CS119492A3 - N-hydroxy-n-/3-/2-/halophenylthio/phenyl/prop-2-enyl/urea and apharmaceutical composition comprising thereof - Google Patents

N-hydroxy-n-/3-/2-/halophenylthio/phenyl/prop-2-enyl/urea and apharmaceutical composition comprising thereof Download PDF

Info

Publication number: CS119492A3
Authority: CS; Czechoslovakia
Prior art keywords: prop; hydroxy; enyl; phenyl; urea
Prior art date: 1991-04-23

Application number

CS921194A

Other languages

Czech (cs)

English (en)

Inventor

Gary Alan Hite

Edward David Mihelich

David Wells Snyder

Tulio Suarez

Original Assignee

Lilly Co Eli

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.)

1991-04-23

Filing date

1992-04-17

Publication date

1992-12-16

1992-04-17 Application filed by Lilly Co Eli filed Critical Lilly Co Eli

1992-12-16 Publication of CS119492A3 publication Critical patent/CS119492A3/cs

Links

239000004202 carbamide Substances 0.000 title claims description 26
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 title claims description 13
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 title claims description 12
239000000203 mixture Substances 0.000 title description 33
150000001875 compounds Chemical class 0.000 claims description 66
-1 4-fluorophenylthio Chemical group 0.000 claims description 59
239000004480 active ingredient Substances 0.000 claims description 22
238000002360 preparation method Methods 0.000 claims description 22
239000008194 pharmaceutical composition Substances 0.000 claims description 19
150000003839 salts Chemical class 0.000 claims description 16
238000000034 method Methods 0.000 claims description 15
108010093579 Arachidonate 5-lipoxygenase Proteins 0.000 claims description 13
230000008569 process Effects 0.000 claims description 11
125000004432 carbon atom Chemical group C* 0.000 claims description 9
230000002401 inhibitory effect Effects 0.000 claims description 8
208000022559 Inflammatory bowel disease Diseases 0.000 claims description 7
238000011282 treatment Methods 0.000 claims description 7
208000026935 allergic disease Diseases 0.000 claims description 6
206010003246 arthritis Diseases 0.000 claims description 6
208000006673 asthma Diseases 0.000 claims description 6
239000000546 pharmaceutical excipient Substances 0.000 claims description 6
206010010904 Convulsion Diseases 0.000 claims description 5
239000000010 aprotic solvent Substances 0.000 claims description 5
239000003153 chemical reaction reagent Substances 0.000 claims description 5
229910052801 chlorine Inorganic materials 0.000 claims description 5
239000003085 diluting agent Substances 0.000 claims description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
229910052744 lithium Inorganic materials 0.000 claims description 5
206010001052 Acute respiratory distress syndrome Diseases 0.000 claims description 4
201000004681 Psoriasis Diseases 0.000 claims description 4
125000001309 chloro group Chemical group Cl* 0.000 claims description 4
229910052731 fluorine Inorganic materials 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 4
208000028867 ischemia Diseases 0.000 claims description 4
208000013616 Respiratory Distress Syndrome Diseases 0.000 claims description 3
239000003795 chemical substances by application Substances 0.000 claims description 3
239000003937 drug carrier Substances 0.000 claims description 3
239000011737 fluorine Substances 0.000 claims description 3
OZOYGQPOXFKXHD-UHFFFAOYSA-N 2-(2-fluorophenyl)-4,4-dimethyl-5h-1,3-oxazole Chemical compound CC1(C)COC(C=2C(=CC=CC=2)F)=N1 OZOYGQPOXFKXHD-UHFFFAOYSA-N 0.000 claims description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
206010020751 Hypersensitivity Diseases 0.000 claims description 2
230000007815 allergy Effects 0.000 claims description 2
125000001153 fluoro group Chemical group F* 0.000 claims description 2
239000003586 protic polar solvent Substances 0.000 claims description 2
102000001381 Arachidonate 5-Lipoxygenase Human genes 0.000 claims 2
UGNSMKDDFAUGFT-UHFFFAOYSA-N 4,4-dimethyl-2-phenyl-5h-1,3-oxazole Chemical compound CC1(C)COC(C=2C=CC=CC=2)=N1 UGNSMKDDFAUGFT-UHFFFAOYSA-N 0.000 claims 1
YIBBMDDEXKBIAM-UHFFFAOYSA-M potassium;pentoxymethanedithioate Chemical compound [K+].CCCCCOC([S-])=S YIBBMDDEXKBIAM-UHFFFAOYSA-M 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 77
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 38
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 37
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 33
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239000011541 reaction mixture Substances 0.000 description 29
239000000243 solution Substances 0.000 description 27
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CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 18
238000006243 chemical reaction Methods 0.000 description 18
239000002904 solvent Substances 0.000 description 17
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
239000012267 brine Substances 0.000 description 15
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 15
102100022364 Polyunsaturated fatty acid 5-lipoxygenase Human genes 0.000 description 14
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
239000000284 extract Substances 0.000 description 13
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239000012442 inert solvent Substances 0.000 description 11
238000012360 testing method Methods 0.000 description 11
239000002253 acid Substances 0.000 description 10
YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
