DE3429415C2 - - Google Patents
Info
- Publication number
- DE3429415C2 DE3429415C2 DE3429415A DE3429415A DE3429415C2 DE 3429415 C2 DE3429415 C2 DE 3429415C2 DE 3429415 A DE3429415 A DE 3429415A DE 3429415 A DE3429415 A DE 3429415A DE 3429415 C2 DE3429415 C2 DE 3429415C2
- Authority
- DE
- Germany
- Prior art keywords
- prazosin hydrochloride
- boiling point
- water
- prazosin
- hydrochloride
- 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.)
- Expired - Lifetime
Links
- WFXFYZULCQKPIP-UHFFFAOYSA-N prazosin hydrochloride Chemical compound [H+].[Cl-].N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N(CC1)CCN1C(=O)C1=CC=CO1 WFXFYZULCQKPIP-UHFFFAOYSA-N 0.000 claims description 36
- 229960002386 prazosin hydrochloride Drugs 0.000 claims description 35
- 238000009835 boiling Methods 0.000 claims description 19
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 3
- 150000001924 cycloalkanes Chemical class 0.000 claims description 3
- 150000008282 halocarbons Chemical class 0.000 claims description 3
- 238000002844 melting Methods 0.000 claims description 3
- 230000008018 melting Effects 0.000 claims description 3
- 238000002425 crystallisation Methods 0.000 claims 1
- 230000008025 crystallization Effects 0.000 claims 1
- 238000004821 distillation Methods 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- 150000004683 dihydrates Chemical class 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 238000002329 infrared spectrum Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 3
- 238000010533 azeotropic distillation Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- 238000004455 differential thermal analysis Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 150000004682 monohydrates Chemical class 0.000 description 2
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FI842544A FI79107C (fi) | 1984-06-25 | 1984-06-25 | Foerfarande foer framstaellning av stabil -form av prazosinhydroklorid. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3429415A1 DE3429415A1 (de) | 1986-01-02 |
| DE3429415C2 true DE3429415C2 (en:Method) | 1990-05-03 |
Family
ID=8519293
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19843429415 Granted DE3429415A1 (de) | 1984-06-25 | 1984-08-09 | Wasserfreie, stabile und kristalline form von prazosinhydrochlorid und verfahren zu dessen herstellung |
Country Status (17)
| Country | Link |
|---|---|
| US (2) | US4739055A (en:Method) |
| JP (1) | JPS6115881A (en:Method) |
| AT (1) | AT389117B (en:Method) |
| AU (1) | AU566814B2 (en:Method) |
| BE (1) | BE900925A (en:Method) |
| CH (1) | CH661045A5 (en:Method) |
| DE (1) | DE3429415A1 (en:Method) |
| FI (1) | FI79107C (en:Method) |
| FR (1) | FR2567124B1 (en:Method) |
| GB (1) | GB2160861B (en:Method) |
| IL (1) | IL73267A (en:Method) |
| IT (1) | IT1224142B (en:Method) |
| LU (1) | LU85616A1 (en:Method) |
| NL (1) | NL8403250A (en:Method) |
| NZ (1) | NZ209962A (en:Method) |
| PT (1) | PT79411B (en:Method) |
| ZA (1) | ZA85910B (en:Method) |
