JP2010180242A5 - - Google Patents
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- Publication number
- JP2010180242A5 JP2010180242A5 JP2010098844A JP2010098844A JP2010180242A5 JP 2010180242 A5 JP2010180242 A5 JP 2010180242A5 JP 2010098844 A JP2010098844 A JP 2010098844A JP 2010098844 A JP2010098844 A JP 2010098844A JP 2010180242 A5 JP2010180242 A5 JP 2010180242A5
- Authority
- JP
- Japan
- Prior art keywords
- acid
- compound
- formula
- malic
- chemical formula
- 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.)
- Granted
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- 150000001875 compounds Chemical class 0.000 claims 35
- -1 ethylcarbonyloxy, isopropylcarbonyloxy, t-butylcarbonyloxy, cyclopropylcarbonyloxy, cyclobutylcarbonyloxy Chemical group 0.000 claims 14
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 12
- QIAFMBKCNZACKA-UHFFFAOYSA-N N-benzoylglycine Chemical compound OC(=O)CNC(=O)C1=CC=CC=C1 QIAFMBKCNZACKA-UHFFFAOYSA-N 0.000 claims 12
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims 12
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims 12
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims 12
- BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 claims 12
- NMHMNPHRMNGLLB-UHFFFAOYSA-N phloretic acid Chemical compound OC(=O)CCC1=CC=C(O)C=C1 NMHMNPHRMNGLLB-UHFFFAOYSA-N 0.000 claims 12
- 239000000126 substance Substances 0.000 claims 12
- 239000002253 acid Substances 0.000 claims 9
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 claims 8
- SMNDYUVBFMFKNZ-UHFFFAOYSA-N 2-furoic acid Chemical compound OC(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-N 0.000 claims 8
- NGSWKAQJJWESNS-UHFFFAOYSA-N 4-coumaric acid Chemical compound OC(=O)C=CC1=CC=C(O)C=C1 NGSWKAQJJWESNS-UHFFFAOYSA-N 0.000 claims 8
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims 8
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 8
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 8
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 8
- LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 claims 8
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 claims 8
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims 8
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims 8
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims 6
- 150000007524 organic acids Chemical class 0.000 claims 6
- PXQPEWDEAKTCGB-UHFFFAOYSA-N orotic acid Chemical compound OC(=O)C1=CC(=O)NC(=O)N1 PXQPEWDEAKTCGB-UHFFFAOYSA-N 0.000 claims 6
- 239000003795 chemical substances by application Substances 0.000 claims 5
- 238000000034 method Methods 0.000 claims 5
- BJEPYKJPYRNKOW-UWTATZPHSA-N (R)-malic acid Chemical compound OC(=O)[C@H](O)CC(O)=O BJEPYKJPYRNKOW-UWTATZPHSA-N 0.000 claims 4
- CIWBSHSKHKDKBQ-SZSCBOSDSA-N 2-[(1s)-1,2-dihydroxyethyl]-3,4-dihydroxy-2h-furan-5-one Chemical compound OC[C@H](O)C1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-SZSCBOSDSA-N 0.000 claims 4
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 claims 4
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Natural products OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims 4
