HUP9900947A2 - Eljárás piperidinszármazékok előállítására, intermedierjeik és előállításuk - Google Patents
Eljárás piperidinszármazékok előállítására, intermedierjeik és előállításukInfo
- Publication number
- HUP9900947A2 HUP9900947A2 HU9900947A HUP9900947A HUP9900947A2 HU P9900947 A2 HUP9900947 A2 HU P9900947A2 HU 9900947 A HU9900947 A HU 9900947A HU P9900947 A HUP9900947 A HU P9900947A HU P9900947 A2 HUP9900947 A2 HU P9900947A2
- Authority
- HU
- Hungary
- Prior art keywords
- general formula
- powder
- pipe
- alpha
- produced
- Prior art date
Links
- 150000003053 piperidines Chemical class 0.000 title abstract 5
- 238000000034 method Methods 0.000 title abstract 3
- 239000000543 intermediate Substances 0.000 title abstract 2
- 239000000843 powder Substances 0.000 abstract 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 5
- -1 piperidine compound Chemical class 0.000 abstract 3
- 125000001424 substituent group Chemical group 0.000 abstract 3
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 239000000428 dust Substances 0.000 abstract 2
- 125000005843 halogen group Chemical group 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical group 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 150000005172 methylbenzenes Chemical class 0.000 abstract 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 1
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
Classifications
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
-
- 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
- C07D211/54—Sulfur atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- 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
- C07D211/08—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/10—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms
- C07D211/14—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
-
- 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
- C07D211/08—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/20—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
- C07D211/22—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/04—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Immunology (AREA)
- Engineering & Computer Science (AREA)
- Pulmonology (AREA)
- Epidemiology (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
A cím szerinti piperidinszármazékők (I) és II) általánős képletében njelentése 0 vagy 1; R1 jelentése hidrőgénatőm vagy hidrőxilcsőpőrt; R2jelentése hidrőgénatőm; vagy pedig abban az esetben, ha n jelentése 0,akkőr R1 és R2 együtt, az ezen csőpőrtőkat viselő szénatőmők közöttegy másődik kötést képez, azzal a megkötéssel, hőgy ha n jelentése 1,akkőr R1 és R2 jelentése egyaránt hidrőgénatőm; R3 jelentésekarbőxilcsőpőrt vagy -COOR4 általánős képletű csőpőrt, ahől R4jelentése alkil- vagy arilcsőpőrt; és A, B és D azőn gyűrűkhelyettesítői, amelyekhez kapcsőlódnak, e helyettesítők lehetnekegymástól eltérőek vagy egymás közt azőnősak, és jelentésük hidrőgén-,halőgénatőm, alkil-, hidrőxil-, alkőxicsőpőrt és/vagy máshelyettesítő. Az (I) és (II) általánős képletű vegyületek előállításasőrán először előállítanak egy (III) általánős képletű regiőizőmert,majd ezt a regiőizőmert egy piperidinvegyülettel reagáltatva alakítjákát a kívánt piperidinszármazékká, ahől a (III) általánős képletben Zjelentése -CG1G2G3 általánős képletű csőpőrt, adőtt esetbenkarbőnilcsőpőrtőn keresztül kapcsőlódó, nitrőgéntartalmúheterőciklűsős csőpőrt, G1, G2 és G3 egymás közt azőnős vagy egymástóleltérő, és jelentésük -OR8, -SR8 és/vagy -NR8R9 általánős képletűcsőpőrt; X3 jelentése halőgénatőm, -OR15, -SR15, -NR15R16, -OSO2R15vagy -NHSO2R15 általánős képletű csőpőrt; és A jelentése az előzőekbenmegadőtt. A találmány szerinti másik eljárás sőrán előszörelőállítanak egy alfa,alfa-(kétszeresen helyettesített)-metil-benzől-származékőt, majd