NO329855B1 - Kystallforbindelse for fast oralt medikament samt fast oralt medikament omfattende denne til behandling av dysuria - Google Patents
Kystallforbindelse for fast oralt medikament samt fast oralt medikament omfattende denne til behandling av dysuria Download PDFInfo
- Publication number
- NO329855B1 NO329855B1 NO20051709A NO20051709A NO329855B1 NO 329855 B1 NO329855 B1 NO 329855B1 NO 20051709 A NO20051709 A NO 20051709A NO 20051709 A NO20051709 A NO 20051709A NO 329855 B1 NO329855 B1 NO 329855B1
- Authority
- NO
- Norway
- Prior art keywords
- agent
- dysuria
- crystal
- drug
- kmd
- Prior art date
Links
- 206010013990 dysuria Diseases 0.000 title claims abstract description 41
- 239000007787 solid Substances 0.000 title claims abstract description 39
- 150000001875 compounds Chemical class 0.000 title abstract description 9
- 229940126701 oral medication Drugs 0.000 title 2
- 239000013078 crystal Substances 0.000 claims abstract description 111
- 239000003814 drug Substances 0.000 claims abstract description 76
- 239000004480 active ingredient Substances 0.000 claims abstract description 39
- -1 indoline compound Chemical class 0.000 claims abstract description 7
- 238000000634 powder X-ray diffraction Methods 0.000 claims abstract description 7
- 229940079593 drug Drugs 0.000 claims description 65
- 239000002775 capsule Substances 0.000 claims description 28
- 239000003795 chemical substances by application Substances 0.000 claims description 26
- 239000002981 blocking agent Substances 0.000 claims description 12
- 239000000463 material Substances 0.000 claims description 12
- 229940121948 Muscarinic receptor antagonist Drugs 0.000 claims description 11
- 239000003242 anti bacterial agent Substances 0.000 claims description 11
- 239000000812 cholinergic antagonist Substances 0.000 claims description 11
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 11
- 229940123934 Reductase inhibitor Drugs 0.000 claims description 10
- 229940121363 anti-inflammatory agent Drugs 0.000 claims description 10
- 239000002260 anti-inflammatory agent Substances 0.000 claims description 10
- 239000002249 anxiolytic agent Substances 0.000 claims description 10
- 230000001713 cholinergic effect Effects 0.000 claims description 10
- 239000003163 gonadal steroid hormone Substances 0.000 claims description 10
- 230000000694 effects Effects 0.000 claims description 9
- 239000003112 inhibitor Substances 0.000 claims description 9
- 239000011248 coating agent Substances 0.000 claims description 8
- 238000000576 coating method Methods 0.000 claims description 8
- 201000010099 disease Diseases 0.000 claims description 8
- 230000027939 micturition Effects 0.000 claims description 6
- 210000005036 nerve Anatomy 0.000 claims description 6
- 206010046459 urethral obstruction Diseases 0.000 claims description 5
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 4
- 208000012931 Urologic disease Diseases 0.000 claims description 4
- 239000002552 dosage form Substances 0.000 claims description 4
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 claims description 4
- 208000014001 urinary system disease Diseases 0.000 claims description 4
- 206010007026 Calculus urethral Diseases 0.000 claims description 3
- 208000000693 Neurogenic Urinary Bladder Diseases 0.000 claims description 3
- 206010029279 Neurogenic bladder Diseases 0.000 claims description 3
- 206010060862 Prostate cancer Diseases 0.000 claims description 3
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 3
- 206010065584 Urethral stenosis Diseases 0.000 claims description 3
- 208000035475 disorder Diseases 0.000 claims description 3
- 201000009160 urethral calculus Diseases 0.000 claims description 3
- 201000001988 urethral stricture Diseases 0.000 claims description 3
- 206010020880 Hypertrophy Diseases 0.000 claims description 2
- 150000002476 indolines Chemical class 0.000 claims description 2
- 210000002307 prostate Anatomy 0.000 claims description 2
