SK16232003A3 - Spôsob prípravy N-[3-(3-kyanopyrazolo [1,5-a]pyrimidín-7- yl)genyl]-N-etylacetamidu (zaleplonu) - Google Patents

Spôsob prípravy N-[3-(3-kyanopyrazolo [1,5-a]pyrimidín-7- yl)genyl]-N-etylacetamidu (zaleplonu) Download PDF

Info

Publication number: SK16232003A3
Authority: SK; Slovakia
Prior art keywords: acid; zaleplon; water; reaction medium; mixture
Prior art date: 2001-06-12

Application number

SK1623-2003A

Other languages

English (en)

Slovak (sk)

Inventor

Ferenc Korodi

Erika Feher

Erika Magyar

Original Assignee

Biogal Gyogyszergyar Rt.

Priority date (The priority date 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 date listed.)

2001-06-12

Filing date

2002-06-12

Publication date

2004-12-01

2002-06-12 Application filed by Biogal Gyogyszergyar Rt. filed Critical Biogal Gyogyszergyar Rt.

2004-12-01 Publication of SK16232003A3 publication Critical patent/SK16232003A3/sk

Links

HUNXMJYCHXQEGX-UHFFFAOYSA-N zaleplon Chemical compound CCN(C(C)=O)C1=CC=CC(C=2N3N=CC(=C3N=CC=2)C#N)=C1 HUNXMJYCHXQEGX-UHFFFAOYSA-N 0.000 title claims abstract description 64
229960004010 zaleplon Drugs 0.000 title claims abstract description 62
238000000034 method Methods 0.000 title claims abstract description 50
238000004519 manufacturing process Methods 0.000 title abstract description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 48
239000000203 mixture Substances 0.000 claims abstract description 39
239000012429 reaction media Substances 0.000 claims abstract description 26
FFNKBQRKZRMYCL-UHFFFAOYSA-N 5-amino-1h-pyrazole-4-carbonitrile Chemical compound NC1=NNC=C1C#N FFNKBQRKZRMYCL-UHFFFAOYSA-N 0.000 claims abstract description 19
UXWJJVRASIHSQS-MDZDMXLPSA-N n-[3-[(e)-3-(dimethylamino)prop-2-enoyl]phenyl]-n-ethylacetamide Chemical compound CCN(C(C)=O)C1=CC=CC(C(=O)\C=C\N(C)C)=C1 UXWJJVRASIHSQS-MDZDMXLPSA-N 0.000 claims abstract description 10
150000003839 salts Chemical class 0.000 claims abstract description 10
230000002378 acidificating effect Effects 0.000 claims abstract description 9
150000002894 organic compounds Chemical class 0.000 claims abstract description 9
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 70
239000002253 acid Substances 0.000 claims description 41
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 28
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 27
238000006243 chemical reaction Methods 0.000 claims description 21
238000004128 high performance liquid chromatography Methods 0.000 claims description 21
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 14
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 13
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 13
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 13
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 8
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 8
238000002360 preparation method Methods 0.000 claims description 8
229910000147 aluminium phosphate Inorganic materials 0.000 claims description 7
239000002244 precipitate Substances 0.000 claims description 7
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 6
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 6
230000015572 biosynthetic process Effects 0.000 claims description 5
239000007788 liquid Substances 0.000 claims description 5
150000007524 organic acids Chemical class 0.000 claims description 5
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 4
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 4
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
235000011054 acetic acid Nutrition 0.000 claims description 4
VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 claims description 4
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 claims description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 4
150000007522 mineralic acids Chemical class 0.000 claims description 4
ZMUMYMWAIXXLIY-UHFFFAOYSA-N n-[3-(3-cyanopyrazolo[1,5-a]pyrimidin-5-yl)phenyl]-n-ethylacetamide Chemical compound CCN(C(C)=O)C1=CC=CC(C2=NC3=C(C#N)C=NN3C=C2)=C1 ZMUMYMWAIXXLIY-UHFFFAOYSA-N 0.000 claims description 4
239000003480 eluent Substances 0.000 claims description 3
235000005985 organic acids Nutrition 0.000 claims description 3
239000011368 organic material Substances 0.000 claims description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 2
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 2
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 2
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 2
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims description 2
150000001408 amides Chemical class 0.000 claims description 2
KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 2
239000004327 boric acid Substances 0.000 claims description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 2
150000002170 ethers Chemical class 0.000 claims description 2
235000019253 formic acid Nutrition 0.000 claims description 2
DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 claims description 2
150000002825 nitriles Chemical class 0.000 claims description 2
150000002828 nitro derivatives Chemical class 0.000 claims description 2
MCSAJNNLRCFZED-UHFFFAOYSA-N nitroethane Chemical compound CC[N+]([O-])=O MCSAJNNLRCFZED-UHFFFAOYSA-N 0.000 claims description 2
LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 claims description 2
235000006408 oxalic acid Nutrition 0.000 claims description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 2
235000019260 propionic acid Nutrition 0.000 claims description 2
FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 claims description 2
150000003462 sulfoxides Chemical class 0.000 claims description 2
235000002906 tartaric acid Nutrition 0.000 claims description 2
