AU2010324249B2 - Azilsartan organic amine salts, preparation method and use thereof - Google Patents
Azilsartan organic amine salts, preparation method and use thereof Download PDFInfo
- Publication number
- AU2010324249B2 AU2010324249B2 AU2010324249A AU2010324249A AU2010324249B2 AU 2010324249 B2 AU2010324249 B2 AU 2010324249B2 AU 2010324249 A AU2010324249 A AU 2010324249A AU 2010324249 A AU2010324249 A AU 2010324249A AU 2010324249 B2 AU2010324249 B2 AU 2010324249B2
- Authority
- AU
- Australia
- Prior art keywords
- organic amine
- azilsartan
- amine salt
- preparation
- amine salts
- 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.)
- Ceased
Links
- 239000005485 Azilsartan Substances 0.000 title claims abstract description 30
- KGSXMPPBFPAXLY-UHFFFAOYSA-N azilsartan Chemical compound CCOC1=NC2=CC=CC(C(O)=O)=C2N1CC(C=C1)=CC=C1C1=CC=CC=C1C1=NOC(=O)N1 KGSXMPPBFPAXLY-UHFFFAOYSA-N 0.000 title claims abstract description 30
- 229960002731 azilsartan Drugs 0.000 title claims abstract description 30
- -1 amine salts Chemical class 0.000 title claims abstract description 16
- 238000002360 preparation method Methods 0.000 title claims abstract description 13
- 239000003814 drug Substances 0.000 claims abstract description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 7
- 230000003276 anti-hypertensive effect Effects 0.000 claims abstract description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
- 206010020772 Hypertension Diseases 0.000 claims description 9
- 239000004480 active ingredient Substances 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- 229960001231 choline Drugs 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 5
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 238000011282 treatment Methods 0.000 claims description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 230000008569 process Effects 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 2
- 150000003248 quinolines Chemical group 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 abstract description 15
- 229940079593 drug Drugs 0.000 abstract description 8
- 230000036772 blood pressure Effects 0.000 description 17
- 241000282472 Canis lupus familiaris Species 0.000 description 9
- 238000002474 experimental method Methods 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- 239000002552 dosage form Substances 0.000 description 8
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 241001465754 Metazoa Species 0.000 description 6
- 239000004698 Polyethylene Substances 0.000 description 5
- WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 5
- 229920000573 polyethylene Polymers 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 238000001356 surgical procedure Methods 0.000 description 4
- 102000005862 Angiotensin II Human genes 0.000 description 3
- 101800000733 Angiotensin-2 Proteins 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- CZGUSIXMZVURDU-JZXHSEFVSA-N Ile(5)-angiotensin II Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC=1C=CC=CC=1)C([O-])=O)NC(=O)[C@@H](NC(=O)[C@H](CCCNC(N)=[NH2+])NC(=O)[C@@H]([NH3+])CC([O-])=O)C(C)C)C1=CC=C(O)C=C1 CZGUSIXMZVURDU-JZXHSEFVSA-N 0.000 description 3
- 239000004105 Penicillin G potassium Substances 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 229950006323 angiotensin ii Drugs 0.000 description 3
- 229920000609 methyl cellulose Polymers 0.000 description 3
- 239000001923 methylcellulose Substances 0.000 description 3
- 235000010981 methylcellulose Nutrition 0.000 description 3
- 235000019368 penicillin G potassium Nutrition 0.000 description 3
- 229940056360 penicillin g Drugs 0.000 description 3
- 229960001412 pentobarbital Drugs 0.000 description 3
- 239000006187 pill Substances 0.000 description 3
- 229920002635 polyurethane Polymers 0.000 description 3
- 239000004814 polyurethane Substances 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- 210000003462 vein Anatomy 0.000 description 3
