UA62966C2 - Quaternary ammonuim compounds as tachykinin antagonists - Google Patents
Quaternary ammonuim compounds as tachykinin antagonists Download PDFInfo
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- UA62966C2 UA62966C2 UA99126551A UA99126551A UA62966C2 UA 62966 C2 UA62966 C2 UA 62966C2 UA 99126551 A UA99126551 A UA 99126551A UA 99126551 A UA99126551 A UA 99126551A UA 62966 C2 UA62966 C2 UA 62966C2
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- UA
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- Prior art keywords
- phenyl
- dichlorophenyl
- disease
- compound
- group
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 140
- 239000005557 antagonist Substances 0.000 title abstract description 7
- 102000003141 Tachykinin Human genes 0.000 title abstract description 4
- 108060008037 tachykinin Proteins 0.000 title abstract description 4
- -1 2,3-dihydrobenzo[b]furanyl Chemical group 0.000 claims abstract description 99
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 69
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 18
- 150000001450 anions Chemical class 0.000 claims abstract description 16
- 125000001424 substituent group Chemical group 0.000 claims abstract description 16
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 13
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 9
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 8
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims abstract description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 7
- 125000001544 thienyl group Chemical group 0.000 claims abstract description 7
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 5
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims abstract description 5
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000005977 Ethylene Substances 0.000 claims abstract description 3
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 3
- 125000001041 indolyl group Chemical group 0.000 claims abstract description 3
- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract 6
- 239000000203 mixture Substances 0.000 claims description 142
- 238000000034 method Methods 0.000 claims description 41
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 38
- 201000010099 disease Diseases 0.000 claims description 27
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 241000282414 Homo sapiens Species 0.000 claims description 14
- 230000003042 antagnostic effect Effects 0.000 claims description 14
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 13
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 12
- 102000007124 Tachykinin Receptors Human genes 0.000 claims description 12
- 108010072901 Tachykinin Receptors Proteins 0.000 claims description 12
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
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- 150000002367 halogens Chemical class 0.000 claims description 10
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 9
- 239000000460 chlorine Substances 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 8
- 229910052731 fluorine Inorganic materials 0.000 claims description 8
- 239000011737 fluorine Substances 0.000 claims description 8
- 230000002496 gastric effect Effects 0.000 claims description 8
- 201000004624 Dermatitis Diseases 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000002541 furyl group Chemical group 0.000 claims description 7
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- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 5
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- 241000208225 Rhus Species 0.000 claims description 5
- 235000014220 Rhus chinensis Nutrition 0.000 claims description 5
- 108010046334 Urease Proteins 0.000 claims description 5
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- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
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- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
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- 206010036376 Postherpetic Neuralgia Diseases 0.000 claims description 4
- 201000008937 atopic dermatitis Diseases 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
- 125000006239 protecting group Chemical group 0.000 claims description 4
