NO313831B1 - Diaryl-5,6-kondenserte, heterosykliske syrer som leukotrienantagonister - Google Patents

Diaryl-5,6-kondenserte, heterosykliske syrer som leukotrienantagonister Download PDF

Info

Publication number: NO313831B1
Authority: NO; Norway
Prior art keywords: mmol; methyl; phenyl; added; carbon atoms
Prior art date: 1992-12-22

Application number

NO19952495A

Other languages

English (en)

Norwegian (no)

Other versions

NO952495L (no

NO952495D0 (no

Inventor

Robert N Young

Marc Labelle

Yves Leblanc

Yi Bin Xiang

Cheuk L Lau

Claude Dufresne

Yves Gareau

Original Assignee

Merck Frosst Canada Inc

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.)

1992-12-22

Filing date

1995-06-21

Publication date

2002-12-09

1995-06-21 Application filed by Merck Frosst Canada Inc filed Critical Merck Frosst Canada Inc

1995-06-21 Publication of NO952495D0 publication Critical patent/NO952495D0/no

1995-08-22 Publication of NO952495L publication Critical patent/NO952495L/no

2002-12-09 Publication of NO313831B1 publication Critical patent/NO313831B1/no

Links

239000003199 leukotriene receptor blocking agent Substances 0.000 title claims description 9
125000000623 heterocyclic group Chemical group 0.000 title description 4
150000001875 compounds Chemical class 0.000 claims abstract description 137
150000002617 leukotrienes Chemical class 0.000 claims abstract description 16
239000005557 antagonist Substances 0.000 claims abstract description 3
-1 heterocyclic radical Chemical class 0.000 claims description 61
150000003839 salts Chemical class 0.000 claims description 28
125000004432 carbon atom Chemical group C* 0.000 claims description 24
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 23
229920006395 saturated elastomer Polymers 0.000 claims description 19
239000004480 active ingredient Substances 0.000 claims description 18
239000000825 pharmaceutical preparation Substances 0.000 claims description 16
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 15
229910052736 halogen Inorganic materials 0.000 claims description 15
150000002367 halogens Chemical class 0.000 claims description 15
229910052757 nitrogen Inorganic materials 0.000 claims description 15
125000005842 heteroatom Chemical group 0.000 claims description 12
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 12
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 11
229910052717 sulfur Inorganic materials 0.000 claims description 11
125000006701 (C1-C7) alkyl group Chemical group 0.000 claims description 8
125000000217 alkyl group Chemical group 0.000 claims description 8
229940124599 anti-inflammatory drug Drugs 0.000 claims description 7
229930195733 hydrocarbon Natural products 0.000 claims description 7
230000003637 steroidlike Effects 0.000 claims description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
239000004215 Carbon black (E152) Substances 0.000 claims description 6
239000003814 drug Substances 0.000 claims description 6
239000003937 drug carrier Substances 0.000 claims description 6
150000002430 hydrocarbons Chemical class 0.000 claims description 6
125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 6
125000001424 substituent group Chemical group 0.000 claims description 6
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 5
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230000015572 biosynthetic process Effects 0.000 claims description 5
229910052799 carbon Inorganic materials 0.000 claims description 5
125000004429 atom Chemical group 0.000 claims description 4
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229910052739 hydrogen Inorganic materials 0.000 claims description 4
125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 claims description 4
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125000002619 bicyclic group Chemical group 0.000 claims description 3
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239000001301 oxygen Substances 0.000 claims description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
125000002015 acyclic group Chemical group 0.000 claims description 2
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238000000034 method Methods 0.000 description 73
238000005481 NMR spectroscopy Methods 0.000 description 70
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 62
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 60
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125000000446 sulfanediyl group Chemical group *S* 0.000 description 38