- PNCPYILNMDWPEY-QGZVFWFLSA-N silodosin Chemical compound N([C@@H](CC=1C=C(C=2N(CCCO)CCC=2C=1)C(N)=O)C)CCOC1=CC=CC=C1OCC(F)(F)F PNCPYILNMDWPEY-QGZVFWFLSA-N 0.000 abstract description 53
- 229940124597 therapeutic agent Drugs 0.000 abstract description 4
- 230000000903 blocking effect Effects 0.000 abstract description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 32
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 239000000203 mixture Substances 0.000 description 14
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- 239000002904 solvent Substances 0.000 description 11
- 238000000034 method Methods 0.000 description 9
- 238000007796 conventional method Methods 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 6
- 239000003826 tablet Substances 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- 238000009776 industrial production Methods 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000012046 mixed solvent Substances 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000008194 pharmaceutical composition Substances 0.000 description 3
- 239000000546 pharmaceutical excipient Substances 0.000 description 3
- 239000013557 residual solvent Substances 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- 206010004446 Benign prostatic hyperplasia Diseases 0.000 description 2
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 206010020853 Hypertonic bladder Diseases 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 208000004403 Prostatic Hyperplasia Diseases 0.000 description 2
- 208000034189 Sclerosis Diseases 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000036772 blood pressure Effects 0.000 description 2
- 210000003679 cervix uteri Anatomy 0.000 description 2
- 208000013507 chronic prostatitis Diseases 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000002198 insoluble material Substances 0.000 description 2
- 238000004811 liquid chromatography Methods 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 201000004240 prostatic hypertrophy Diseases 0.000 description 2
- 201000007094 prostatitis Diseases 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000012453 solvate Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 210000003708 urethra Anatomy 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 206010005060 Bladder obstruction Diseases 0.000 description 1
- 208000003174 Brain Neoplasms Diseases 0.000 description 1
- 208000014644 Brain disease Diseases 0.000 description 1
- 206010063057 Cystitis noninfective Diseases 0.000 description 1
- 208000032274 Encephalopathy Diseases 0.000 description 1
- 208000015824 Fowler syndrome Diseases 0.000 description 1
- 208000026602 Hinman syndrome Diseases 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 208000001089 Multiple system atrophy Diseases 0.000 description 1
- 206010031127 Orthostatic hypotension Diseases 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 206010036968 Prostatic pain Diseases 0.000 description 1
- 206010037195 Psychogenic dysuria Diseases 0.000 description 1
- 208000029033 Spinal Cord disease Diseases 0.000 description 1
- 208000028484 Urethral disease Diseases 0.000 description 1
- 206010046477 Urethral syndrome Diseases 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 208000026106 cerebrovascular disease Diseases 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 201000003139 chronic cystitis Diseases 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 230000001077 hypotensive effect Effects 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 229910000403 monosodium phosphate Inorganic materials 0.000 description 1
- 235000019799 monosodium phosphate Nutrition 0.000 description 1
- 239000008184 oral solid dosage form Substances 0.000 description 1
- 210000000578 peripheral nerve Anatomy 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 238000004080 punching Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000007873 sieving Methods 0.000 description 1
- 210000002460 smooth muscle Anatomy 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- 229940126589 solid medicine Drugs 0.000 description 1