- 239000005711 Benzoic acid Substances 0.000 claims 4
- CKLJMWTZIZZHCS-UHFFFAOYSA-N D-OH-Asp Natural products OC(=O)C(N)CC(O)=O CKLJMWTZIZZHCS-UHFFFAOYSA-N 0.000 claims 4
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims 4
- DSLZVSRJTYRBFB-UHFFFAOYSA-N Galactaric acid Natural products OC(=O)C(O)C(O)C(O)C(O)C(O)=O DSLZVSRJTYRBFB-UHFFFAOYSA-N 0.000 claims 4
- 239000001358 L(+)-tartaric acid Substances 0.000 claims 4
- 235000011002 L(+)-tartaric acid Nutrition 0.000 claims 4
- FEWJPZIEWOKRBE-LWMBPPNESA-N L-(+)-Tartaric acid Natural products OC(=O)[C@@H](O)[C@H](O)C(O)=O FEWJPZIEWOKRBE-LWMBPPNESA-N 0.000 claims 4
- CKLJMWTZIZZHCS-UWTATZPHSA-N L-Aspartic acid Natural products OC(=O)[C@H](N)CC(O)=O CKLJMWTZIZZHCS-UWTATZPHSA-N 0.000 claims 4
- 239000002211 L-ascorbic acid Substances 0.000 claims 4
- 235000000069 L-ascorbic acid Nutrition 0.000 claims 4
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims 4
- FEWJPZIEWOKRBE-XIXRPRMCSA-N Mesotartaric acid Chemical compound OC(=O)[C@@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-XIXRPRMCSA-N 0.000 claims 4
- 235000021314 Palmitic acid Nutrition 0.000 claims 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 4
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 claims 4
- 235000021355 Stearic acid Nutrition 0.000 claims 4
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims 4
- 235000011054 acetic acid Nutrition 0.000 claims 4
- 229960005261 aspartic acid Drugs 0.000 claims 4
- 235000010233 benzoic acid Nutrition 0.000 claims 4
- 229960004365 benzoic acid Drugs 0.000 claims 4
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims 4
- 229960004106 citric acid Drugs 0.000 claims 4
- DZAUWHJDUNRCTF-UHFFFAOYSA-N dihydrocaffeic acid Natural products OC(=O)CCC1=CC=C(O)C(O)=C1 DZAUWHJDUNRCTF-UHFFFAOYSA-N 0.000 claims 4
- 229940048879 dl tartaric acid Drugs 0.000 claims 4
- 239000001530 fumaric acid Substances 0.000 claims 4
- DSLZVSRJTYRBFB-DUHBMQHGSA-N galactaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)C(O)=O DSLZVSRJTYRBFB-DUHBMQHGSA-N 0.000 claims 4
- 229940074391 gallic acid Drugs 0.000 claims 4
- 235000004515 gallic acid Nutrition 0.000 claims 4
- AUONNNVJUCSETH-UHFFFAOYSA-N icosanoyl icosanoate Chemical compound CCCCCCCCCCCCCCCCCCCC(=O)OC(=O)CCCCCCCCCCCCCCCCCCC AUONNNVJUCSETH-UHFFFAOYSA-N 0.000 claims 4
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims 4
- 239000011976 maleic acid Substances 0.000 claims 4
- 229940098779 methanesulfonic acid Drugs 0.000 claims 4
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 claims 4
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims 4
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims 4
- 235000006408 oxalic acid Nutrition 0.000 claims 4
- 235000019260 propionic acid Nutrition 0.000 claims 4
- YQUVCSBJEUQKSH-UHFFFAOYSA-N protochatechuic acid Natural products OC(=O)C1=CC=C(O)C(O)=C1 YQUVCSBJEUQKSH-UHFFFAOYSA-N 0.000 claims 4
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims 4
- 229960004889 salicylic acid Drugs 0.000 claims 4
