NO317371B1 - 4-Fenylpiperidinforbindelser - Google Patents
4-Fenylpiperidinforbindelser Download PDFInfo
- Publication number
- NO317371B1 NO317371B1 NO19995455A NO995455A NO317371B1 NO 317371 B1 NO317371 B1 NO 317371B1 NO 19995455 A NO19995455 A NO 19995455A NO 995455 A NO995455 A NO 995455A NO 317371 B1 NO317371 B1 NO 317371B1
- Authority
- NO
- Norway
- Prior art keywords
- group
- compound according
- alkyl
- formula
- paroxetine
- Prior art date
Links
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 title claims abstract description 10
- 150000003839 salts Chemical class 0.000 claims abstract description 21
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 15
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 7
- -1 methylsulphonyl Chemical group 0.000 claims abstract description 7
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims abstract description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 5
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 4
- 125000004950 trifluoroalkyl group Chemical group 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 57
- AHOUBRCZNHFOSL-YOEHRIQHSA-N (+)-Casbol Chemical group C1=CC(F)=CC=C1[C@H]1[C@H](COC=2C=C3OCOC3=CC=2)CNCC1 AHOUBRCZNHFOSL-YOEHRIQHSA-N 0.000 claims description 25
- AHOUBRCZNHFOSL-UHFFFAOYSA-N Paroxetine hydrochloride Chemical group C1=CC(F)=CC=C1C1C(COC=2C=C3OCOC3=CC=2)CNCC1 AHOUBRCZNHFOSL-UHFFFAOYSA-N 0.000 claims description 23
- 229960002296 paroxetine Drugs 0.000 claims description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 11
- 239000003814 drug Substances 0.000 claims description 10
- 150000002431 hydrogen Chemical group 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- SHIJTGJXUHTGGZ-RVXRQPKJSA-N (3s,4r)-3-(1,3-benzodioxol-5-yloxymethyl)-4-(4-fluorophenyl)piperidin-1-ium;methanesulfonate Chemical compound CS(O)(=O)=O.C1=CC(F)=CC=C1[C@H]1[C@H](COC=2C=C3OCOC3=CC=2)CNCC1 SHIJTGJXUHTGGZ-RVXRQPKJSA-N 0.000 claims description 6
- 125000001153 fluoro group Chemical group F* 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 239000003153 chemical reaction reagent Substances 0.000 claims description 5
- 239000012453 solvate Substances 0.000 claims description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
- 208000022531 anorexia Diseases 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 206010061428 decreased appetite Diseases 0.000 claims description 4
- 229940079593 drug Drugs 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 3
- 208000024827 Alzheimer disease Diseases 0.000 claims description 2
- 208000032841 Bulimia Diseases 0.000 claims description 2
- 206010006550 Bulimia nervosa Diseases 0.000 claims description 2
- 208000020401 Depressive disease Diseases 0.000 claims description 2
- 208000019695 Migraine disease Diseases 0.000 claims description 2
- 208000008589 Obesity Diseases 0.000 claims description 2
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims description 2
- 208000002193 Pain Diseases 0.000 claims description 2
- 206010036618 Premenstrual syndrome Diseases 0.000 claims description 2
- 206010039966 Senile dementia Diseases 0.000 claims description 2
- 206010041250 Social phobia Diseases 0.000 claims description 2
