PL192097B1 - 4-(2-chloroetoksy)-acetylooctan etylu, 4-(2-jodoetoksy)-acetylooctan etylu, 4-(2-chloroetoksy)-2-(2-chlorobenzylideno)-acetylooctan etylu i 4-(2-jodoetoksy)-2-(2-chlorobenzylideno)-acetylooctan etylu - Google Patents
4-(2-chloroetoksy)-acetylooctan etylu, 4-(2-jodoetoksy)-acetylooctan etylu, 4-(2-chloroetoksy)-2-(2-chlorobenzylideno)-acetylooctan etylu i 4-(2-jodoetoksy)-2-(2-chlorobenzylideno)-acetylooctan etyluInfo
- Publication number
- PL192097B1 PL192097B1 PL375449A PL37544998A PL192097B1 PL 192097 B1 PL192097 B1 PL 192097B1 PL 375449 A PL375449 A PL 375449A PL 37544998 A PL37544998 A PL 37544998A PL 192097 B1 PL192097 B1 PL 192097B1
- Authority
- PL
- Poland
- Prior art keywords
- ethyl
- acetoacetate
- iodoetoxy
- chloroetoxy
- chlorobenzylidene
- Prior art date
Links
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 title claims description 11
- WDJHALXBUFZDSR-UHFFFAOYSA-M acetoacetate Chemical compound CC(=O)CC([O-])=O WDJHALXBUFZDSR-UHFFFAOYSA-M 0.000 title 4
- RZLNMUWYERBPLK-UHFFFAOYSA-N CCOC(CC(C=CC(C=CC(OCCI)=C1)=C1Cl)=O)=O Chemical compound CCOC(CC(C=CC(C=CC(OCCI)=C1)=C1Cl)=O)=O RZLNMUWYERBPLK-UHFFFAOYSA-N 0.000 claims description 3
- MVEHLCXZIFKFGT-UHFFFAOYSA-N OC(CC(C=CC(C=CC(OCCCl)=C1)=C1Cl)=O)=O Chemical compound OC(CC(C=CC(C=CC(OCCCl)=C1)=C1Cl)=O)=O MVEHLCXZIFKFGT-UHFFFAOYSA-N 0.000 claims description 2
- RSBOYMJARBOYMP-UHFFFAOYSA-N ethyl 2-[(2-chlorophenyl)methylidene]-4-(2-iodoethoxy)-3-oxobutanoate Chemical compound ICCOCC(=O)C(C(=O)OCC)=CC1=CC=CC=C1Cl RSBOYMJARBOYMP-UHFFFAOYSA-N 0.000 abstract 1
- ZEYZVDNRETZDPT-UHFFFAOYSA-N ethyl 4-(2-chloroethoxy)-2-[(2-chlorophenyl)methylidene]-3-oxobutanoate Chemical compound ClCCOCC(=O)C(C(=O)OCC)=CC1=CC=CC=C1Cl ZEYZVDNRETZDPT-UHFFFAOYSA-N 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 238000000921 elemental analysis Methods 0.000 description 4
- GIGQADAFYQQKLX-UHFFFAOYSA-N ethyl 4-(2-chloroethoxy)-3-oxobutanoate Chemical compound CCOC(=O)CC(=O)COCCCl GIGQADAFYQQKLX-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- FPYUJUBAXZAQNL-UHFFFAOYSA-N 2-chlorobenzaldehyde Chemical compound ClC1=CC=CC=C1C=O FPYUJUBAXZAQNL-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- RAIYODFGMLZUDF-UHFFFAOYSA-N piperidin-1-ium;acetate Chemical compound CC([O-])=O.C1CC[NH2+]CC1 RAIYODFGMLZUDF-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 1
- -1 3-ethyl-5-methyl-2- (2-aminoethoxy-methyl) -4- (2-chloro-phenyl) -6-methyl-benzenesulfonate Chemical compound 0.000 description 1
- FOOZJOPUAHMPQR-UHFFFAOYSA-N CCOC(CC(C=CC(C=CC(OCCCl)=C1)=C1Cl)=O)=O Chemical compound CCOC(CC(C=CC(C=CC(OCCCl)=C1)=C1Cl)=O)=O FOOZJOPUAHMPQR-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 229960000528 amlodipine Drugs 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
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- MPFLRYZEEAQMLQ-UHFFFAOYSA-N dinicotinic acid Chemical compound OC(=O)C1=CN=CC(C(O)=O)=C1 MPFLRYZEEAQMLQ-UHFFFAOYSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- LLKNNWAVRRHMMC-UHFFFAOYSA-N ethyl 4-(2-iodoethoxy)-3-oxobutanoate Chemical compound CCOC(=O)CC(=O)COCCI LLKNNWAVRRHMMC-UHFFFAOYSA-N 0.000 description 1
- RQCOPVYEHVOEMR-UHFFFAOYSA-N ethyl 4-ethoxy-3-oxobutanoate Chemical class CCOCC(=O)CC(=O)OCC RQCOPVYEHVOEMR-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/67—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids
