UA75369C2 - Phenoxyphenyl alkane sulfonates, a method for the preparation thereof and medicament based thereon - Google Patents

Phenoxyphenyl alkane sulfonates, a method for the preparation thereof and medicament based thereon Download PDF

Info

Publication number: UA75369C2
Authority: UA; Ukraine
Prior art keywords: group; compounds; compounds according; trifluoromethyl; salts
Prior art date: 2000-09-26

Application number

UA2003043896A

Other languages

English (en)

Ukrainian (uk)

Original Assignee

Bayer Ag

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.)

2000-09-26

Filing date

2001-09-13

Publication date

2006-04-17

2001-09-13 Application filed by Bayer Ag filed Critical Bayer Ag

2006-04-17 Publication of UA75369C2 publication Critical patent/UA75369C2/uk

Links

238000000034 method Methods 0.000 title claims abstract description 47
-1 Phenoxyphenyl alkane sulfonates Chemical class 0.000 title claims abstract description 13
239000003814 drug Substances 0.000 title abstract description 5
238000002360 preparation method Methods 0.000 title description 4
125000000217 alkyl group Chemical group 0.000 claims abstract description 11
229910052731 fluorine Inorganic materials 0.000 claims abstract description 10
239000011737 fluorine Substances 0.000 claims abstract description 8
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 7
239000000460 chlorine Substances 0.000 claims abstract description 7
229910052801 chlorine Inorganic materials 0.000 claims abstract description 7
125000001153 fluoro group Chemical group F* 0.000 claims abstract description 3
150000001875 compounds Chemical class 0.000 claims description 65
238000006243 chemical reaction Methods 0.000 claims description 19
150000003839 salts Chemical class 0.000 claims description 13
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 11
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 11
125000004432 carbon atom Chemical group C* 0.000 claims description 10
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
125000004093 cyano group Chemical group *C#N 0.000 claims description 8
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 8
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 7
239000012442 inert solvent Substances 0.000 claims description 7
239000003054 catalyst Substances 0.000 claims description 6
125000005843 halogen group Chemical group 0.000 claims description 6
150000003868 ammonium compounds Chemical class 0.000 claims description 5
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
230000016507 interphase Effects 0.000 claims description 4
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
125000004430 oxygen atom Chemical group O* 0.000 claims description 4
238000012546 transfer Methods 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 3
229940126601 medicinal product Drugs 0.000 claims description 3
125000001424 substituent group Chemical group 0.000 claims description 3
125000001309 chloro group Chemical group Cl* 0.000 claims description 2
231100000252 nontoxic Toxicity 0.000 claims description 2
230000003000 nontoxic effect Effects 0.000 claims description 2
239000003085 diluting agent Substances 0.000 claims 1
238000012876 topography Methods 0.000 claims 1
208000002193 Pain Diseases 0.000 abstract description 16
238000011282 treatment Methods 0.000 abstract description 12
230000036407 pain Effects 0.000 abstract description 10
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 8
201000010099 disease Diseases 0.000 abstract description 7
230000004770 neurodegeneration Effects 0.000 abstract description 6
208000015122 neurodegenerative disease Diseases 0.000 abstract description 6
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
239000001301 oxygen Substances 0.000 abstract 1
229910052760 oxygen Inorganic materials 0.000 abstract 1
238000011321 prophylaxis Methods 0.000 abstract 1
150000003871 sulfonates Chemical class 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 78
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 54
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 26
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
239000000126 substance Substances 0.000 description 23
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
238000004128 high performance liquid chromatography Methods 0.000 description 20
239000000203 mixture Substances 0.000 description 20
239000000243 solution Substances 0.000 description 20
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 19
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 16
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
241000700159 Rattus Species 0.000 description 14
238000002474 experimental method Methods 0.000 description 13
229910052943 magnesium sulfate Inorganic materials 0.000 description 13
235000019341 magnesium sulphate Nutrition 0.000 description 13
230000014759 maintenance of location Effects 0.000 description 13
238000001819 mass spectrum Methods 0.000 description 13
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
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210000004027 cell Anatomy 0.000 description 12
239000012071 phase Substances 0.000 description 11
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 10
239000012074 organic phase Substances 0.000 description 10
239000002904 solvent Substances 0.000 description 10
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 9
239000000741 silica gel Substances 0.000 description 9
229910002027 silica gel Inorganic materials 0.000 description 9
241001465754 Metazoa Species 0.000 description 8
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 8
230000015572 biosynthetic process Effects 0.000 description 8
230000000694 effects Effects 0.000 description 8
229910000027 potassium carbonate Inorganic materials 0.000 description 8
238000003786 synthesis reaction Methods 0.000 description 8
238000005160 1H NMR spectroscopy Methods 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical class C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 7
229960003742 phenol Drugs 0.000 description 7
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
238000003756 stirring Methods 0.000 description 7
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
238000005481 NMR spectroscopy Methods 0.000 description 6
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
239000012300 argon atmosphere Substances 0.000 description 6
239000002585 base Substances 0.000 description 6
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 6
229910052796 boron Inorganic materials 0.000 description 6
239000002609 medium Substances 0.000 description 6
239000011780 sodium chloride Substances 0.000 description 6
208000011580 syndromic disease Diseases 0.000 description 6
238000012360 testing method Methods 0.000 description 6
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
230000001684 chronic effect Effects 0.000 description 5
230000003993 interaction Effects 0.000 description 5
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
ASHGTJPOSUFTGB-UHFFFAOYSA-N 3-methoxyphenol Chemical compound COC1=CC=CC(O)=C1 ASHGTJPOSUFTGB-UHFFFAOYSA-N 0.000 description 4
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102000009132 CB1 Cannabinoid Receptor Human genes 0.000 description 4
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CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
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OHCQJHSOBUTRHG-KGGHGJDLSA-N FORSKOLIN Chemical compound O=C([C@@]12O)C[C@](C)(C=C)O[C@]1(C)[C@@H](OC(=O)C)[C@@H](O)[C@@H]1[C@]2(C)[C@@H](O)CCC1(C)C OHCQJHSOBUTRHG-KGGHGJDLSA-N 0.000 description 4
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239000005089 Luciferase Substances 0.000 description 4
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VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 4
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HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 3
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SDHMEUVUMPVLQY-UHFFFAOYSA-N 1-(3-methoxyphenoxy)-3-methyl-2-nitrobenzene Chemical compound COC1=CC=CC(OC=2C(=C(C)C=CC=2)[N+]([O-])=O)=C1 SDHMEUVUMPVLQY-UHFFFAOYSA-N 0.000 description 2
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/63—Esters of sulfonic acids
- C07C309/64—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms
- C07C309/65—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms of a saturated carbon skeleton
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- A61P37/02—Immunomodulators
- A—HUMAN NECESSITIES
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- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/02—Sulfonic acids having sulfo groups bound to acyclic carbon atoms
- C07C309/20—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic unsaturated carbon skeleton
- C07C309/22—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic unsaturated carbon skeleton containing carboxyl groups bound to the carbon skeleton
- 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
- C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
- C07C311/02—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C311/08—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton 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
- 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
- C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
- C07C311/02—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C311/09—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton the carbon skeleton being further substituted by at least two halogen atoms