- 239000002195 soluble material Substances 0.000 description 1
- 210000000278 spinal cord Anatomy 0.000 description 1
- 208000020431 spinal cord injury Diseases 0.000 description 1
- 208000005198 spinal stenosis Diseases 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 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
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
- A61K31/404—Indoles, e.g. pindolol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2300/00—Mixtures or combinations of active ingredients, wherein at least one active ingredient is fully defined in groups A61K31/00 - A61K41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Urology & Nephrology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Indole Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines Containing Plant Substances (AREA)
- Steroid Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2002262157 | 2002-09-06 | ||
| PCT/JP2003/011345 WO2004022538A1 (ja) | 2002-09-06 | 2003-09-05 | 経口用固形医薬用結晶およびそれを含む排尿障害治療用経口用固形医薬 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO20051709L NO20051709L (no) | 2005-06-06 |
| NO329855B1 true NO329855B1 (no) | 2011-01-10 |
Family
ID=31973150
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20051709A NO329855B1 (no) | 2002-09-06 | 2005-04-06 | Kystallforbindelse for fast oralt medikament samt fast oralt medikament omfattende denne til behandling av dysuria |
| NO2011011C NO2011011I1 (no) | 2002-09-06 | 2011-07-11 | Silodosin (Indolinforbindelse representert ved strukturformelen vist i krav 1 i norsk patent 329855) |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO2011011C NO2011011I1 (no) | 2002-09-06 | 2011-07-11 | Silodosin (Indolinforbindelse representert ved strukturformelen vist i krav 1 i norsk patent 329855) |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US20060142374A1 (pl) |
| EP (1) | EP1541554B1 (pl) |
| JP (1) | JP4532274B2 (pl) |
| KR (1) | KR100670592B1 (pl) |
| CN (1) | CN1321111C (pl) |
| AT (1) | ATE416159T1 (pl) |
| AU (1) | AU2003264385B2 (pl) |
| BR (1) | BR0314338A (pl) |
| CA (1) | CA2496780C (pl) |
| DE (1) | DE60325074D1 (pl) |
| ES (1) | ES2316858T3 (pl) |
| HK (1) | HK1084396A1 (pl) |
| HR (1) | HRP20050214B1 (pl) |
| IL (1) | IL167168A (pl) |
| IS (1) | IS2640B (pl) |
| MX (1) | MXPA05002549A (pl) |
| NO (2) | NO329855B1 (pl) |
| NZ (1) | NZ538598A (pl) |
| PL (1) | PL375701A1 (pl) |
| RU (1) | RU2347774C2 (pl) |
| TW (1) | TW200407126A (pl) |
| UA (1) | UA78854C2 (pl) |
| WO (1) | WO2004022538A1 (pl) |
| ZA (1) | ZA200501884B (pl) |
Families Citing this family (40)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101072909B1 (ko) * | 2002-12-16 | 2011-10-17 | 깃세이 야쿠힌 고교 가부시키가이샤 | 경구고형의약 |
| US20070167511A1 (en) * | 2004-03-05 | 2007-07-19 | Kissei Pharmaceutical Co,. Ltd. | Medicinal composition for prevention or treatment of overactive bladder accompanying nervous disorder |
| CN101027052A (zh) * | 2004-10-05 | 2007-08-29 | 橘生药品工业株式会社 | 用于伴下尿路梗阻的集尿障碍的预防和/或治疗剂 |
| ES2378240T3 (es) * | 2004-10-06 | 2012-04-10 | Kissei Pharmaceutical Co., Ltd. | Composición medicinal para evitar la transición al tratamiento operatorio de la hipertrofia prostática |
| NZ556156A (en) * | 2005-02-02 | 2010-03-26 | Teva Pharma | Process for producing acetate salts of polypeptides using hydrogenolysis |
| PT1848415E (pt) * | 2005-02-17 | 2013-06-27 | Teva Pharma | Terapia de combinação com acetato de glatirâmero e rasagilina para o tratamento da esclerose múltipla |
| ES2375761T3 (es) * | 2006-12-14 | 2012-03-06 | Teva Pharmaceutical Industries Ltd. | Base de rasagilina cristalina sólida. |
| US20100076010A1 (en) * | 2007-02-26 | 2010-03-25 | Concert Pharmaceuticals, Inc. | Alpha 1a-adrenoceptor antagonists |
| US8013007B2 (en) * | 2007-02-26 | 2011-09-06 | Concert Pharmaceuticals, Inc. | Alpha 1A-adrenoceptor antagonists |
| MX2009009230A (es) * | 2007-02-28 | 2009-11-26 | Kissei Pharmaceutical | Uso de silodosina en una administracion diaria para tratar hiperplasia prostatica benigna. |
