SI9420016B - Enantioselektivna sinteza 5,6 -dihidro-(S)-4-(etilamino)-(S)-6-metil-4H-tieno /2,3-b/ tiopiran-2- sulfonamid 7,7- dioksida in sorodnih spojin - Google Patents
Enantioselektivna sinteza 5,6 -dihidro-(S)-4-(etilamino)-(S)-6-metil-4H-tieno /2,3-b/ tiopiran-2- sulfonamid 7,7- dioksida in sorodnih spojin Download PDFInfo
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- SI9420016B SI9420016B SI9420016A SI9420016A SI9420016B SI 9420016 B SI9420016 B SI 9420016B SI 9420016 A SI9420016 A SI 9420016A SI 9420016 A SI9420016 A SI 9420016A SI 9420016 B SI9420016 B SI 9420016B
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Ophthalmology & Optometry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Seasonings (AREA)
- Cephalosporin Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Claims (8)
- PATENTNI ZAHTEVKI 1. Postopek za pripravo spojine s strukturno formulo I: NHI in njene hidrokloridne soli, pri čemer je kiralnost pri C-6 fiksna in je trans-s tereokemična povezava med C-4 in C-6 substituenti ohranjena, spojina je kristalinična in R in R1 sta enaka ali različna in sta alkil, ki obsega stopnje: A) obdelovanje spojine s formulo II z HOo2 II R» nitrilom s formulo RCN in količina prisotne vode, v kisline, od 0,5 do 10 mas strukturo III: močno kislino, tako da je odvisnosti od uporabljene %, da se tvori spojina s -2- R ΟR1 ΝΗIII \ ο. Β) obdelovanje spojine III s klorosulfonsko kislino, da se tvori spojina s strukturo IV: O A NHC) obdelovanje spojine IV s tionilovim kloridom, da se tvori spojina s strukturo V: O NH SO?CI Γϊν R1^s-^s o, D) obdelovanje spojine V z amoniakom, da se tvori spojina s strukturo VI:VI -3- E) obdelovanje spojine VI z natrijevim borohidridom in močno kislino ali boran-tetrahidrofuranom, da se tvori spojina s strukturo VIIF) izolacija spojine VII kot maleatna sol VIII; G) pretvorba spojine VIII v hidrokloridno sol spojine I; in H) čiščenje hidrokloridne soli spojine I.
- 2. Postopek iz zahtevka 1, pri čemer sta R in R1 metil.
- 3. Postopek iz zahtevka 1, pri čemer je R metil in R1 n-propil.
- 4. Postopek za pripravo spojine s strukturno formulo III:III pri čemer je kiralnost pri C-6 fiksna in je trans-stereokemična -4- povezava med C-4 in C-6 substituenti ohranjena, R in R1 pa sta enaka ali različna in sta C1-3 alkil, ki obsega: obdelovanje spojine s formulo II z HOII nitrilom s formulo RCN in močno anorgansko kislino, tako da je količina prisotne vode, v odvisnosti od uporabljene kisline, od 0,5 do 10 mas. %.
- 5. Postopek iz zahtevka 4, pri čemer sta R in R1 metil.
- 6. Postopek iz zahtevka 4, pri čemer je R metil in R1 je n-propil.
- 7. Postopek iz zahtevka 1, pri čemer je močna kislina koncentrirana žveplova kislina ali zmes koncentrirane žveplove kisline in kadeče se žveplove kisline ali metansulfonska kislina, trifluoroocetna kislina ali borotrifluorid eterat in količina prisotne vode je od 1 do 2 mas. %.