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Chemical & Material Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Neurosurgery (AREA)
Neurology (AREA)
Biomedical Technology (AREA)
Pain & Pain Management (AREA)
Pulmonology (AREA)
Immunology (AREA)
Ophthalmology & Optometry (AREA)
Hospice & Palliative Care (AREA)
Psychiatry (AREA)
Vascular Medicine (AREA)
Anesthesiology (AREA)
Otolaryngology (AREA)
Rheumatology (AREA)
Nutrition Science (AREA)
Urology & Nephrology (AREA)
Psychology (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

UA2003043896A 2000-09-26 2001-09-13 Phenoxyphenyl alkane sulfonates, a method for the preparation thereof and medicament based thereon UA75369C2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE10047486A DE10047486A1 (de)	2000-09-26	2000-09-26	Phenoxyphenyl Alkansulfonate
PCT/EP2001/010564 WO2002026702A1 (de)	2000-09-26	2001-09-13	Phenoxyphenyl alkansulfonate

Publications (1)

Publication Number	Publication Date
UA75369C2 true UA75369C2 (en)	2006-04-17

Family

ID=7657564

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
UA2003043896A UA75369C2 (en)	2000-09-26	2001-09-13	Phenoxyphenyl alkane sulfonates, a method for the preparation thereof and medicament based thereon

Country Status (34)