- OVFCSRJZUQAXOA-UHFFFAOYSA-N 1-azoniabicyclo[2.2.2]octane;methanesulfonate Chemical compound CS([O-])(=O)=O.C1CC2CC[NH+]1CC2 OVFCSRJZUQAXOA-UHFFFAOYSA-N 0.000 claims description 3
- 206010039085 Rhinitis allergic Diseases 0.000 claims description 3
- 201000010105 allergic rhinitis Diseases 0.000 claims description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
- 229940126601 medicinal product Drugs 0.000 claims description 3
- 125000005948 methanesulfonyloxy group Chemical group 0.000 claims description 3
- 125000005951 trifluoromethanesulfonyloxy group Chemical group 0.000 claims description 3
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 3
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 2
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 2
- 229910002651 NO3 Inorganic materials 0.000 claims description 2
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 239000013543 active substance Substances 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 229940077388 benzenesulfonate Drugs 0.000 claims description 2
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
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- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 claims description 2
- 208000023783 Genitourinary tract disease Diseases 0.000 claims 2
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims 2
- 241000588653 Neisseria Species 0.000 claims 1
- SZMUSGRLLRWRIV-UHFFFAOYSA-N [4-methoxy-3-propan-2-yloxy-2-(trifluoromethoxy)phenyl] hypofluorite Chemical compound COC1=C(C(=C(OF)C=C1)OC(F)(F)F)OC(C)C SZMUSGRLLRWRIV-UHFFFAOYSA-N 0.000 claims 1
- JFSPBVWPKOEZCB-UHFFFAOYSA-N fenfuram Chemical compound O1C=CC(C(=O)NC=2C=CC=CC=2)=C1C JFSPBVWPKOEZCB-UHFFFAOYSA-N 0.000 claims 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract description 7
- 125000005843 halogen group Chemical group 0.000 abstract description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract description 3
- 125000002252 acyl group Chemical group 0.000 abstract description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 7
- 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 abstract 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
- 125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 243
- 238000002360 preparation method Methods 0.000 description 157
- 230000002829 reductive effect Effects 0.000 description 113
- 239000002904 solvent Substances 0.000 description 111
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 105
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-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
- C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Pulmonology (AREA)
- Psychiatry (AREA)
- Urology & Nephrology (AREA)
- Dermatology (AREA)
- Virology (AREA)
- Pain & Pain Management (AREA)
- Immunology (AREA)
- Endocrinology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Reproductive Health (AREA)
- Hospice & Palliative Care (AREA)
- Physical Education & Sports Medicine (AREA)
- Rheumatology (AREA)
- Heart & Thoracic Surgery (AREA)
- Otolaryngology (AREA)
- Ophthalmology & Optometry (AREA)
- Cardiology (AREA)
- Gynecology & Obstetrics (AREA)
- Vascular Medicine (AREA)
- Molecular Biology (AREA)
- Orthopedic Medicine & Surgery (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9712882.1A GB9712882D0 (en) | 1997-06-18 | 1997-06-18 | Quaternary ammonium compounds |
| PCT/EP1998/003500 WO1998057972A1 (en) | 1997-06-18 | 1998-06-05 | Quaternary ammonium compounds as tachykinin antagonists |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UA62966C2 true UA62966C2 (en) | 2004-01-15 |
Family
ID=10814535
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UA99126551A UA62966C2 (en) | 1997-06-18 | 1998-05-06 | Quaternary ammonuim compounds as tachykinin antagonists |
Country Status (43)
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999033489A1 (fr) * | 1997-12-26 | 1999-07-08 | Yamanouchi Pharmaceutical Co., Ltd. | Compositions medicinales a liberation prolongee |
| JP4546589B2 (ja) * | 1998-04-23 | 2010-09-15 | 武田薬品工業株式会社 | ナフタレン誘導体 |
| NZ523310A (en) * | 2000-06-12 | 2005-07-29 | Univ Rochester | Tachykinin receptor antagonist to block receptors NK1, NK2, and NK3 and treat symptoms of hormonal variation |
| WO2002046156A2 (en) * | 2000-12-06 | 2002-06-13 | Sepracor, Inc. | 4,4-disubstituted piperidines for use as dopamine, serotonin and norepinephrine ligands |
| AU2003243353A1 (en) * | 2002-05-29 | 2003-12-19 | The Regents Of The University Of California | Antagonizing nk1 receptors inhibits consumption of substances of abuse |
| WO2004091597A2 (en) * | 2003-04-15 | 2004-10-28 | Pharmacia & Upjohn Company Llc | Method of treating irritable bowel syndrome (ibs) |
| WO2005110998A1 (en) * | 2004-05-07 | 2005-11-24 | Janssen Pharmaceutica N.V. | Scalable synthesis of imidazole derivatives |
| WO2008090114A1 (en) | 2007-01-24 | 2008-07-31 | Glaxo Group Limited | Pharmaceutical compositions comprising 2-methoxy-5- (5-trifluoromethyl-tetrazol-i-yl-benzyl) - (2s-phenyl-piperidin-3s-yl-) |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3991201A (en) * | 1974-06-27 | 1976-11-09 | Janssen Pharmaceutica N.V. | 1-(β-Aryl-β-R-ethyl)imidazoles as antimicrobial agents |
| US5583134A (en) * | 1992-09-30 | 1996-12-10 | Sanofi | 1-azoniabicyclo[2.2.2] octanes and pharmaceutical compositions in which they are present |
| FR2696178B1 (fr) * | 1992-09-30 | 1994-12-30 | Sanofi Elf | Amides basiques quaternaires, procédé pour leur préparation et compositions pharmaceutiques en contenant. |
-
1997
- 1997-06-18 GB GBGB9712882.1A patent/GB9712882D0/en active Pending
-
1998
- 1998-05-06 UA UA99126551A patent/UA62966C2/uk unknown
- 1998-05-19 TW TW087107720A patent/TW479055B/zh not_active IP Right Cessation
- 1998-06-04 HN HN1998000087A patent/HN1998000087A/es unknown
- 1998-06-04 PA PA19988452501A patent/PA8452501A1/es unknown
- 1998-06-05 CA CA002291975A patent/CA2291975C/en not_active Expired - Fee Related
- 1998-06-05 EP EP98932148A patent/EP0994876B1/en not_active Expired - Lifetime
- 1998-06-05 ID IDW991633A patent/ID23410A/id unknown
- 1998-06-05 TR TR1999/03135T patent/TR199903135T2/xx unknown
- 1998-06-05 WO PCT/EP1998/003500 patent/WO1998057972A1/en not_active Application Discontinuation
- 1998-06-05 PL PL98337713A patent/PL189557B1/pl not_active IP Right Cessation
- 1998-06-05 JP JP50368799A patent/JP3280993B2/ja not_active Expired - Fee Related
- 1998-06-05 HU HU0003962A patent/HUP0003962A3/hu unknown
- 1998-06-05 NZ NZ501286A patent/NZ501286A/xx unknown
- 1998-06-05 SK SK1744-99A patent/SK283346B6/sk unknown
- 1998-06-05 SI SI9830692T patent/SI0994876T1/xx unknown
- 1998-06-05 PT PT98932148T patent/PT994876E/pt unknown
- 1998-06-05 CN CNB988063425A patent/CN1199971C/zh not_active Expired - Fee Related
- 1998-06-05 AT AT98932148T patent/ATE275564T1/de not_active IP Right Cessation
- 1998-06-05 IL IL15562198A patent/IL155621A0/xx not_active IP Right Cessation
- 1998-06-05 DE DE69826129T patent/DE69826129T2/de not_active Expired - Fee Related
- 1998-06-05 YU YU64699A patent/YU64699A/sh unknown
- 1998-06-05 IL IL13307998A patent/IL133079A/en not_active IP Right Cessation
- 1998-06-05 EA EA199900986A patent/EA002424B1/ru not_active IP Right Cessation
- 1998-06-05 ES ES98932148T patent/ES2227856T3/es not_active Expired - Lifetime
- 1998-06-05 US US09/380,370 patent/US6207678B1/en not_active Expired - Fee Related
- 1998-06-05 KR KR1019997011931A patent/KR100345389B1/ko not_active IP Right Cessation
- 1998-06-05 BR BR9810619-8A patent/BR9810619A/pt not_active Application Discontinuation
- 1998-06-05 AU AU82153/98A patent/AU726027B2/en not_active Ceased
- 1998-06-08 PE PE1998000468A patent/PE80099A1/es not_active Application Discontinuation
- 1998-06-11 AP APAP/P/1998/001262A patent/AP947A/en active
- 1998-06-15 UY UY25045A patent/UY25045A1/es unknown
- 1998-06-16 MY MYPI98002689A patent/MY136376A/en unknown
- 1998-06-16 AR ARP980102853A patent/AR012249A1/es active IP Right Grant
- 1998-06-17 MA MA25118A patent/MA26509A1/fr unknown
- 1998-06-17 ZA ZA9805239A patent/ZA985239B/xx unknown
- 1998-06-17 DZ DZ980134A patent/DZ2524A1/xx active
- 1998-06-17 TN TNTNSN98089A patent/TNSN98089A1/fr unknown
- 1998-06-18 CO CO98034807A patent/CO4940478A1/es unknown
- 1998-06-18 HR HR980337A patent/HRP980337B1/xx not_active IP Right Cessation
-
1999
- 1999-11-23 IS IS5269A patent/IS5269A/is unknown
- 1999-11-23 BG BG103919A patent/BG63341B1/bg unknown
- 1999-11-25 NO NO995782A patent/NO995782L/no not_active Application Discontinuation
- 1999-12-15 OA OA9900281A patent/OA11235A/en unknown
-
2000
- 2000-12-11 US US09/734,266 patent/US6380396B1/en not_active Expired - Fee Related
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