- 8. Postopek iz zahtevka 1, pri čemer spojina s strukturno formulo I kristalizira po raztapljanju surove spojine s strukturno formulo I v vodni raztopini pri temperaturi 90 °C do 95 °C; po dodajanju aktivnega oglja, mešanju zmesi, filtriranju zmesi skozi plast filtrirnega pomožnega sredstva, izpiranju filtrskega kolača z vročo vodno raztopino, kombiniranju filtrata in kolača, kristaliziranju spojine s strukturno formulo I, ko se raztopina ohladi na 1 °C do 5 °C, filtriranju zmesi, zbiranju kolača in sušenju kolača. Za Merck & Co., Inc. Rahway New Jersey 07065-0900 ZDA : ODVETNICA ALEKSANDRA JANEŽIČ Ljubljana, Resljeva c. 24 teL; 300 76 60, tar433 70 98
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US3552393A | 1993-03-22 | 1993-03-22 | |
| US19588694A | 1994-02-10 | 1994-02-10 | |
| PCT/US1994/002852 WO1994021645A1 (en) | 1993-03-22 | 1994-03-16 | ENANTIOSELECTIVE SYNTHESIS OF 5,6-DIHYDRO-(S)-4-(ETHYLAMINO)-(S)-6-METHYL-4H-THIENO[2,3-b]THIOPYRAN-2-SULFONAMIDE 7,7-DIOXIDE AND RELATED COMPOUNDS |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SI9420016A SI9420016A (en) | 1996-06-30 |
| SI9420016B true SI9420016B (sl) | 2002-12-31 |
Family
ID=26712200
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SI9420016A SI9420016B (sl) | 1993-03-22 | 1994-03-16 | Enantioselektivna sinteza 5,6 -dihidro-(S)-4-(etilamino)-(S)-6-metil-4H-tieno /2,3-b/ tiopiran-2- sulfonamid 7,7- dioksida in sorodnih spojin |
Country Status (29)
| Country | Link |
|---|---|
| US (1) | US5688968A (sl) |
| EP (1) | EP0617037B1 (sl) |
| JP (1) | JP3273096B2 (sl) |
| KR (1) | KR0157162B1 (sl) |
| CN (1) | CN1046732C (sl) |
| AT (1) | ATE163291T1 (sl) |
| AU (1) | AU673409B2 (sl) |
| BR (1) | BR9406017A (sl) |
| CA (1) | CA2119218C (sl) |
| CY (1) | CY2108B1 (sl) |
| CZ (1) | CZ281390B6 (sl) |
| DE (1) | DE69408550T2 (sl) |
| DK (1) | DK0617037T3 (sl) |
| ES (1) | ES2112482T3 (sl) |
| FI (1) | FI107384B (sl) |
| GR (1) | GR3026178T3 (sl) |
| HK (1) | HK1009063A1 (sl) |
| HR (1) | HRP940182B1 (sl) |
| HU (1) | HU217363B (sl) |
| NO (1) | NO313240B1 (sl) |
| NZ (1) | NZ263092A (sl) |
| PL (1) | PL176373B1 (sl) |
| RO (1) | RO115264B1 (sl) |
| SI (1) | SI9420016B (sl) |
| SK (1) | SK280831B6 (sl) |
| TW (1) | TW265343B (sl) |
| UA (1) | UA41921C2 (sl) |
| WO (1) | WO1994021645A1 (sl) |
| YU (1) | YU48951B (sl) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5760249A (en) * | 1995-08-29 | 1998-06-02 | Merck & Co., Inc. | Synthesis of hydroxysulfone and related compounds |
| ES2177415B1 (es) * | 2000-09-04 | 2004-10-16 | Ragactives, S.L. | Procedimiento para la obtencion de 4-alquilamino-5, 6-dihidro-4h-tieno-(2,3b)-tiopiran-2-sulfonamida-7-dioxidos, e intermedios. |
| ES2204306B1 (es) * | 2002-08-16 | 2005-08-01 | Ragactives, S.L. | Formas polimorficas de clorhidrato de dorzolamida, su obtencion y composiciones farmaceuticas que las contienen. |
| US7053115B2 (en) * | 2003-04-07 | 2006-05-30 | Hetero Drugs Limited | Crystalline form of dorzolamide hydrochloride |
| ATE380190T1 (de) * | 2004-07-09 | 2007-12-15 | Fdc Ltd | Verbessertes verfahren zur herstellung von 5,6 - dihydro -4h-4(s)-ethylamin-6(s)-methylthieno(2,3- b) thiopyran-2-sulfonamid- 7,7 -dioxid und seinen salzen |
| ES2253112B1 (es) | 2004-11-05 | 2007-03-16 | Ragactives, S.L. | Procedimiento para la obtencion de derivados de 4-(n-alquilamino)-5, 6-dihidro-4h-tieno-(2,3-b)-tiopirano. |
| US7109353B2 (en) | 2004-12-28 | 2006-09-19 | Council Of Scientific And Industrial Research | Process for preparing 5,6-dihydro-4-(S)-(ethylamino)-6-(S) methyl-4H-thieno[2,3b]thiopyran-2-sulphonamide-7,7-dioxide HCl |
| EP1841774A1 (en) * | 2004-12-28 | 2007-10-10 | Usv Limited | PROCESS FOR PREPARING 5,6-DIHYDRO-4-(S)-(ETHYLAMINO)-6-(S) METHYL-4H-THIENOÝ2,3b¨THIOPYRAN-2-SULPHONAMIDE-7,7-DIOXIDE HCI |
| US20060155132A1 (en) * | 2005-01-06 | 2006-07-13 | Kovacs Laszlo Z | Method of making dorzolamide hydrochloride |