239000011975 tartaric acid Substances 0.000 claims description 2
239000000376 reactant Substances 0.000 claims 2
150000001732 carboxylic acid derivatives Chemical group 0.000 claims 1
125000002843 carboxylic acid group Chemical group 0.000 claims 1
RRHORVAOECWFPT-UHFFFAOYSA-N pyrazolo[1,5-a]pyrimidine-3-carbonitrile Chemical compound C1=CC=NC2=C(C#N)C=NN21 RRHORVAOECWFPT-UHFFFAOYSA-N 0.000 claims 1
208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 abstract 1
239000004480 active ingredient Substances 0.000 abstract 1
206010022437 insomnia Diseases 0.000 abstract 1
239000000047 product Substances 0.000 description 16
239000011541 reaction mixture Substances 0.000 description 14
239000000543 intermediate Substances 0.000 description 12
150000002466 imines Chemical class 0.000 description 11
239000003960 organic solvent Substances 0.000 description 10
239000012535 impurity Substances 0.000 description 9
150000001875 compounds Chemical class 0.000 description 7
239000002904 solvent Substances 0.000 description 7
239000007858 starting material Substances 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
239000000523 sample Substances 0.000 description 6
239000006184 cosolvent Substances 0.000 description 5
238000001914 filtration Methods 0.000 description 5
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
PMDCZENCAXMSOU-UHFFFAOYSA-N N-ethylacetamide Chemical compound CCNC(C)=O PMDCZENCAXMSOU-UHFFFAOYSA-N 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
238000004458 analytical method Methods 0.000 description 4
238000001816 cooling Methods 0.000 description 4
239000000243 solution Substances 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
238000011109 contamination Methods 0.000 description 3
238000004090 dissolution Methods 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
238000005755 formation reaction Methods 0.000 description 3
229910052500 inorganic mineral Inorganic materials 0.000 description 3
238000002955 isolation Methods 0.000 description 3
238000004949 mass spectrometry Methods 0.000 description 3
239000011707 mineral Substances 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
229910002027 silica gel Inorganic materials 0.000 description 3
238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
WGZYVHFXLPDNDL-UHFFFAOYSA-N 4-benzoyl-2-phenylpyrazole-3-carbonitrile Chemical compound C=1C=CC=CC=1C(=O)C(=C1C#N)C=NN1C1=CC=CC=C1 WGZYVHFXLPDNDL-UHFFFAOYSA-N 0.000 description 2
238000005481 NMR spectroscopy Methods 0.000 description 2
238000009835 boiling Methods 0.000 description 2
238000004440 column chromatography Methods 0.000 description 2
238000003379 elimination reaction Methods 0.000 description 2
238000000605 extraction Methods 0.000 description 2
238000002347 injection Methods 0.000 description 2
239000007924 injection Substances 0.000 description 2
239000012035 limiting reagent Substances 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
238000004445 quantitative analysis Methods 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
239000013074 reference sample Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
238000005160 1H NMR spectroscopy Methods 0.000 description 1
102100027324 2-hydroxyacyl-CoA lyase 1 Human genes 0.000 description 1
ZBBUUZBCGCQPBJ-UHFFFAOYSA-N 5-amino-1h-pyrazole-4-carbonitrile;hydrochloride Chemical compound Cl.NC1=NNC=C1C#N ZBBUUZBCGCQPBJ-UHFFFAOYSA-N 0.000 description 1
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
101001009252 Homo sapiens 2-hydroxyacyl-CoA lyase 1 Proteins 0.000 description 1
238000006845 Michael addition reaction Methods 0.000 description 1
ZSXGLVDWWRXATF-UHFFFAOYSA-N N,N-dimethylformamide dimethyl acetal Chemical compound COC(OC)N(C)C ZSXGLVDWWRXATF-UHFFFAOYSA-N 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
FKCBLVCOSCZFHV-UHFFFAOYSA-N acetonitrile;ethanol Chemical compound CCO.CC#N FKCBLVCOSCZFHV-UHFFFAOYSA-N 0.000 description 1
239000008186 active pharmaceutical agent Substances 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
235000011114 ammonium hydroxide Nutrition 0.000 description 1
239000000010 aprotic solvent Substances 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
238000013475 authorization Methods 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
238000012512 characterization method Methods 0.000 description 1
239000007806 chemical reaction intermediate Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
230000003749 cleanliness Effects 0.000 description 1
229940125782 compound 2 Drugs 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
150000004656 dimethylamines Chemical class 0.000 description 1
239000003814 drug Substances 0.000 description 1
229940088679 drug related substance Drugs 0.000 description 1
230000000694 effects Effects 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000010828 elution Methods 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
238000011141 high resolution liquid chromatography Methods 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
239000003586 protic polar solvent Substances 0.000 description 1
125000003226 pyrazolyl group Chemical group 0.000 description 1
125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
238000007614 solvation Methods 0.000 description 1
238000004611 spectroscopical analysis Methods 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
-1 tetrahydrofuran) Chemical class 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Chemical Kinetics & Catalysis (AREA)
Veterinary Medicine (AREA)
Medicinal Chemistry (AREA)
Engineering & Computer Science (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Anesthesiology (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