- 229940077388 benzenesulfonate Drugs 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 206010027599 migraine Diseases 0.000 claims description 2
- 235000020824 obesity Nutrition 0.000 claims description 2
- 208000019906 panic disease Diseases 0.000 claims description 2
- 201000000484 premenstrual tension Diseases 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 239000007787 solid Substances 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims 4
- 239000011737 fluorine Substances 0.000 claims 4
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 1
- RJWBTWIBUIGANW-UHFFFAOYSA-N 4-chlorobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(Cl)C=C1 RJWBTWIBUIGANW-UHFFFAOYSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 claims 1
- 125000000068 chlorophenyl group Chemical group 0.000 claims 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 1
- 125000003944 tolyl group Chemical group 0.000 claims 1
- UTBULQCHEUWJNV-UHFFFAOYSA-N 4-phenylpiperidine Chemical class C1CNCCC1C1=CC=CC=C1 UTBULQCHEUWJNV-UHFFFAOYSA-N 0.000 abstract description 3
- 125000001475 halogen functional group Chemical group 0.000 abstract 3
- 125000004442 acylamino group Chemical group 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 abstract 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 abstract 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 7
- 239000002585 base Substances 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000012512 characterization method Methods 0.000 description 4
- 239000012458 free base Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- AEIUZSKXSWGSRU-QXGDPHCHSA-N paroxetine maleate Chemical compound OC(=O)\C=C/C(O)=O.C1=CC(F)=CC=C1[C@H]1[C@H](COC=2C=C3OCOC3=CC=2)CNCC1 AEIUZSKXSWGSRU-QXGDPHCHSA-N 0.000 description 3
- 150000003460 sulfonic acids Chemical class 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- RQBJOWKBGCDPOS-RVXRQPKJSA-N acetic acid;(3s,4r)-3-(1,3-benzodioxol-5-yloxymethyl)-4-(4-fluorophenyl)piperidine Chemical compound CC(O)=O.C1=CC(F)=CC=C1[C@H]1[C@H](COC=2C=C3OCOC3=CC=2)CNCC1 RQBJOWKBGCDPOS-RVXRQPKJSA-N 0.000 description 2
- 150000007942 carboxylates Chemical class 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 150000004677 hydrates Chemical class 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229960005183 paroxetine hydrochloride Drugs 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- 229940127557 pharmaceutical product Drugs 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 229910006069 SO3H Inorganic materials 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 159000000021 acetate salts Chemical class 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 125000002102 aryl alkyloxo group Chemical group 0.000 description 1
- 208000028683 bipolar I disease Diseases 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000001938 differential scanning calorimetry curve Methods 0.000 description 1
- 238000007907 direct compression Methods 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 238000007908 dry granulation Methods 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007909 solid dosage form Substances 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/06—Antimigraine agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity 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
- C07D211/18—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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Pain & Pain Management (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Psychiatry (AREA)
- Child & Adolescent Psychology (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/NL1997/000328 WO1998056787A1 (en) | 1997-06-10 | 1997-06-10 | 4-Phenylpiperidine compounds |
| US08/872,023 US5874447A (en) | 1997-06-10 | 1997-06-10 | 4-Phenylpiperidine compounds for treating depression |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO995455D0 NO995455D0 (no) | 1999-11-08 |
| NO995455L NO995455L (no) | 2000-02-09 |
| NO317371B1 true NO317371B1 (no) | 2004-10-18 |
Family
ID=26647319
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19995455A NO317371B1 (no) | 1997-06-10 | 1999-11-08 | 4-Fenylpiperidinforbindelser |
| NO20033766A NO20033766D0 (no) | 1997-06-10 | 2003-08-25 | 4-Fenylpiperidinforbindelser |
| NO20033765A NO20033765D0 (no) | 1997-06-10 | 2003-08-25 | 4-Fenylpiperidinforbindelser |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20033766A NO20033766D0 (no) | 1997-06-10 | 2003-08-25 | 4-Fenylpiperidinforbindelser |
| NO20033765A NO20033765D0 (no) | 1997-06-10 | 2003-08-25 | 4-Fenylpiperidinforbindelser |
Country Status (25)
| Country | Link |
|---|---|
| US (4) | US5874447A (cs) |
| EP (2) | EP0994872B9 (cs) |
| JP (1) | JP2002503248A (cs) |
| KR (1) | KR100543614B1 (cs) |
| AT (1) | ATE200781T1 (cs) |
| AU (1) | AU3108097A (cs) |
| BG (1) | BG64315B1 (cs) |
| BR (1) | BR9714787A (cs) |
| CA (1) | CA2293247C (cs) |
| CZ (1) | CZ295301B6 (cs) |
| DE (2) | DE69704679T2 (cs) |
| DK (1) | DK0994872T3 (cs) |
| EE (2) | EE200200633A (cs) |
| ES (1) | ES2155995T3 (cs) |
| GR (1) | GR3035784T3 (cs) |
| HU (1) | HUP0003141A3 (cs) |
| IL (1) | IL133366A (cs) |
| IS (2) | IS1927B (cs) |
| NO (3) | NO317371B1 (cs) |
| PL (1) | PL188450B1 (cs) |
| PT (1) | PT994872E (cs) |
| SI (1) | SI0994872T1 (cs) |
| SK (1) | SK283394B6 (cs) |
| TR (2) | TR199903025T2 (cs) |
| WO (1) | WO1998056787A1 (cs) |
Families Citing this family (52)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU221921B1 (hu) * | 1996-07-08 | 2003-02-28 | Richter Gedeon Vegyészeti Gyár Rt. | N-benzil-piperidin- és tetrahidropiridinszármazékok és eljárás azok előállítására |
| AU3433499A (en) * | 1998-04-09 | 1999-11-01 | Smithkline Beecham Plc | Paroxetine maleate |
| GB9814316D0 (en) * | 1998-07-02 | 1998-09-02 | Smithkline Beecham Plc | Novel compounds |
| US20010023252A1 (en) * | 1998-07-02 | 2001-09-20 | Smithkline Beecham Plc | Novel compound |
| CH689805A8 (fr) * | 1998-07-02 | 2000-02-29 | Smithkline Beecham Plc | Méthanesulfonate de paroxétine, procédé pour sa préparation et compositions pharmaceutiques le contenant. |
| AU724845B3 (en) * | 1998-07-02 | 2000-09-28 | Smithkline Beecham Plc | Novel compound |
| WO2000008016A1 (en) * | 1998-08-08 | 2000-02-17 | Smithkline Beecham Plc | Paroxetine salts |
| GB9827431D0 (en) * | 1998-12-11 | 1999-02-03 | Smithkline Beecham Plc | Novel compound |
| GB9828779D0 (en) * | 1998-12-29 | 1999-02-17 | Smithkline Beecham Plc | Novel process |
| GB9828781D0 (en) * | 1998-12-29 | 1999-02-17 | Smithkline Beecham Plc | Novel process |
| GB9828780D0 (en) * | 1998-12-29 | 1999-02-17 | Smithkline Beecham Plc | Novel process |
| ES2159260B1 (es) * | 1999-06-22 | 2002-05-01 | Smithkline Beechan Plc | Nueva composicion de metanosulfonato de paroxetina |
| WO2000078290A2 (en) * | 1999-06-22 | 2000-12-28 | Smithkline Beecham P.L.C. | Pharmaceutical composition comprising a salt of paroxetine |
| GB9914585D0 (en) * | 1999-06-22 | 1999-08-25 | Smithkline Beecham Plc | Novel process |
| AU5535900A (en) * | 1999-07-01 | 2001-01-22 | Italfarmaco S.P.A. | Complexes of paroxetine, with cyclodextrins or cyclodextrin derivatives |
| GB9919052D0 (en) * | 1999-08-12 | 1999-10-13 | Smithkline Beecham Plc | Novel compound composition and process |
| US6503927B1 (en) * | 1999-10-28 | 2003-01-07 | Pentech Pharmaceuticals, Inc. | Amorphous paroxetine composition |
| USRE46117E1 (en) | 1999-12-22 | 2016-08-23 | Teva Pharmaceuticals International Gmbh | Modulators of dopamine neurotransmission |
| DE60007782T2 (de) * | 2000-05-12 | 2004-12-09 | Synthon B.V. | Piperidinverbindungen und verfahren zu deren herstellung |
| WO2001085688A1 (en) * | 2000-05-12 | 2001-11-15 | Synthon B.V. | TOSYLATE SALTS OF 4-(p-FLUOROPHENYL)-PIPERIDINE-3-CARBINOLS |
| US6645523B2 (en) * | 2000-08-28 | 2003-11-11 | Synthon Bct Technologies, Llc | Paroxetine compositions and processes for making the same |
| AU2001286232A1 (en) * | 2000-09-14 | 2002-03-26 | Asahi Glass Company, Limited | Process for producing paroxetine salt containing substantially no organic solvent |
| DE20100529U1 (de) * | 2001-01-11 | 2001-05-10 | Synthon Bv | Pharmazeutische Tablette umfassend Paroxetinmesylat |
| US6720003B2 (en) * | 2001-02-16 | 2004-04-13 | Andrx Corporation | Serotonin reuptake inhibitor formulations |
| NL1017421C2 (nl) * | 2001-02-21 | 2002-01-15 | Synthon Bv | Werkwijze voor het vervaardigen van paroxetine. |
| US20030032809A1 (en) * | 2001-04-25 | 2003-02-13 | Subhash P. Upadhyaya | Optimized procedures for the manufacture of paroxetine salts |
| US6930186B2 (en) | 2001-06-13 | 2005-08-16 | Teva Pharmacetical Industries Ltd. | Process for the preparation of paroxetine substantially free of alkoxy impurities |
| IL159280A0 (en) * | 2001-06-14 | 2004-06-01 | Teva Pharma | A process for preparing paroxetine hcl which limits formation of pink colored compounds |
| US20040225128A1 (en) * | 2001-08-02 | 2004-11-11 | Callewaert George Leo | Paroxetine isethionate salt, process of preparation and use in the treatment of depression |
| US20030181488A1 (en) | 2002-03-07 | 2003-09-25 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Administration form for the oral application of 3-[(2-{[4-(hexyloxycarbonylamino-imino-methyl)-phenylamino]-methyl}-1-methyl-1H-benzimidazol-5-carbonyl)-pyridin-2-yl-amino]-propionic acid ethyl ester and the salts thereof |
| AR039163A1 (es) * | 2002-03-28 | 2005-02-09 | Synthon Bv | Besilato de venlafaxina |
| US20040220153A1 (en) * | 2002-09-24 | 2004-11-04 | Jost-Price Edward Roydon | Methods and reagents for the treatment of diseases and disorders associated with increased levels of proinflammatory cytokines |
