SI2860175T1 - Method for producing 4,4,7-trifluoro-1,2,3,4-tetrahydro-5h-1-benzazepine compound and intermediate for synthesis thereof - Google Patents
Method for producing 4,4,7-trifluoro-1,2,3,4-tetrahydro-5h-1-benzazepine compound and intermediate for synthesis thereof Download PDFInfo
- Publication number
- SI2860175T1 SI2860175T1 SI201330925T SI201330925T SI2860175T1 SI 2860175 T1 SI2860175 T1 SI 2860175T1 SI 201330925 T SI201330925 T SI 201330925T SI 201330925 T SI201330925 T SI 201330925T SI 2860175 T1 SI2860175 T1 SI 2860175T1
- Authority
- SI
- Slovenia
- Prior art keywords
- formula
- compound
- produced
- preparation
- making
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 33
- 238000004519 manufacturing process Methods 0.000 title claims 4
- WGQWRLLENSTDAH-UHFFFAOYSA-N 4,4,7-trifluoro-1,2,3,5-tetrahydro-1-benzazepine Chemical compound N1CCC(F)(F)CC2=CC(F)=CC=C21 WGQWRLLENSTDAH-UHFFFAOYSA-N 0.000 title claims 2
- 230000015572 biosynthetic process Effects 0.000 title claims 2
- 238000003786 synthesis reaction Methods 0.000 title claims 2
- 150000001875 compounds Chemical class 0.000 claims 77
- 238000002360 preparation method Methods 0.000 claims 18
- 238000006243 chemical reaction Methods 0.000 claims 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 6
- WKXZJCKWUCBECD-GSVOUGTGSA-N (2r)-2-fluoropropan-1-ol Chemical compound C[C@@H](F)CO WKXZJCKWUCBECD-GSVOUGTGSA-N 0.000 claims 4
- -1 p-toluenesulfonyl Chemical group 0.000 claims 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- 238000002955 isolation Methods 0.000 claims 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims 2
- QDSFNOHWQKVVEB-UHFFFAOYSA-N 4-(diethoxyphosphorylmethyl)morpholine Chemical compound CCOP(=O)(OCC)CN1CCOCC1 QDSFNOHWQKVVEB-UHFFFAOYSA-N 0.000 claims 2
- CDXVUROVRIFQMV-UHFFFAOYSA-N oxo(diphenoxy)phosphanium Chemical compound C=1C=CC=CC=1O[P+](=O)OC1=CC=CC=C1 CDXVUROVRIFQMV-UHFFFAOYSA-N 0.000 claims 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims 2
- STJVIACOQKGCFT-HJPCULJESA-N (2z)-2-[4,4,7-trifluoro-1-[4-[(2r)-2-fluoropropoxy]-2-(trifluoromethyl)benzoyl]-2,3-dihydro-1-benzazepin-5-ylidene]acetyl chloride Chemical compound FC(F)(F)C1=CC(OC[C@H](F)C)=CC=C1C(=O)N1C2=CC=C(F)C=C2C(=C/C(Cl)=O)/C(F)(F)CC1 STJVIACOQKGCFT-HJPCULJESA-N 0.000 claims 1
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 claims 1
- 238000006546 Horner-Wadsworth-Emmons reaction Methods 0.000 claims 1
- AIHIHVZYAAMDPM-QMMMGPOBSA-N [(2s)-oxiran-2-yl]methyl 3-nitrobenzenesulfonate Chemical compound [O-][N+](=O)C1=CC=CC(S(=O)(=O)OC[C@H]2OC2)=C1 AIHIHVZYAAMDPM-QMMMGPOBSA-N 0.000 claims 1
- 230000002862 amidating effect Effects 0.000 claims 1
- 239000012043 crude product Substances 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 238000005984 hydrogenation reaction Methods 0.000 claims 1
- 239000000543 intermediate Substances 0.000 claims 1
- ZZUYIRISBMWFMV-UHFFFAOYSA-N methyl 4-chlorobutanoate Chemical compound COC(=O)CCCCl ZZUYIRISBMWFMV-UHFFFAOYSA-N 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/14—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D223/16—Benzazepines; Hydrogenated benzazepines
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/36—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids
- C07C303/40—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids by reactions not involving the formation of sulfonamide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
- C07C311/21—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/367—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of functional groups containing oxygen only in singly bound form
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/31—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by introduction of functional groups containing oxygen only in singly bound form
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Urology & Nephrology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2012131504 | 2012-06-11 | ||
| EP13804693.3A EP2860175B1 (en) | 2012-06-11 | 2013-06-11 | Method for producing 4,4,7-trifluoro-1,2,3,4-tetrahydro-5h-1-benzazepine compound and intermediate for synthesis thereof |
| PCT/JP2013/066076 WO2013187406A1 (ja) | 2012-06-11 | 2013-06-11 | 4,4,7-トリフルオロ-1,2,3,4-テトラヒドロ-5h-1-ベンゾアゼピン化合物の製造方法及びその合成中間体 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SI2860175T1 true SI2860175T1 (en) | 2018-04-30 |