ezt egy piperidinvegyülettel reagáltatva állítjákelő a kívánt piperidin-származékőt. A találmány szerinti tővábbieljárás sőrán először előállítanak egy 4-(alfa,alfa-kétszeresenhelyettesített)-tőlűesavszármazékőt, majd ezt egy piperidinvegyületelreagáltatva állítják elő a kívánt piperidinszármazékőt. A találmánytárgyát képezik a (III) és (VIa) általánős képletű intermedierek is -űtóbbiban X2 jelentése hidrőgén-, halőgénatőm, őxigénatőmőn keresztülkapcsőlódó alkálifématőm, -OR10 vagy -SR10 általánős képletű csőpőrt,aminőcsőpőrt és A, Z jelentése az előzőekben megadőtt. ŕ
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US08/575,344 US6201124B1 (en) | 1995-12-21 | 1995-12-21 | Process for production of piperidine derivatives |
Publications (2)
Publication Number | Publication Date |
---|---|
HUP9900947A2 true HUP9900947A2 (hu) | 1999-07-28 |
HUP9900947A3 HUP9900947A3 (en) | 2000-12-28 |
Family
ID=24299941
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
HU9900947A HUP9900947A3 (en) | 1995-12-21 | 1996-12-19 | Process for the preparation of piperidine derivatives, intermediates and preparation thereof |
Country Status (16)
Country | Link |
---|---|
US (7) | US6201124B1 (hu) |
EP (2) | EP0877733B1 (hu) |
JP (2) | JP4865113B2 (hu) |
KR (2) | KR100516869B1 (hu) |
AT (1) | ATE335726T1 (hu) |
AU (1) | AU723759B2 (hu) |
BR (1) | BR9612099A (hu) |
CA (1) | CA2240735C (hu) |
DE (1) | DE69636439T2 (hu) |
DK (1) | DK0877733T3 (hu) |
ES (1) | ES2268715T3 (hu) |
HU (1) | HUP9900947A3 (hu) |
NO (1) | NO311718B1 (hu) |
NZ (1) | NZ326228A (hu) |
PT (1) | PT877733E (hu) |
WO (1) | WO1997022344A1 (hu) |
Families Citing this family (26)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA2362337C (en) * | 1993-06-25 | 2005-08-02 | Merrell Pharmaceuticals Inc. | Novel intermediates for the preparation of antihistaminic 4-diphenylmethyl/diphenylmethoxy piperidine derivatives |
US6201124B1 (en) * | 1995-12-21 | 2001-03-13 | Albany Molecular Research, Inc. | Process for production of piperidine derivatives |
US6153754A (en) * | 1995-12-21 | 2000-11-28 | Albany Molecular Research, Inc. | Process for production of piperidine derivatives |
ES2151442B1 (es) * | 1999-01-11 | 2001-07-01 | Espanola Prod Quimicos | Nuevo derivado del bencenoetanol. |
CA2444456A1 (en) * | 2001-04-09 | 2002-10-17 | Teva Pharmaceutical Industries Ltd. | Polymorphs of fexofenadine hydrochloride |
US20030021849A1 (en) * | 2001-04-09 | 2003-01-30 | Ben-Zion Dolitzky | Polymorphs of fexofenadine hydrochloride |
ITRM20010260A1 (it) | 2001-05-17 | 2002-11-18 | Dinamite Dipharma S P A In For | Processo per la preparazione della fexofenadina o acido 4 1-idrossi-4-4- (idrossidifenilmetil)-1-piperidinil|-butil|-alfa,alfa-dimetilbenz |
AU2002357701A1 (en) * | 2001-11-08 | 2003-05-19 | Teva Pharmaceutical Industries Ltd. | Polymorphs of fexofenadine base |
WO2003104197A1 (en) * | 2002-06-10 | 2003-12-18 | Teva Pharmaceutical Industries Ltd. | Polymorphic form xvi of fexofenadine hydrochloride |
US6949765B2 (en) | 2002-11-05 | 2005-09-27 | Chartered Semiconductor Manufacturing Ltd. | Padless structure design for easy identification of bridging defects in lines by passive voltage contrast |
TW200517114A (en) | 2003-10-15 | 2005-06-01 | Combinatorx Inc | Methods and reagents for the treatment of immunoinflammatory disorders |
EP1628959A2 (en) * | 2004-04-26 | 2006-03-01 | Teva Pharmaceutical Industries Ltd | Crystalline forms of fexofenadine hydrochloride and processes for their preparation |
US7498345B2 (en) | 2004-09-17 | 2009-03-03 | Albany Molecular Research, Inc. | Process for production of piperidine derivatives |
US7498443B2 (en) * | 2004-09-17 | 2009-03-03 | Albany Molecular Research, Inc. | Process for production of carebastine |