| US7202259B2 (en) * | 2002-11-18 | 2007-04-10 | Euro-Celtique S.A. | Therapeutic agents useful for treating pain |
| EP2343073A3 (en) | 2003-12-11 | 2011-10-12 | Sepracor Inc. | Combination of a sedative and a neurotransmitter modulator, and methods for improving sleep quality and treating depression |
| EP1778183B1 (en) * | 2004-08-18 | 2018-06-27 | Synthon B.V. | Liquid paroxetine compositions |
| WO2006023347A1 (en) * | 2004-08-20 | 2006-03-02 | Alpharma, Inc. | Paroxetine formulations |
| US20080033011A1 (en) * | 2005-07-29 | 2008-02-07 | Concert Pharmaceuticals Inc. | Novel benzo[d][1,3]-dioxol derivatives |
| EA014432B1 (ru) * | 2005-07-29 | 2010-12-30 | Консерт Фармасьютикалс Инк. | Дейтерированные производные 1,3-бензодиоксола |
| SE529246C2 (sv) | 2005-10-13 | 2007-06-12 | Neurosearch Sweden Ab | Nya disubstituerade fenyl-piperidiner som modulatorer för dopaminneurotransmission |
| EP1948646A2 (en) * | 2005-11-14 | 2008-07-30 | Auspex Pharmaceuticals Inc. | Substituted phenylpiperidines with serotoninergic activity and enhanced therapeutic properties |
| US20080033050A1 (en) | 2006-08-04 | 2008-02-07 | Richards Patricia Allison Tewe | Method of treating thermoregulatory disfunction with paroxetine |
| EP2727915B1 (en) * | 2007-09-13 | 2016-04-13 | Concert Pharmaceuticals Inc. | Synthesis of deuterated catechols and benzo[d][1,3]dioxoles and derivatives thereof |
| US9138430B2 (en) * | 2007-12-27 | 2015-09-22 | Mylan Specialty L.P. | Formulation and method for the release of paroxetine in the large intestine |
| ES2705950T3 (es) | 2011-06-03 | 2019-03-27 | Eisai R&D Man Co Ltd | Biomarcadores para predecir y valorar la capacidad de respuesta de sujetos con cáncer de tiroides y de riñón a compuestos de lenvatinib |
| CN104039777B (zh) | 2012-01-31 | 2016-03-02 | 卫材R&D管理有限公司 | 帕罗西汀衍生物 |
| NZ630560A (en) | 2012-04-04 | 2016-11-25 | Teva Pharmaceuticals Int Gmbh | Pharmaceutical compositions for combination therapy |
| EP3825305A1 (en) | 2014-08-28 | 2021-05-26 | Eisai R&D Management Co., Ltd. | Process for preparing lenvatinib |
| DK3263106T3 (da) | 2015-02-25 | 2024-01-08 | Eisai R&D Man Co Ltd | Fremgangsmåde til undertrykkelse af bitterhed af quinolinderivat |
| CN107801379B (zh) | 2015-06-16 | 2021-05-25 | 卫材R&D管理有限公司 | 抗癌剂 |
| JP6553726B2 (ja) | 2015-08-20 | 2019-07-31 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | 腫瘍治療剤 |
| CN110072528B (zh) | 2017-02-08 | 2022-04-26 | 卫材R&D管理有限公司 | 治疗肿瘤的药物组合物 |
| JP2020519576A (ja) | 2017-05-16 | 2020-07-02 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | 肝細胞癌の治療 |
Family Cites Families (47)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT99678B (de) * | 1921-09-21 | 1925-04-10 | Hoechst Ag | Verfahren zur Darstellung arzneilich wirksamer Quecksilberverbindungen. |
| GB1422263A (en) * | 1973-01-30 | 1976-01-21 | Ferrosan As | 4-phenyl-piperidine compounds |
| US4585777A (en) * | 1984-02-07 | 1986-04-29 | A/S Ferrosan | (-)-Trans-4-(4-fluorophenyl)-3-(4-methoxyphenoxy)methylpiperidine for potentiating 5-HT |
| GB8430581D0 (en) * | 1984-12-04 | 1985-01-09 | Ferrosan As | Treatment |