- CPKVUHPKYQGHMW-UHFFFAOYSA-N 1-ethenylpyrrolidin-2-one;molecular iodine Chemical compound II.C=CN1CCCC1=O CPKVUHPKYQGHMW-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 210000000709 aorta Anatomy 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000017531 blood circulation Effects 0.000 description 2
- 239000006172 buffering agent Substances 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 210000001105 femoral artery Anatomy 0.000 description 2
- 210000003191 femoral vein Anatomy 0.000 description 2
- 230000001631 hypertensive effect Effects 0.000 description 2
- 239000003701 inert diluent Substances 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 230000005923 long-lasting effect Effects 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 230000002503 metabolic effect Effects 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 230000003389 potentiating effect Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000007920 subcutaneous administration Methods 0.000 description 2
- 230000035488 systolic blood pressure Effects 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- GRWKNBPOGBTZMN-UHFFFAOYSA-N 2-benzyl-3-phenylpropane-1,2-diamine Chemical compound C=1C=CC=CC=1CC(N)(CN)CC1=CC=CC=C1 GRWKNBPOGBTZMN-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 108010064733 Angiotensins Proteins 0.000 description 1
- 102000015427 Angiotensins Human genes 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 239000004381 Choline salt Substances 0.000 description 1
- 241000725101 Clea Species 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 1
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 240000005578 Rivina humilis Species 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 210000001015 abdomen Anatomy 0.000 description 1
- 210000003815 abdominal wall Anatomy 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 230000002421 anti-septic effect Effects 0.000 description 1
- 239000002220 antihypertensive agent Substances 0.000 description 1
- 229940030600 antihypertensive agent Drugs 0.000 description 1
- 229940124572 antihypotensive agent Drugs 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 229940064004 antiseptic throat preparations Drugs 0.000 description 1
- XRWSZZJLZRKHHD-WVWIJVSJSA-N asunaprevir Chemical compound O=C([C@@H]1C[C@H](CN1C(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)(C)C)OC1=NC=C(C2=CC=C(Cl)C=C21)OC)N[C@]1(C(=O)NS(=O)(=O)C2CC2)C[C@H]1C=C XRWSZZJLZRKHHD-WVWIJVSJSA-N 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000007385 chemical modification Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 235000019417 choline salt Nutrition 0.000 description 1
- 229940125773 compound 10 Drugs 0.000 description 1
- 229940125961 compound 24 Drugs 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000001647 drug administration Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002169 ethanolamines Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 229960002897 heparin Drugs 0.000 description 1
- 229920000669 heparin Polymers 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 229960003194 meglumine Drugs 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 210000002464 muscle smooth vascular Anatomy 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000006201 parenteral dosage form Substances 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 230000036470 plasma concentration Effects 0.000 description 1
- 230000002980 postoperative effect Effects 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000036584 pressor response Effects 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000007909 solid dosage form Substances 0.000 description 1
- 238000013222 sprague-dawley male rat Methods 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 239000003206 sterilizing agent Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 238000002627 tracheal intubation Methods 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