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238000003818 flash chromatography Methods 0.000 description 33
239000011734 sodium Substances 0.000 description 33
238000006243 chemical reaction Methods 0.000 description 32
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 30
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239000002253 acid Substances 0.000 description 30
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239000002904 solvent Substances 0.000 description 23
239000000377 silicon dioxide Substances 0.000 description 22
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
239000011541 reaction mixture Substances 0.000 description 19
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 19
LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 description 18
239000007787 solid Substances 0.000 description 17
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 16
JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 16
ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 16
229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 16
150000004714 phosphonium salts Chemical class 0.000 description 16
238000002360 preparation method Methods 0.000 description 16
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 15
239000000725 suspension Substances 0.000 description 15
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 14
239000000443 aerosol Substances 0.000 description 14
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 13
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 13
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 13
239000000427 antigen Substances 0.000 description 13
108091007433 antigens Proteins 0.000 description 13
102000036639 antigens Human genes 0.000 description 13
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 13
150000001299 aldehydes Chemical class 0.000 description 12
150000002148 esters Chemical class 0.000 description 12
239000000741 silica gel Substances 0.000 description 12
229910002027 silica gel Inorganic materials 0.000 description 12
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UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 10
238000001704 evaporation Methods 0.000 description 10
230000008020 evaporation Effects 0.000 description 10
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 10
150000004702 methyl esters Chemical class 0.000 description 10
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 9
241000700159 Rattus Species 0.000 description 9
230000000202 analgesic effect Effects 0.000 description 9
239000012267 brine Substances 0.000 description 9
230000000694 effects Effects 0.000 description 9
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 9
238000012360 testing method Methods 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
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WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 8
CMSYDJVRTHCWFP-UHFFFAOYSA-N triphenylphosphane;hydrobromide Chemical compound Br.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 CMSYDJVRTHCWFP-UHFFFAOYSA-N 0.000 description 8
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KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 6
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ZDYVRSLAEXCVBX-UHFFFAOYSA-N pyridinium p-toluenesulfonate Chemical compound C1=CC=[NH+]C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 ZDYVRSLAEXCVBX-UHFFFAOYSA-N 0.000 description 6
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GLPNQKYLIJFZPY-OAQYLSRUSA-N methyl 2-[1-[[(1r)-3-(2-bromophenyl)-1-[3-(hydroxymethyl)phenyl]propoxy]methyl]cyclopropyl]acetate Chemical compound O([C@H](CCC=1C(=CC=CC=1)Br)C=1C=C(CO)C=CC=1)CC1(CC(=O)OC)CC1 GLPNQKYLIJFZPY-OAQYLSRUSA-N 0.000 description 1
NOFUKZJRODVAIO-IKOFQBKESA-N methyl 2-[[(1r)-3-(2-bromophenyl)-1-[3-(oxan-2-yloxymethyl)phenyl]propoxy]methyl]prop-2-enoate Chemical compound C([C@@H](OCC(=C)C(=O)OC)C=1C=C(COC2OCCCC2)C=CC=1)CC1=CC=CC=C1Br NOFUKZJRODVAIO-IKOFQBKESA-N 0.000 description 1
TWEQNZZOOFKOER-UHFFFAOYSA-N methyl 3-aminothiophene-2-carboxylate Chemical compound COC(=O)C=1SC=CC=1N TWEQNZZOOFKOER-UHFFFAOYSA-N 0.000 description 1
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239000003380 propellant Substances 0.000 description 1
230000000069 prophylactic effect Effects 0.000 description 1
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150000003180 prostaglandins Chemical class 0.000 description 1
230000005588 protonation Effects 0.000 description 1