- C07C69/716—Esters of keto-carboxylic acids or aldehydo-carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
- C07C69/738—Esters of keto-carboxylic acids or aldehydo-carboxylic acids
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Hydrogenated Pyridines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
1. 4-(2-chloroetoksy)-acetylooctan etylu (I). 2. 4-(2-jodoetoksy)-acetylooctan etylu (II). 2. 4-(2-chloroetoksy)-2-(2-chlorobenzylideno)-acetylooctan etylu (III). 3. 4-(2-jodoetoksy)-2-(2-chlorobenzylideno)-acetylooctan etylu (IV). PL PL PL PL PL PL PL
Description
Opis wynalazku
Przedmiotem wynalazku są nowe związki, będące pochodnymi etoksy-acetylooctanu etylu, powstające w czasie otrzymywania benzenosulfonianu 3-etylo-5-metylo-2-(2-aminoetoksy-metylo)-4-(2-chloro-fenylo)-6-metylo-1,4-dwuwodoropirydyno-3,5-dwukarboksylanu sposobem opisanym w węgierskim głoszeniu wynalazku HU9701379. Związek ten jest znanym aktywnym składnikiem leków, posiadającym nazwę międzynarodową (INN) benzenosulfonian amlodypiny.
Nowymi związkami, stanowiącymi przedmiot wynalazku są:
4-(2-chloroetoksy)-acetylooctan etylu (I).
4-(2-jodoetoksy)-acetylooctan etylu (II).
4-(2-chloroetoksy)-2-(2-chlorobenzylideno)-acetylooctan etylu (III).
4-(2-jodo-etoksy)-2-(2-chloro-benzylideno)-acetylooctan etylu (IV).
oraz ich izomery optyczne (prawo- i lewo- skrętne izomery) i ich mieszaniny (włącznie z mieszaninami racemicznymi). Poniższe przykłady przedstawiają sposoby otrzymywania związków według wynalazku, nie wyczerpując wszystkich możliwości.
P r z y k ł a d 1.
Otrzymywanie 4-(2-chloroetoksy)-acetylooctanu etylu (I)
Do 10,38 g (0,25 mola) 5,8% wodorku sodu dodaje się 110 ml czterowodorofuranu. Mieszaninę schładza się do temperatury pomiędzy -10°C a -20°C, po czym w temperaturze tej dodaje się kroplami etylenochlorohydrynę w atmosferze azotu. Mieszaninę miesza się przez 20 minut, po czym w tej samej temperaturze dodaje się roztwór 26,18 g (0,125 mola) 4-bromoacetylooctanu etylu i 35 ml czterowodorofuranu. Mieszaninę reakcyjną miesza się przez 20 minut, pozostawia do ogrzania do temperatury pokojowej, trzyma w tej temperaturze przez 6 godzin, wlewa do 270 ml 1 N kwasu solnego z równoczesnym chłodzeniem i poddaje ekstrakcji przy użyciu dwuchlorometanu. Warstwę organiczną osusza się i odparowuje. Oleistą pozostałość uwalnia się od parafiny przez potraktowanie mieszaniną 1:1 acetonitrylu i benzenu. Produkt oddestylowuje się in vacuo.
W ten sposób otrzymuje się 17,47 g pożądanego związku, wydajność 67%, temperatura wrzenia: 110°C/2,7 hPa.
Analiza elementarna: dla wzoru C8H13CIO4 (208.41)
Obliczone: C 46,05% H 6,28% C I 16,99%
Otrzymane: C 46,45% H6,11% C 16,,52%
P r z y k ł a d 2.
Otrzymywanie 4-(2-jodoetoksy)-acetylooctanu etylu (II)
Do mieszaniny 19 g (91 milimoli) 4-(2-chloroetoksy)-acetylooctanu etylu (I) i 380 ml acetonu dodano 134,4 g (910 milimoli) jodku sodowego. Mieszaninę reakcyjną ogrzewano do wrzenia przez 13 godzin. Substancje nieorganiczne odsączono, a filtrat odparowano in vacuo. Olej pozostałościowy rozpuszczono w dwuchlorometanie, roztwór przemyto wodą, suszono i odparowano. Produkt w stanie surowym poddano destylacji frakcyjnej in vacuo.