- 239000005526 vasoconstrictor agent Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4245—Oxadiazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C215/04—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated
- C07C215/06—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic
- C07C215/08—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic with only one hydroxy group and one amino group bound to the carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Epidemiology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN200910246554.9 | 2009-11-30 | ||
| CN200910246554 | 2009-11-30 | ||
| PCT/CN2010/079222 WO2011063764A1 (zh) | 2009-11-30 | 2010-11-29 | 阿齐沙坦有机胺盐及其制备方法和用途 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2010324249A1 AU2010324249A1 (en) | 2012-05-03 |
| AU2010324249B2 true AU2010324249B2 (en) | 2014-08-28 |
Family
ID=44065877
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2010324249A Ceased AU2010324249B2 (en) | 2009-11-30 | 2010-11-29 | Azilsartan organic amine salts, preparation method and use thereof |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US20120238606A1 (cg-RX-API-DMAC7.html) |
| EP (1) | EP2508522A4 (cg-RX-API-DMAC7.html) |
| JP (1) | JP2013512199A (cg-RX-API-DMAC7.html) |
| CN (1) | CN102548988B (cg-RX-API-DMAC7.html) |
| AU (1) | AU2010324249B2 (cg-RX-API-DMAC7.html) |
| BR (1) | BR112012012484A2 (cg-RX-API-DMAC7.html) |
| CA (1) | CA2782224A1 (cg-RX-API-DMAC7.html) |
| MX (1) | MX2012005776A (cg-RX-API-DMAC7.html) |
| RU (1) | RU2554947C2 (cg-RX-API-DMAC7.html) |
| WO (1) | WO2011063764A1 (cg-RX-API-DMAC7.html) |
| ZA (1) | ZA201202683B (cg-RX-API-DMAC7.html) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102603723B (zh) * | 2011-01-20 | 2014-10-08 | 江苏豪森医药集团有限公司 | 阿齐沙坦有机胺盐及其制备方法和用途 |
| CN103930419B (zh) | 2011-09-30 | 2016-06-01 | 广东东阳光药业有限公司 | 阿齐沙坦的晶型及其制备方法 |
| JP2017036215A (ja) * | 2013-12-27 | 2017-02-16 | トーアエイヨー株式会社 | アンジオテンシンｉｉ受容体拮抗物質の塩 |
| CN105037341B (zh) * | 2014-04-04 | 2019-12-03 | 江苏豪森药业集团有限公司 | 阿齐沙坦醇铵晶型及其制备方法 |
| CN105503848A (zh) * | 2014-10-13 | 2016-04-20 | 江苏豪森药业集团有限公司 | 阿齐沙坦有机胺盐复合物及其制备方法和用途 |
| CZ2014702A3 (cs) | 2014-10-15 | 2016-04-27 | Zentiva, K.S. | Způsob přípravy vysoce čistého azilsartanu |
| KR102220011B1 (ko) * | 2020-05-15 | 2021-02-25 | 대봉엘에스 주식회사 | 친환경 용매를 이용한 아질사탄의 제조방법 및 이에 관한 핵심 중간체 화합물 |
| KR102862852B1 (ko) * | 2022-09-19 | 2025-09-22 | 대봉엘에스 주식회사 | 안지오텐신 ⅱ 길항제로서의 아질사르탄 디시클로헥실아민 및 이를 유효성분으로 하는 심혈관질환 치료 또는 예방용 약학적 조성물 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1452176A1 (en) * | 2001-12-03 | 2004-09-01 | Takeda Chemical Industries, Ltd. | Insulin resistance improving agents |
| WO2006038722A1 (en) * | 2004-10-07 | 2006-04-13 | Takeda Pharmaceutical Company Limited | Agent for prophylaxis or treatment of metabolic syndrome |
| CN101035524A (zh) * | 2004-10-07 | 2007-09-12 | 武田药品工业株式会社 | 预防或治疗代谢综合征的药剂 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA924666B (en) * | 1991-06-27 | 1993-12-24 | Takeda Chemical Industries Ltd | Heterocyclic compounds, their production and use |
| TW251288B (cg-RX-API-DMAC7.html) * | 1991-06-27 | 1995-07-11 | Takeda Dharm Industry Co Ltd | |
| AU2002336267B2 (en) * | 2001-03-08 | 2006-10-05 | Merck & Co., Inc. | Antihypertensive agent and cholesterol absorption inhibitor combination therapy |
| JP4484427B2 (ja) * | 2001-12-03 | 2010-06-16 | 武田薬品工業株式会社 | インスリン抵抗性改善剤 |
| US20090239882A1 (en) * | 2004-12-17 | 2009-09-24 | Astrazeneca Ab | Thiazolopyramidine Compounds for the Modulation of Chemokine Receptor Activity |
-
2010
- 2010-11-29 US US13/512,652 patent/US20120238606A1/en not_active Abandoned
- 2010-11-29 CA CA2782224A patent/CA2782224A1/en not_active Abandoned
- 2010-11-29 MX MX2012005776A patent/MX2012005776A/es not_active Application Discontinuation
- 2010-11-29 CN CN2010800449716A patent/CN102548988B/zh not_active Expired - Fee Related
- 2010-11-29 RU RU2012124332/04A patent/RU2554947C2/ru active
- 2010-11-29 JP JP2012540278A patent/JP2013512199A/ja active Pending
- 2010-11-29 WO PCT/CN2010/079222 patent/WO2011063764A1/zh not_active Ceased
- 2010-11-29 AU AU2010324249A patent/AU2010324249B2/en not_active Ceased
- 2010-11-29 EP EP10832671.1A patent/EP2508522A4/en not_active Withdrawn
- 2010-11-29 BR BR112012012484A patent/BR112012012484A2/pt not_active IP Right Cessation
-
2012
- 2012-04-13 ZA ZA2012/02683A patent/ZA201202683B/en unknown
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1452176A1 (en) * | 2001-12-03 | 2004-09-01 | Takeda Chemical Industries, Ltd. | Insulin resistance improving agents |
| WO2006038722A1 (en) * | 2004-10-07 | 2006-04-13 | Takeda Pharmaceutical Company Limited | Agent for prophylaxis or treatment of metabolic syndrome |
| CN101035524A (zh) * | 2004-10-07 | 2007-09-12 | 武田药品工业株式会社 | 预防或治疗代谢综合征的药剂 |
Also Published As
| Publication number | Publication date |
|---|---|
| CN102548988A (zh) | 2012-07-04 |
| BR112012012484A2 (pt) | 2016-04-12 |
| HK1164310A1 (en) | 2012-09-21 |
| MX2012005776A (es) | 2012-06-13 |
| EP2508522A4 (en) | 2013-05-08 |
| CA2782224A1 (en) | 2011-06-03 |
| WO2011063764A1 (zh) | 2011-06-03 |
| EP2508522A1 (en) | 2012-10-10 |
| AU2010324249A1 (en) | 2012-05-03 |
| CN102548988B (zh) | 2013-10-23 |
| ZA201202683B (en) | 2013-08-28 |
| RU2012124332A (ru) | 2014-01-10 |
| JP2013512199A (ja) | 2013-04-11 |
| US20120238606A1 (en) | 2012-09-20 |
| RU2554947C2 (ru) | 2015-07-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| AU2010324249B2 (en) | Azilsartan organic amine salts, preparation method and use thereof | |
| FI108637B (fi) | Menetelmä lääkeaineena käyttökelpoisen (+)-(S)-2-(3-bentsoyylifenyyli)propaanihapon trometamiinisuolan valmistamiseksi | |
| AU2012255935B2 (en) | Compounds for use in treatment of mucositis | |
| KR20020012169A (ko) | 프로스타글란딘 화합물, 조성물 및 말초혈관질병 및폐고혈압증의 치료방법 | |
| JP2016128481A (ja) | 肺高血圧症の処置のためのニトロキシル供与体 | |
| US7638556B2 (en) | Freeze-dried product of N-[o-(p-pivaloyloxy benzenesulfonylamino)benzoyl]glycine monosodium salt tetra-hydrate and a process for the manufacture thereof | |
| CN107382966B (zh) | 一类荜茇酰胺-川芎嗪杂合物、制备方法及医药用途 | |
| CN103717219B (zh) | 左心室舒张功能改善剂 | |
| RU2600986C2 (ru) | Органические аминные соли азилсартана, способ их получения и применение | |
| JP2019503993A (ja) | テトラサイクリンの塩 | |
| US11008311B2 (en) | Potassium salt of benzimidazole compound and preparation method therefor, composition and application thereof | |
| WO2020185982A9 (en) | Polymorphs and cocrystals of a cardiac troponin activator | |
| JPH04264030A (ja) | 抗喘息剤 | |
| US20070048252A1 (en) | Conjugates of the hydrophilic polymer and the molecules from boxwood extraction, and pharmaceutical compositions of the conjugates | |
| JPS6348217A (ja) | 麻酔薬組成物 | |
| US20140228319A1 (en) | Water soluble salts of aldose reductase inhibitors for treatment of diabetic complications | |
| JP2025534851A (ja) | 複素環化合物、ならびにその調製方法および使用 | |
| HK1164310B (en) | Azilsartan organic amine salts, preparation method and use thereof | |
| AU2016212555A1 (en) | Sunitinib prodrug and pharmaceutical composition | |
| WO2020030648A1 (en) | Tissue transglutaminase modulators for medicinal use | |
| CN101921264A (zh) | 坎地沙坦有机胺盐及其制备方法和用途 | |
| US11413273B2 (en) | Prophylactic or therapeutic agent for pulmonary hypertension comprising unsaturated 5-membered heterocycle-containing compound | |
| US20090062295A1 (en) | Pharmaceutical Products | |
| CN110483372A (zh) | 布比卡因的盐 | |
| US20040048776A1 (en) | Medicament for preventive and therapeutic treatment of fibrosis |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FGA | Letters patent sealed or granted (standard patent) | ||
| MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |