JP2010535185A5 - - Google Patents
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- Publication number
- JP2010535185A5 JP2010535185A5 JP2010518741A JP2010518741A JP2010535185A5 JP 2010535185 A5 JP2010535185 A5 JP 2010535185A5 JP 2010518741 A JP2010518741 A JP 2010518741A JP 2010518741 A JP2010518741 A JP 2010518741A JP 2010535185 A5 JP2010535185 A5 JP 2010535185A5
- Authority
- JP
- Japan
- Prior art keywords
- alfuzosin
- amino
- dimethoxyquinazol
- acid
- base
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 238000000034 method Methods 0.000 claims 23
- WNMJYKCGWZFFKR-UHFFFAOYSA-N alfuzosin Chemical compound N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N(C)CCCNC(=O)C1CCCO1 WNMJYKCGWZFFKR-UHFFFAOYSA-N 0.000 claims 10
- 229960004607 alfuzosin Drugs 0.000 claims 9
- CCOVXHZDHACRNQ-UHFFFAOYSA-N 3-[(4-amino-6,7-dimethoxyquinazolin-2-yl)-methylamino]propanenitrile Chemical compound N#CCCN(C)C1=NC(N)=C2C=C(OC)C(OC)=CC2=N1 CCOVXHZDHACRNQ-UHFFFAOYSA-N 0.000 claims 8
- 239000002585 base Substances 0.000 claims 8
- 150000003839 salts Chemical class 0.000 claims 8
- 239000002253 acid Substances 0.000 claims 7
- FBRFWJRUZCTMPR-UHFFFAOYSA-N 2-n-(2-aminopropyl)-6,7-dimethoxy-2-n-methylquinazoline-2,4-diamine Chemical compound CC(N)CN(C)C1=NC(N)=C2C=C(OC)C(OC)=CC2=N1 FBRFWJRUZCTMPR-UHFFFAOYSA-N 0.000 claims 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims 4
- -1 4-amino-6,7-dimethoxyquinazol-2-yl Chemical group 0.000 claims 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
- 229960003103 alfuzosin hydrochloride Drugs 0.000 claims 3
- YTNKWDJILNVLGX-UHFFFAOYSA-N alfuzosin hydrochloride Chemical compound [H+].[Cl-].N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N(C)CCCNC(=O)C1CCCO1 YTNKWDJILNVLGX-UHFFFAOYSA-N 0.000 claims 3
- 229910052783 alkali metal Inorganic materials 0.000 claims 3
- 150000001340 alkali metals Chemical class 0.000 claims 3
- 239000012320 chlorinating reagent Substances 0.000 claims 3
- HWIIAAVGRHKSOJ-UHFFFAOYSA-N 2-chloro-6,7-dimethoxyquinazolin-4-amine Chemical compound ClC1=NC(N)=C2C=C(OC)C(OC)=CC2=N1 HWIIAAVGRHKSOJ-UHFFFAOYSA-N 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- 150000001450 anions Chemical group 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 238000006482 condensation reaction Methods 0.000 claims 2
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 claims 2
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical group C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
- 238000005984 hydrogenation reaction Methods 0.000 claims 2
- 150000007522 mineralic acids Chemical class 0.000 claims 2
- 150000007524 organic acids Chemical class 0.000 claims 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 claims 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims 2
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical group ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- UNIJBMUBHBAUET-UHFFFAOYSA-N 3-(methylamino)propanenitrile Chemical compound CNCCC#N UNIJBMUBHBAUET-UHFFFAOYSA-N 0.000 claims 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims 1
- DCXYFEDJOCDNAF-UHFFFAOYSA-N Asparagine Natural products OC(=O)C(N)CC(N)=O DCXYFEDJOCDNAF-UHFFFAOYSA-N 0.000 claims 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 1
- DCXYFEDJOCDNAF-REOHCLBHSA-N L-asparagine Chemical compound OC(=O)[C@@H](N)CC(N)=O DCXYFEDJOCDNAF-REOHCLBHSA-N 0.000 claims 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims 1
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 claims 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
- 239000007868 Raney catalyst Substances 0.000 claims 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical group [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims 1
- 229910000564 Raney nickel Inorganic materials 0.000 claims 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims 1
- 230000001476 alcoholic effect Effects 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 1
- 235000011114 ammonium hydroxide Nutrition 0.000 claims 1
- 229960001230 asparagine Drugs 0.000 claims 1