- 239000008117 stearic acid Substances 0.000 claims 4
- WKOLLVMJNQIZCI-UHFFFAOYSA-N vanillic acid Chemical compound COC1=CC(C(O)=O)=CC=C1O WKOLLVMJNQIZCI-UHFFFAOYSA-N 0.000 claims 4
- TUUBOHWZSQXCSW-UHFFFAOYSA-N vanillic acid Natural products COC1=CC(O)=CC(C(O)=O)=C1 TUUBOHWZSQXCSW-UHFFFAOYSA-N 0.000 claims 4
- NLSNLUSGBGHEII-UHFFFAOYSA-N 2-acetamidoacetic acid Chemical compound CC(=O)NCC(O)=O.CC(=O)NCC(O)=O NLSNLUSGBGHEII-UHFFFAOYSA-N 0.000 claims 3
- WUECABRAWUKURJ-UHFFFAOYSA-N 3-(2-methyl-1h-indol-3-yl)-3-oxopropanenitrile Chemical compound C1=CC=C2C(C(=O)CC#N)=C(C)NC2=C1 WUECABRAWUKURJ-UHFFFAOYSA-N 0.000 claims 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- AEMOLEFTQBMNLQ-UHFFFAOYSA-N beta-D-galactopyranuronic acid Natural products OC1OC(C(O)=O)C(O)C(O)C1O AEMOLEFTQBMNLQ-UHFFFAOYSA-N 0.000 claims 3
- 239000003638 chemical reducing agent Substances 0.000 claims 3
- 150000002148 esters Chemical class 0.000 claims 3
- 229960005010 orotic acid Drugs 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- HWKRAUXFMLQKLS-UHFFFAOYSA-N 2-oxidanylidenepropanoic acid Chemical compound CC(=O)C(O)=O.CC(=O)C(O)=O HWKRAUXFMLQKLS-UHFFFAOYSA-N 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 229940107700 pyruvic acid Drugs 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- CWIFYQQOFPQJEW-JOCHJYFZSA-N 2-[2-[(1r)-3-[di(propan-2-yl)amino]-1-phenylpropyl]-4-(hydroxymethyl)phenyl]-2-methylpropanoic acid Chemical compound C1([C@@H](CCN(C(C)C)C(C)C)C=2C(=CC=C(CO)C=2)C(C)(C)C(O)=O)=CC=CC=C1 CWIFYQQOFPQJEW-JOCHJYFZSA-N 0.000 claims 1
- CLWAIIWRVCYDAC-UHFFFAOYSA-N C(C)(=O)NCC(=O)O.C(C)(=O)O Chemical compound C(C)(=O)NCC(=O)O.C(C)(=O)O CLWAIIWRVCYDAC-UHFFFAOYSA-N 0.000 claims 1
- 239000007868 Raney catalyst Substances 0.000 claims 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims 1
- 229910000564 Raney nickel Inorganic materials 0.000 claims 1
- 230000002378 acidificating effect Effects 0.000 claims 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-M fumarate(1-) Chemical compound OC(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-M 0.000 claims 1
- 150000007522 mineralic acids Chemical class 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 0 CC(C)*(CCC(C(C=C(C)C(ONC)=O)=C(C)OCc1ccccc1)c1ccccc1)C(C)C Chemical compound CC(C)*(CCC(C(C=C(C)C(ONC)=O)=C(C)OCc1ccccc1)c1ccccc1)C(C)C 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19955190A DE19955190A1 (de) | 1999-11-16 | 1999-11-16 | Stabile Salze neuartiger Derivate von 3,3-Diphenylpropylaminen |
| DE19955190.1 | 1999-11-16 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007042774A Division JP2007137895A (ja) | 1999-11-16 | 2007-02-22 | ３，３−ジフェニルプロピルアミン類の新規誘導体の安定な塩 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011096911A Division JP5290351B2 (ja) | 1999-11-16 | 2011-04-25 | ３，３−ジフェニルプロピルアミン類の新規誘導体の安定な塩 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2010180242A JP2010180242A (ja) | 2010-08-19 |
| JP2010180242A5 true JP2010180242A5 (OSRAM) | 2011-09-08 |
| JP5650924B2 JP5650924B2 (ja) | 2015-01-07 |
Family
ID=7929277