150000003212 purines Chemical class 0.000 description 1
VMXUWOKSQNHOCA-LCYFTJDESA-N ranitidine Chemical compound [O-][N+](=O)/C=C(/NC)NCCSCC1=CC=C(CN(C)C)O1 VMXUWOKSQNHOCA-LCYFTJDESA-N 0.000 description 1
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GVHKSMYWAFEEBI-UHFFFAOYSA-N s-(pyridin-3-ylmethyl) 2-[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]ethanethioate Chemical compound CC1=C(CC(=O)SCC=2C=NC=CC=2)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 GVHKSMYWAFEEBI-UHFFFAOYSA-N 0.000 description 1
UTKQJRWEYCKICG-UHFFFAOYSA-N s-[[1-(cyanomethyl)cyclopropyl]methyl] ethanethioate Chemical compound CC(=O)SCC1(CC#N)CC1 UTKQJRWEYCKICG-UHFFFAOYSA-N 0.000 description 1
LCXASZQUGJCXBG-SUMWQHHRSA-N s057 Chemical compound C1([C@]23OC[C@@H](O3)CN3C4=CC=CC=C4N=C23)=CC=CC=C1 LCXASZQUGJCXBG-SUMWQHHRSA-N 0.000 description 1
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230000035939 shock Effects 0.000 description 1
HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 1
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FGTJJHCZWOVVNH-UHFFFAOYSA-N tert-butyl-[tert-butyl(dimethyl)silyl]oxy-dimethylsilane Chemical compound CC(C)(C)[Si](C)(C)O[Si](C)(C)C(C)(C)C FGTJJHCZWOVVNH-UHFFFAOYSA-N 0.000 description 1
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238000010998 test method Methods 0.000 description 1
125000004187 tetrahydropyran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
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229960000278 theophylline Drugs 0.000 description 1
238000011287 therapeutic dose Methods 0.000 description 1
CUWHXIJMTMMRTI-UHFFFAOYSA-N thiadiazol-4-amine Chemical class NC1=CSN=N1 CUWHXIJMTMMRTI-UHFFFAOYSA-N 0.000 description 1
YJSKZIATOGOJEB-UHFFFAOYSA-N thieno[2,3-b]pyrazine Chemical compound C1=CN=C2SC=CC2=N1 YJSKZIATOGOJEB-UHFFFAOYSA-N 0.000 description 1
SMZMHUCIDGHERP-UHFFFAOYSA-N thieno[2,3-b]pyridine Chemical compound C1=CN=C2SC=CC2=C1 SMZMHUCIDGHERP-UHFFFAOYSA-N 0.000 description 1
DKGYESBFCGKOJC-UHFFFAOYSA-N thiophen-3-amine Chemical compound NC=1C=CSC=1 DKGYESBFCGKOJC-UHFFFAOYSA-N 0.000 description 1
210000000115 thoracic cavity Anatomy 0.000 description 1
RZWIIPASKMUIAC-VQTJNVASSA-N thromboxane Chemical compound CCCCCCCC[C@H]1OCCC[C@@H]1CCCCCCC RZWIIPASKMUIAC-VQTJNVASSA-N 0.000 description 1
229960001312 tiaprofenic acid Drugs 0.000 description 1
229950000140 tiflamizole Drugs 0.000 description 1
229950002345 tiopinac Drugs 0.000 description 1
210000001519 tissue Anatomy 0.000 description 1
229960002905 tolfenamic acid Drugs 0.000 description 1
YEZNLOUZAIOMLT-UHFFFAOYSA-N tolfenamic acid Chemical compound CC1=C(Cl)C=CC=C1NC1=CC=CC=C1C(O)=O YEZNLOUZAIOMLT-UHFFFAOYSA-N 0.000 description 1
229950005382 tolpadol Drugs 0.000 description 1
238000002691 topical anesthesia Methods 0.000 description 1
239000012049 topical pharmaceutical composition Substances 0.000 description 1
125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
125000005490 tosylate group Chemical group 0.000 description 1
239000003053 toxin Substances 0.000 description 1
231100000765 toxin Toxicity 0.000 description 1
108700012359 toxins Proteins 0.000 description 1
ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 description 1
XYTOSDBNRCWJEF-UHFFFAOYSA-N trimethyl-(5-methylfuro[3,2-b]pyridin-2-yl)silane Chemical compound CC1=CC=C2OC([Si](C)(C)C)=CC2=N1 XYTOSDBNRCWJEF-UHFFFAOYSA-N 0.000 description 1
YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
229960000281 trometamol Drugs 0.000 description 1
102000003390 tumor necrosis factor Human genes 0.000 description 1
229950010121 ufenamate Drugs 0.000 description 1
230000001562 ulcerogenic effect Effects 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
229960001722 verapamil Drugs 0.000 description 1
238000010792 warming Methods 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
229960003414 zomepirac Drugs 0.000 description 1
ZXVNMYWKKDOREA-UHFFFAOYSA-N zomepirac Chemical compound C1=C(CC(O)=O)N(C)C(C(=O)C=2C=CC(Cl)=CC=2)=C1C ZXVNMYWKKDOREA-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- 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
- 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]
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Pulmonology (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Rheumatology (AREA)
Pain & Pain Management (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (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)
Pyridine Compounds (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