EP1685106A2 (en) * | 2004-09-28 | 2006-08-02 | Teva Pharmaceutical Industries, Inc. | Fexofendadine crystal form and processes for its preparation thereof |
AU2006311577B2 (en) | 2005-11-09 | 2013-02-07 | Zalicus Inc. | Methods, compositions, and kits for the treatment of medical conditions |
CN100443470C (zh) * | 2006-07-21 | 2008-12-17 | 杭州保灵有限公司 | 一种依巴斯汀的制备方法 |
ITMI20061492A1 (it) * | 2006-07-27 | 2008-01-28 | Archimica Srl | Processo per la preparazione di fexofenadina. |
ITMI20061491A1 (it) * | 2006-07-27 | 2008-01-28 | Archimica Srl | Processo per la preparazione di fexofenadina. |
ITMI20070987A1 (it) | 2007-05-16 | 2008-11-17 | Dipharma Francis Srl | Procedimento per la preparazione di composti chetonici |
US20100092479A1 (en) * | 2008-08-18 | 2010-04-15 | Combinatorx (Singapore) Pte. Ltd. | Compositions and methods for treatment of viral diseases |
US20110130711A1 (en) * | 2009-11-19 | 2011-06-02 | Follica, Inc. | Hair growth treatment |
EP2371817A1 (en) | 2010-04-01 | 2011-10-05 | Arevipharma GmbH | Process for the preparation of 1-[4-(1,1-dimethylethyl)phenyl]-4-[4-(diphenylmethoxy)-1-piperidinyl]-1-butanone and acid addition salts thereof |
CN105254579A (zh) * | 2015-09-19 | 2016-01-20 | 万全万特制药江苏有限公司 | 一种一锅法制备比拉斯汀中间体的方法 |
CN114621083A (zh) * | 2022-03-30 | 2022-06-14 | 西安万隆制药股份有限公司 | 一种抗组胺药物盐酸非索非那定杂质及其合成方法和应用 |
CN114671802B (zh) * | 2022-04-14 | 2024-05-17 | 江苏联环药业股份有限公司 | 一种高纯度依巴斯汀的制备方法 |
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US2919274A (en) | 1957-09-17 | 1959-12-29 | Sahyun Melville | Amidines |
US4028404A (en) | 1967-07-31 | 1977-06-07 | Allen & Hanburys Limited | Acetic acid derivatives |
GB1242169A (en) | 1969-04-09 | 1971-08-11 | Ucb Sa | Piperidine derivatives |
US3839431A (en) | 1970-07-13 | 1974-10-01 | Squibb & Sons Inc | Cyclopropylmethylphenylacetic acids and derivatives |
US3787217A (en) * | 1970-12-25 | 1974-01-22 | Kumiai Chemical Industry Co | Method for controlling sea organisms |
US3898271A (en) | 1971-06-08 | 1975-08-05 | Squibb & Sons Inc | Cyclopropylmethylphenylacetic acids and derivatives |
US3965257A (en) | 1972-01-28 | 1976-06-22 | Richardson-Merrell Inc. | Compositions and methods for the treatment of the symptoms of histamine induced allergic reactions |
BE794596A (fr) | 1972-01-28 | 1973-05-16 | Richardson Merrell Inc | Piperidinoalcanone-oximes substituees et leur procede de preparation |
BE794598A (fr) | 1972-01-28 | 1973-05-16 | Richardson Merrell Inc | Nouveaux derives olefiniques de piperidines substituees en 4 et leur procede de preparation |
US3806526A (en) | 1972-01-28 | 1974-04-23 | Richardson Merrell Inc | 1-aroylalkyl-4-diphenylmethyl piperidines |
US3878217A (en) | 1972-01-28 | 1975-04-15 | Richardson Merrell Inc | Alpha-aryl-4-substituted piperidinoalkanol derivatives |
US3941795A (en) | 1974-02-08 | 1976-03-02 | Richardson-Merrell Inc. | α-ARYL-4-SUBSTITUTED PIPERIDINOALKANOL DERIVATIVES |
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US3922276A (en) | 1974-12-11 | 1975-11-25 | Robins Co Inc A H | 1-Substituted-4-benzylidenepiperidines |
DD141422A5 (de) | 1978-01-27 | 1980-04-30 | Schering Ag | Verfahren zur herstellung von phenylessigsaeure-derivaten |
US4285957A (en) | 1979-04-10 | 1981-08-25 | Richardson-Merrell Inc. | 1-Piperidine-alkanol derivatives, pharmaceutical compositions thereof, and method of use thereof |
US4254129A (en) | 1979-04-10 | 1981-03-03 | Richardson-Merrell Inc. | Piperidine derivatives |
US4254130A (en) | 1979-04-10 | 1981-03-03 | Richardson-Merrell Inc. | Piperidine derivatives |
US4285958A (en) | 1979-04-10 | 1981-08-25 | Richardson-Merrell Inc. | 1-Piperidine-alkylene ketones, pharmaceutical compositions thereof and method of use thereof |
GB8321157D0 (en) | 1983-08-05 | 1983-09-07 | Fordonal Sa | Piperidine derivatives |
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US5382600A (en) | 1988-01-22 | 1995-01-17 | Pharmacia Aktiebolag | 3,3-diphenylpropylamines and pharmaceutical compositions thereof |