| EP1838717A2 (en) * | 2005-01-18 | 2007-10-03 | Teva Gyógyszergyár Zártköruen Muködo Részvenytarsaság | Amorphous and crystalline forms of dorzolamide hydrochloride and processes of making same |
| WO2008135770A2 (en) * | 2007-05-07 | 2008-11-13 | Cipla Limited | Process for preparing dorzolam ide |
| SI2683724T1 (sl) | 2011-03-10 | 2015-08-31 | Zach System S.P.A. | Asimetrični redukcijski proces |
| ITMI20121165A1 (it) * | 2012-07-03 | 2014-01-04 | Zach System Spa | Processo di riduzione asimmetrica |
| JP2016536295A (ja) * | 2013-10-17 | 2016-11-24 | ダウ アグロサイエンシィズ エルエルシー | 有害生物防除性化合物の製造方法 |
| CN105636445B (zh) * | 2013-10-17 | 2018-12-07 | 美国陶氏益农公司 | 制备杀虫化合物的方法 |
| CN103497202B (zh) * | 2013-10-23 | 2015-12-02 | 武汉武药科技有限公司 | 盐酸多佐胺中间体的合成方法 |
| CN108822127B (zh) * | 2018-05-30 | 2020-05-15 | 沈阳药科大学 | 4-羟亚胺基噻吩并[2,3-b]噻喃-2-甲酰胺类化合物及其用途 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4863922A (en) * | 1984-12-12 | 1989-09-05 | Merck & Co., Inc. | Substituted aromatic sulfonamides as antiglaucoma agents, compositions and use |
| US4797413A (en) * | 1986-05-14 | 1989-01-10 | Merck & Co., Inc. | Thieno thiopyran sulfonamide derivatives, pharmaceutical compositions and use |
| US4968814A (en) * | 1990-04-18 | 1990-11-06 | Merck & Co., Inc. | (S)-Alkyl 3-(thien-2-ylthio)butyrate and analogs and synthesis thereof |
| US5091409A (en) * | 1990-05-17 | 1992-02-25 | Merck & Co., Inc. | 4-alkylamino-6-(C3-5 -hydrocarbyl)thieno[2,3-B]thiopyran-2-sulfonamide-7,7-dioxides |
-
1994
- 1994-03-15 TW TW083102219A patent/TW265343B/zh not_active IP Right Cessation
- 1994-03-16 SK SK1169-95A patent/SK280831B6/sk not_active IP Right Cessation
- 1994-03-16 KR KR1019950703996A patent/KR0157162B1/ko not_active IP Right Cessation
- 1994-03-16 CA CA002119218A patent/CA2119218C/en not_active Expired - Fee Related
- 1994-03-16 SI SI9420016A patent/SI9420016B/sl unknown
- 1994-03-16 CN CN94191502A patent/CN1046732C/zh not_active Expired - Lifetime
- 1994-03-16 WO PCT/US1994/002852 patent/WO1994021645A1/en active IP Right Grant
- 1994-03-16 HU HU9502772A patent/HU217363B/hu unknown
- 1994-03-16 RO RO95-01639A patent/RO115264B1/ro unknown
- 1994-03-16 UA UA95094239A patent/UA41921C2/uk unknown
- 1994-03-16 NZ NZ263092A patent/NZ263092A/en not_active IP Right Cessation
- 1994-03-16 CZ CZ952418A patent/CZ281390B6/cs not_active IP Right Cessation
- 1994-03-16 PL PL94310633A patent/PL176373B1/pl unknown
- 1994-03-16 BR BR9406017A patent/BR9406017A/pt unknown
- 1994-03-17 DK DK94301933.1T patent/DK0617037T3/da active
- 1994-03-17 EP EP94301933A patent/EP0617037B1/en not_active Expired - Lifetime
- 1994-03-17 AT AT94301933T patent/ATE163291T1/de active
- 1994-03-17 ES ES94301933T patent/ES2112482T3/es not_active Expired - Lifetime
- 1994-03-17 DE DE69408550T patent/DE69408550T2/de not_active Expired - Lifetime
- 1994-03-17 JP JP04730794A patent/JP3273096B2/ja not_active Expired - Lifetime
- 1994-03-18 AU AU57871/94A patent/AU673409B2/en not_active Expired
- 1994-03-21 YU YU13194A patent/YU48951B/sh unknown
- 1994-03-21 HR HR08/195,886A patent/HRP940182B1/xx not_active IP Right Cessation
-
1995
- 1995-01-06 US US08/369,557 patent/US5688968A/en not_active Expired - Fee Related
- 1995-09-20 FI FI954438A patent/FI107384B/fi not_active IP Right Cessation
- 1995-09-21 NO NO19953733A patent/NO313240B1/no not_active IP Right Cessation
-
1998
- 1998-02-19 GR GR980400202T patent/GR3026178T3/el unknown
- 1998-07-23 CY CY9800020A patent/CY2108B1/xx unknown
- 1998-08-07 HK HK98109764A patent/HK1009063A1/xx not_active IP Right Cessation
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| IF | Valid on the event date | ||
| SP73 | Change of data on owner |
Owner name: MERCK SHARP & DOHME CORP.; US Effective date: 20021015 |
|
| SP73 | Change of data on owner |
Owner name: MERCK SHARP & DOHME CORP.; US Effective date: 20121127 |