| JP2011525489A (ja) * | 2008-06-19 | 2011-09-22 | テバ ファーマシューティカル インダストリーズ リミティド | ラサリジン塩基の精製方法 |
| ES2471076T3 (es) | 2010-06-28 | 2014-06-25 | Ratiopharm Gmbh | Compuestos de inclusión de silodoxina-ciclodextrina |
| JP2013532651A (ja) | 2010-07-23 | 2013-08-19 | ラティオファルム ゲー・エム・ベー・ハー | シロドシンと塩基性コポリマーとの混合物を含む経口投与用医薬品 |
| WO2012014186A1 (en) | 2010-07-30 | 2012-02-02 | Ranbaxy Laboratories Limited | Process for the preparation of silodosin and its novel intermediates |
| CN102229557B (zh) * | 2010-08-05 | 2013-03-27 | 南京海纳医药科技有限公司 | 西洛多辛的半水合物晶体、制备方法和包含它的药物组合物 |
| CN102229558B (zh) * | 2010-08-05 | 2013-05-08 | 南京海纳医药科技有限公司 | 西洛多辛的晶型δ、它的制备方法和包含它的药物组合物 |
| CN102010359B (zh) * | 2010-09-10 | 2013-01-23 | 北京阳光诺和药物研究有限公司 | β晶型西洛多辛的制备方法 |
| WO2012077138A1 (en) | 2010-12-09 | 2012-06-14 | Panacea Biotec Limited | Methods of crystallizing (r) -1- (3 -hydroxypropyl) -5- [2- [2- [2- ( 2, 2, 2 - trifluoroethoxy) phenoxy] ethylamino] propyl] indoline-7 -carboxamide |
| SI2474529T1 (sl) | 2010-12-23 | 2014-12-31 | Sandoz Ag | Kristalne oblike aktivne farmacevtske učinkovine |
| CN102283816B (zh) * | 2011-08-05 | 2013-09-11 | 北京海步国际医药科技发展有限公司 | 西洛多辛缓释片剂及其制备方法 |
| WO2013061338A1 (en) * | 2011-08-24 | 2013-05-02 | Cadila Healthcare Limited | Pharmaceutical compositions of silodosin |
| WO2013072935A2 (en) | 2011-10-10 | 2013-05-23 | Cadila Healthcare Limited | Process for the preparation of silodosin |
| TWI659752B (zh) * | 2013-03-26 | 2019-05-21 | 日商橘生藥品工業股份有限公司 | 經遮蔽西羅多辛（Ｓｉｌｏｄｏｓｉｎ）苦味之經口投與製劑 |
| CN103159664B (zh) * | 2013-03-29 | 2016-03-23 | 深圳市海滨制药有限公司 | 一种赛洛多辛原料药及其制备方法、药物组合物 |
| WO2015015512A2 (en) * | 2013-07-29 | 2015-02-05 | Ind-Swift Laboratories Limited | Process for the preparation of silodosin and its gamma form |
| JP2015117192A (ja) * | 2013-12-17 | 2015-06-25 | 東和薬品株式会社 | シロドシンγ型結晶及びその製造方法 |
| JP6225998B2 (ja) | 2014-02-06 | 2017-11-08 | 宇部興産株式会社 | インドリン化合物の製造方法 |
| KR20150127996A (ko) * | 2014-05-08 | 2015-11-18 | 한미정밀화학주식회사 | 실로도신 감마형 결정의 제조방법 |
| KR101725393B1 (ko) * | 2014-07-24 | 2017-04-27 | 주식회사 경보제약 | 실로도신의 제조 방법 및 신규 중간체 |
| KR101673160B1 (ko) | 2014-10-24 | 2016-11-07 | 보령제약 주식회사 | 실로도신 γ 결정형의 제조방법 |
| JP2016147811A (ja) * | 2015-02-10 | 2016-08-18 | ダイト株式会社 | シロドシンγ型結晶の製造方法 |
| ES2607639B1 (es) | 2015-09-30 | 2018-02-28 | Urquima, S.A | Sal de ácido maleico de un intermedio de silodosina |
| KR101733084B1 (ko) | 2016-07-27 | 2017-05-08 | (주)다산메디켐 | 실로도신의 결정형의 제조방법 |
| EP3354283B1 (en) | 2017-06-20 | 2019-08-07 | Alfred E. Tiefenbacher (GmbH & Co. KG) | Pharmaceutical capsule composition comprising silodosin |
| JP2018035199A (ja) * | 2017-12-07 | 2018-03-08 | 東和薬品株式会社 | シロドシンγ型結晶及びその製造方法 |
| CN107903201B (zh) * | 2017-12-27 | 2020-09-25 | 浙江天宇药业股份有限公司 | 一种β晶型西洛多辛的制备方法 |
| CN111410626B (zh) * | 2019-01-04 | 2022-11-04 | 上海汇伦医药股份有限公司 | 赛洛多辛α-晶型的制备方法 |
| CN109824569B (zh) * | 2019-04-04 | 2022-09-20 | 重庆医药高等专科学校 | 一种西罗多辛晶型i及其制备方法 |
| WO2020237643A1 (zh) * | 2019-05-31 | 2020-12-03 | 上海汇伦生命科技有限公司 | 赛洛多辛α-晶型的制备方法 |
| CN114601826B (zh) * | 2022-03-31 | 2024-06-04 | 乐泰药业有限公司 | 一种用于治疗前列腺增生的药物制剂及其制备方法和质量检测方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0600675B1 (en) * | 1992-12-02 | 1998-07-08 | Kissei Pharmaceutical Co., Ltd. | Indoline compounds for the treatment of dysuria |
| JP3331048B2 (ja) * | 1994-06-01 | 2002-10-07 | キッセイ薬品工業株式会社 | インドール誘導体 |
| WO1999015202A1 (fr) * | 1997-09-22 | 1999-04-01 | Kissei Pharmaceutical Co., Ltd. | Medicaments contre la dysurie resultant d'une hypertrophie de la prostate |
| WO1999048530A1 (en) * | 1998-03-23 | 1999-09-30 | Merck & Co., Inc. | Combination therapy for the treatment of benign prostatic hyperplasia |
| JP4324266B2 (ja) * | 1999-02-26 | 2009-09-02 | キッセイ薬品工業株式会社 | α１Ａアドレナリン受容体の変異体、当該変異体を用いた測定方法及び前立腺肥大に伴う排尿困難症治療剤 |
| JP4921646B2 (ja) * | 2001-03-08 | 2012-04-25 | キッセイ薬品工業株式会社 | １−（３−ベンジルオキシプロピル）−５−（２−置換プロピル）インドリン誘導体およびその使用方法 |
| ES2362788T3 (es) * | 2004-10-27 | 2011-07-13 | Kissei Pharmaceutical Co., Ltd. | Compuesto de indolina y proceso para la producción del mismo. |
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