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3683760D1 (de) * | 1986-03-21 | 1992-03-12 | Heumann Pharma Gmbh & Co | Kristalline, wasserfreie sigma -form von 2-(4-(2-furoyl-(2-piperazin)-1-yl)-4-amino-6,7-dimethoxychinazolinhydrochlorid und verfahren zu ihrer herstellung. |
| JP2756846B2 (ja) * | 1989-12-28 | 1998-05-25 | 住化ファインケム株式会社 | 無水のε型結晶体２―〔４―（２―フロイル）ピペラジン―１―イル〕―４―アミノ―６，７―ジメトキシキナゾリン塩酸塩及びその製造方法 |
| JPH07206857A (ja) * | 1993-12-28 | 1995-08-08 | Synthelabo Sa | アルフゾシン塩酸塩の二水和物 |
| EP1953162B9 (de) * | 2001-02-24 | 2012-10-31 | Boehringer Ingelheim Pharma GmbH & Co. KG | Xanthinderivate, deren Herstellung und deren Verwendung als Arzneimittel |
| US7407955B2 (en) | 2002-08-21 | 2008-08-05 | Boehringer Ingelheim Pharma Gmbh & Co., Kg | 8-[3-amino-piperidin-1-yl]-xanthines, the preparation thereof and their use as pharmaceutical compositions |
| US7501426B2 (en) * | 2004-02-18 | 2009-03-10 | Boehringer Ingelheim International Gmbh | 8-[3-amino-piperidin-1-yl]-xanthines, their preparation and their use as pharmaceutical compositions |
| DE102004054054A1 (de) | 2004-11-05 | 2006-05-11 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Verfahren zur Herstellung chiraler 8-(3-Amino-piperidin-1-yl)-xanthine |
| DE102005035891A1 (de) * | 2005-07-30 | 2007-02-08 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | 8-(3-Amino-piperidin-1-yl)-xanthine, deren Herstellung und deren Verwendung als Arzneimittel |
| EP1852108A1 (en) * | 2006-05-04 | 2007-11-07 | Boehringer Ingelheim Pharma GmbH & Co.KG | DPP IV inhibitor formulations |
| PE20080251A1 (es) * | 2006-05-04 | 2008-04-25 | Boehringer Ingelheim Int | Usos de inhibidores de dpp iv |
| EP2016079A1 (de) | 2006-05-04 | 2009-01-21 | Boehringer Ingelheim International GmbH | Polymorphe |
| JP5769966B2 (ja) * | 2007-08-17 | 2015-08-26 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | Ｆａｂ関連疾患治療用プリン誘導体 |
| AR071175A1 (es) | 2008-04-03 | 2010-06-02 | Boehringer Ingelheim Int | Composicion farmaceutica que comprende un inhibidor de la dipeptidil-peptidasa-4 (dpp4) y un farmaco acompanante |
| PE20100156A1 (es) * | 2008-06-03 | 2010-02-23 | Boehringer Ingelheim Int | Tratamiento de nafld |
| UY32030A (es) | 2008-08-06 | 2010-03-26 | Boehringer Ingelheim Int | "tratamiento para diabetes en pacientes inapropiados para terapia con metformina" |
| KR20190016601A (ko) | 2008-08-06 | 2019-02-18 | 베링거 인겔하임 인터내셔날 게엠베하 | 메트포르민 요법이 부적합한 환자에서의 당뇨병 치료 |
| ES2764251T3 (es) * | 2008-08-15 | 2020-06-02 | Boehringer Ingelheim Int | Inhibidores de DPP-4 para uso en el tratamiento de curación de heridas en pacientes diabéticos |
| JP2012502081A (ja) | 2008-09-10 | 2012-01-26 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | 糖尿病及び関連症状の治療のための組み合わせ治療 |
| US20200155558A1 (en) | 2018-11-20 | 2020-05-21 | Boehringer Ingelheim International Gmbh | Treatment for diabetes in patients with insufficient glycemic control despite therapy with an oral antidiabetic drug |
| AU2009331471B2 (en) | 2008-12-23 | 2015-09-03 | Boehringer Ingelheim International Gmbh | Salt forms of organic compound |
| AR074990A1 (es) | 2009-01-07 | 2011-03-02 | Boehringer Ingelheim Int | Tratamiento de diabetes en pacientes con un control glucemico inadecuado a pesar de la terapia con metformina |