Country	Link
US (2)	US6756409B2 (ko)
EP (1)	EP1334086B1 (ko)
JP (1)	JP2004509946A (ko)
KR (1)	KR20030039372A (ko)
CN (1)	CN1476427A (ko)
AR (1)	AR033575A1 (ko)
AT (1)	ATE292621T1 (ko)
AU (2)	AU2054702A (ko)
BG (1)	BG107634A (ko)
BR (1)	BR0114182A (ko)
CA (1)	CA2423171A1 (ko)
DE (2)	DE10047486A1 (ko)
EE (1)	EE200300117A (ko)
ES (1)	ES2240543T3 (ko)
GT (1)	GT200100193A (ko)
HN (1)	HN2001000214A (ko)
HR (1)	HRP20030326A2 (ko)
HU (1)	HUP0302258A3 (ko)
IL (1)	IL154968A0 (ko)
MA (1)	MA26053A1 (ko)
MX (1)	MXPA03002546A (ko)
NO (1)	NO20031357L (ko)
NZ (1)	NZ524886A (ko)
PE (1)	PE20020408A1 (ko)
PL (1)	PL361015A1 (ko)
PT (1)	PT1334086E (ko)
RU (1)	RU2278853C2 (ko)
SI (1)	SI1334086T1 (ko)
SK (1)	SK3442003A3 (ko)
SV (1)	SV2002000639A (ko)
UA (1)	UA75369C2 (ko)
UY (1)	UY26945A1 (ko)
WO (1)	WO2002026702A1 (ko)
ZA (1)	ZA200302275B (ko)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2003061699A1 (fr) *	2001-12-27	2003-07-31	Japan Tobacco, Inc.	Remedes pour affections allergiques
EP2313093A4 (en)	2008-07-10	2012-03-28	Angion Biomedica Corp	METHOD AND COMPOSITIONS FOR LOW-MOLECULAR MODULATORS OF THE HEPATOCYTE GROWTH FACTOR (SCATTER FACTOR) ACTIVITY
US10709497B2 (en) *	2017-09-22	2020-07-14	Covidien Lp	Electrosurgical tissue sealing device with non-stick coating
MX2021012250A (es)	2019-04-11	2022-01-18	Angion Biomedica Corp	Formas solidas de (e)-3-[2-(2-tienil)vinil]-1h-pirazol.

Family Cites Families (14)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE216642C (ko) *
BE786644A (fr) *	1971-07-23	1973-01-24	Hoechst Ag	Derives d'acides phenoxy-4 phenoxy-alcane-carboxyliques leur preparation et les medicaments qui en contiennent
US3914418A (en) *	1971-09-02	1975-10-21	Merck & Co Inc	Methods of controlling liver fluke infections
GB8914660D0 (en) *	1989-06-26	1989-08-16	Fujisawa Pharmaceutical Co	Aniline derivatives,processes for production thereof and pharmaceutical compositions comprising the same
IN186119B (ko) *	1996-07-25	2001-06-23	Lg Chemical Ltd
US6090839A (en) *	1996-12-23	2000-07-18	Merck & Co., Inc.	Antidiabetic agents
NZ337331A (en) *	1997-02-21	2001-05-25	Bayer Ag	Aryl-sulfonamides and analogues thereof and their use in the treatment of neurodegenerative diseases
US5925654A (en) *	1997-03-12	1999-07-20	G.D. Searle & Co.	LTA4 , hydrolase inhibitors
DK1031556T3 (da) *	1997-10-20	2003-02-24	Taisho Pharmaceutical Co Ltd	2-phenoxyanilinderivater
US6231875B1 (en) *	1998-03-31	2001-05-15	Johnson & Johnson Consumer Companies, Inc.	Acidified composition for topical treatment of nail and skin conditions
NL1008795C2 (nl) *	1998-04-02	1999-10-05	Rene Werenfridus Lodewijk Vroo	Samenstelling voor het behandelen van hoeven en werkwijze voor het vervaardigen van de samenstelling.
HN1998000027A (es) *	1998-08-19	1999-06-02	Bayer Ip Gmbh	Arilsulfonamidas y analagos
DE19837627A1 (de) *	1998-08-19	2000-02-24	Bayer Ag	Neue Aminosäureester von Arylsulfonamiden und Analoga
US6242422B1 (en) *	1998-10-22	2001-06-05	Idun Pharmacueticals, Inc.	(Substituted)Acyl dipeptidyl inhibitors of the ice/ced-3 family of cysteine proteases

