ZA200004927B - Pyridazinone hydrochlorine compound and method for producing the same. - Google Patents
Pyridazinone hydrochlorine compound and method for producing the same. Download PDFInfo
- Publication number
- ZA200004927B ZA200004927B ZA200004927A ZA200004927A ZA200004927B ZA 200004927 B ZA200004927 B ZA 200004927B ZA 200004927 A ZA200004927 A ZA 200004927A ZA 200004927 A ZA200004927 A ZA 200004927A ZA 200004927 B ZA200004927 B ZA 200004927B
- Authority
- ZA
- South Africa
- Prior art keywords
- hydrochloride
- compound
- pyridazinone
- solvent
- methanol
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims description 28
- 238000004519 manufacturing process Methods 0.000 title claims description 14
- AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical compound OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 title claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 42
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 39
- 239000002904 solvent Substances 0.000 claims description 36
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 34
- 239000000203 mixture Substances 0.000 claims description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 13
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 12
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 12
- QYWHYLNYDQJLNO-UHFFFAOYSA-N 4-[[3-[2-(4-benzylpiperazin-1-yl)-2-oxoethoxy]-4-methoxyphenyl]methylamino]-5-chloro-1h-pyridazin-6-one Chemical compound C1=C(OCC(=O)N2CCN(CC=3C=CC=CC=3)CC2)C(OC)=CC=C1CNC=1C=NNC(=O)C=1Cl QYWHYLNYDQJLNO-UHFFFAOYSA-N 0.000 claims description 6
- UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical group OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 claims description 5
- LJQKCYFTNDAAPC-UHFFFAOYSA-N ethanol;ethyl acetate Chemical group CCO.CCOC(C)=O LJQKCYFTNDAAPC-UHFFFAOYSA-N 0.000 claims description 4
- -1 HYDROCHLORIDE COMPOUND Chemical class 0.000 description 25
- 239000013078 crystal Substances 0.000 description 24
- 239000000243 solution Substances 0.000 description 23
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- 238000002425 crystallisation Methods 0.000 description 17
- 230000008025 crystallization Effects 0.000 description 17
- 239000007858 starting material Substances 0.000 description 11
- 239000000825 pharmaceutical preparation Substances 0.000 description 7
- 229940127557 pharmaceutical product Drugs 0.000 description 7
- 239000011369 resultant mixture Substances 0.000 description 7
- 238000001914 filtration Methods 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- DZGCGKFAPXFTNM-UHFFFAOYSA-N ethanol;hydron;chloride Chemical compound Cl.CCO DZGCGKFAPXFTNM-UHFFFAOYSA-N 0.000 description 5
- FUKUFMFMCZIRNT-UHFFFAOYSA-N hydron;methanol;chloride Chemical compound Cl.OC FUKUFMFMCZIRNT-UHFFFAOYSA-N 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 238000002441 X-ray diffraction Methods 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 230000003266 anti-allergic effect Effects 0.000 description 3
- 230000006502 antiplatelets effects Effects 0.000 description 3
- 238000000634 powder X-ray diffraction Methods 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 230000007883 bronchodilation Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 230000004526 pharmaceutical effect Effects 0.000 description 2
- 238000001144 powder X-ray diffraction data Methods 0.000 description 2
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 230000003750 conditioning effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
- 229940011051 isopropyl acetate Drugs 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D237/22—Nitrogen and oxygen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D237/12—Halogen atoms or nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Pulmonology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Immunology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8592098 | 1998-03-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200004927B true ZA200004927B (en) | 2001-12-24 |
Family
ID=13872231
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200004927A ZA200004927B (en) | 1998-03-31 | 2000-09-15 | Pyridazinone hydrochlorine compound and method for producing the same. |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US6310065B1 (fr) |
| EP (1) | EP1066265A1 (fr) |
| JP (1) | JP2002509919A (fr) |
| KR (1) | KR20010042078A (fr) |
| CN (1) | CN1293661A (fr) |
| AU (1) | AU742553B2 (fr) |
| CA (1) | CA2326506A1 (fr) |
| IL (1) | IL138521A0 (fr) |
| NO (1) | NO20004896L (fr) |
| NZ (1) | NZ506959A (fr) |
| SK (1) | SK14742000A3 (fr) |
| TW (1) | TW499425B (fr) |
| WO (1) | WO1999050248A1 (fr) |
| ZA (1) | ZA200004927B (fr) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| PE20080251A1 (es) | 2006-05-04 | 2008-04-25 | Boehringer Ingelheim Int | Usos de inhibidores de dpp iv |
| EP1852108A1 (fr) | 2006-05-04 | 2007-11-07 | Boehringer Ingelheim Pharma GmbH & Co.KG | Compositions d'inhibiteurs de la DPP IV |
| CN102838599A (zh) | 2006-05-04 | 2012-12-26 | 贝林格尔.英格海姆国际有限公司 | 多晶型 |
| PE20140960A1 (es) | 2008-04-03 | 2014-08-15 | Boehringer Ingelheim Int | Formulaciones que comprenden un inhibidor de dpp4 |
| BRPI0916997A2 (pt) | 2008-08-06 | 2020-12-15 | Boehringer Ingelheim International Gmbh | Inibidor de dpp-4 e seu uso |
| UY32030A (es) | 2008-08-06 | 2010-03-26 | Boehringer Ingelheim Int | "tratamiento para diabetes en pacientes inapropiados para terapia con metformina" |
| AU2009290911A1 (en) | 2008-09-10 | 2010-03-18 | Boehringer Ingelheim International Gmbh | Combination therapy for the treatment of diabetes and related conditions |
| US8978895B2 (en) * | 2008-10-01 | 2015-03-17 | Rickey E. Wark | Self-cleaning coal separator grids with multiple cleaning combs |
| 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 |
| KR102668834B1 (ko) | 2009-11-27 | 2024-05-24 | 베링거 인겔하임 인터내셔날 게엠베하 | 리나글립틴과 같은 ｄｐｐ－ｉｖ 억제제를 사용한 유전자형 검사된 당뇨병 환자의 치료 |
| ES2935300T3 (es) | 2010-05-05 | 2023-03-03 | Boehringer Ingelheim Int | Combiterapia |
| KR20230051307A (ko) | 2010-06-24 | 2023-04-17 | 베링거 인겔하임 인터내셔날 게엠베하 | 당뇨병 요법 |
| US9034883B2 (en) | 2010-11-15 | 2015-05-19 | Boehringer Ingelheim International Gmbh | Vasoprotective and cardioprotective antidiabetic therapy |
| EA030121B1 (ru) | 2011-07-15 | 2018-06-29 | Бёрингер Ингельхайм Интернациональ Гмбх | Замещенные хиназолины, их получение и их применение в фармацевтических композициях |
| US9555001B2 (en) | 2012-03-07 | 2017-01-31 | Boehringer Ingelheim International Gmbh | Pharmaceutical composition and uses thereof |
| WO2013171167A1 (fr) | 2012-05-14 | 2013-11-21 | Boehringer Ingelheim International Gmbh | Dérivé de xanthine en tant qu'inhibiteur de dpp-4 pour l'utilisation dans le traitement de troubles associés aux podocytes et/ou un syndrome néphrotique |
| WO2013174767A1 (fr) | 2012-05-24 | 2013-11-28 | Boehringer Ingelheim International Gmbh | Dérivé de xanthine en tant qu'inhibiteur de la dpp-4 à utiliser dans la modification de l'apport alimentaire et dans la régulation des préférences alimentaires |
| ES2950384T3 (es) | 2014-02-28 | 2023-10-09 | Boehringer Ingelheim Int | Uso médico de un inhibidor de DPP-4 |
| EP4233840A3 (fr) | 2016-06-10 | 2023-10-18 | Boehringer Ingelheim International GmbH | Combinaisons de linagliptine et de metformine |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3080131B2 (ja) * | 1993-06-29 | 2000-08-21 | 日産化学工業株式会社 | ピリダジノン誘導体 |
| IL110040A (en) * | 1993-06-29 | 2000-07-16 | Nissan Chemical Ind Ltd | Pyridazinone derivatives their preparation and pharmaceutical compositions comprising them |
-
1999
- 1999-03-30 CN CN99804120A patent/CN1293661A/zh active Pending
- 1999-03-30 IL IL13852199A patent/IL138521A0/xx unknown
- 1999-03-30 SK SK1474-2000A patent/SK14742000A3/sk unknown
- 1999-03-30 US US09/646,127 patent/US6310065B1/en not_active Expired - Fee Related
- 1999-03-30 JP JP2000541153A patent/JP2002509919A/ja not_active Withdrawn
- 1999-03-30 EP EP99910776A patent/EP1066265A1/fr not_active Withdrawn
- 1999-03-30 WO PCT/JP1999/001629 patent/WO1999050248A1/fr not_active Application Discontinuation
- 1999-03-30 CA CA002326506A patent/CA2326506A1/fr not_active Abandoned
- 1999-03-30 KR KR1020007010430A patent/KR20010042078A/ko not_active Application Discontinuation
- 1999-03-30 TW TW088105033A patent/TW499425B/zh active
- 1999-03-30 NZ NZ506959A patent/NZ506959A/en unknown
- 1999-03-30 AU AU29606/99A patent/AU742553B2/en not_active Ceased
-
2000
- 2000-09-15 ZA ZA200004927A patent/ZA200004927B/en unknown
- 2000-09-29 NO NO20004896A patent/NO20004896L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| NZ506959A (en) | 2002-02-01 |
| AU742553B2 (en) | 2002-01-03 |
| JP2002509919A (ja) | 2002-04-02 |
| KR20010042078A (ko) | 2001-05-25 |
| IL138521A0 (en) | 2001-10-31 |
| AU2960699A (en) | 1999-10-18 |
| CA2326506A1 (fr) | 1999-10-07 |
| SK14742000A3 (sk) | 2001-03-12 |
| TW499425B (en) | 2002-08-21 |
| NO20004896L (no) | 2000-10-12 |
| EP1066265A1 (fr) | 2001-01-10 |
| NO20004896D0 (no) | 2000-09-29 |
| US6310065B1 (en) | 2001-10-30 |
| WO1999050248A1 (fr) | 1999-10-07 |
| CN1293661A (zh) | 2001-05-02 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| ZA200004927B (en) | Pyridazinone hydrochlorine compound and method for producing the same. | |
| US8696868B2 (en) | Disulfo-type fluorescent whitening agent compositions | |
| US7067669B2 (en) | Substantially pure cilostazol and processes for making same | |
| US20070208164A1 (en) | Methods of synthesizing radiolabeled 3-cyano[14C]quinolines | |
| CN109232537A (zh) | 一种沃诺拉赞的制备方法 | |
| US20210139433A1 (en) | Crystal form of 3-(4-methyl-1h-imidazol-1-yl)-5-trifluoromethylaniline monohydrochloride and use thereof | |
| US6740669B1 (en) | Crystal modification of 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxamide and its use as antiepileptic | |
| US6977306B2 (en) | Citalopram hydrobromide crystal and method for crystallization thereof | |
| US20060047124A1 (en) | Process for preparing 2-aminopyridine derivatives | |
| EP1159254B1 (fr) | Intermediaire aminophenol a substitution oxyalkylene | |
| NZ204536A (en) | 1,4-dihydropyridine derivatives and pharmaceutical compositions | |
| CN107586267A (zh) | 一种牛磺酰胺盐酸盐(2‑氨基乙基磺酰胺盐酸盐)的合成方法 | |
| NZ585833A (en) | Stable crystalline salt of (r)-3-fluorophenyl-3,4,5-trifluorobenzylcarbamic acid 1-azabicyclo [2.2.2]oct-yl ester | |
| EP0008759B1 (fr) | Procédé de préparation de dérivés de l'acide 1H-indazole-3-yl-acétique | |
| CZ13998A3 (cs) | Způsob výroby esterů kyseliny 1-alkyl-pyrazol-5-karboxylové | |
| CN113549025B (zh) | 一种1,4,7,10-四氮杂环十二烷-1,4,7-三乙酸及其钠盐的制备方法 | |
| CZ20003446A3 (cs) | Pyridazinonová hydrochloridová sloučenina a způsob její přípravy | |
| EP1932835B1 (fr) | Procédé de production d'un composé 2,3-dihydropyridazine | |
| CN118206536A (zh) | N-取代苯基磺酰胺类化合物的固体形式 | |
| CN109400588A (zh) | 一种含氟三唑喹喔啉类杀菌剂、制备方法及其应用 | |
| US4143049A (en) | Method for preparing 2h-tetrazolium chloride and 2h-tetrazolium chloride hydrochloride | |
| TW202311224A (zh) | 製備非對稱線狀碳酸酯的方法 | |
| CN118324664A (zh) | 一种丝氨酸衍生物的制备方法 | |
| CN110305135A (zh) | 一种培美曲塞二钠中间体及其制备方法 | |
| CN110305137A (zh) | 一种培美曲塞二钠中间体及其制备方法 |