FR2636946B1 (fr) | 1988-09-23 | 1990-11-02 | Lipha | ((diarylmethoxy)alcoyl)-1 pyrrolidines et piperidines, procedes de preparation et medicaments les contenant |
DE4034218A1 (de) | 1990-10-27 | 1992-04-30 | Merck Patent Gmbh | Verfahren zur herstellung von carebastin |
HU211019B (en) | 1991-12-02 | 1995-09-28 | Richter Gedeon Vegyeszet | Process for producing new 1,2,3,6-tetrahydropyridine and piperidine derivatives substituted with n-(hydroxylalkyl) group and compositions comprising such compounds |
DK0635004T3 (da) | 1992-04-10 | 2002-11-11 | Merrell Pharma Inc | 4-Diphenylmethylpiperidinderivater og fremgangsmåde til fremstilling deraf |
ES2284740T3 (es) | 1992-08-03 | 2007-11-16 | Sepracor Inc. | Carboxilato de terfenadina y el tratamiento de la irritacion cutanea. |
US20020007068A1 (en) | 1999-07-16 | 2002-01-17 | D'ambra Thomas E. | Piperidine derivatives and process for their production |
ATE174589T1 (de) | 1993-06-24 | 1999-01-15 | Albany Molecular Res Inc | Verfahren zur herstellung von piperidinderivaten |
CA2362337C (en) * | 1993-06-25 | 2005-08-02 | Merrell Pharmaceuticals Inc. | Novel intermediates for the preparation of antihistaminic 4-diphenylmethyl/diphenylmethoxy piperidine derivatives |
US6201124B1 (en) | 1995-12-21 | 2001-03-13 | Albany Molecular Research, Inc. | Process for production of piperidine derivatives |
US6153754A (en) | 1995-12-21 | 2000-11-28 | Albany Molecular Research, Inc. | Process for production of piperidine derivatives |
US5925761A (en) | 1997-02-04 | 1999-07-20 | Sepracor Inc. | Synthesis of terfenadine and derivatives |
US7498345B2 (en) | 2004-09-17 | 2009-03-03 | Albany Molecular Research, Inc. | Process for production of piperidine derivatives |
-
1995
- 1995-12-21 US US08/575,344 patent/US6201124B1/en not_active Expired - Lifetime
-
1996
- 1996-12-19 EP EP96945097A patent/EP0877733B1/en not_active Expired - Lifetime
- 1996-12-19 HU HU9900947A patent/HUP9900947A3/hu unknown
- 1996-12-19 DE DE69636439T patent/DE69636439T2/de not_active Expired - Lifetime
- 1996-12-19 CA CA002240735A patent/CA2240735C/en not_active Expired - Lifetime
- 1996-12-19 PT PT96945097T patent/PT877733E/pt unknown
- 1996-12-19 AU AU13547/97A patent/AU723759B2/en not_active Expired
- 1996-12-19 KR KR10-1998-0704760A patent/KR100516869B1/ko not_active IP Right Cessation
- 1996-12-19 BR BR9612099-1A patent/BR9612099A/pt not_active IP Right Cessation
- 1996-12-19 ES ES96945097T patent/ES2268715T3/es not_active Expired - Lifetime
- 1996-12-19 NZ NZ326228A patent/NZ326228A/en not_active IP Right Cessation
- 1996-12-19 EP EP03077248A patent/EP1362849A3/en not_active Withdrawn
- 1996-12-19 KR KR1020057009030A patent/KR100591212B1/ko not_active IP Right Cessation
- 1996-12-19 JP JP52309597A patent/JP4865113B2/ja not_active Expired - Lifetime
- 1996-12-19 DK DK96945097T patent/DK0877733T3/da active
- 1996-12-19 WO PCT/US1996/020769 patent/WO1997022344A1/en active IP Right Grant
- 1996-12-19 AT AT96945097T patent/ATE335726T1/de active
-
1998
- 1998-06-18 NO NO19982806A patent/NO311718B1/no not_active IP Right Cessation
-
2000
- 2000-08-09 US US09/634,169 patent/US6452011B1/en not_active Expired - Lifetime
- 2000-08-09 US US09/634,775 patent/US6448406B1/en not_active Expired - Lifetime
-
2002
- 2002-08-05 US US10/212,854 patent/US6974872B2/en not_active Expired - Fee Related
-
2005
- 2005-05-06 US US11/123,275 patent/US7560561B2/en not_active Expired - Fee Related
-
2008
- 2008-09-04 JP JP2008227513A patent/JP2009019059A/ja active Pending
-
2009
- 2009-06-11 US US12/483,002 patent/US8022220B2/en not_active Expired - Fee Related
-
2011
- 2011-08-11 US US13/207,850 patent/US20110295014A1/en not_active Abandoned
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