CA2060825A1 - Therapeutic agent - Google Patents
Therapeutic agentInfo
- Publication number
- CA2060825A1 CA2060825A1 CA002060825A CA2060825A CA2060825A1 CA 2060825 A1 CA2060825 A1 CA 2060825A1 CA 002060825 A CA002060825 A CA 002060825A CA 2060825 A CA2060825 A CA 2060825A CA 2060825 A1 CA2060825 A1 CA 2060825A1
- Authority
- CA
- Canada
- Prior art keywords
- compound
- ethyl
- biphenyl
- tetrazol
- methoxy
- Prior art date
- Legal status (The legal status 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 status listed.)
- Abandoned
Links
- 239000003814 drug Substances 0.000 title abstract description 3
- 229940124597 therapeutic agent Drugs 0.000 title abstract 2
- 238000000034 method Methods 0.000 claims abstract description 39
- 230000008569 process Effects 0.000 claims abstract description 19
- 238000004519 manufacturing process Methods 0.000 claims abstract description 9
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 33
- 239000000203 mixture Substances 0.000 claims description 32
- 150000001875 compounds Chemical class 0.000 claims description 30
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 24
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical group CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 18
- 239000002904 solvent Substances 0.000 claims description 15
- 238000010438 heat treatment Methods 0.000 claims description 12
- 238000009835 boiling Methods 0.000 claims description 8
- 238000001816 cooling Methods 0.000 claims description 7
- 238000002844 melting Methods 0.000 claims description 7
- 230000008018 melting Effects 0.000 claims description 7
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 7
- -1 2'-(1H-1,2,3,4-tetrazol-5-yl)biphenyl-4-yl Chemical group 0.000 claims description 6
- 238000001704 evaporation Methods 0.000 claims description 6
- 230000008020 evaporation Effects 0.000 claims description 6
- 239000003085 diluting agent Substances 0.000 claims description 4
- 239000003495 polar organic solvent Substances 0.000 claims description 4
- PSXRWZBTVAZNSF-UHFFFAOYSA-N hydron;quinoline;chloride Chemical compound Cl.N1=CC=CC2=CC=CC=C21 PSXRWZBTVAZNSF-UHFFFAOYSA-N 0.000 claims description 3
- 230000036961 partial effect Effects 0.000 claims description 3
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 claims description 2
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- 238000004508 fractional distillation Methods 0.000 claims description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 2
- FSJCYXPMWQPVOS-UHFFFAOYSA-N 2-ethyl-4-[[4-[2-(2h-tetrazol-5-yl)phenyl]phenyl]methoxy]quinoline Chemical compound C=12C=CC=CC2=NC(CC)=CC=1OCC(C=C1)=CC=C1C1=CC=CC=C1C=1N=NNN=1 FSJCYXPMWQPVOS-UHFFFAOYSA-N 0.000 claims 7
- 239000002798 polar solvent Substances 0.000 claims 2
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- 230000003389 potentiating effect Effects 0.000 abstract description 2
- 125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 abstract 1
- 229940126062 Compound A Drugs 0.000 description 40
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- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
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- 102000005862 Angiotensin II Human genes 0.000 description 3
- 101800000733 Angiotensin-2 Proteins 0.000 description 3
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- 239000011928 denatured alcohol Substances 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 229960003883 furosemide Drugs 0.000 description 1
- 230000013632 homeostatic process Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 241001515942 marmosets Species 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 102000006240 membrane receptors Human genes 0.000 description 1
- 108020004084 membrane receptors Proteins 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000004452 microanalysis Methods 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229960002748 norepinephrine Drugs 0.000 description 1
- SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- 239000003791 organic solvent mixture Substances 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 210000002381 plasma Anatomy 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000011165 process development Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 230000029865 regulation of blood pressure Effects 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 230000000894 saliuretic effect Effects 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 238000007614 solvation Methods 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000003506 spasmogen Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 235000015096 spirit Nutrition 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
- 239000007916 tablet composition Substances 0.000 description 1
- FMUBFLCMVLZYPU-UHFFFAOYSA-N tributyl-[5-[2-[4-[(2-ethylquinolin-4-yl)oxymethyl]phenyl]phenyl]tetrazol-2-yl]stannane Chemical compound CCCC[Sn](CCCC)(CCCC)N1N=NC(C=2C(=CC=CC=2)C=2C=CC(COC=3C4=CC=CC=C4N=C(CC)C=3)=CC=2)=N1 FMUBFLCMVLZYPU-UHFFFAOYSA-N 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 230000009723 vascular congestion Effects 0.000 description 1
- 210000005166 vasculature Anatomy 0.000 description 1
- 239000005526 vasoconstrictor agent Substances 0.000 description 1
- 229960003726 vasopressin Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB919102727A GB9102727D0 (en) | 1991-02-08 | 1991-02-08 | Pharmaceutical agent |
| GB9102727.6 | 1991-02-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2060825A1 true CA2060825A1 (en) | 1992-08-09 |
Family
ID=10689748
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002060825A Abandoned CA2060825A1 (en) | 1991-02-08 | 1992-02-07 | Therapeutic agent |
Country Status (12)
| Country | Link |
|---|---|
| CN (1) | CN1064809A (zh) |
| AP (1) | AP9200355A0 (zh) |
| AU (1) | AU1189392A (zh) |
| CA (1) | CA2060825A1 (zh) |
| GB (2) | GB9102727D0 (zh) |
| HU (1) | HUT60489A (zh) |
| IE (1) | IE920243A1 (zh) |
| IL (1) | IL100793A0 (zh) |
| MX (1) | MX9200532A (zh) |
| PT (1) | PT100097A (zh) |
| WO (1) | WO1992013853A1 (zh) |
| ZA (1) | ZA92729B (zh) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW297025B (zh) * | 1992-02-14 | 1997-02-01 | Squibb & Sons Inc | |
| US8969514B2 (en) | 2007-06-04 | 2015-03-03 | Synergy Pharmaceuticals, Inc. | Agonists of guanylate cyclase useful for the treatment of hypercholesterolemia, atherosclerosis, coronary heart disease, gallstone, obesity and other cardiovascular diseases |
| EA020466B1 (ru) | 2007-06-04 | 2014-11-28 | Синерджи Фармасьютикалз Инк. | Агонисты гуанилатциклазы, пригодные для лечения желудочно-кишечных нарушений, воспаления, рака и других заболеваний |
| EP2810951B1 (en) | 2008-06-04 | 2017-03-15 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase useful for the treatment of gastrointestinal disorders, inflammation, cancer and other disorders |
| ES2624828T3 (es) | 2008-07-16 | 2017-07-17 | Synergy Pharmaceuticals Inc. | Agonistas de la guanilato ciclasa útiles para el tratamiento de trastornos gastrointestinales, inflamación, cáncer y otros |
| US9616097B2 (en) | 2010-09-15 | 2017-04-11 | Synergy Pharmaceuticals, Inc. | Formulations of guanylate cyclase C agonists and methods of use |
| CA2905438A1 (en) | 2013-03-15 | 2014-09-25 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase and their uses |
| CA2905435A1 (en) | 2013-03-15 | 2014-09-25 | Synergy Pharmaceuticals Inc. | Compositions useful for the treatment of gastrointestinal disorders |
| PT3004138T (pt) | 2013-06-05 | 2024-06-18 | Bausch Health Ireland Ltd | Agonistas ultrapuros de guanilato ciclase c, método de produção e utilização dos mesmos |
| LT3046584T (lt) | 2013-09-16 | 2017-10-10 | Astrazeneca Ab | Terapinės polimerinės nanodalelės ir jų gamybos būdai ir panaudojimas |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4920132A (en) * | 1987-11-03 | 1990-04-24 | Rorer Pharmaceutical Corp. | Quinoline derivatives and use thereof as antagonists of leukotriene D4 |
| NZ234854A (en) * | 1989-08-11 | 1993-02-25 | Ici Plc | Quinoline derivatives, preparation, intermediates and pharmaceutical compositions thereof |
-
1991
- 1991-02-08 GB GB919102727A patent/GB9102727D0/en active Pending
-
1992
- 1992-01-27 IE IE024392A patent/IE920243A1/en unknown
- 1992-01-28 IL IL100793A patent/IL100793A0/xx unknown
- 1992-01-31 ZA ZA92729A patent/ZA92729B/xx unknown
- 1992-02-03 AP APAP/P/1992/000355A patent/AP9200355A0/en unknown
- 1992-02-05 AU AU11893/92A patent/AU1189392A/en not_active Abandoned
- 1992-02-05 WO PCT/GB1992/000214 patent/WO1992013853A1/en active Application Filing
- 1992-02-05 HU HU9200354A patent/HUT60489A/hu unknown
- 1992-02-05 GB GB9202377A patent/GB2252557A/en not_active Withdrawn
- 1992-02-06 PT PT100097A patent/PT100097A/pt not_active Application Discontinuation
- 1992-02-07 MX MX9200532A patent/MX9200532A/es unknown
- 1992-02-07 CA CA002060825A patent/CA2060825A1/en not_active Abandoned
- 1992-02-08 CN CN92101425A patent/CN1064809A/zh active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| AU1189392A (en) | 1992-09-07 |
| CN1064809A (zh) | 1992-09-30 |
| MX9200532A (es) | 1992-08-01 |
| HUT60489A (en) | 1992-09-28 |
| GB9202377D0 (en) | 1992-03-18 |
| HU9200354D0 (en) | 1992-04-28 |
| GB2252557A (en) | 1992-08-12 |
| GB9102727D0 (en) | 1991-03-27 |
| ZA92729B (en) | 1992-11-25 |
| IE920243A1 (en) | 1992-08-12 |
| IL100793A0 (en) | 1992-09-06 |
| PT100097A (pt) | 1993-04-30 |
| AP9200355A0 (en) | 1993-08-03 |
| WO1992013853A1 (en) | 1992-08-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |