU2519601A (en) *	1999-12-30	2001-07-16	Orion Corporation	A process for preparing 3-((3-chloro-4-(methylsulfonyl)-phenyl)methylene)-2,4- pentanedione
FI20011386A0 (fi) *	2001-06-28	2001-06-28	Orion Corp	Inhalaatiopartikkeleja
FI20020126A0 (fi) *	2002-01-23	2002-01-23	Orion Corp	Koostumuksia pulmonaaliseen antoon
WO2013008002A1 (en) *	2011-07-12	2013-01-17	Astrazeneca Ab	N- (6- ( (2r,3s) -3,4-dihydroxybutan-2-yloxy) -2- (4 - fluorobenzylthio) pyrimidin- 4 - yl) -3- methylazetidine- 1 - sulfonamide as chemokine receptor modulator

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS6230767A (ja)	1985-08-01	1987-02-09	Taisho Pharmaceut Co Ltd	イミダゾ−ル誘導体
US4741769A (en)	1986-06-09	1988-05-03	Stauffer Chemical Company	Certain 1-phenyl-3-alkyl-1,3-propanediones
YU213587A (en)	1986-11-28	1989-06-30	Orion Yhtymae Oy	Process for obtaining new pharmacologic active cateholic derivatives
MTP1031B (en)	1987-12-24	1990-10-04	Orion Yhtymae Oy	New use of cathecol-o-methyl transferase (comt) inhibitors and their physiologically acceptable salts and esters
GB9002337D0 (en) *	1990-02-02	1990-04-04	Orion Yhtymae Oy	Compounds useful in treating inflammatory bowel disease
US5185370A (en) *	1988-09-01	1993-02-09	Orion-Yhtyma Oy	Substituted β-diketones and their use
IL91382A (en)	1988-09-01	1995-06-29	Orion Yhtymae Oy	Alkenyl or arylmethylene-substituted beta-diketones their preparation and pharmaceutical compositions containing them
US5804532A (en) *	1991-01-25	1998-09-08	Rhone-Poulenc Agriculture Limited	Herbicidal 2-cyano-1,3-diones

1998
- 1998-07-01 FI FI981521A patent/FI981521A0/fi unknown
1999
- 1999-06-30 DK DK99934722T patent/DK1091933T3/da active
- 1999-06-30 PL PL99344856A patent/PL195216B1/pl not_active IP Right Cessation
- 1999-06-30 EA EA200100094A patent/EA002693B1/ru unknown
- 1999-06-30 CN CNB998080535A patent/CN1258526C/zh not_active Expired - Fee Related
- 1999-06-30 HU HU0103006A patent/HUP0103006A3/hu unknown
- 1999-06-30 HR HR20000911A patent/HRP20000911B1/xx not_active IP Right Cessation
- 1999-06-30 SI SI9930503T patent/SI1091933T1/xx unknown
- 1999-06-30 TR TR2000/03773T patent/TR200003773T2/xx unknown
- 1999-06-30 CZ CZ20004774A patent/CZ296378B6/cs not_active IP Right Cessation
- 1999-06-30 EP EP99934722A patent/EP1091933B1/de not_active Expired - Lifetime
- 1999-06-30 WO PCT/FI1999/000575 patent/WO2000001667A1/en not_active Ceased
- 1999-06-30 EE EEP200000789A patent/EE200000789A/xx unknown
- 1999-06-30 AT AT99934722T patent/ATE255088T1/de not_active IP Right Cessation
- 1999-06-30 BR BR9911626-0A patent/BR9911626A/pt not_active Application Discontinuation
- 1999-06-30 ES ES99934722T patent/ES2212590T3/es not_active Expired - Lifetime
- 1999-06-30 AU AU50392/99A patent/AU745338B2/en not_active Ceased
- 1999-06-30 JP JP2000558072A patent/JP2002519407A/ja active Pending
- 1999-06-30 CA CA002336300A patent/CA2336300A1/en not_active Abandoned
- 1999-06-30 IL IL13996399A patent/IL139963A0/xx not_active IP Right Cessation
- 1999-06-30 PT PT99934722T patent/PT1091933E/pt unknown
- 1999-06-30 DE DE69913145T patent/DE69913145T2/de not_active Expired - Fee Related
- 1999-06-30 SK SK1985-2000A patent/SK284934B6/sk unknown
- 1999-07-01 US US09/346,397 patent/US6201027B1/en not_active Expired - Fee Related
2000
- 2000-11-27 ZA ZA200006961A patent/ZA200006961B/en unknown
- 2000-12-21 BG BG105080A patent/BG64529B1/bg unknown
- 2000-12-27 NO NO20006665A patent/NO20006665L/no not_active Application Discontinuation
- 2000-12-27 IS IS5793A patent/IS2037B/is unknown