| EP0190496A3 (en) * | 1984-12-13 | 1987-05-27 | Beecham Group Plc | Piperidine derivatives having a gastro-intestinal activity |
| GB8520154D0 (en) * | 1985-08-10 | 1985-09-18 | Beecham Group Plc | Chemical process |
| DE3680184D1 (de) * | 1985-08-10 | 1991-08-14 | Beecham Group Plc | Verfahren zur herstellung von arylpiperidincarbinol. |
| DE3688827T2 (de) * | 1985-10-25 | 1994-03-31 | Beecham Group Plc | Piperidinderivat, seine Herstellung und seine Verwendung als Arzneimittel. |
| US5258388A (en) | 1986-03-17 | 1993-11-02 | University Of Florida | Anticholinergic compounds, compositions and methods of treatment |
| IE66332B1 (en) * | 1986-11-03 | 1995-12-27 | Novo Nordisk As | Piperidine compounds and their preparation and use |
| GB8626936D0 (en) * | 1986-11-11 | 1986-12-10 | Ferrosan As | Treatment |
| GB8714707D0 (en) * | 1987-06-23 | 1987-07-29 | Beecham Group Plc | Chemical process |
| DK715988D0 (da) * | 1988-12-22 | 1988-12-22 | Ferrosan As | Etherifikation og dealkylering af piperidin-derivater samt intermediater |
| DK716088D0 (da) * | 1988-12-22 | 1988-12-22 | Ferrosan As | Reduktion af piperidin-dion-derivater samt intermediat |
| EP0558679A1 (en) * | 1990-11-24 | 1993-09-08 | BEECHAM GROUP plc | Use of paroxetine for the treatment of senile dementia, bulimia, migraine or anorexia |
| GB9209687D0 (en) * | 1992-05-06 | 1992-06-17 | Smithkline Beecham Plc | Novel process |
| US5258517A (en) * | 1992-08-06 | 1993-11-02 | Sepracor, Inc. | Method of preparing optically pure precursors of paroxetine |
| JP2773587B2 (ja) * | 1992-11-30 | 1998-07-09 | 東レ株式会社 | Ｏ，ｏ´−ジアシル酒石酸無水物の製造法 |
| US5276042A (en) | 1993-04-16 | 1994-01-04 | Crenshaw Roger T | Treatment of premature ejaculation |
| US5546683A (en) * | 1993-09-29 | 1996-08-20 | Clark; George J. | Bucket attachment device with remote controlled retractable pins |
| IT1274241B (it) * | 1993-12-03 | 1997-07-15 | Smithkline Beecham Farma | Complessi agente terapeutico/matrice polimerica dotati di migliorate caratteristiche di sapore e composizioni farmaceutiche che li contengono |
| GB9325644D0 (en) | 1993-12-15 | 1994-02-16 | Smithkline Beecham Plc | Novel formulation |
| US5668134A (en) * | 1994-01-28 | 1997-09-16 | G. D. Searle & Co. | Method for preventing or reducing photosensitivity and/or phototoxicity reactions to medications |
| GB9402029D0 (en) * | 1994-02-03 | 1994-03-30 | Smithkline Beecham Plc | Novel formulation |
| CA2143070C (en) * | 1994-02-22 | 2001-12-18 | Pankaj Modi | Oral controlled release liquid suspension pharmaceutical formulation |
| EP0714663A3 (en) * | 1994-11-28 | 1997-01-15 | Lilly Co Eli | Potentiation of drug responses by serotonin 1A receptor antagonists |
| JPH08220486A (ja) * | 1994-12-14 | 1996-08-30 | Kato Kogei:Kk | 眼鏡フレーム |
| US5856493A (en) * | 1995-02-06 | 1999-01-05 | Smithkline Beecham Corporation | Process for making novel form of paroxeting hydrochloride anhydrate |
| SK283608B6 (sk) * | 1995-02-06 | 2003-10-07 | Smithkline Beecham Plc | Bezvodý hydrochlorid paroxetínu, spôsob jeho výroby a použitie |
| GB2297550B (en) * | 1995-02-06 | 1997-04-09 | Smithkline Beecham Plc | Paroxetine hydrochloride anhydrate substantially free of bound organic solvent |