Temperatura wrzenia: 170°C/13,3 Pa. W ten sposób otrzymano się 18,3 g pożądanego produktu, wydajność 67%.
Analiza elementarna: dla wzoru C8H13lO4 (300.091)
Obliczone: C 32,02% H 4,37%
Otrzymane: C 31,86% H 4,36%
P r z y k ł a d 3.
Otrzymywanie 4-(2-chloroetoksy)-2-(2-chlorobenzylideno)-acetylooctanu etylu(III).
16,64 g (0,118 milimola) 2-chloro-benzaldehydu i 24,7 g (0,118 mola) 4-(2-chloroetoksy)-acetylooctanu etylu (I) poddano reakcji z 365 ml izopropanolu w obecności octanu piperydyny jako katalizatora [10 g (11,8 milimola) piperydyny + 0,7 g (11,8 milimola) kwasu octowego] w temperaturze pokojowej przez 10 godzin. Mieszaninę reakcyjną odparowano, pozostałościowy olej rozpuszczono w dwuchlorometanie, przemyto wodą i osuszono. Fazę organiczną odparowano w próżni. W ten sposób otrzymano 37,9 g pożądanego produktu w formie żółtego oleju, wydajność 97%.
Analiza elementarna: dla wzoru C15H16CfO4 (331.203)
Obliczone: C 54,39% H 4,87% C 2 21.41%
Otrzymane: C 53,69% H 5,03% 0^^,,8%%
PL 192 097 B1
P r z y k ł a d 4.
Otrzymywanie 4-(2-jodo-etoksy)-2-(2-chloro-benzylideno)-acetylooctanu etylu (IV) g (33 milimole) 4-(2-jodoetoksy)-acetylooctanu etylu (II) i 4,64 g (33 milimole) 2-chlorobenzaldehydu poddano reakcji z 100 ml izopropanolu w obecności octanu piperydyny [0,28 g (3,3 milimola) piperydyny + 0,198 g (3,3 milimola) kwasu octowego] jako katalizatora, w temperaturze pokojowej przez 10 godzin. Mieszaninę reakcyjną odparowano, oleistą pozostałość rozpuszczono w dwuchlorometanie, przemyto wodą i osuszono. Fazę organiczną odparowano w próżni. W ten sposób otrzymano 11,55 g pożądanego produktu w postaci czerwonawo brązowego oleju, wydajność 83%.
Analiza elementarna: dla wzoru C15H16CIIO4 (422.643)
Obliczone: C 42,63% H 3,82% C I 8,39%
Otrzymane: C 43,00% H4,12% C 118,13%
Claims (4)
1.4-(2-chloroetoksy)-acetylooctan etylu (I).
2. 4-(2-chloroetoksy)-2-(2-chlorobenzylideno)-acetylooctan etylu (III).
2. 4-(2-jodoetoksy)-acetylooctan etylu (II).
3.
4-(2-jodoetoksy)-2-(2-chlorobenzylideno)-acetylooctan etylu (IV).
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU9701379A HU221810B1 (hu) | 1997-08-12 | 1997-08-12 | Eljárás amlodipin-bezilát előállítására és az eljárás intermedierjei |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL192097B1 true PL192097B1 (pl) | 2006-08-31 |
Family
ID=89995490
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL375449A PL192097B1 (pl) | 1997-08-12 | 1998-08-11 | 4-(2-chloroetoksy)-acetylooctan etylu, 4-(2-jodoetoksy)-acetylooctan etylu, 4-(2-chloroetoksy)-2-(2-chlorobenzylideno)-acetylooctan etylu i 4-(2-jodoetoksy)-2-(2-chlorobenzylideno)-acetylooctan etylu |
| PL327952A PL191995B1 (pl) | 1997-08-12 | 1998-08-11 | Sposób otrzymywania soli kwasu benzenosulfonowego 3-etylo-5-metylo-2-(2-aminoetoksymetylo)-4-(2-chlorofenylo)-6-metylo-1,4-dihydropirydyno-3,5-dikarboksylanu oraz związki przejściowe |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL327952A PL191995B1 (pl) | 1997-08-12 | 1998-08-11 | Sposób otrzymywania soli kwasu benzenosulfonowego 3-etylo-5-metylo-2-(2-aminoetoksymetylo)-4-(2-chlorofenylo)-6-metylo-1,4-dihydropirydyno-3,5-dikarboksylanu oraz związki przejściowe |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US6046337A (pl) |
| EP (1) | EP0902016B1 (pl) |
| AT (1) | ATE216988T1 (pl) |
| CZ (1) | CZ291430B6 (pl) |