Family Applications (6)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001537950A Expired - Lifetime JP4083431B2 (ja) | 1999-11-16 | 2000-11-15 | ３，３−ジフェニルプロピルアミン類の新規誘導体の安定な塩 |
| JP2007042774A Pending JP2007137895A (ja) | 1999-11-16 | 2007-02-22 | ３，３−ジフェニルプロピルアミン類の新規誘導体の安定な塩 |
| JP2010098844A Expired - Lifetime JP5650924B2 (ja) | 1999-11-16 | 2010-04-22 | ３，３−ジフェニルプロピルアミン類の新規誘導体の安定な塩 |
| JP2010098845A Expired - Lifetime JP5503393B2 (ja) | 1999-11-16 | 2010-04-22 | ３，３−ジフェニルプロピルアミン類の新規誘導体の安定な塩 |
| JP2011096911A Expired - Lifetime JP5290351B2 (ja) | 1999-11-16 | 2011-04-25 | ３，３−ジフェニルプロピルアミン類の新規誘導体の安定な塩 |
| JP2013229622A Expired - Lifetime JP5717824B2 (ja) | 1999-11-16 | 2013-11-05 | ３，３−ジフェニルプロピルアミン類の新規誘導体の安定な塩 |
Family Applications Before (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001537950A Expired - Lifetime JP4083431B2 (ja) | 1999-11-16 | 2000-11-15 | ３，３−ジフェニルプロピルアミン類の新規誘導体の安定な塩 |
| JP2007042774A Pending JP2007137895A (ja) | 1999-11-16 | 2007-02-22 | ３，３−ジフェニルプロピルアミン類の新規誘導体の安定な塩 |
Family Applications After (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010098845A Expired - Lifetime JP5503393B2 (ja) | 1999-11-16 | 2010-04-22 | ３，３−ジフェニルプロピルアミン類の新規誘導体の安定な塩 |
| JP2011096911A Expired - Lifetime JP5290351B2 (ja) | 1999-11-16 | 2011-04-25 | ３，３−ジフェニルプロピルアミン類の新規誘導体の安定な塩 |
| JP2013229622A Expired - Lifetime JP5717824B2 (ja) | 1999-11-16 | 2013-11-05 | ３，３−ジフェニルプロピルアミン類の新規誘導体の安定な塩 |
Country Status (30)
| Country | Link |
|---|---|
| US (1) | US6858650B1 (OSRAM) |
| EP (3) | EP1690536B1 (OSRAM) |
| JP (6) | JP4083431B2 (OSRAM) |
| KR (2) | KR100536095B1 (OSRAM) |
| CN (1) | CN1215045C (OSRAM) |
| AT (3) | ATE395056T1 (OSRAM) |
| AU (1) | AU778132B2 (OSRAM) |
| BR (1) | BRPI0015610C1 (OSRAM) |
| CA (1) | CA2389749C (OSRAM) |
| CY (2) | CY1106204T1 (OSRAM) |
| CZ (2) | CZ302967B6 (OSRAM) |
| DE (5) | DE19955190A1 (OSRAM) |
| DK (3) | DK1230209T3 (OSRAM) |
| EA (1) | EA005588B1 (OSRAM) |
| ES (3) | ES2303708T3 (OSRAM) |
| GE (1) | GEP20084430B (OSRAM) |
| HK (1) | HK1045148B (OSRAM) |
| HU (2) | HU227608B1 (OSRAM) |
| IL (2) | IL149567A0 (OSRAM) |
| IS (2) | IS2124B (OSRAM) |
| MX (1) | MXPA02004603A (OSRAM) |
| NO (2) | NO323920B1 (OSRAM) |
| NZ (1) | NZ519230A (OSRAM) |
| PL (1) | PL201422B1 (OSRAM) |
| PT (3) | PT1481964E (OSRAM) |
| SI (3) | SI1690536T1 (OSRAM) |
| SK (3) | SK288185B6 (OSRAM) |
| UA (2) | UA73324C2 (OSRAM) |
| WO (1) | WO2001035957A1 (OSRAM) |
| ZA (1) | ZA200203315B (OSRAM) |
Families Citing this family (48)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0957073A1 (en) * | 1998-05-12 | 1999-11-17 | Schwarz Pharma Ag | Novel derivatives of 3,3-diphenylpropylamines |
| DE19955190A1 (de) * | 1999-11-16 | 2001-06-21 | Sanol Arznei Schwarz Gmbh | Stabile Salze neuartiger Derivate von 3,3-Diphenylpropylaminen |
| DE10028443C1 (de) * | 2000-06-14 | 2002-05-29 | Sanol Arznei Schwarz Gmbh | Verfahren zur Herstellung von 3,3-Diarylpropylaminen, (R,S)- und (R)-4-Phenyl-2-chromanon-6-carbonsäure sowie (R)-4-Phenyl-2-chromanon-carbonsäure-cinchonidinsalz und deren Verwendung zur Herstellung eines rechtsdrehenden Hydroxybenzylalkohols und von pharmazeutischen Zusammensetzungen |