| WO1996031197A1 (en) * | 1995-04-03 | 1996-10-10 | Abbott Laboratories | Homogeneous mixtures of low temperature-melting drugs and additives for controlled release |
| AU721257B2 (en) * | 1995-05-17 | 2000-06-29 | Novo Nordisk A/S | Process for preparing 4-aryl-piperidine derivatives |
| JP2813768B2 (ja) * | 1995-05-24 | 1998-10-22 | 農林水産省家畜衛生試験場長 | 口蹄疫診断用ペプチドおよび当該ペプチドを含有する口蹄疫診断用抗原 |
| GB9514842D0 (en) * | 1995-07-20 | 1995-09-20 | Smithkline Beecham Plc | Novel formulation |
| EP0858460A1 (en) * | 1995-10-31 | 1998-08-19 | Merck & Co., Inc. | Process for preparing substituted azetidinones |
| IT1276160B1 (it) * | 1995-11-22 | 1997-10-27 | Recordati Chem Pharm | Composizioni farmaceutiche orali a pronto rilascio per sospensioni estemporanee |
| GB9526645D0 (en) * | 1995-12-28 | 1996-02-28 | Chiroscience Ltd | Stereoselective synthesis |
| ES2117557B1 (es) * | 1996-02-29 | 1999-07-01 | Ferrer Int | Nuevo procedimiento de obtencion de (-)-trans -n-p-fluorobenzoilmetil-4-(p-fluorofenil)-3- ((3,4-(metilendioxi)fenoxi ) metil)-piperidina. |
| JP3446468B2 (ja) * | 1996-04-15 | 2003-09-16 | 旭硝子株式会社 | ピペリジンカルビノール類の製造方法 |
| CA2206592A1 (en) * | 1996-05-30 | 1997-11-30 | Shu-Zhong Wang | Method of producing amorphous paroxetine hydrochloride |
| JP3882224B2 (ja) * | 1996-05-31 | 2007-02-14 | 旭硝子株式会社 | パロキセチンの製造方法 |
| EP1384711A1 (en) * | 1996-06-13 | 2004-01-28 | SUMIKA FINE CHEMICALS Co., Ltd. | Optical resolution of a piperidine derivative |
| HU221921B1 (hu) * | 1996-07-08 | 2003-02-28 | Richter Gedeon Vegyészeti Gyár Rt. | N-benzil-piperidin- és tetrahidropiridinszármazékok és eljárás azok előállítására |
| US5672609A (en) * | 1996-07-18 | 1997-09-30 | Eli Lilly And Company | Pyridine compounds, intermediates compositions and methods of use |
| CA2187128A1 (en) * | 1996-10-04 | 1997-06-26 | K. S. Keshava Murthy | New and useful polymorph of anhydrous paroxetine hydrochloride |
| US5955475A (en) * | 1997-06-30 | 1999-09-21 | Endo Pharmaceuticals Inc. | Process for manufacturing paroxetine solid dispersions |
| CH689805A8 (fr) | 1998-07-02 | 2000-02-29 | Smithkline Beecham Plc | Méthanesulfonate de paroxétine, procédé pour sa préparation et compositions pharmaceutiques le contenant. |
-
1997
- 1997-06-10 KR KR1019997011625A patent/KR100543614B1/ko not_active Expired - Fee Related
- 1997-06-10 SI SI9730138T patent/SI0994872T1/xx unknown
- 1997-06-10 ES ES97926276T patent/ES2155995T3/es not_active Expired - Lifetime
- 1997-06-10 DE DE69704679T patent/DE69704679T2/de not_active Expired - Lifetime
- 1997-06-10 EP EP97926276A patent/EP0994872B9/en not_active Expired - Lifetime
- 1997-06-10 IL IL13336697A patent/IL133366A/xx not_active IP Right Cessation
- 1997-06-10 TR TR1999/03025T patent/TR199903025T2/xx unknown
- 1997-06-10 AU AU31080/97A patent/AU3108097A/en not_active Abandoned
- 1997-06-10 SK SK1619-99A patent/SK283394B6/sk unknown
- 1997-06-10 EP EP00203910A patent/EP1078925A1/en not_active Withdrawn
- 1997-06-10 CA CA002293247A patent/CA2293247C/en not_active Expired - Lifetime
- 1997-06-10 TR TR2002/01156T patent/TR200201156T2/xx unknown
- 1997-06-10 EE EEP200200633A patent/EE200200633A/xx unknown
- 1997-06-10 CZ CZ19994295A patent/CZ295301B6/cs not_active IP Right Cessation
- 1997-06-10 PT PT97926276T patent/PT994872E/pt unknown