| DE (1) | DE69805143T2 (pl) |
| ES (1) | ES2175573T3 (pl) |
| HR (1) | HRP980440B1 (pl) |
| HU (1) | HU221810B1 (pl) |
| PL (2) | PL192097B1 (pl) |
| RU (1) | RU2163597C2 (pl) |
| SI (1) | SI0902016T1 (pl) |
| SK (1) | SK283422B6 (pl) |
| UA (1) | UA57722C2 (pl) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| UA72768C2 (en) * | 1999-07-05 | 2005-04-15 | Richter Gedeon Vegyeszet | A method for obtaining amilodipine benzenesulphonate |
| US7266501B2 (en) * | 2000-03-02 | 2007-09-04 | Akiba Electronics Institute Llc | Method and apparatus for accommodating primary content audio and secondary content remaining audio capability in the digital audio production process |
| MXPA03005882A (es) * | 2000-12-29 | 2005-04-19 | Pfizer Ltd | Derivado amida de amlodipina. |
| US7335380B2 (en) * | 2000-12-29 | 2008-02-26 | Synthon Ip Inc. | Amlodipine free base |
| ATE315026T1 (de) | 2000-12-29 | 2006-02-15 | Pfizer Ltd | Amlodipin-hemimaleat |
| CN1272319C (zh) * | 2000-12-29 | 2006-08-30 | 辉瑞有限公司 | 制备氨氯地平马来酸盐的工艺、所制得的氨氯地平马来酸盐、其药物组合物和用途 |
| WO2002054062A2 (en) | 2000-12-29 | 2002-07-11 | Pfizer Limited | Reference standards and processes for determining the purity or stability of amlodipine maleate |
| EP1309554A1 (en) | 2000-12-29 | 2003-05-14 | Synthon Licensing, Ltd. | Amide derivative of amlodipine |
| AT5874U1 (de) | 2000-12-29 | 2003-01-27 | Bioorg Bv | Pharmazeutische zubereitungen enthaltend amlodipinmaleat |
| EP1309556B1 (en) | 2000-12-29 | 2004-11-24 | Pfizer Limited | Amlodipine fumarate |
| BR0116553A (pt) | 2000-12-29 | 2004-02-03 | Pfizer Ltd | Composto, composição farmacêutica para tratamento de angina ou hipertensão, processo, processo para tratamento ou prevenção de angina ou hipertensão, composição de ingredientes farmaceuticamente ativos, composição farmacêutica para tratamento ou prevenção de angina ou hipertensão e processo para tratar ou prevenir angina ou hipertensão |
| US6653481B2 (en) | 2000-12-29 | 2003-11-25 | Synthon Bv | Process for making amlodipine |
| KR100374767B1 (ko) * | 2001-03-13 | 2003-03-03 | 한미약품공업 주식회사 | 개선된 암로디핀의 제조 방법 |
| WO2003004025A1 (en) * | 2001-07-06 | 2003-01-16 | Lek Pharmaceutical And Chemical Company D.D. | High purity amlodipine benzenesulfonate and a process for its preparation |
| US6680334B2 (en) | 2001-08-28 | 2004-01-20 | Pfizer Inc | Crystalline material |
| US6828339B2 (en) * | 2001-11-21 | 2004-12-07 | Synthon Bv | Amlodipine salt forms and processes for preparing them |
| US6699892B2 (en) | 2002-06-04 | 2004-03-02 | Yung Shin Pharmaceutical Industrial Co., Ltd. | Pharmaceutically acceptable salt of amlodipine and method of preparing the same |
| US6784297B2 (en) | 2002-09-04 | 2004-08-31 | Kopran Limited | Process for the preparation of anti-ischemic and anti-hypertensive drug amlodipine besylate |
| US6608206B1 (en) * | 2002-10-30 | 2003-08-19 | Council Of Scientific & Industrial Research | Process for making S(-) Amlodipine salts |
| US20060030602A1 (en) * | 2004-03-16 | 2006-02-09 | Sepracor Inc. | (S)-amlodipine malate |
| KR100807336B1 (ko) | 2006-10-23 | 2008-02-28 | 명문제약주식회사 | 암로디핀의 제조를 위한 신규한 중간체 화합물, 이의 제조방법 및 이를 이용한 암로디핀의 제조 방법 |
| HU230877B1 (hu) * | 2008-09-30 | 2018-11-29 | EGIS Gyógyszergyár NyR | Stabil kombinációs gyógyszerkészítmény |
| CN102070516A (zh) * | 2011-02-22 | 2011-05-25 | 广东东阳光药业有限公司 | 一种制备氨氯地平的方法 |