SK1623-2003A 2001-06-12 2002-06-12 Spôsob prípravy N-[3-(3-kyanopyrazolo [1,5-a]pyrimidín-7- yl)genyl]-N-etylacetamidu (zaleplonu) SK16232003A3 (sk)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US29763501P	2001-06-12	2001-06-12
PCT/US2002/018567 WO2002100828A2 (fr)	2001-06-12	2002-06-12	Procede pour la production de n-[3-(3-cyanopyrazolo[1,5-a] pyrimidine-7-yle)phenyle]-n-ethylacetamide (zaleplon)

Publications (1)

Publication Number	Publication Date
SK16232003A3 true SK16232003A3 (sk)	2004-12-01

Family

ID=23147125

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK1623-2003A SK16232003A3 (sk)	2001-06-12	2002-06-12	Spôsob prípravy N-[3-(3-kyanopyrazolo [1,5-a]pyrimidín-7- yl)genyl]-N-etylacetamidu (zaleplonu)

Country Status (20)

Country	Link
US (2)	US6884888B2 (fr)
EP (1)	EP1406871A4 (fr)
JP (1)	JP2005507858A (fr)
KR (1)	KR20040007683A (fr)
CN (1)	CN1537113A (fr)
CA (1)	CA2450384A1 (fr)
CZ (1)	CZ20033544A3 (fr)
DE (1)	DE02778962T1 (fr)
ES (1)	ES2223311T1 (fr)
HR (1)	HRP20040016A2 (fr)
HU (1)	HUP0402257A2 (fr)
IL (1)	IL159281A0 (fr)
IS (1)	IS7069A (fr)
MX (1)	MXPA03011485A (fr)
NO (1)	NO20035538D0 (fr)
PL (1)	PL372942A1 (fr)
SK (1)	SK16232003A3 (fr)
TR (1)	TR200402588T3 (fr)
WO (1)	WO2002100828A2 (fr)
ZA (1)	ZA200309677B (fr)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US20050032818A1 (en) *	2001-06-12	2005-02-10	Entire Interest	N-[3-(3-cyanopyrazolo[1,5-a]pyrimidin-5-yl)phenyl]-N-ethylacetamide and crystalline forms of zaleplon
DE02778962T1 (de) *	2001-06-12	2005-02-10	Biogal Gyogyszergyar Rt.	VERFAHREN ZUR HERSTELLUNG VON N ç3 (3 CYANOPYRAZOLOç1,5 A!PYRIMIDIN 7 YL)PHENYL!-N-ETHYLACETAMID (ZALEPLON)
PL374176A1 (en)	2001-08-01	2005-10-03	Biogal Gyogyszergyar Rt	Process for purifying n-[3-(3-cyanopyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-n-ethylacetamide(zaleplon) and crystalline forms of zaleplon accessible with the process
HRP20040764A2 (en) *	2002-02-15	2005-02-28	Biogal Gyogyszergyar Rt.	Powder composition comprising zaleplon of defined particle size distribution and pharmaceutical products made therefrom
PL207322B1 (pl) *	2002-05-14	2010-11-30	Adamed Społka Z Ograniczoną Odpowiedzialnością	Sposób wytwarzania zaleplonu
AU2002343201A1 (en) *	2002-10-16	2004-05-04	Sanmar Speciality Chemicals Limited	Synthesis of zaleplon
CZ293015B6 (cs) *	2002-10-25	2004-01-14	Léčiva, A.S.	Způsob výroby N-ethyl-N-[3-(3-methyl-pyrazolo[1,5-a]pyrimidin-7-yl)-fenyl]-acetamidu (zaleplonu)
WO2005023813A1 (fr) *	2003-09-04	2005-03-17	Cipla Limited	Synthese du zaleplon
US7498434B2 (en) *	2004-01-14	2009-03-03	Mallinckrodt Inc	Two-phase method for the synthesis of selected pyrazolopyrimidines
HUP0400325A3 (en)	2004-02-02	2005-11-28	Richter Gedeon Vegyeszet	Pure n-[3-(-cyanopyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-n-ethyl-acetamide, process for its preparation and intermediates
WO2005099712A2 (fr) *	2004-04-19	2005-10-27	Sanmar Speciality Chemicals Limited	Procede de preparation de n-[3-(3-cyanopyrazolo [1,5-a]pyrimidin-7-yl)phenyl]-n-ethylacetamide
WO2006070244A2 (fr) *	2004-11-22	2006-07-06	Bakulesh Mafatlal Khamar	Processus de preparation de zaleplon
CN102816163A (zh) *	2012-08-20	2012-12-12	四川禾邦阳光制药股份有限公司	扎来普隆的新晶型及制备方法

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Publication number	Priority date	Publication date	Assignee	Title
US4626538A (en) *	1983-06-23	1986-12-02	American Cyanamid Company	[7-(3-disubstituted amino)phenyl]pyrazolo[1,5-a]pyrimidines
US5714607A (en) *	1995-12-01	1998-02-03	American Cyanamid Company	Process improvement in the synthesis of N- 3-(3-cyano-pyrazolo 1,5-a!pyrimidin-7-yl)phenyl!-N-ethylacetamide
US6485746B1 (en) *	2000-08-25	2002-11-26	Neurocrine Biosciences, Inc.	Controlled-release sedative-hypnotic compositions and methods related thereto
US6384221B1 (en) *	1999-09-02	2002-05-07	Neurocrine Biosciences, Inc.	Polymorphs of N-methyl-N-(3-{3-[2-thienylcarbonyl]-pyrazol-[1,5-α]-pyrimidin-7-yl}phenyl)acetamide and compositions and methods related thereto
SG125971A1 (en) *	2000-08-03	2006-10-30	Wyeth Corp	Variable water hydrates of zaleplon and method forthe preparation thereof
AR029780A1 (es) *	2000-12-13	2003-07-16	Gador Sa	Procedimiento mejorado para la obtencion de n-[3(3-ciano-pirazolo[1,5-a]pirimidin-7-il)fenil]-n-etil-acetamida
DE02778962T1 (de) *	2001-06-12	2005-02-10	Biogal Gyogyszergyar Rt.	VERFAHREN ZUR HERSTELLUNG VON N ç3 (3 CYANOPYRAZOLOç1,5 A!PYRIMIDIN 7 YL)PHENYL!-N-ETHYLACETAMID (ZALEPLON)
PL374176A1 (en) *	2001-08-01	2005-10-03	Biogal Gyogyszergyar Rt	Process for purifying n-[3-(3-cyanopyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-n-ethylacetamide(zaleplon) and crystalline forms of zaleplon accessible with the process
PL207322B1 (pl) *	2002-05-14	2010-11-30	Adamed Społka Z Ograniczoną Odpowiedzialnością	Sposób wytwarzania zaleplonu

