PH26259A - Tetrazole derivatives and their use as leukotriene antagonist - Google Patents
Tetrazole derivatives and their use as leukotriene antagonist Download PDFInfo
- Publication number
- PH26259A PH26259A PH37399A PH37399A PH26259A PH 26259 A PH26259 A PH 26259A PH 37399 A PH37399 A PH 37399A PH 37399 A PH37399 A PH 37399A PH 26259 A PH26259 A PH 26259A
- Authority
- PH
- Philippines
- Prior art keywords
- tetrazole
- hydroxy
- propyl
- mmol
- phenoxy
- Prior art date
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- 150000003536 tetrazoles Chemical class 0.000 title description 58
- 239000003199 leukotriene receptor blocking agent Substances 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 68
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 67
- -1 2H-tetrazolyl ring Chemical class 0.000 claims description 65
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- 125000001118 alkylidene group Chemical group 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 5
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 3
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 256
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 237
- 239000000047 product Substances 0.000 description 98
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 94
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 85
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 85
- 239000000203 mixture Substances 0.000 description 79
- 238000006243 chemical reaction Methods 0.000 description 73
- 235000013350 formula milk Nutrition 0.000 description 63
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 59
- 238000010992 reflux Methods 0.000 description 56
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 54
- 238000000034 method Methods 0.000 description 51
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 46
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- 239000000243 solution Substances 0.000 description 45
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
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- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 34
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 34
- 238000004458 analytical method Methods 0.000 description 33
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 32
- 230000000875 corresponding effect Effects 0.000 description 31
- 239000003153 chemical reaction reagent Substances 0.000 description 27
- 229910000027 potassium carbonate Inorganic materials 0.000 description 27
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- 238000002425 crystallisation Methods 0.000 description 26
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- 239000002253 acid Substances 0.000 description 25
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 21
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 21
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 21
- 239000000543 intermediate Substances 0.000 description 21
- 238000003756 stirring Methods 0.000 description 21
- KJUGUADJHNHALS-UHFFFAOYSA-N 1H-tetrazole Substances C=1N=NNN=1 KJUGUADJHNHALS-UHFFFAOYSA-N 0.000 description 20
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 20
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- 239000011591 potassium Substances 0.000 description 20
- 235000007686 potassium Nutrition 0.000 description 20
- 229960003975 potassium Drugs 0.000 description 20
- 150000002617 leukotrienes Chemical class 0.000 description 19
- 239000013078 crystal Substances 0.000 description 18
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 18
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
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- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
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- HJHVQCXHVMGZNC-JCJNLNMISA-M sodium;(2z)-2-[(3r,4s,5s,8s,9s,10s,11r,13r,14s,16s)-16-acetyloxy-3,11-dihydroxy-4,8,10,14-tetramethyl-2,3,4,5,6,7,9,11,12,13,15,16-dodecahydro-1h-cyclopenta[a]phenanthren-17-ylidene]-6-methylhept-5-enoate Chemical compound [Na+].O[C@@H]([C@@H]12)C[C@H]3\C(=C(/CCC=C(C)C)C([O-])=O)[C@@H](OC(C)=O)C[C@]3(C)[C@@]2(C)CC[C@@H]2[C@]1(C)CC[C@@H](O)[C@H]2C HJHVQCXHVMGZNC-JCJNLNMISA-M 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 229960005078 sorbitan sesquioleate Drugs 0.000 description 1
- 235000019337 sorbitan trioleate Nutrition 0.000 description 1
- 229960000391 sorbitan trioleate Drugs 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000008925 spontaneous activity Effects 0.000 description 1
- 238000013222 sprague-dawley male rat Methods 0.000 description 1
- 208000024794 sputum Diseases 0.000 description 1
- 210000003802 sputum Anatomy 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000012058 sterile packaged powder Substances 0.000 description 1
- 239000006190 sub-lingual tablet Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 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
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- 125000001701 trimethoxybenzyl group Chemical group 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D257/04—Five-membered rings
-
- 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
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pulmonology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Immunology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/085,588 US4820723A (en) | 1987-08-14 | 1987-08-14 | Disubstituted tetrazole leukotriene antagonists and methods for their use thereas |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PH26259A true PH26259A (en) | 1992-04-01 |
Family
ID=22192636
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PH37399A PH26259A (en) | 1987-08-14 | 1988-08-11 | Tetrazole derivatives and their use as leukotriene antagonist |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US4820723A (fr) |
| EP (1) | EP0303478B1 (fr) |
| JP (1) | JPS6466174A (fr) |
| KR (1) | KR890003716A (fr) |
| CN (1) | CN1012434B (fr) |
| AU (1) | AU610218B2 (fr) |
| DE (1) | DE3875030T2 (fr) |
| DK (1) | DK449388A (fr) |
| ES (1) | ES2052730T3 (fr) |
| HU (1) | HUT50462A (fr) |
| NZ (1) | NZ225791A (fr) |
| PH (1) | PH26259A (fr) |
| PT (1) | PT88244B (fr) |
| ZA (1) | ZA885887B (fr) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4820722A (en) * | 1987-08-14 | 1989-04-11 | Eli Lilly And Company | Disubstituted tetrazoles and their use as leukotriene antagonists |
| DK0408509T3 (da) * | 1989-07-14 | 1996-04-01 | Ciba Geigy Ag | Substituerede benzonitriler |
| DE4124942A1 (de) * | 1991-07-27 | 1993-01-28 | Thomae Gmbh Dr K | 5-gliedrige heterocyclen, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| CN101544614B (zh) * | 2008-03-24 | 2011-07-20 | 合肥合源药业有限公司 | 磷酸二酯酶ⅲ抑制剂、其制法及其医药用途 |
| MX2016008247A (es) | 2013-12-20 | 2016-10-21 | Novartis Ag | Derivados de acido heteroaril butanoico como inhibidores de lta4h. |
| TWI834581B (zh) | 2018-07-31 | 2024-03-01 | 瑞士商諾華公司 | Lta4h抑制劑的晶型 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4661505A (en) * | 1982-11-03 | 1987-04-28 | Eli Lilly And Company | Leukotriene antagonists |
| US4663332A (en) * | 1985-10-10 | 1987-05-05 | Hoffman-La Roche Inc. | 5-substituted N-alkylated tetrazoles |
| PT85110A (en) * | 1986-06-23 | 1987-07-01 | Merck Frosst Canada Inc | Process for preparing benzenealkanoic acid derivatives useful as leukotriene antagonists |
| CA1315279C (fr) * | 1987-01-12 | 1993-03-30 | Nancy Grace Bollinger | Agents antiinflammatoires |
-
1987
- 1987-08-14 US US07/085,588 patent/US4820723A/en not_active Expired - Fee Related
-
1988
- 1988-08-10 JP JP63202627A patent/JPS6466174A/ja active Pending
- 1988-08-10 ZA ZA885887A patent/ZA885887B/xx unknown
- 1988-08-11 DE DE8888307429T patent/DE3875030T2/de not_active Expired - Fee Related
- 1988-08-11 PH PH37399A patent/PH26259A/en unknown
- 1988-08-11 NZ NZ225791A patent/NZ225791A/xx unknown
- 1988-08-11 ES ES88307429T patent/ES2052730T3/es not_active Expired - Lifetime
- 1988-08-11 PT PT88244A patent/PT88244B/pt not_active IP Right Cessation
- 1988-08-11 DK DK449388A patent/DK449388A/da not_active Application Discontinuation
- 1988-08-11 AU AU20967/88A patent/AU610218B2/en not_active Expired - Fee Related
- 1988-08-11 EP EP88307429A patent/EP0303478B1/fr not_active Expired - Lifetime
- 1988-08-12 CN CN88106046A patent/CN1012434B/zh not_active Expired
- 1988-08-12 HU HU884343A patent/HUT50462A/hu unknown
- 1988-08-12 KR KR1019880010274A patent/KR890003716A/ko not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| EP0303478B1 (fr) | 1992-09-30 |
| DK449388A (da) | 1989-02-15 |
| PT88244A (pt) | 1989-06-30 |
| AU2096788A (en) | 1989-02-16 |
| JPS6466174A (en) | 1989-03-13 |
| NZ225791A (en) | 1990-10-26 |
| DE3875030D1 (de) | 1992-11-05 |
| CN1012434B (zh) | 1991-04-24 |
| DE3875030T2 (de) | 1993-03-04 |
| DK449388D0 (da) | 1988-08-11 |
| ZA885887B (en) | 1990-04-25 |
| AU610218B2 (en) | 1991-05-16 |
| EP0303478A1 (fr) | 1989-02-15 |
| ES2052730T3 (es) | 1994-07-16 |
| KR890003716A (ko) | 1989-04-17 |
| HUT50462A (en) | 1990-02-28 |
| CN1031224A (zh) | 1989-02-22 |
| US4820723A (en) | 1989-04-11 |
| PT88244B (pt) | 1995-03-01 |
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