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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- Prior art keywords
- compound
- acid
- methyl
- treating
- iii
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- 150000001875 compounds Chemical class 0.000 title claims abstract 17
- IAVUPMFITXYVAF-XPUUQOCRSA-N dorzolamide Chemical compound CCN[C@H]1C[C@H](C)S(=O)(=O)C2=C1C=C(S(N)(=O)=O)S2 IAVUPMFITXYVAF-XPUUQOCRSA-N 0.000 title abstract 3
- 230000015572 biosynthetic process Effects 0.000 title abstract 2
- 238000003786 synthesis reaction Methods 0.000 title abstract 2
- 238000000034 method Methods 0.000 claims 8
- 239000002253 acid Substances 0.000 claims 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 239000000203 mixture Substances 0.000 claims 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 3
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 claims 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims 2
- 239000007864 aqueous solution Substances 0.000 claims 2
- 238000001914 filtration Methods 0.000 claims 2
- 238000002156 mixing Methods 0.000 claims 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 2
- 150000002825 nitriles Chemical class 0.000 claims 2
- 238000002360 preparation method Methods 0.000 claims 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 claims 1
- FCSKOFQQCWLGMV-UHFFFAOYSA-N 5-{5-[2-chloro-4-(4,5-dihydro-1,3-oxazol-2-yl)phenoxy]pentyl}-3-methylisoxazole Chemical compound O1N=C(C)C=C1CCCCCOC1=CC=C(C=2OCCN=2)C=C1Cl FCSKOFQQCWLGMV-UHFFFAOYSA-N 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 229910021529 ammonia Inorganic materials 0.000 claims 1
- UWTDFICHZKXYAC-UHFFFAOYSA-N boron;oxolane Chemical compound [B].C1CCOC1 UWTDFICHZKXYAC-UHFFFAOYSA-N 0.000 claims 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 claims 1
- 238000001035 drying Methods 0.000 claims 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 claims 1
- 239000012065 filter cake Substances 0.000 claims 1
- 239000000706 filtrate Substances 0.000 claims 1
- 150000003840 hydrochlorides Chemical class 0.000 claims 1
- 150000002688 maleic acid derivatives Chemical class 0.000 claims 1
- 229940098779 methanesulfonic acid Drugs 0.000 claims 1
- 150000007522 mineralic acids Chemical class 0.000 claims 1
- 229910000033 sodium borohydride Inorganic materials 0.000 claims 1
- 239000012279 sodium borohydride Substances 0.000 claims 1
- 239000000243 solution Substances 0.000 claims 1
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 claims 1
- 238000006434 Ritter amidation reaction Methods 0.000 abstract 1
- 229960003933 dorzolamide Drugs 0.000 abstract 1
- 230000014759 maintenance of location Effects 0.000 abstract 1
Classifications
-
- 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
Landscapes
- 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)
- Cephalosporin Compounds (AREA)
- Seasonings (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
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 (28)
| Country | Link |
|---|---|
| US (1) | US5688968A (cs) |
| EP (1) | EP0617037B1 (cs) |
| JP (1) | JP3273096B2 (cs) |
| KR (1) | KR0157162B1 (cs) |
| CN (1) | CN1046732C (cs) |
| AT (1) | ATE163291T1 (cs) |
| AU (1) | AU673409B2 (cs) |
| BR (1) | BR9406017A (cs) |
| CA (1) | CA2119218C (cs) |
| CY (1) | CY2108B1 (cs) |
| CZ (1) | CZ281390B6 (cs) |
| DE (1) | DE69408550T2 (cs) |
| DK (1) | DK0617037T3 (cs) |
| ES (1) | ES2112482T3 (cs) |
| FI (1) | FI107384B (cs) |
| GR (1) | GR3026178T3 (cs) |
| HR (1) | HRP940182B1 (cs) |
| HU (1) | HU217363B (cs) |
| NO (1) | NO313240B1 (cs) |
| NZ (1) | NZ263092A (cs) |