| RU2755349C1 (ru) * | 2021-02-16 | 2021-09-15 | Федеральное государственное автономное образовательное учреждение высшего образования "Белгородский государственный национальный исследовательский университет" (НИУ "БелГУ") | Применение бензил 6-({ 2-[(3,4-диметилфенил)амино]-2-оксоэтил} тио)-2-метил-4-(4-хлорфенил)-5-циано-1,4-дигидропиридин-3-карбоксилата в качестве гепатопротекторного средства |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK161312C (da) * | 1982-03-11 | 1991-12-09 | Pfizer | Analogifremgangsmaade til fremstilling af 2-aminoalkoxymethyl-4-phenyl-6-methyl-1,4-dihydropyridin-3,5-dicarboxylsyreestere eller syreadditionssalte deraf samt phthalimidoderivater til anvendelse som udgangsmateriale ved fremgangsmaaden |
| GB8608335D0 (en) * | 1986-04-04 | 1986-05-08 | Pfizer Ltd | Pharmaceutically acceptable salts |
| US5001119A (en) * | 1987-11-25 | 1991-03-19 | Schwartz Arthur G | 16-substituted androstanes and 16-substituted androstenes |
| CA2080127A1 (en) * | 1990-04-10 | 1991-10-11 | Peter Zimmermann | Pyridines as medicaments |
| SI9200344B (sl) * | 1992-11-26 | 1998-06-30 | Lek, | Postopek za pripravo amlodipin benzensulfonata |
| US5389654A (en) * | 1992-11-26 | 1995-02-14 | Lek, Tovarna, Farmacevtskih In Kemicnih . . . | 3-ethyl 5-methyl(±)2-[2-(N-tritylamino)ethoxymethyl]-4-(2-chlorophenyl)-1,4-dihydro-6-methyl-6-methyl-3,5-pyridinedicarboxylate |
-
1997
- 1997-08-12 HU HU9701379A patent/HU221810B1/hu not_active IP Right Cessation
-
1998
- 1998-07-30 CZ CZ19982396A patent/CZ291430B6/cs not_active IP Right Cessation
- 1998-08-03 SK SK1045-98A patent/SK283422B6/sk unknown
- 1998-08-10 UA UA98084353A patent/UA57722C2/uk unknown
- 1998-08-11 HR HR980440A patent/HRP980440B1/xx not_active IP Right Cessation
- 1998-08-11 PL PL375449A patent/PL192097B1/pl not_active IP Right Cessation
- 1998-08-11 RU RU98115586/04A patent/RU2163597C2/ru not_active IP Right Cessation
- 1998-08-11 PL PL327952A patent/PL191995B1/pl not_active IP Right Cessation
- 1998-08-12 DE DE69805143T patent/DE69805143T2/de not_active Expired - Fee Related
- 1998-08-12 ES ES98115155T patent/ES2175573T3/es not_active Expired - Lifetime
- 1998-08-12 SI SI9830190T patent/SI0902016T1/xx unknown
- 1998-08-12 EP EP98115155A patent/EP0902016B1/en not_active Expired - Lifetime
- 1998-08-12 AT AT98115155T patent/ATE216988T1/de not_active IP Right Cessation
- 1998-08-12 US US09/133,108 patent/US6046337A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| HRP980440A2 (en) | 1999-06-30 |
| RU2163597C2 (ru) | 2001-02-27 |
| US6046337A (en) | 2000-04-04 |
| DE69805143D1 (de) | 2002-06-06 |
| ES2175573T3 (es) | 2002-11-16 |
| EP0902016A1 (en) | 1999-03-17 |
| DE69805143T2 (de) | 2002-11-28 |
| EP0902016B1 (en) | 2002-05-02 |
| CZ239698A3 (cs) | 1999-02-17 |
| UA57722C2 (uk) | 2003-07-15 |
| HUP9701379A2 (hu) | 2000-05-28 |
| PL191995B1 (pl) | 2006-08-31 |
| SK283422B6 (sk) | 2003-07-01 |
| HU221810B1 (hu) | 2003-01-28 |
| HU9701379D0 (en) | 1997-10-28 |
| HUP9701379A3 (en) | 2000-06-28 |
| EP0902016A3 (en) | 2000-01-05 |
| CZ291430B6 (cs) | 2003-03-12 |
| SI0902016T1 (en) | 2002-08-31 |
| HRP980440B1 (en) | 2003-06-30 |
| PL327952A1 (en) | 1999-02-15 |
| ATE216988T1 (de) | 2002-05-15 |
| SK104598A3 (en) | 1999-03-12 |
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Effective date: 20080811 |