NO19952495A 1992-12-22 1995-06-21 Diaryl-5,6-kondenserte, heterosykliske syrer som leukotrienantagonister NO313831B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US99486992A	1992-12-22	1992-12-22
PCT/CA1993/000541 WO1994014815A1 (fr)	1992-12-22	1993-12-15	Acides di-aryle 5,6 fusionnes heterocycliques en tant qu'antagonistes des leucotrienes

Publications (3)

Publication Number	Publication Date
NO952495D0 NO952495D0 (no)	1995-06-21
NO952495L NO952495L (no)	1995-08-22
NO313831B1 true NO313831B1 (no)	2002-12-09

Family

ID=25541163

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO19952495A NO313831B1 (no)	1992-12-22	1995-06-21	Diaryl-5,6-kondenserte, heterosykliske syrer som leukotrienantagonister

Country Status (23)

Country	Link
EP (1)	EP0604114B1 (fr)
KR (1)	KR100310552B1 (fr)
CN (1)	CN1040213C (fr)
AT (1)	ATE192448T1 (fr)
AU (1)	AU672837B2 (fr)
CA (1)	CA2111372C (fr)
CZ (1)	CZ290829B6 (fr)
DE (1)	DE69328540T2 (fr)
DK (1)	DK0604114T3 (fr)
ES (1)	ES2145765T3 (fr)
FI (1)	FI111368B (fr)
GR (1)	GR3033985T3 (fr)
HU (1)	HU222274B1 (fr)
IL (1)	IL108050A (fr)
MX (1)	MX9400022A (fr)
NO (1)	NO313831B1 (fr)
NZ (1)	NZ258835A (fr)
PL (1)	PL177967B1 (fr)
PT (1)	PT604114E (fr)
RU (1)	RU2154065C2 (fr)
SK (1)	SK282409B6 (fr)
WO (1)	WO1994014815A1 (fr)
ZA (1)	ZA939560B (fr)

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US5472964A (en) *	1992-12-22	1995-12-05	Merck Frosst Canada, Inc.	Diaryl 5,6-fused heterocyclic acids as leukotriene antagonists
US5350760A (en) *	1993-08-04	1994-09-27	Merck Frosst Canada, Inc.	Aza-5,5-fused hetrocyclic acids as leukotriene antagonists
TW416948B (en) *	1993-12-28	2001-01-01	Merck & Co Inc	Process for the preparation of leukotriene antagonists
US5427933A (en) *	1994-07-20	1995-06-27	Merck & Co., Inc.	Reduction of phenylalkyl ketones to the corresponding (S)-hydroxy derivatives using mucor hiemalis IFO 5834
US5491077A (en) *	1994-07-20	1996-02-13	Merck & Co., Inc.	Microbial method
US5523477A (en) *	1995-01-23	1996-06-04	Merck & Co., Inc.	Process for the preparation of 1-(thiomethyl)-cyclopropaneacetic acid
US5750539A (en) *	1995-06-07	1998-05-12	Merck Frosst Canada	Heteroaryl diol acids as leukotriene antagonists
RU2196772C1 (ru) *	2001-10-08	2003-01-20	Кубанский государственный технологический университет	6-МЕТИЛ-8-МЕТОКСИМЕТИЛ-3-ФЕНИЛИЗОКСАЗОЛО[3',4':4,5]ТИЕНО-[2,3-b]ПИРИДИН, ПРОЯВЛЯЮЩИЙ РОСТОРЕГУЛИРУЮЩУЮ И АНТИСТРЕССОВУЮ АКТИВНОСТЬ
CN1318400C (zh) *	2002-02-06	2007-05-30	戴尔玛化学品股份有限公司	制备1－(巯基甲基)－环丙烷乙酸的方法
US7271268B1 (en)	2006-12-22	2007-09-18	Formosa Laboratories Inc.	Process for preparation of [1-(mercaptomethyl)cyclopropyl]acetic acid and related derivatives
RU2449807C2 (ru) *	2009-11-16	2012-05-10	Государственное образовательное учреждение высшего профессионального образования "Дагестанская государственная медицинская академия федерального агентства по здравоохранению и социальному развитию"	Способ лечения эндотоксикоза при хроническом пиелонефрите

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WO1984001576A1 (fr) *	1982-10-07	1984-04-26	Takeda Chemical Industries Ltd	Derives de pyrrolidone fondus
US4957932A (en) *	1987-11-25	1990-09-18	Merck Frosst Canada, Inc.	Benzoheterazoles
CA2053216C (fr) *	1990-10-12	2003-04-08	Michel L. Belley	Derives acides d'hyroxyalkylquinoline saturee comme antagonistes des leucotrienes
ATE165088T1 (de) *	1990-10-12	1998-05-15	Merck Frosst Canada Inc	Ungesättigte hydroxyalkylchinolinsäuren als leukotrien-antagonisten
US5308850A (en) *	1991-09-30	1994-05-03	Merck Frosst Canada, Inc.	(Bicyclic-hetero-arylmethoxy)indoles as inhibitors of leukotriene biosynthesis

1993
- 1993-12-14 CA CA002111372A patent/CA2111372C/fr not_active Expired - Fee Related
- 1993-12-15 WO PCT/CA1993/000541 patent/WO1994014815A1/fr not_active Ceased
- 1993-12-15 DK DK93310127T patent/DK0604114T3/da active
- 1993-12-15 NZ NZ258835A patent/NZ258835A/en unknown
- 1993-12-15 RU RU95113598/04A patent/RU2154065C2/ru not_active IP Right Cessation
- 1993-12-15 DE DE69328540T patent/DE69328540T2/de not_active Expired - Fee Related
- 1993-12-15 ES ES93310127T patent/ES2145765T3/es not_active Expired - Lifetime
- 1993-12-15 AT AT93310127T patent/ATE192448T1/de not_active IP Right Cessation
- 1993-12-15 SK SK822-95A patent/SK282409B6/sk unknown
- 1993-12-15 CZ CZ19951653A patent/CZ290829B6/cs not_active IP Right Cessation
- 1993-12-15 PT PT93310127T patent/PT604114E/pt unknown
- 1993-12-15 EP EP93310127A patent/EP0604114B1/fr not_active Expired - Lifetime
- 1993-12-15 KR KR1019950702546A patent/KR100310552B1/ko not_active Expired - Fee Related
- 1993-12-15 PL PL93309408A patent/PL177967B1/pl unknown
- 1993-12-15 HU HU9501842A patent/HU222274B1/hu not_active IP Right Cessation
- 1993-12-16 IL IL108050A patent/IL108050A/en active IP Right Grant
- 1993-12-21 ZA ZA939560A patent/ZA939560B/xx unknown
- 1993-12-21 CN CN93119928A patent/CN1040213C/zh not_active Expired - Fee Related
- 1993-12-21 AU AU52579/93A patent/AU672837B2/en not_active Ceased
1994
- 1994-01-03 MX MX9400022A patent/MX9400022A/es not_active IP Right Cessation
1995
- 1995-06-21 FI FI953104A patent/FI111368B/fi active
- 1995-06-21 NO NO19952495A patent/NO313831B1/no unknown
2000
- 2000-07-19 GR GR20000401670T patent/GR3033985T3/el not_active IP Right Cessation

