SK282736B6 - Spôsob prípravy amlodipín benzénsulfonátu - Google Patents
Spôsob prípravy amlodipín benzénsulfonátu Download PDFInfo
- Publication number
- SK282736B6 SK282736B6 SK1698-99A SK169899A SK282736B6 SK 282736 B6 SK282736 B6 SK 282736B6 SK 169899 A SK169899 A SK 169899A SK 282736 B6 SK282736 B6 SK 282736B6
- Authority
- SK
- Slovakia
- Prior art keywords
- amlodipine
- benzenesulfonate
- water
- preparation
- mixture
- Prior art date
Links
- ZPBWCRDSRKPIDG-UHFFFAOYSA-N amlodipine benzenesulfonate Chemical compound OS(=O)(=O)C1=CC=CC=C1.CCOC(=O)C1=C(COCCN)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1Cl ZPBWCRDSRKPIDG-UHFFFAOYSA-N 0.000 title claims abstract description 45
- 238000000034 method Methods 0.000 title claims abstract description 23
- 230000008569 process Effects 0.000 title claims abstract description 16
- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- 239000000203 mixture Substances 0.000 claims abstract description 14
- -1 alkali metal benzenesulphonate Chemical class 0.000 claims abstract description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 5
- 239000012736 aqueous medium Substances 0.000 claims abstract description 4
- 150000007522 mineralic acids Chemical class 0.000 claims abstract description 3
- 150000007524 organic acids Chemical class 0.000 claims abstract description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 13
- 229940077386 sodium benzenesulfonate Drugs 0.000 claims description 13
- MZSDGDXXBZSFTG-UHFFFAOYSA-M sodium;benzenesulfonate Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC=C1 MZSDGDXXBZSFTG-UHFFFAOYSA-M 0.000 claims description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical group CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 5
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 claims description 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 3
- 229910002651 NO3 Inorganic materials 0.000 claims description 3
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 3
- 229940077388 benzenesulfonate Drugs 0.000 claims description 3
- FOCAUTSVDIKZOP-UHFFFAOYSA-M chloroacetate Chemical compound [O-]C(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-M 0.000 claims description 3
- 229940089960 chloroacetate Drugs 0.000 claims description 3
- 229960000528 amlodipine Drugs 0.000 abstract description 15
- 150000003839 salts Chemical class 0.000 abstract description 7
- 239000003814 drug Substances 0.000 abstract description 3
- 208000037849 arterial hypertension Diseases 0.000 abstract description 2
- 208000029078 coronary artery disease Diseases 0.000 abstract description 2
- 230000008061 calcium-channel-blocking effect Effects 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 8
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- 239000002244 precipitate Substances 0.000 description 6
- 229940092714 benzenesulfonic acid Drugs 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- SWKVSFPUHCMFJY-UHFFFAOYSA-N 6-methyl-2-oxo-5-pyridin-4-yl-1h-pyridine-3-carboxamide Chemical compound N1C(=O)C(C(N)=O)=CC(C=2C=CN=CC=2)=C1C SWKVSFPUHCMFJY-UHFFFAOYSA-N 0.000 description 1
- 229940127291 Calcium channel antagonist Drugs 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 201000001068 Prinzmetal angina Diseases 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 208000009325 Variant Angina Pectoris Diseases 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- HTIQEAQVCYTUBX-UHFFFAOYSA-N amlodipine Chemical compound CCOC(=O)C1=C(COCCN)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1Cl HTIQEAQVCYTUBX-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 210000002565 arteriole Anatomy 0.000 description 1
