GB1459606A - Phthalazone compounds - Google Patents
Phthalazone compoundsInfo
- Publication number
- GB1459606A GB1459606A GB3870874A GB3870874A GB1459606A GB 1459606 A GB1459606 A GB 1459606A GB 3870874 A GB3870874 A GB 3870874A GB 3870874 A GB3870874 A GB 3870874A GB 1459606 A GB1459606 A GB 1459606A
- Authority
- GB
- United Kingdom
- Prior art keywords
- dimethyl
- phthalazone
- formula
- acid
- diethoxycarbonyl
- 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.)
- Expired
Links
- IJAPPYDYQCXOEF-UHFFFAOYSA-N phthalazin-1(2H)-one Chemical class C1=CC=C2C(=O)NN=CC2=C1 IJAPPYDYQCXOEF-UHFFFAOYSA-N 0.000 title abstract 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 3
- 238000010438 heat treatment Methods 0.000 abstract 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 abstract 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000004494 ethyl ester group Chemical group 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- -1 methylene, ethylidene Chemical group 0.000 abstract 2
- 235000011149 sulphuric acid Nutrition 0.000 abstract 2
- 239000001117 sulphuric acid Substances 0.000 abstract 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 abstract 1
- KHAGPMWRGXECEJ-UHFFFAOYSA-N 1-hydroxy-1,4,6-trimethyl-3-oxo-2-benzofuran-5-carboxylic acid Chemical compound C(=O)(O)C1=C(C=C2C(OC(=O)C2=C1C)(C)O)C KHAGPMWRGXECEJ-UHFFFAOYSA-N 0.000 abstract 1
- PETJMENJXKEBGC-UHFFFAOYSA-N 2,4-bis(ethoxycarbonyl)-3,5-dimethylbenzoic acid Chemical compound CCOC(=O)C1=C(C)C=C(C(O)=O)C(C(=O)OCC)=C1C PETJMENJXKEBGC-UHFFFAOYSA-N 0.000 abstract 1
- WJQIUUAUVMYNQA-UHFFFAOYSA-N 4,6-dimethyl-1,3-dioxo-2-benzofuran-5-carboxylic acid Chemical compound C(=O)(O)C1=C(C=C2C(=C1C)C(=O)OC2=O)C WJQIUUAUVMYNQA-UHFFFAOYSA-N 0.000 abstract 1
- 239000004342 Benzoyl peroxide Substances 0.000 abstract 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 abstract 1
- IVOMOUWHDPKRLL-KQYNXXCUSA-N Cyclic adenosine monophosphate Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=CN=C2N)=C2N=C1 IVOMOUWHDPKRLL-KQYNXXCUSA-N 0.000 abstract 1
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 abstract 1
- 206010020772 Hypertension Diseases 0.000 abstract 1
- 208000007536 Thrombosis Diseases 0.000 abstract 1
- IVOMOUWHDPKRLL-UHFFFAOYSA-N UNPD107823 Natural products O1C2COP(O)(=O)OC2C(O)C1N1C(N=CN=C2N)=C2N=C1 IVOMOUWHDPKRLL-UHFFFAOYSA-N 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 230000003143 atherosclerotic effect Effects 0.000 abstract 1
- 235000019400 benzoyl peroxide Nutrition 0.000 abstract 1
- 229940095074 cyclic amp Drugs 0.000 abstract 1
- 150000005690 diesters Chemical class 0.000 abstract 1
- WAYWGPOOTWZAIT-UHFFFAOYSA-N diethyl 4-carbonochloridoyl-2,6-dimethylbenzene-1,3-dicarboxylate Chemical compound CC=1C=C(C(=O)Cl)C(=C(C1C(=O)OCC)C)C(=O)OCC WAYWGPOOTWZAIT-UHFFFAOYSA-N 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- 201000010099 disease Diseases 0.000 abstract 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 230000001631 hypertensive effect Effects 0.000 abstract 1
- 229910001507 metal halide Inorganic materials 0.000 abstract 1
- 150000005309 metal halides Chemical class 0.000 abstract 1
- 238000007911 parenteral administration Methods 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/87—Benzo [c] furans; Hydrogenated benzo [c] furans
- C07D307/89—Benzo [c] furans; Hydrogenated benzo [c] furans with two oxygen atoms directly attached in positions 1 and 3
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12126073A JPS5732065B2 (https=) | 1973-10-30 | 1973-10-30 | |
| JP12175773A JPS5724786B2 (https=) | 1973-10-31 | 1973-10-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1459606A true GB1459606A (en) | 1976-12-22 |