- 235000009582 asparagine Nutrition 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 150000004985 diamines Chemical class 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- 229910052744 lithium Inorganic materials 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 claims 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 claims 1
- 239000003880 polar aprotic solvent Substances 0.000 claims 1
- 229910052700 potassium Inorganic materials 0.000 claims 1
- 239000011591 potassium Substances 0.000 claims 1
- 239000000376 reactant Substances 0.000 claims 1
- 229910052710 silicon Inorganic materials 0.000 claims 1
- 239000010703 silicon Substances 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN1493MU2007 | 2007-08-02 | ||
| PCT/GB2008/002632 WO2009016387A2 (en) | 2007-08-02 | 2008-08-01 | Process for the preparation of alfuzosin hydrochloride |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2010535185A JP2010535185A (ja) | 2010-11-18 |
| JP2010535185A5 true JP2010535185A5 (enExample) | 2011-09-15 |
Family
ID=40304963
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010518741A Pending JP2010535185A (ja) | 2007-08-02 | 2008-08-01 | アルフゾシン塩酸塩の製造方法 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US8716476B2 (enExample) |
| EP (1) | EP2178864B1 (enExample) |
| JP (1) | JP2010535185A (enExample) |
| KR (1) | KR20100044239A (enExample) |
| AU (1) | AU2008281567B2 (enExample) |
| CA (1) | CA2695076A1 (enExample) |
| NZ (1) | NZ582950A (enExample) |
| WO (1) | WO2009016387A2 (enExample) |
| ZA (1) | ZA201000802B (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2178864B1 (en) | 2007-08-02 | 2014-07-23 | Cipla Limited | Process for the preparation of alfuzosin hydrochloride |
| CN104893626B (zh) | 2010-03-09 | 2017-08-08 | 汉高知识产权控股有限责任公司 | 用于压敏粘合剂的阳离子的可uv交联的丙烯酸聚合物 |
| AR107672A1 (es) * | 2016-02-22 | 2018-05-23 | Hoffmann La Roche | Proceso para la fabricación de derivados de 3-piperazin-1-il-propilamina |
| CN113801069B (zh) * | 2020-06-15 | 2024-03-15 | 鲁南制药集团股份有限公司 | 一种盐酸阿夫唑嗪中间体化合物 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2421888A1 (fr) * | 1978-02-06 | 1979-11-02 | Synthelabo | Amides d'alkylene-diamines et leur application en therapeutique |
| YU70890A (en) | 1989-04-21 | 1992-05-28 | Egyt Gyogyszervegyeszeti Gyar | Process for obtaining quinazoline derivatives |
| JPH07206857A (ja) | 1993-12-28 | 1995-08-08 | Synthelabo Sa | アルフゾシン塩酸塩の二水和物 |
| WO2006090268A2 (en) * | 2005-02-28 | 2006-08-31 | Glenmark Pharmaceuticals Limited | Processes for the preparation of alfuzosin and salts thereof and novel crystalline forms of alfuzosin |
| US20070066824A1 (en) | 2005-09-22 | 2007-03-22 | Anumula Raghupathi R | Preparation of alfuzosin |
| US20070105880A1 (en) * | 2005-11-08 | 2007-05-10 | Torrent Pharmaceuticals Limited | Process for the preparation of alfuzosin |
| EP1968970A2 (en) * | 2005-12-16 | 2008-09-17 | Wockhardt Limited | Processes for the preparation of alfuzosin |
| WO2007074364A1 (en) * | 2005-12-26 | 2007-07-05 | Aurobindo Pharma Limited | Process for the preparation of alfuzosin |
| WO2008114272A2 (en) * | 2007-03-22 | 2008-09-25 | Cadila Healthcare Limited | Process for preparing alpuzosin and crystalline alfuzosin hydrochloride |
| EP2178864B1 (en) | 2007-08-02 | 2014-07-23 | Cipla Limited | Process for the preparation of alfuzosin hydrochloride |
-
2008
- 2008-08-01 EP EP08788253.6A patent/EP2178864B1/en not_active Not-in-force
- 2008-08-01 KR KR1020107004281A patent/KR20100044239A/ko not_active Withdrawn
- 2008-08-01 AU AU2008281567A patent/AU2008281567B2/en not_active Ceased
- 2008-08-01 US US12/671,418 patent/US8716476B2/en not_active Expired - Fee Related
- 2008-08-01 WO PCT/GB2008/002632 patent/WO2009016387A2/en not_active Ceased
- 2008-08-01 JP JP2010518741A patent/JP2010535185A/ja active Pending
- 2008-08-01 NZ NZ582950A patent/NZ582950A/en not_active IP Right Cessation
- 2008-08-01 CA CA2695076A patent/CA2695076A1/en not_active Abandoned
-
2010
- 2010-02-03 ZA ZA2010/00802A patent/ZA201000802B/en unknown
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