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150000002617 leukotrienes Chemical class 0.000 description 8
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238000000921 elemental analysis Methods 0.000 description 7
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YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
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239000012043 crude product Substances 0.000 description 6
230000005764 inhibitory process Effects 0.000 description 6
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NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 5
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 5
229920000168 Microcrystalline cellulose Polymers 0.000 description 5
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239000000460 chlorine Chemical group 0.000 description 5
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 5
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230000004044 response Effects 0.000 description 5
235000015424 sodium Nutrition 0.000 description 5
239000012453 solvate Substances 0.000 description 5
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CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
241000700198 Cavia Species 0.000 description 4
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MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 4
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AIXAANGOTKPUOY-UHFFFAOYSA-N carbachol Chemical compound [Cl-].C[N+](C)(C)CCOC(N)=O AIXAANGOTKPUOY-UHFFFAOYSA-N 0.000 description 4
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150000007522 mineralic acids Chemical class 0.000 description 4
239000011734 sodium Substances 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
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GQUCMPNYHIRLTH-UHFFFAOYSA-N 1-(2-bromophenyl)prop-2-en-1-ol Chemical compound C=CC(O)C1=CC=CC=C1Br GQUCMPNYHIRLTH-UHFFFAOYSA-N 0.000 description 3
IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 description 3
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239000000556 agonist Substances 0.000 description 3
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239000003054 catalyst Substances 0.000 description 3
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239000001257 hydrogen Substances 0.000 description 3
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239000000543 intermediate Substances 0.000 description 3
238000007912 intraperitoneal administration Methods 0.000 description 3
NIZHERJWXFHGGU-UHFFFAOYSA-N isocyanato(trimethyl)silane Chemical compound C[Si](C)(C)N=C=O NIZHERJWXFHGGU-UHFFFAOYSA-N 0.000 description 3
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NLXXVSKHVGDQAT-UHFFFAOYSA-N o-(oxan-2-yl)hydroxylamine Chemical compound NOC1CCCCO1 NLXXVSKHVGDQAT-UHFFFAOYSA-N 0.000 description 3
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ONCRBHOAKAAJAD-UHFFFAOYSA-N 2-[1-(2-bromophenyl)prop-2-enoxy]oxane Chemical compound BrC1=CC=CC=C1C(C=C)OC1OCCCC1 ONCRBHOAKAAJAD-UHFFFAOYSA-N 0.000 description 2
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BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
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125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 1
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239000005720 sucrose Substances 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
229910021653 sulphate ion Inorganic materials 0.000 description 1
238000001356 surgical procedure Methods 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Substances SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
229930195735 unsaturated hydrocarbon Chemical group 0.000 description 1
230000035899 viability Effects 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
229940071104 xylenesulfonate Drugs 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/39—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton at least one of the nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom
- C07C323/43—Y being a hetero atom
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/46—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having at least one of the nitrogen atoms, not being part of nitro or nitroso groups, further bound to other hetero atoms
- C07C323/47—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having at least one of the nitrogen atoms, not being part of nitro or nitroso groups, further bound to other hetero atoms to oxygen atoms
- 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
- A61P17/00—Drugs for dermatological disorders
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- 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
- A61P37/08—Antiallergic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- 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

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Engineering & Computer Science (AREA)
Pharmacology & Pharmacy (AREA)
Veterinary Medicine (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Pulmonology (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Immunology (AREA)
Urology & Nephrology (AREA)
Vascular Medicine (AREA)
Pain & Pain Management (AREA)
Rheumatology (AREA)
Dermatology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

CS921194A 1991-04-23 1992-04-17 N-hydroxy-n-/3-/2-/halophenylthio/phenyl/prop-2-enyl/urea and apharmaceutical composition comprising thereof CS119492A3 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US69020491A	1991-04-23	1991-04-23

Publications (1)

Publication Number	Publication Date
CS119492A3 true CS119492A3 (en)	1992-12-16

Family

ID=24771539

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS921194A CS119492A3 (en)	1991-04-23	1992-04-17	N-hydroxy-n-/3-/2-/halophenylthio/phenyl/prop-2-enyl/urea and apharmaceutical composition comprising thereof

Country Status (17)

Country	Link
US (1)	US5283361A (de)
EP (1)	EP0510948A1 (de)
JP (1)	JPH05117227A (de)
KR (1)	KR920019740A (de)
CN (1)	CN1066062A (de)
AU (1)	AU638641B2 (de)
BR (1)	BR9201452A (de)
CA (1)	CA2066508A1 (de)
CS (1)	CS119492A3 (de)
FI (1)	FI921786A7 (de)
HU (1)	HUT62557A (de)
IE (1)	IE921279A1 (de)
IL (1)	IL101625A0 (de)
MX (1)	MX9201808A (de)
NO (1)	NO921530L (de)
TW (1)	TW199141B (de)
ZA (1)	ZA922873B (de)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPH05294921A (ja) *	1992-04-17	1993-11-09	Pfizer Pharmaceut Co Ltd	新規なフェニル置換シクロアルキル尿素誘導体および組成物
CA2178833A1 (en) *	1993-12-22	1995-06-29	Akiyoshi Kawai	Phenylthiophenyl cycloalkenyl hydroxyureas as lipoxygenase inhibitors
US5891460A (en) *	1995-06-07	1999-04-06	University Of Southern California University Park Campus	Method for reducing or preventing post-surgical adhesion formation using ketotifen and analogs thereof
JP3929140B2 (ja)	1997-10-27	2007-06-13	日本碍子株式会社	耐蝕性部材およびその製造方法
NZ720946A (en)	2009-04-29	2017-09-29	Amarin Pharmaceuticals Ie Ltd	Pharmaceutical compositions comprising epa and a cardiovascular agent and methods of using the same
CN102659637B (zh) *	2012-05-21	2014-05-14	上海大学	一种制备双羟基脲的新方法

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NZ215487A (en) *	1985-03-16	1990-01-29	Wellcome Found	Aryl derivatives, pharmaceutical compositions thereof and preservation of cut flowers
US5185363A (en) *	1986-04-25	1993-02-09	Abbott Laboratories	Urea based lipoxygenase inhibiting compounds
GB8619593D0 (en) *	1986-08-12	1986-09-24	Roussel Lab Ltd	Chemical compounds
EP0279263B1 (de) *	1987-02-10	1993-08-04	Abbott Laboratories	Indol, Benzofuran, Benzothiophen enthaltende, Lipoxygenase hemmende Verbindungen
NZ232350A (en) *	1989-02-03	1992-04-28	Wellcome Found	N-(1-methyl-3-((halophenoxy)phenyl)prop-2-en-1-yl)-n-hydroxyurea derivatives and pharmaceutical compositions
WO1990012008A1 (en) *	1989-03-30	1990-10-18	Abbott Laboratories	Urea based lipoxygenase inhibiting compounds
US5130485A (en) *	1991-04-23	1992-07-14	Eli Lilly And Company	N-hydroxy-N-(3-(2-substituted phenyl)prop-2-enyl)ureas and thioureas useful as 5-lipoxygenase inhibiting agents

1992
- 1992-04-08 US US07/865,005 patent/US5283361A/en not_active Expired - Fee Related
- 1992-04-16 IL IL101625A patent/IL101625A0/xx unknown
- 1992-04-17 TW TW081103011A patent/TW199141B/zh active
- 1992-04-17 CS CS921194A patent/CS119492A3/cs unknown
- 1992-04-20 MX MX9201808A patent/MX9201808A/es unknown
- 1992-04-20 BR BR929201452A patent/BR9201452A/pt not_active Application Discontinuation
- 1992-04-21 KR KR1019920006703A patent/KR920019740A/ko not_active Withdrawn
- 1992-04-21 CA CA002066508A patent/CA2066508A1/en not_active Abandoned
- 1992-04-21 AU AU15009/92A patent/AU638641B2/en not_active Ceased
- 1992-04-21 ZA ZA922873A patent/ZA922873B/xx unknown
- 1992-04-21 NO NO92921530A patent/NO921530L/no unknown
- 1992-04-22 IE IE127992A patent/IE921279A1/en not_active Application Discontinuation
- 1992-04-22 HU HU9201343A patent/HUT62557A/hu unknown
- 1992-04-22 FI FI921786A patent/FI921786A7/fi not_active Application Discontinuation
- 1992-04-22 CN CN92102892A patent/CN1066062A/zh active Pending
- 1992-04-22 EP EP92303615A patent/EP0510948A1/de not_active Ceased
- 1992-04-22 JP JP4102841A patent/JPH05117227A/ja not_active Withdrawn

Also Published As

Publication number	Publication date
CA2066508A1 (en)	1992-10-24
NO921530L (no)	1992-10-26
US5283361A (en)	1994-02-01
FI921786A0 (fi)	1992-04-22
KR920019740A (ko)	1992-11-19
IL101625A0 (en)	1992-12-30
NO921530D0 (no)	1992-04-21
IE921279A1 (en)	1992-11-04
JPH05117227A (ja)	1993-05-14
BR9201452A (pt)	1992-12-01
MX9201808A (es)	1994-05-31
ZA922873B (en)	1993-10-21
TW199141B (de)	1993-02-01
CN1066062A (zh)	1992-11-11
AU1500992A (en)	1992-10-29
HUT62557A (en)	1993-05-28
FI921786A7 (fi)	1992-10-24
HU9201343D0 (en)	1992-07-28
AU638641B2 (en)	1993-07-01
EP0510948A1 (de)	1992-10-28

Publication	Publication Date	Title
WO2003014064A1 (en)	2003-02-20	Naphthylurea and naphthylacetamide derivatives as vanilloid receptor 1 (vr1) antagonists
JPH08508741A (ja)	1996-09-17	虚血および関連疾患の処置におけるヘテロ環誘導体類
JPH0637443B2 (ja)	1994-05-18	１−フェニル−３−ナフタレニルオキシプロパンアミン類
US6107328A (en)	2000-08-22	Use of 5HT1B receptor antagonist for the treatment of vascular disease
JPS6051138A (ja)	1985-03-22	ロイコトリエン拮抗物質
US4341793A (en)	1982-07-27	Secondary amines and their use in pharmaceutical compositions
EP0091795A1 (de)	1983-10-19	Olefinische Benzimidazole
IE58352B1 (en)	1993-09-08	Benzocycloalkane derivatives
US4749701A (en)	1988-06-07	Aminostyryl compound, leukotriene antagonistic composition containing the same as effective ingredients and method of antagonizing SRS by employing the same
CZ159893A3 (en)	1994-03-16	Derivatives of 1,4-benzodioxan, process of their preparation and pharmaceutical preparations in which they are comprised
US5283361A (en)	1994-02-01	N-hydroxy-N-[3-[2-(halophenylthio)phenyl]prop-2-enyl]ureas as lipoxygenase inhibitors
US4255575A (en)	1981-03-10	2-Hydroxy-5-(1-hydroxy-2-piperazinylethyl)-benzoic acid derivatives
AU647911B2 (en)	1994-03-31	N-hydroxy-N-{3-(2-substituted phenyl)prop-2-enyl} ureas and thioureas, compositions thereof and methods of use
US4876282A (en)	1989-10-24	1-Phenylalkylamines as selective serotonin uptake inhibitors
US4764521A (en)	1988-08-16	Leukotriene antagonists and a method of use there as
US4562199A (en)	1985-12-31	Imidazole derivatives, compositions and use
US5354769A (en)	1994-10-11	Benzofuranylimidazole derivatives and therapeutical compositions containing the same
SU1600627A3 (ru)	1990-10-15	Способ получени 2-замещенных 1-нафтолов
EP0106060B1 (de)	1988-09-28	Imidazol-Derivate und Salze, deren Herstellung und pharmazeutische Zusammenstellungen
CZ453699A3 (cs)	2000-07-12	Způsob a meziprodukty pro přípravu inhibitorů 5-lipoxygenasy
EP0034752B1 (de)	1983-06-08	Phenoxyalkanderivat und Verfahren zu dessen Herstellung
WO2016023039A1 (en)	2016-02-11	Bisamidinium-based inhibitors for the treatment of myotonic dystrophy
JP3269658B2 (ja)	2002-03-25	フェノール誘導体
GB2126218A (en)	1984-03-21	Imidazoles
JPS63290852A (ja)	1988-11-28	化合物