Also Published As

Publication number	Publication date
SK82295A3 (en)	1995-12-06
EP0604114A1 (fr)	1994-06-29
DE69328540D1 (de)	2000-06-08
NO952495L (no)	1995-08-22
HU222274B1 (hu)	2003-05-28
CZ290829B6 (cs)	2002-10-16
FI953104A0 (fi)	1995-06-21
SK282409B6 (sk)	2002-01-07
PT604114E (pt)	2000-09-29
FI953104L (fi)	1995-06-21
NZ258835A (en)	1997-06-24
CA2111372C (fr)	2007-01-16
NO952495D0 (no)	1995-06-21
ES2145765T3 (es)	2000-07-16
PL177967B1 (pl)	2000-02-29
ZA939560B (en)	1994-08-11
IL108050A0 (en)	1994-04-12
FI111368B (fi)	2003-07-15
PL309408A1 (en)	1995-10-02
KR100310552B1 (ko)	2001-12-17
DE69328540T2 (de)	2001-01-04
HU9501842D0 (en)	1995-08-28
RU2154065C2 (ru)	2000-08-10
WO1994014815A1 (fr)	1994-07-07
AU672837B2 (en)	1996-10-17
AU5257993A (en)	1994-07-07
CN1094051A (zh)	1994-10-26
HUT71810A (en)	1996-02-28
MX9400022A (es)	1995-01-31
RU95113598A (ru)	1997-06-10
DK0604114T3 (da)	2000-08-07
IL108050A (en)	1998-06-15
CZ165395A3 (en)	1996-01-17
EP0604114B1 (fr)	2000-05-03
GR3033985T3 (en)	2000-11-30
CN1040213C (zh)	1998-10-14
KR950704325A (ko)	1995-11-17
ATE192448T1 (de)	2000-05-15
CA2111372A1 (fr)	1994-06-23

Publication	Publication Date	Title
US5506227A (en)	1996-04-09	Pyridine-substituted benzyl alcohols as leukotriene antagonists
SI9111647A (en)	1997-12-31	Unsaturated hydroxyalkylquinoline acids
EP0480716A1 (fr)	1992-04-15	Acides hydroxyalkylquinoliniques saturés comme antagonistes de leukotriène
US5472964A (en)	1995-12-05	Diaryl 5,6-fused heterocyclic acids as leukotriene antagonists
EP0500360B1 (fr)	1997-06-25	Des céto-acides contenant une quinoléine comme antagonistes des leukotriènes
EP0604114B1 (fr)	2000-05-03	Acides hétérocycliques 5,6-condensés diaryliques comme antagonistes de leucotriene
WO1993021168A1 (fr)	1993-10-28	Alcools benzyliques a substitution thiazole utilises comme antagonistes de leucotrienes
CA2163244C (fr)	2006-07-11	Derives de la quinoleine, antagonistes de la leucotriene
EP0480708B1 (fr)	1995-10-11	Hydroxyalkylquinoline ether acide comme antagoniste leukotriènes
US5750539A (en)	1998-05-12	Heteroaryl diol acids as leukotriene antagonists
AU683290B2 (en)	1997-11-06	Aza-5,5-fused heterocyclic acids as leukotriene antagonists
WO1993021169A1 (fr)	1993-10-28	Alcools benzyliques substitues par benzothiazole, utilises comme antagonistes de leucotrienes
WO1994005657A1 (fr)	1994-03-17	Acides heteroarylnaphtalene hydroxy utiles comme inhibiteurs de la biosynthese du leucotriene
WO1994005658A1 (fr)	1994-03-17	Lactones d'heteroarylnaphtalene utiles comme inhibiteurs de la biosynthese de leucotrienes
US5212180A (en)	1993-05-18	Quinoline-containing ketoacids as leukotriene antagonists
CA2223414C (fr)	2007-08-14	Acides d'heteroaryle diol antagonistes des leucotrienes