| DE10315878B4 (de) | 2003-04-08 | 2009-06-04 | Schwarz Pharma Ag | Vorrichtung zur transdermalen Verabreichung von Fesoterodin und Verwendung |
| DE10315917A1 (de) * | 2003-04-08 | 2004-11-18 | Schwarz Pharma Ag | Hochreine Basen von 3,3-Diphenylpropylaminmonoestern |
| WO2005012227A2 (en) * | 2003-08-05 | 2005-02-10 | Ranbaxy Laboratories Limited | Process for preparation of 2-(3-diisopropylamino-1-phenylpropyl)-4-hydroxymethyl-phenol, a metabolite of tolterodine |
| ES2235648B1 (es) * | 2003-12-22 | 2006-11-01 | Ragactives, S.L. | Procedimiento para la obtencion de tolterodina. |
| US8034823B2 (en) * | 2005-02-22 | 2011-10-11 | Savvipharm Inc | Method of increasing drug oral bioavailability and compositions of less toxic orotate salts |
| KR100647068B1 (ko) | 2005-09-15 | 2006-11-23 | 하나제약 주식회사 | 라세믹ｎ,ｎ-디이소프로필-3-(2-히드록시-5-메틸페닐)-3-페닐프로판아민의 제조방법 |
| DK2029567T3 (da) * | 2006-05-24 | 2010-11-29 | Pfizer Ltd | Fremgangsmåde til frembringelse af benzopyran-2-ol-derivater |
| BRPI0711881B1 (pt) * | 2006-05-31 | 2016-09-27 | Schwarz Pharma Ltd | síntese de hidroximetil fenóis substituídos |
| EP1862449A1 (en) * | 2006-05-31 | 2007-12-05 | Schwarz Pharma Ltd. | A shortened synthesis of substituted hydroxymethyl phenols |
| IES20060424A2 (en) * | 2006-06-08 | 2007-10-31 | Schwarz Pharma Ltd | Accelerated synthesis of (3-Diisopropylamino-1-phenylpropyl)-4-(hydroxymethyl)phenol and its phenolic monoesters |
| US7807715B2 (en) | 2006-06-09 | 2010-10-05 | Ucb Pharma Gmbh | Pharmaceutical compositions comprising fesoterodine |
| CA2648333C (en) * | 2006-06-09 | 2014-04-29 | Schwarz Pharma Ltd | Synthesis of phenolic esters of hydroxymethyl phenols |
| ATE517619T1 (de) * | 2006-06-09 | 2011-08-15 | Ucb Pharma Gmbh | Stabilisierte pharmazeutische zusammensetzung mit fesoterodin |
| IES20060435A2 (en) * | 2006-06-12 | 2007-12-12 | Schwarz Pharma Ltd | Shortened synthesis using paraformaldehyde or trioxane |
| AU2007260267B2 (en) | 2006-06-12 | 2012-09-06 | Ucb Pharma Gmbh | New chiral intermediate, process for producing the same and its use in the manufacture of tolterodine, fesoterodine, or the active metabolite thereof |
| US20100217034A1 (en) * | 2007-09-21 | 2010-08-26 | Actavis Group Ptc Ehf | Process for the Preparation of Fesoterodine |
| US20100297241A1 (en) * | 2007-10-01 | 2010-11-25 | Actavis Group Ptc Ehf | Amorphous Fesoterodine Fumarate |
| EP2294047A2 (en) * | 2008-04-04 | 2011-03-16 | Actavis Group PTC EHF | Novel mandelate salt of fesoterodine |
| US20110171274A1 (en) * | 2008-07-21 | 2011-07-14 | Actavis Group Ptc Ehf | Fesoterodine Substantially Free of Dehydroxy Impurity |
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| JPH0483431A (ja) * | 1990-07-26 | 1992-03-17 | Seiko Epson Corp | 選択呼出受信機 |
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| SE9701144D0 (sv) * | 1997-03-27 | 1997-03-27 | Pharmacia & Upjohn Ab | Novel compounds, their use and preparation |
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1999
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