| JP2013512229A (ja) | 2009-11-27 | 2013-04-11 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | 遺伝子型が同定された糖尿病患者のリナグリプチン等のｄｄｐ−ｉｖ阻害薬による治療 |
| EP2566469B1 (en) | 2010-05-05 | 2022-12-21 | Boehringer Ingelheim International GmbH | Combination therapy |
| EP3366304B1 (en) | 2010-06-24 | 2020-05-13 | Boehringer Ingelheim International GmbH | Diabetes therapy |
| AR083878A1 (es) | 2010-11-15 | 2013-03-27 | Boehringer Ingelheim Int | Terapia antidiabetica vasoprotectora y cardioprotectora, linagliptina, metodo de tratamiento |
| DK2731947T3 (en) | 2011-07-15 | 2019-04-23 | Boehringer Ingelheim Int | SUBSTITUTED DIMERIC QUINAZOLINE DERIVATIVE, PREPARATION AND USE thereof IN PHARMACEUTICAL COMPOSITIONS FOR TREATMENT OF TYPE I AND TYPE II DIABETES |
| US9555001B2 (en) | 2012-03-07 | 2017-01-31 | Boehringer Ingelheim International Gmbh | Pharmaceutical composition and uses thereof |
| US20130303462A1 (en) | 2012-05-14 | 2013-11-14 | Boehringer Ingelheim International Gmbh | Use of a dpp-4 inhibitor in podocytes related disorders and/or nephrotic syndrome |
| ES2929025T3 (es) | 2012-05-14 | 2022-11-24 | Boehringer Ingelheim Int | Linagliptina, un derivado de xantina como inhibidor de dpp-4, para su uso en el tratamiento del SRIS y/o de la septicemia |
| WO2013174767A1 (en) | 2012-05-24 | 2013-11-28 | Boehringer Ingelheim International Gmbh | A xanthine derivative as dpp -4 inhibitor for use in modifying food intake and regulating food preference |
| JP6615109B2 (ja) | 2014-02-28 | 2019-12-04 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | Ｄｐｐ−４阻害薬の医学的使用 |
| CN109310697A (zh) | 2016-06-10 | 2019-02-05 | 勃林格殷格翰国际有限公司 | 利格列汀和二甲双胍的组合 |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE156532C (en:Method) * | ||||
| US2969375A (en) * | 1961-01-24 | Certification of correction | ||
| NL54420C (en:Method) * | 1937-05-25 | |||
| GB1156973A (en) * | 1965-07-06 | 1969-07-02 | Quinazoline Derivatives | |
| US3433788A (en) * | 1966-04-27 | 1969-03-18 | Union Carbide Corp | Process for recovery of amines from aqueous solutions by solvent treatment and distillation |
| US3421983A (en) * | 1967-03-07 | 1969-01-14 | Lummus Co | Azeotropic distillation of aqueous toluene diamine |
| US3511836A (en) * | 1967-12-13 | 1970-05-12 | Pfizer & Co C | 2,4,6,7-tetra substituted quinazolines |
| US3743672A (en) * | 1970-05-27 | 1973-07-03 | Halcon International Inc | Separation of water in alkylene glycol mono and diester purification by azeotropic distillation |
| GB1308718A (en) * | 1970-07-01 | 1973-03-07 | Sir Soc Italiana Resine Spa | Method of separating vinyl acetate from liquid mixtures |
| IT956765B (it) * | 1972-06-22 | 1973-10-10 | Montedison Spa | Procedimento per la purificazione di 1 3 diossolano |
| US3935213A (en) * | 1973-12-05 | 1976-01-27 | Pfizer Inc. | Process for hypotensive 4-amino-2-(piperazin-1-yl) quinazoline derivatives |
| US4026894A (en) * | 1975-10-14 | 1977-05-31 | Abbott Laboratories | Antihypertensive agents |
| US4001237A (en) * | 1976-02-18 | 1977-01-04 | Bristol-Myers Company | Oxazole, isoxazole, thiazole and isothiazole amides |
| US4092315A (en) * | 1976-03-01 | 1978-05-30 | Pfizer Inc. | Novel crystalline forms of prazosin hydrochloride |
| FI67699C (fi) * | 1979-01-31 | 1985-05-10 | Orion Yhtymae Oy | Foerfarande foer framstaellning av 6,7-dimetoxi-4-amino-2-(4-(2-furoyl)-1-piperazinyl)kinazolinhydroklorid med blodtryckssaenkande verkan |
| FI64367C (fi) * | 1980-02-26 | 1986-08-05 | Orion Yhtymae Oy | Foerfarande foer framstaellning av alfa-form av prazosinhydroklorid |
-
1984
- 1984-06-25 FI FI842544A patent/FI79107C/fi not_active IP Right Cessation
- 1984-08-09 DE DE19843429415 patent/DE3429415A1/de active Granted
- 1984-10-03 GB GB08424999A patent/GB2160861B/en not_active Expired
- 1984-10-15 US US06/660,871 patent/US4739055A/en not_active Expired - Lifetime
- 1984-10-19 IL IL73267A patent/IL73267A/xx not_active IP Right Cessation
- 1984-10-19 AU AU34510/84A patent/AU566814B2/en not_active Ceased
- 1984-10-23 NZ NZ209962A patent/NZ209962A/en unknown
- 1984-10-24 IT IT23292/84A patent/IT1224142B/it active
- 1984-10-25 NL NL8403250A patent/NL8403250A/nl not_active Application Discontinuation
- 1984-10-26 CH CH5142/84A patent/CH661045A5/de not_active IP Right Cessation
- 1984-10-26 FR FR8416401A patent/FR2567124B1/fr not_active Expired - Lifetime
- 1984-10-26 PT PT79411A patent/PT79411B/pt not_active IP Right Cessation
- 1984-10-29 BE BE0/213911A patent/BE900925A/fr not_active IP Right Cessation
- 1984-10-29 JP JP59227640A patent/JPS6115881A/ja active Granted
- 1984-10-29 LU LU85616A patent/LU85616A1/fr unknown
- 1984-10-30 AT AT0344184A patent/AT389117B/de not_active IP Right Cessation
-
1985
- 1985-02-06 ZA ZA85910A patent/ZA85910B/xx unknown
-
1988
- 1988-02-08 US US07/153,780 patent/US4873330A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| LU85616A1 (fr) | 1985-06-04 |
| FR2567124A1 (fr) | 1986-01-10 |
| FI842544L (fi) | 1985-12-26 |
| FR2567124B1 (fr) | 1990-09-21 |
| FI79107C (fi) | 1989-11-10 |
| GB2160861B (en) | 1987-11-18 |
| IT1224142B (it) | 1990-09-26 |
| FI842544A0 (fi) | 1984-06-25 |
| AU566814B2 (en) | 1987-10-29 |
| FI79107B (fi) | 1989-07-31 |
| US4873330A (en) | 1989-10-10 |
| PT79411B (en) | 1986-09-15 |
| GB2160861A (en) | 1986-01-02 |
| JPH0481993B2 (en:Method) | 1992-12-25 |
| GB8424999D0 (en) | 1984-11-07 |
| ATA344184A (de) | 1989-03-15 |
| AU3451084A (en) | 1986-01-02 |
| BE900925A (fr) | 1985-02-15 |
| AT389117B (de) | 1989-10-25 |
| PT79411A (en) | 1984-11-01 |
| NZ209962A (en) | 1987-06-30 |
| DE3429415A1 (de) | 1986-01-02 |
| NL8403250A (nl) | 1986-01-16 |
| ZA85910B (en) | 1985-09-25 |
| US4739055A (en) | 1988-04-19 |
| CH661045A5 (de) | 1987-06-30 |
| JPS6115881A (ja) | 1986-01-23 |
| IL73267A0 (en) | 1985-01-31 |
| IL73267A (en) | 1988-06-30 |
| IT8423292A0 (it) | 1984-10-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8328 | Change in the person/name/address of the agent |
Free format text: BARZ, P., DIPL.-CHEM. DR.RER.NAT., PAT.-ANW., 80803 MUENCHEN |
|
| 8339 | Ceased/non-payment of the annual fee |