2000
- 2000-09-26 DE DE10047486A patent/DE10047486A1/de not_active Withdrawn
2001
- 2001-09-13 AU AU2054702A patent/AU2054702A/xx active Pending
- 2001-09-13 EP EP01985700A patent/EP1334086B1/de not_active Expired - Lifetime
- 2001-09-13 HU HU0302258A patent/HUP0302258A3/hu unknown
- 2001-09-13 MX MXPA03002546A patent/MXPA03002546A/es active IP Right Grant
- 2001-09-13 PL PL01361015A patent/PL361015A1/xx not_active Application Discontinuation
- 2001-09-13 CN CNA01819527XA patent/CN1476427A/zh active Pending
- 2001-09-13 UA UA2003043896A patent/UA75369C2/uk unknown
- 2001-09-13 SI SI200130356T patent/SI1334086T1/xx unknown
- 2001-09-13 NZ NZ524886A patent/NZ524886A/en unknown
- 2001-09-13 KR KR10-2003-7003902A patent/KR20030039372A/ko not_active Application Discontinuation
- 2001-09-13 DE DE50105857T patent/DE50105857D1/de not_active Expired - Fee Related
- 2001-09-13 SK SK344-2003A patent/SK3442003A3/sk unknown
- 2001-09-13 JP JP2002531088A patent/JP2004509946A/ja active Pending
- 2001-09-13 PT PT01985700T patent/PT1334086E/pt unknown
- 2001-09-13 RU RU2003112454/04A patent/RU2278853C2/ru not_active IP Right Cessation
- 2001-09-13 AT AT01985700T patent/ATE292621T1/de not_active IP Right Cessation
- 2001-09-13 IL IL15496801A patent/IL154968A0/xx unknown
- 2001-09-13 ES ES01985700T patent/ES2240543T3/es not_active Expired - Lifetime
- 2001-09-13 EE EEP200300117A patent/EE200300117A/xx unknown
- 2001-09-13 WO PCT/EP2001/010564 patent/WO2002026702A1/de active IP Right Grant
- 2001-09-13 CA CA002423171A patent/CA2423171A1/en not_active Abandoned
- 2001-09-13 AU AU2002220547A patent/AU2002220547B2/en not_active Ceased
- 2001-09-13 BR BR0114182-1A patent/BR0114182A/pt not_active IP Right Cessation
- 2001-09-24 AR ARP010104486A patent/AR033575A1/es not_active Application Discontinuation
- 2001-09-24 UY UY26945A patent/UY26945A1/es not_active Application Discontinuation
- 2001-09-24 GT GT200100193A patent/GT200100193A/es unknown
- 2001-09-25 HN HN2001000214A patent/HN2001000214A/es unknown
- 2001-09-25 SV SV2001000639A patent/SV2002000639A/es unknown
- 2001-09-25 PE PE2001000958A patent/PE20020408A1/es not_active Application Discontinuation
- 2001-09-26 US US09/965,708 patent/US6756409B2/en not_active Expired - Fee Related
2003
- 2003-03-13 BG BG107634A patent/BG107634A/bg unknown
- 2003-03-24 ZA ZA200302275A patent/ZA200302275B/en unknown
- 2003-03-25 MA MA27075A patent/MA26053A1/fr unknown
- 2003-03-25 NO NO20031357A patent/NO20031357L/no not_active Application Discontinuation
- 2003-04-25 HR HR20030326A patent/HRP20030326A2/hr not_active Application Discontinuation
2004
- 2004-05-20 US US10/850,507 patent/US20040214886A1/en not_active Abandoned

Also Published As

Publication number	Publication date
CN1476427A (zh)	2004-02-18
CA2423171A1 (en)	2003-03-21
HN2001000214A (es)	2001-10-25
ES2240543T3 (es)	2005-10-16
GT200100193A (es)	2002-06-04
HUP0302258A2 (hu)	2003-11-28
UY26945A1 (es)	2002-04-26
NZ524886A (en)	2005-09-30
AU2054702A (en)	2002-04-08
US20040214886A1 (en)	2004-10-28
KR20030039372A (ko)	2003-05-17
US6756409B2 (en)	2004-06-29
DE50105857D1 (de)	2005-05-12
EP1334086A1 (de)	2003-08-13
IL154968A0 (en)	2003-10-31
WO2002026702A1 (de)	2002-04-04
EE200300117A (et)	2005-04-15
BG107634A (bg)	2003-12-31
MXPA03002546A (es)	2004-04-20
EP1334086B1 (de)	2005-04-06
SI1334086T1 (en)	2005-10-31
SV2002000639A (es)	2002-10-24
SK3442003A3 (en)	2003-10-07
NO20031357D0 (no)	2003-03-25
PE20020408A1 (es)	2002-06-08
RU2278853C2 (ru)	2006-06-27
JP2004509946A (ja)	2004-04-02
HRP20030326A2 (en)	2005-02-28
HUP0302258A3 (en)	2006-02-28
NO20031357L (no)	2003-03-25
ATE292621T1 (de)	2005-04-15
BR0114182A (pt)	2003-07-29
DE10047486A1 (de)	2002-04-11
AR033575A1 (es)	2003-12-26
MA26053A1 (fr)	2004-04-01
PL361015A1 (en)	2004-09-20
AU2002220547B2 (en)	2006-11-02
PT1334086E (pt)	2005-08-31
US20030022934A1 (en)	2003-01-30
ZA200302275B (en)	2004-03-24

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