2002
- 2002-06-12 DE DE02778962T patent/DE02778962T1/de active Pending
- 2002-06-12 KR KR10-2003-7016185A patent/KR20040007683A/ko not_active Ceased
- 2002-06-12 HR HR20040016A patent/HRP20040016A2/hr not_active Application Discontinuation
- 2002-06-12 EP EP02778962A patent/EP1406871A4/fr not_active Withdrawn
- 2002-06-12 CZ CZ20033544A patent/CZ20033544A3/cs unknown
- 2002-06-12 TR TR2004/02588T patent/TR200402588T3/xx unknown
- 2002-06-12 JP JP2003503597A patent/JP2005507858A/ja active Pending
- 2002-06-12 SK SK1623-2003A patent/SK16232003A3/sk unknown
- 2002-06-12 US US10/170,673 patent/US6884888B2/en not_active Expired - Fee Related
- 2002-06-12 IL IL15928102A patent/IL159281A0/xx unknown
- 2002-06-12 PL PL02372942A patent/PL372942A1/xx not_active Application Discontinuation
- 2002-06-12 HU HU0402257A patent/HUP0402257A2/hu unknown
- 2002-06-12 ES ES02778962T patent/ES2223311T1/es active Pending
- 2002-06-12 CN CNA028150112A patent/CN1537113A/zh active Pending
- 2002-06-12 WO PCT/US2002/018567 patent/WO2002100828A2/fr not_active Ceased
- 2002-06-12 MX MXPA03011485A patent/MXPA03011485A/es not_active Application Discontinuation
- 2002-06-12 CA CA002450384A patent/CA2450384A1/fr not_active Abandoned
2003
- 2003-12-10 IS IS7069A patent/IS7069A/is unknown
- 2003-12-11 NO NO20035538A patent/NO20035538D0/no not_active Application Discontinuation
- 2003-12-12 ZA ZA200309677A patent/ZA200309677B/en unknown
2005
- 2005-02-25 US US11/067,044 patent/US20050187225A1/en not_active Abandoned

Also Published As

Publication number	Publication date
NO20035538D0 (no)	2003-12-11
CZ20033544A3 (cs)	2004-11-10
CN1537113A (zh)	2004-10-13
HUP0402257A2 (hu)	2005-02-28
ES2223311T1 (es)	2005-03-01
ZA200309677B (en)	2004-12-13
CA2450384A1 (fr)	2002-12-19
TR200402588T3 (tr)	2004-11-22
WO2002100828A2 (fr)	2002-12-19
US20030040522A1 (en)	2003-02-27
EP1406871A4 (fr)	2005-01-26
US6884888B2 (en)	2005-04-26
JP2005507858A (ja)	2005-03-24
WO2002100828A3 (fr)	2003-05-01
MXPA03011485A (es)	2004-06-11
IS7069A (is)	2003-12-10
HRP20040016A2 (en)	2004-10-31
DE02778962T1 (de)	2005-02-10
PL372942A1 (en)	2005-08-08
US20050187225A1 (en)	2005-08-25
IL159281A0 (en)	2004-06-01
EP1406871A2 (fr)	2004-04-14
KR20040007683A (ko)	2004-01-24

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