| PL (1) | PL176373B1 (cs) |
| RO (1) | RO115264B1 (cs) |
| SI (1) | SI9420016B (cs) |
| SK (1) | SK280831B6 (cs) |
| TW (1) | TW265343B (cs) |
| UA (1) | UA41921C2 (cs) |
| WO (1) | WO1994021645A1 (cs) |
| YU (1) | YU48951B (cs) |
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. |
| WO2004089957A1 (en) * | 2003-04-07 | 2004-10-21 | Hetero Drugs Limited | A novel crystalline form of dorzolamide hydrochloride |
| MXPA06015274A (es) * | 2004-07-09 | 2007-09-27 | Fdc Ltd | Un procedimiento mejorado para la preparacion de 5,6-dihidro-4h-4(s)-etilamino-6(s)-metiltieno [2,3-b] tiopiran-2-sulfonamida-7,7-dioxido y sus sales. |
| 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. |
| AU2004326111A1 (en) * | 2004-12-28 | 2006-07-06 | 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 HCI |
| 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 |
| US20060155132A1 (en) * | 2005-01-06 | 2006-07-13 | Kovacs Laszlo Z | Method of making dorzolamide hydrochloride |
| WO2006078731A2 (en) * | 2005-01-18 | 2006-07-27 | Teva Gyogyszergyar Zartkoruen Mukodo Reszvenytarsasag | Amorphous and crystalline forms of dorzolamide hydrochloride and processes of making same |
| US8263787B2 (en) | 2007-05-07 | 2012-09-11 | Cipla Limited | Process for preparing dorzolamide |
| CN103415524B (zh) | 2011-03-10 | 2015-11-25 | Zach系统股份公司 | 不对称还原方法 |
| ITMI20121165A1 (it) * | 2012-07-03 | 2014-01-04 | Zach System Spa | Processo di riduzione asimmetrica |
| EP3057427B1 (en) * | 2013-10-17 | 2018-07-18 | Dow AgroSciences LLC | Processes for the preparation of pesticidal compounds |
| 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 CZ CZ952418A patent/CZ281390B6/cs not_active IP Right Cessation
- 1994-03-16 NZ NZ263092A patent/NZ263092A/en not_active IP Right Cessation
- 1994-03-16 UA UA95094239A patent/UA41921C2/uk unknown
- 1994-03-16 BR BR9406017A patent/BR9406017A/pt unknown
- 1994-03-16 WO PCT/US1994/002852 patent/WO1994021645A1/en active IP Right Grant
- 1994-03-16 CN CN94191502A patent/CN1046732C/zh not_active Expired - Lifetime
- 1994-03-16 KR KR1019950703996A patent/KR0157162B1/ko not_active Expired - Lifetime
- 1994-03-16 SI SI9420016A patent/SI9420016B/sl unknown
- 1994-03-16 CA CA002119218A patent/CA2119218C/en not_active Expired - Fee Related
- 1994-03-16 PL PL94310633A patent/PL176373B1/pl unknown
- 1994-03-16 RO RO95-01639A patent/RO115264B1/ro unknown
- 1994-03-16 SK SK1169-95A patent/SK280831B6/sk not_active IP Right Cessation
- 1994-03-16 HU HU9502772A patent/HU217363B/hu unknown
- 1994-03-17 EP EP94301933A patent/EP0617037B1/en not_active Expired - Lifetime
- 1994-03-17 DK DK94301933.1T patent/DK0617037T3/da active
- 1994-03-17 ES ES94301933T patent/ES2112482T3/es not_active Expired - Lifetime
- 1994-03-17 AT AT94301933T patent/ATE163291T1/de active
- 1994-03-17 JP JP04730794A patent/JP3273096B2/ja not_active Expired - Lifetime
- 1994-03-17 DE DE69408550T patent/DE69408550T2/de not_active Expired - Lifetime
- 1994-03-18 AU AU57871/94A patent/AU673409B2/en not_active Expired
- 1994-03-21 HR HR08/195,886A patent/HRP940182B1/xx not_active IP Right Cessation
- 1994-03-21 YU YU13194A patent/YU48951B/sh unknown
-
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
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Legal Events
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| IF | Valid on the event date | ||
| SP73 | Change of data on owner |
Owner name: MERCK SHARP & DOHME CORP.; US Effective date: 20021015 |
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| SP73 | Change of data on owner |
Owner name: MERCK SHARP & DOHME CORP.; US Effective date: 20121127 |