- WWLOCCUNZXBJFR-UHFFFAOYSA-N azanium;benzenesulfonate Chemical compound [NH4+].[O-]S(=O)(=O)C1=CC=CC=C1 WWLOCCUNZXBJFR-UHFFFAOYSA-N 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000000480 calcium channel blocker Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 210000004351 coronary vessel Anatomy 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 229940126601 medicinal product Drugs 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/80—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D211/84—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen directly attached to ring carbon atoms
- C07D211/90—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL98325757A PL189666B1 (pl) | 1998-04-09 | 1998-04-09 | Sposób otrzymywania benzenosulfonianu amlodypiny |
| PCT/PL1999/000011 WO1999052873A1 (en) | 1998-04-09 | 1999-04-08 | A process for the preparation of amlodipine benzenesulphonate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SK169899A3 SK169899A3 (en) | 2000-06-12 |
| SK282736B6 true SK282736B6 (sk) | 2002-11-06 |
Family
ID=20071938
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK1698-99A SK282736B6 (sk) | 1998-04-09 | 1999-04-08 | Spôsob prípravy amlodipín benzénsulfonátu |
Country Status (15)
| Country | Link |
|---|---|
| EP (1) | EP0993447B1 (cs) |
| KR (1) | KR100323244B1 (cs) |
| CN (1) | CN1122023C (cs) |
| AT (1) | ATE302187T1 (cs) |
| AU (1) | AU3061399A (cs) |
| CZ (1) | CZ295311B6 (cs) |
| DE (1) | DE69926704D1 (cs) |
| ES (1) | ES2245823T3 (cs) |
| HU (1) | HUP0003300A3 (cs) |
| PL (1) | PL189666B1 (cs) |
| PT (1) | PT993447E (cs) |
| RU (1) | RU2177000C2 (cs) |
| SK (1) | SK282736B6 (cs) |
| UA (1) | UA57091C2 (cs) |
| WO (1) | WO1999052873A1 (cs) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1309558A1 (en) | 2000-12-29 | 2003-05-14 | Synthon Licensing, Ltd. | Aspartate derivative of amlodipine as calcium channel antagonist |
| EP1309556B1 (en) | 2000-12-29 | 2004-11-24 | Pfizer Limited | Amlodipine fumarate |
| WO2002054062A2 (en) | 2000-12-29 | 2002-07-11 | Pfizer Limited | Reference standards and processes for determining the purity or stability of amlodipine maleate |
| OA13133A (en) * | 2000-12-29 | 2006-12-13 | Pfizer Ltd | Process for making amlodipine maleate. |
| AT5874U1 (de) | 2000-12-29 | 2003-01-27 | Bioorg Bv | Pharmazeutische zubereitungen enthaltend amlodipinmaleat |
| US7335380B2 (en) | 2000-12-29 | 2008-02-26 | Synthon Ip Inc. | Amlodipine free base |
| RS53403A (en) * | 2000-12-29 | 2006-10-27 | Pfizer Limited | Process for making amlodipine maleate |
| US6653481B2 (en) | 2000-12-29 | 2003-11-25 | Synthon Bv | Process for making amlodipine |
| WO2002053541A1 (en) | 2000-12-29 | 2002-07-11 | Pfizer Limited | Amide derivative of amlodipine |
| ATE315026T1 (de) | 2000-12-29 | 2006-02-15 | Pfizer Ltd | Amlodipin-hemimaleat |
| MXPA03005882A (es) | 2000-12-29 | 2005-04-19 | Pfizer Ltd | Derivado amida de amlodipina. |
| DE50112189D1 (de) * | 2001-01-09 | 2007-04-26 | Siegfried Generics Int Ag | Salze von Amlodipin-Mesylat |
| DE60235101D1 (de) | 2001-07-06 | 2010-03-04 | Lek Pharmaceuticals | Verfahren zur herstellung hochreines amlodipinbenzolsulfonat |
| US6680334B2 (en) | 2001-08-28 | 2004-01-20 | Pfizer Inc | Crystalline material |
| AR037565A1 (es) * | 2001-11-21 | 2004-11-17 | Synthon Bv | Formas de sales de amlodipina y procedimientos para prepararlas. |
| KR100462304B1 (ko) | 2002-07-30 | 2004-12-17 | 씨제이 주식회사 | 암로디핀의 유기산염 |
| KR100538641B1 (ko) | 2002-07-30 | 2005-12-22 | 씨제이 주식회사 | 암로디핀의 유기산염 |
| KR100496436B1 (ko) | 2002-07-30 | 2005-06-20 | 씨제이 주식회사 | 암로디핀의 유기산염 |
| KR100467669B1 (ko) * | 2002-08-21 | 2005-01-24 | 씨제이 주식회사 | 암로디핀의 유기산염 |
| US6784297B2 (en) | 2002-09-04 | 2004-08-31 | Kopran Limited | Process for the preparation of anti-ischemic and anti-hypertensive drug amlodipine besylate |
| WO2004026834A1 (en) * | 2002-09-19 | 2004-04-01 | Cj Corporation | Crystalline organic acid salt of amlodipine |
| US20060030602A1 (en) * | 2004-03-16 | 2006-02-09 | Sepracor Inc. | (S)-amlodipine malate |
| CN100391946C (zh) * | 2006-05-26 | 2008-06-04 | 苏州东瑞制药有限公司 | 一种苯磺酸氨氯地平的制备方法 |
| KR100913791B1 (ko) * | 2006-07-21 | 2009-08-26 | 한미약품 주식회사 | (ｓ)-(-)-암로디핀 캠실레이트 또는 이의 수화물 및 이를함유하는 약학적 조성물 |
| PL236001B1 (pl) | 2012-12-21 | 2020-11-30 | Adamed Spolka Z Ograniczona Odpowiedzialnoscia | Złożona kompozycja farmaceutyczna zawierająca kandesartan cyleksetylu oraz amlodypinę, sposób jej wytwarzania oraz jednostkowa postać dawkowania zawierająca tę kompozycję |
| CN103044314A (zh) * | 2013-01-06 | 2013-04-17 | 先声药业有限公司 | 马来酸氨氯地平的制备方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8608335D0 (en) * | 1986-04-04 | 1986-05-08 | Pfizer Ltd | Pharmaceutically acceptable salts |
| SI9200344B (sl) * | 1992-11-26 | 1998-06-30 | Lek, | Postopek za pripravo amlodipin benzensulfonata |
-
1998
- 1998-04-09 PL PL98325757A patent/PL189666B1/pl unknown
-
1999
- 1999-04-08 WO PCT/PL1999/000011 patent/WO1999052873A1/en active IP Right Grant
- 1999-04-08 RU RU2000100282/04A patent/RU2177000C2/ru not_active IP Right Cessation
- 1999-04-08 HU HU0003300A patent/HUP0003300A3/hu unknown
- 1999-04-08 ES ES99912189T patent/ES2245823T3/es not_active Expired - Lifetime
- 1999-04-08 SK SK1698-99A patent/SK282736B6/sk not_active IP Right Cessation
- 1999-04-08 CZ CZ19994669A patent/CZ295311B6/cs not_active IP Right Cessation
- 1999-04-08 AU AU30613/99A patent/AU3061399A/en not_active Abandoned
- 1999-04-08 CN CN99800509A patent/CN1122023C/zh not_active Expired - Fee Related
- 1999-04-08 AT AT99912189T patent/ATE302187T1/de not_active IP Right Cessation
- 1999-04-08 DE DE69926704T patent/DE69926704D1/de not_active Expired - Lifetime
- 1999-04-08 EP EP99912189A patent/EP0993447B1/en not_active Expired - Lifetime
- 1999-04-08 KR KR1019997011291A patent/KR100323244B1/ko not_active Expired - Fee Related
- 1999-04-08 PT PT99912189T patent/PT993447E/pt unknown
- 1999-08-04 UA UA2000010042A patent/UA57091C2/uk unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CN1122023C (zh) | 2003-09-24 |
| CZ295311B6 (cs) | 2005-07-13 |
| PL325757A1 (en) | 1999-10-11 |
| ATE302187T1 (de) | 2005-09-15 |
| SK169899A3 (en) | 2000-06-12 |
| ES2245823T3 (es) | 2006-01-16 |
| EP0993447B1 (en) | 2005-08-17 |
| CZ466999A3 (cs) | 2000-04-12 |
| CN1263525A (zh) | 2000-08-16 |
| RU2177000C2 (ru) | 2001-12-20 |
| WO1999052873A1 (en) | 1999-10-21 |
| HUP0003300A2 (en) | 2001-03-28 |
| KR20010013297A (ko) | 2001-02-26 |
| AU3061399A (en) | 1999-11-01 |
| HUP0003300A3 (en) | 2002-11-28 |
| DE69926704D1 (de) | 2005-09-22 |
| UA57091C2 (uk) | 2003-06-16 |
| KR100323244B1 (ko) | 2002-02-19 |
| PT993447E (pt) | 2005-10-31 |
| PL189666B1 (pl) | 2005-09-30 |
| EP0993447A1 (en) | 2000-04-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Patent lapsed due to non-payment of maintenance fees |
Effective date: 20100408 |