Family
ID=26458679
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3870874A Expired GB1459606A (en) | 1973-10-30 | 1974-09-04 | Phthalazone compounds |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US3963716A (https=) |
| AR (1) | AR205004A1 (https=) |
| CA (1) | CA1029377A (https=) |
| CH (2) | CH611282A5 (https=) |
| DD (1) | DD119231A5 (https=) |
| DE (1) | DE2451417C3 (https=) |
| DK (1) | DK134345B (https=) |
| ES (1) | ES431454A1 (https=) |
| FI (1) | FI59402C (https=) |
| FR (1) | FR2248841B1 (https=) |
| GB (1) | GB1459606A (https=) |
| HU (1) | HU168797B (https=) |
| IE (1) | IE39831B1 (https=) |
| IL (1) | IL45675A (https=) |
| IN (1) | IN139552B (https=) |
| LU (1) | LU71191A1 (https=) |
| NL (1) | NL7414186A (https=) |
| PH (1) | PH10519A (https=) |
| SE (1) | SE412389B (https=) |
| YU (1) | YU289774A (https=) |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4120960A (en) * | 1973-10-31 | 1978-10-17 | The Boots Company Limited | Therapeutic agents |
| NL7702763A (nl) * | 1976-03-18 | 1977-09-20 | Takio Shimamoto En Masayuki Is | Werkwijze voor de bereiding van thromboxaan- -antagonisten en van preparaten die deze stof- fen bevatten. |
| IE47592B1 (en) * | 1977-12-29 | 1984-05-02 | Ici Ltd | Enzyme inhibitory phthalazin-4-ylacetic acid derivatives, pharmaceutical compositions thereof,and process for their manufacture |
| US4293553A (en) * | 1978-08-11 | 1981-10-06 | Masayuki Ishikawa | 1-Phthalazone derivatives, and use thereof |
| US4464532A (en) * | 1979-07-31 | 1984-08-07 | Nippon Kayaku Kabushiki Kaisha | Intermediates of 7-alkoxycarbonyl-6,8-dimethyl-4-hydroxymethyl-1-phthalazone |
| JPS5668609A (en) * | 1979-11-07 | 1981-06-09 | Nippon Kayaku Co Ltd | Phthalazinol preparation |
| JPS58116471A (ja) * | 1981-12-29 | 1983-07-11 | Nippon Kayaku Co Ltd | ４−ヒドロキシメチル−１−フタラゾンエステル誘導体およびその塩 |
| GB2127805A (en) * | 1982-09-13 | 1984-04-18 | Showa Denko Kk | Phthalazones |
| US4861778A (en) * | 1986-06-16 | 1989-08-29 | Research Corporation | 2,3-dihydrophthalazine-1,4-diones |
| CA1334969C (en) * | 1988-08-19 | 1995-03-28 | Mark James Suto | Substituted dihydroisoquinoline and phthalazine derivatives as potentiators of the lethal effects of radiation and certain chemotherapeutic agents, selected compounds, analogs andprocess |
| US5177075A (en) * | 1988-08-19 | 1993-01-05 | Warner-Lambert Company | Substituted dihydroisoquinolinones and related compounds as potentiators of the lethal effects of radiation and certain chemotherapeutic agents; selected compounds, analogs and process |
| DE4333761A1 (de) * | 1993-10-04 | 1995-04-06 | Luitpold Pharma Gmbh | Heterocyclische Carbamate, Verfahren zu ihrer Herstellung und Arzneimittel |
| RU2169139C1 (ru) * | 2000-08-02 | 2001-06-20 | Закрытое акционерное общество "Центр современной медицины "Медикор" | Способ получения щелочных и щелочноземельных солей 5-амино-2,3-дигидро-1,4-фталазиндиона |
| US7772188B2 (en) | 2003-01-28 | 2010-08-10 | Ironwood Pharmaceuticals, Inc. | Methods and compositions for the treatment of gastrointestinal disorders |
| EP2527360B1 (en) | 2007-06-04 | 2015-10-28 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase useful for the treatment of gastrointestinal disorders, inflammation, cancer and other disorders |
| 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 |
| 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 |
| EP3241839B1 (en) | 2008-07-16 | 2019-09-04 | Bausch Health Ireland Limited | Agonists of guanylate cyclase useful for the treatment of gastrointestinal, inflammation, cancer and other disorders |
| KR101701943B1 (ko) | 2009-11-13 | 2017-02-02 | 도레이 카부시키가이샤 | 당뇨병의 치료 또는 예방약 |