Family
ID=49758228
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SI201330925T SI2860175T1 (en) | 2012-06-11 | 2013-06-11 | Method for producing 4,4,7-trifluoro-1,2,3,4-tetrahydro-5h-1-benzazepine compound and intermediate for synthesis thereof |
Country Status (16)
| Country | Link |
|---|---|
| US (3) | US9598373B2 (enExample) |
| EP (1) | EP2860175B1 (enExample) |
| JP (2) | JPWO2013187406A1 (enExample) |
| CY (1) | CY1119983T1 (enExample) |
| DK (1) | DK2860175T3 (enExample) |
| ES (1) | ES2659180T3 (enExample) |
| HR (1) | HRP20180032T8 (enExample) |
| HU (1) | HUE035391T2 (enExample) |
| LT (1) | LT2860175T (enExample) |
| NO (1) | NO2860175T3 (enExample) |
| PL (1) | PL2860175T3 (enExample) |
| PT (1) | PT2860175T (enExample) |
| RS (1) | RS56804B1 (enExample) |
| SI (1) | SI2860175T1 (enExample) |
| SM (1) | SMT201800106T1 (enExample) |
| WO (1) | WO2013187406A1 (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MX362478B (es) * | 2012-12-26 | 2019-01-11 | Sanwa Kagaku Kenkyusho Co | Derivado de benzoazepina novedoso y uso medico del mismo. |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2857760B2 (ja) * | 1989-02-17 | 1999-02-17 | 第一製薬株式会社 | プロポキシニトロベンゼン類の製法 |
| CA2263267C (en) * | 1996-09-18 | 2006-05-02 | Daiso Co., Ltd. | Process for the preparation of glycidyl ethers |
| MXPA04004501A (es) | 2001-11-16 | 2004-08-11 | Yamanouchi Pharma Co Ltd | Derivados de 4-4-difluoro-1,2,3,4-tetrahidro-5h-1-benzazepina o sales de los mismos. |
| ATE512951T1 (de) * | 2003-04-28 | 2011-07-15 | Astellas Pharma Inc | 4,4-difluor-1,2,3,4-tetrahydro-5h-1- benzazepinderivat oder salz davon |
| CA2570688A1 (en) | 2004-06-24 | 2006-02-02 | Eli Lilly And Company | Compounds and methods for treating dyslipidemia |
| JP4765546B2 (ja) | 2004-10-27 | 2011-09-07 | アステラス製薬株式会社 | ベンゾアゼピン誘導体又はその塩の製造法 |
| JP4765545B2 (ja) | 2004-10-27 | 2011-09-07 | アステラス製薬株式会社 | ベンゾアゼピン誘導体を有効成分とする医薬組成物 |
| EP2235988B1 (en) * | 2008-02-01 | 2011-11-30 | Interdigital Patent Holdings, Inc. | Method and apparatus for enabling cell reselection for wtru operating in discontinuous reception |
-
2013
- 2013-06-11 NO NO13804693A patent/NO2860175T3/no unknown
- 2013-06-11 SI SI201330925T patent/SI2860175T1/en unknown
- 2013-06-11 US US14/406,568 patent/US9598373B2/en not_active Expired - Fee Related
- 2013-06-11 RS RS20180081A patent/RS56804B1/sr unknown
- 2013-06-11 JP JP2014521349A patent/JPWO2013187406A1/ja not_active Ceased
- 2013-06-11 HU HUE13804693A patent/HUE035391T2/en unknown
- 2013-06-11 EP EP13804693.3A patent/EP2860175B1/en active Active
- 2013-06-11 ES ES13804693.3T patent/ES2659180T3/es active Active
- 2013-06-11 DK DK13804693.3T patent/DK2860175T3/da active
- 2013-06-11 PT PT138046933T patent/PT2860175T/pt unknown
- 2013-06-11 WO PCT/JP2013/066076 patent/WO2013187406A1/ja not_active Ceased
- 2013-06-11 LT LTEP13804693.3T patent/LT2860175T/lt unknown
- 2013-06-11 SM SM20180106T patent/SMT201800106T1/it unknown
- 2013-06-11 PL PL13804693T patent/PL2860175T3/pl unknown
- 2013-06-11 HR HRP20180032TT patent/HRP20180032T8/hr unknown
-
2017
- 2017-02-16 US US15/434,678 patent/US9951022B2/en not_active Expired - Fee Related
-
2018
- 2018-01-24 CY CY20181100092T patent/CY1119983T1/el unknown
- 2018-03-23 US US15/933,804 patent/US10508084B2/en not_active Expired - Fee Related
- 2018-08-15 JP JP2018152818A patent/JP2019014716A/ja not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| JPWO2013187406A1 (ja) | 2016-02-04 |
| ES2659180T3 (es) | 2018-03-14 |
| HUE035391T2 (en) | 2018-05-02 |
| RS56804B1 (sr) | 2018-04-30 |
| DK2860175T3 (da) | 2018-01-29 |
| PL2860175T3 (pl) | 2018-07-31 |
| SMT201800106T1 (it) | 2018-03-08 |
| HRP20180032T8 (hr) | 2018-12-14 |
| NO2860175T3 (enExample) | 2018-04-28 |
| WO2013187406A1 (ja) | 2013-12-19 |
| PT2860175T (pt) | 2018-02-02 |
| EP2860175A1 (en) | 2015-04-15 |
| US9951022B2 (en) | 2018-04-24 |
| CY1119983T1 (el) | 2018-12-12 |
| LT2860175T (lt) | 2018-03-26 |
| US10508084B2 (en) | 2019-12-17 |
| US20150141641A1 (en) | 2015-05-21 |
| EP2860175A4 (en) | 2015-12-09 |
| EP2860175B1 (en) | 2017-11-29 |
| HRP20180032T1 (hr) | 2018-03-23 |
| US20190062280A1 (en) | 2019-02-28 |
| US9598373B2 (en) | 2017-03-21 |
| US20170158639A1 (en) | 2017-06-08 |
| JP2019014716A (ja) | 2019-01-31 |
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