- 1997-06-10 BR BR9714787-7A patent/BR9714787A/pt unknown
- 1997-06-10 AT AT97926276T patent/ATE200781T1/de not_active IP Right Cessation
- 1997-06-10 HU HU0003141A patent/HUP0003141A3/hu unknown
- 1997-06-10 EE EEP199900570A patent/EE03970B1/xx not_active IP Right Cessation
- 1997-06-10 WO PCT/NL1997/000328 patent/WO1998056787A1/en not_active Ceased
- 1997-06-10 US US08/872,023 patent/US5874447A/en not_active Expired - Lifetime
- 1997-06-10 DK DK97926276T patent/DK0994872T3/da active
- 1997-06-10 DE DE29724281U patent/DE29724281U1/de not_active Expired - Lifetime
- 1997-06-10 PL PL97336895A patent/PL188450B1/pl not_active IP Right Cessation
- 1997-06-10 JP JP50212699A patent/JP2002503248A/ja not_active Ceased
-
1998
- 1998-11-30 US US09/200,743 patent/US7598271B1/en not_active Expired - Lifetime
-
1999
- 1999-11-08 NO NO19995455A patent/NO317371B1/no unknown
- 1999-11-16 IS IS5249A patent/IS1927B/is unknown
- 1999-12-10 BG BG103980A patent/BG64315B1/bg unknown
-
2001
- 2001-04-26 GR GR20010400220T patent/GR3035784T3/el not_active IP Right Cessation
- 2001-05-16 US US09/855,710 patent/US6900327B2/en not_active Expired - Lifetime
-
2003
- 2003-08-25 NO NO20033766A patent/NO20033766D0/no not_active Application Discontinuation
- 2003-08-25 NO NO20033765A patent/NO20033765D0/no not_active Application Discontinuation
-
2004
- 2004-01-08 IS IS7098A patent/IS7098A/is unknown
-
2009
- 2009-01-23 US US12/358,997 patent/US20090326233A1/en not_active Abandoned
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| NO317371B1 (no) | 4-Fenylpiperidinforbindelser | |
| EP1731506A1 (en) | 5-hydroxyindole-3-carboxylates derivatives and their use | |
| JP2005514457A (ja) | 統合失調症およびうつ病等の疾患を処置するためのフェノキシピペリジン | |
| JP2004534008A (ja) | 新規なアムロジピンカンファースルホン酸塩及びその製造方法 | |
| JP2003535885A (ja) | 制御された範囲内にｐＨを持つ安定なギャバペンチン | |
| RU2539591C2 (ru) | Антагонисты арилсульфонамида ccr3 | |
| TW200900392A (en) | Novel crystalline bepotastine metal salt hydrate, method for preparing same, and pharmaceutical composition comprising same | |
| JPH0378858B2 (cs) | ||
| RU2451016C2 (ru) | Тозилатная соль транс-n-изобутил-3-фтор-3-[3-фтор-4-(пирролидин-1-илметил)фенил]циклобутанкарбоксамида | |
| KR100779786B1 (ko) | 레복세틴의 제약 염 | |
| EP1732544A2 (en) | Treatment of tremor with histamine h3 inverse agonists or histamine h3 antagonists | |
| TW201536750A (zh) | ３，５－二胺基吡唑激酶抑制劑之醫藥上可接受鹽 | |
| CN1092654C (zh) | 4－苯基哌啶类化合物 | |
| DK200000380U1 (da) | 4-phenyl-piperidin-forbindelser | |
| AU2002301956B2 (en) | 4-phenylpiperidine compounds | |
| SU1456012A3 (ru) | Способ получени N-(1-циклогексенилметил-2-пирролидинилметил)-8-этилсульфонил-1,5-бензодиоксепан-6-карбоксамида или его хлоргидрата | |
| MXPA99011355A (en) | 4-phenylpiperidine compounds | |
| CA2455954A1 (en) | 4-phenylpiperidine compounds | |
| BG104973A (bg) | Пароксетин 10-камфорсулфонат за лечение на cns заболявания | |
| KR20090005271A (ko) | 결정형의 베포타스틴 금속염 수화물, 이의 제조방법 및 이를 포함하는 약학 조성물 | |
| WO2001025201A1 (en) | Process for the preparation of paroxetin intermediate | |
| HK1027352B (en) | 4-phenylpiperidine compounds | |
| ZA200406461B (en) | Venlafaxine besylate | |
| JPH06279373A (ja) | アミノカルボン酸誘導体、その製造方法および用途 |