Also Published As

Publication number	Publication date
HRP20000911B1 (en)	2006-07-31
AU745338B2 (en)	2002-03-21
FI981521A0 (fi)	1998-07-01
DK1091933T3 (da)	2004-03-22
ZA200006961B (en)	2001-08-10
HUP0103006A3 (en)	2002-12-28
HK1036054A1 (en)	2001-12-21
PT1091933E (pt)	2004-04-30
EE200000789A (et)	2002-06-17
SK19852000A3 (sk)	2002-05-09
DE69913145D1 (de)	2004-01-08
EA200100094A1 (ru)	2001-06-25
NO20006665D0 (no)	2000-12-27
IS5793A (is)	2000-12-27
US6201027B1 (en)	2001-03-13
BR9911626A (pt)	2001-03-20
PL195216B1 (pl)	2007-08-31
AU5039299A (en)	2000-01-24
CN1307559A (zh)	2001-08-08
CN1258526C (zh)	2006-06-07
EA002693B1 (ru)	2002-08-29
EP1091933B1 (de)	2003-11-26
HUP0103006A2 (hu)	2002-03-28
SI1091933T1 (en)	2004-04-30
DE69913145T2 (de)	2004-09-02
CZ296378B6 (cs)	2006-03-15
BG105080A (en)	2001-09-28
EP1091933A1 (de)	2001-04-18
SK284934B6 (sk)	2006-02-02
HRP20000911A2 (en)	2001-12-31
IS2037B (is)	2005-08-15
ES2212590T3 (es)	2004-07-16
NO20006665L (no)	2000-12-27
PL344856A1 (en)	2001-11-19
CA2336300A1 (en)	2000-01-13
JP2002519407A (ja)	2002-07-02
TR200003773T2 (tr)	2001-06-21
CZ20004774A3 (en)	2001-06-13
ATE255088T1 (de)	2003-12-15
WO2000001667A1 (en)	2000-01-13
IL139963A0 (en)	2002-02-10

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DE60131750T2 (de)	2008-11-06	6.alpha.,9.alpha.-difluoro-17.alpha.-(2-furanylcarboxyl)oxy-11.beta.-hydroxy-16.alpha.-methyl-3-oxo-androst-1,4-diene-17-carbothioic acid s-fluoromethyl ester als entzündungshemmendes arzneimittel
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WO2005063777A1 (en)	2005-07-14	Benzylphosphate and substituted benzylphosphate prodrugs for the treatment of pulmonary inflammation
CZ175496A3 (en)	1996-11-13	6-(2-imidazolinylamino)quinoxaline compounds usable as alpha-2 adrenoceptor agonists
JP2012528140A (ja)	2012-11-12	新規なグルココルチコイド受容体アゴニスト
EP0038343B1 (de)	1984-12-27	Substituierte oxocarbonsäuren, verfahren zu ihrer herstellung, ihre verwendung und sie enthaltende arzneimittel
WO1984004521A1 (fr)	1984-11-22	Pyridazinones, leur preparation et leur utilisation, ainsi que des medicaments contenant des pyridazinones
EP1091933B1 (de)	2003-11-26	Substituierte beta-diketone und ihre anwendung
JP2005527518A (ja)	2005-09-15	新規なカルコン（ｃｈａｌｃｏｎｅ）誘導体とその使用
CN115974832B (zh)	2023-08-01	一种含有二硫键的n-乙酰- l-半胱氨酸衍生物及其制备方法与应用
HK1036054B (en)	2004-07-02	Substituted beta-diketones and their use
UA64805C2 (uk)	2004-03-15	ЗАМІЩЕНІ <font face="Symbol">b</font>-ДИКЕТОНИ І ЇХ ЗАСТОСУВАННЯ ДЛЯ ЛІКУВАННЯ РЕСПІРАТОРНИХ ЗАХВОРЮВАНЬ
WO2018076568A1 (zh)	2018-05-03	环菠萝烷四环三萜类化合物、其制备方法及其用途
JP2003321368A (ja)	2003-11-11	Ｎ，ｎ’−ジ置換ウレアまたはチオウレア化合物含有医薬
FR2508907A1 (fr)	1983-01-07	Esters d'hydroxybenzenes substitues de 2-thenoylmercaptopropionylglycine utiles notamment comme mucolytiques, procede pour leur preparation et compositions pharmaceutiques les contenant
WO1984004522A1 (fr)	1984-11-22	Pyridazinone, son procede de preparation et son utilisation, medicaments contenant de la pyridazinone
HU181739B (en)	1983-11-28	Process for preparing new digoxin derivatives
JP2000515118A (ja)	2000-11-14	置換６ｈ―１，３，４―チアジアジン―２―アミン、麻酔剤、心臓血管剤および代謝低下剤としてのそれらの使用、およびそれらを含有する医薬組成物
JPS59175485A (ja)	1984-10-04	４，５−ジヒドロキシ−１，３−ジチオラン−２−イリデンマロン酸誘導体の製法
JPH11502519A (ja)	1999-03-02	新規な１−エチル−１，２−ジヒドロ−２−オキソ−３−メチルアミノキノキサリン誘導体、それらの医薬品としての使用、およびそれらを含む医薬組成物