| US9616097B2 (en) | 2010-09-15 | 2017-04-11 | Synergy Pharmaceuticals, Inc. | Formulations of guanylate cyclase C agonists and methods of use |
| ES2664873T3 (es) | 2011-03-01 | 2018-04-23 | Synergy Pharmaceuticals Inc. | Proceso de preparación de agonistas de guanilato ciclasa C |
| US9545446B2 (en) | 2013-02-25 | 2017-01-17 | 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 |
| CA2905438A1 (en) | 2013-03-15 | 2014-09-25 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase and their uses |
| SI3004138T1 (sl) | 2013-06-05 | 2024-07-31 | Bausch Health Ireland Limited | Ultra čisti agonisti gvanilat ciklaze C, postopek za njihovo pripravo in uporabo |
| KR102456567B1 (ko) | 2013-08-09 | 2022-10-19 | 알데릭스, 인코포레이티드 | 인산염 수송을 억제하기 위한 화합물 및 방법 |
| WO2020237096A1 (en) | 2019-05-21 | 2020-11-26 | Ardelyx, Inc. | Combination for lowering serum phosphate in a patient |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5116430B2 (https=) * | 1971-08-05 | 1976-05-24 | ||
| US3870792A (en) * | 1972-07-24 | 1975-03-11 | Michiro Inoue | Certain dihydrophthalizines for treating hemorrhage and thrombosis |
-
1974
- 1974-01-01 AR AR256326A patent/AR205004A1/es active
- 1974-09-03 IE IE1825/74A patent/IE39831B1/en unknown
- 1974-09-04 GB GB3870874A patent/GB1459606A/en not_active Expired
- 1974-09-10 US US05/504,745 patent/US3963716A/en not_active Expired - Lifetime
- 1974-09-16 IL IL45675A patent/IL45675A/xx unknown
- 1974-10-23 FR FR7435550A patent/FR2248841B1/fr not_active Expired
- 1974-10-24 CA CA212,163A patent/CA1029377A/en not_active Expired
- 1974-10-28 DK DK561874AA patent/DK134345B/da not_active IP Right Cessation
- 1974-10-28 LU LU71191A patent/LU71191A1/xx unknown
- 1974-10-28 SE SE7413530A patent/SE412389B/xx not_active IP Right Cessation
- 1974-10-29 YU YU02897/74A patent/YU289774A/xx unknown
- 1974-10-29 ES ES431454A patent/ES431454A1/es not_active Expired
- 1974-10-29 HU HUIO218A patent/HU168797B/hu unknown
- 1974-10-29 DE DE2451417A patent/DE2451417C3/de not_active Expired
- 1974-10-29 FI FI3157/74A patent/FI59402C/fi active
- 1974-10-30 CH CH497878A patent/CH611282A5/xx not_active IP Right Cessation
- 1974-10-30 PH PH16465A patent/PH10519A/en unknown
- 1974-10-30 CH CH1454674A patent/CH610892A5/xx not_active IP Right Cessation
- 1974-10-30 DD DD182046A patent/DD119231A5/xx unknown
- 1974-10-30 NL NL7414186A patent/NL7414186A/xx not_active Application Discontinuation
-
1976
- 1976-02-25 IN IN330/CAL/76A patent/IN139552B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IE39831B1 (en) | 1979-01-03 |
| IL45675A (en) | 1978-10-31 |
| DK561874A (https=) | 1975-07-07 |
| FI59402C (fi) | 1981-08-10 |
| PH10519A (en) | 1977-05-26 |
| IE39831L (en) | 1975-04-30 |
| DE2451417C3 (de) | 1981-01-29 |
| FR2248841B1 (https=) | 1978-07-28 |
| FI59402B (fi) | 1981-04-30 |
| AR205004A1 (es) | 1976-03-31 |
| IN139552B (https=) | 1976-07-03 |
| DK134345C (https=) | 1977-03-21 |
| IL45675A0 (en) | 1974-11-29 |
| DK134345B (da) | 1976-10-25 |
| US3963716A (en) | 1976-06-15 |
| YU289774A (en) | 1983-01-21 |
| FR2248841A1 (https=) | 1975-05-23 |
| DE2451417B2 (de) | 1980-05-14 |
| LU71191A1 (https=) | 1975-04-17 |
| CA1029377A (en) | 1978-04-11 |
| CH611282A5 (https=) | 1979-05-31 |
| SE7413530L (https=) | 1975-05-02 |
| ES431454A1 (es) | 1976-10-16 |
| DE2451417A1 (de) | 1975-05-07 |
| HU168797B (https=) | 1976-07-28 |
| FI315774A7 (https=) | 1975-05-01 |
| SE412389B (sv) | 1980-03-03 |
| NL7414186A (nl) | 1975-05-02 |
| AU7295474A (en) | 1976-03-11 |
| CH610892A5 (https=) | 1979-05-15 |
| DD119231A5 (https=) | 1976-04-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |