NO328873B1 - Fremgansmate for fremstilling av olanzapin. - Google Patents

Fremgansmate for fremstilling av olanzapin. Download PDF

Info

Publication number: NO328873B1
Authority: NO; Norway
Prior art keywords: olanzapine; preparation; borohydride; methyl; reaction
Prior art date: 2002-06-20

Application number

NO20040658A

Other languages

English (en)

Norwegian (no)

Other versions

NO20040658L (no

Inventor

Maciej Wieczorek

Zbigniew Majka

Tomasz Stawinski

Justyna Rechnio

Original Assignee

Adamed Sp Zoo

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.)

2002-06-20

Filing date

2004-02-13

Publication date

2010-06-07

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=29997625&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=NO328873(B1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

2004-02-13 Application filed by Adamed Sp Zoo filed Critical Adamed Sp Zoo

2004-02-13 Publication of NO20040658L publication Critical patent/NO20040658L/no

2010-06-07 Publication of NO328873B1 publication Critical patent/NO328873B1/no

Links

KVWDHTXUZHCGIO-UHFFFAOYSA-N olanzapine Chemical compound C1CN(C)CCN1C1=NC2=CC=CC=C2NC2=C1C=C(C)S2 KVWDHTXUZHCGIO-UHFFFAOYSA-N 0.000 title claims abstract description 19
229960005017 olanzapine Drugs 0.000 title claims abstract description 18
238000002360 preparation method Methods 0.000 title claims abstract description 7
239000002243 precursor Substances 0.000 title 1
238000000034 method Methods 0.000 claims abstract description 23
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 14
FHPIXVHJEIZKJW-UHFFFAOYSA-N 4'-N-desmethylolanzapine Chemical compound S1C(C)=CC2=C1NC1=CC=CC=C1N=C2N1CCNCC1 FHPIXVHJEIZKJW-UHFFFAOYSA-N 0.000 claims description 8
238000007069 methylation reaction Methods 0.000 claims description 5
230000002829 reductive effect Effects 0.000 claims description 5
239000003638 chemical reducing agent Substances 0.000 claims description 4
239000012279 sodium borohydride Substances 0.000 claims description 4
229910000033 sodium borohydride Inorganic materials 0.000 claims description 4
229910052783 alkali metal Inorganic materials 0.000 claims description 2
150000001340 alkali metals Chemical class 0.000 claims description 2
229910052751 metal Inorganic materials 0.000 claims description 2
239000002184 metal Substances 0.000 claims description 2
150000001875 compounds Chemical class 0.000 abstract description 4
SFWJCBPXQCTXTO-UHFFFAOYSA-N 4-(2-methyl-10H-thieno[2,3-b][1,5]benzodiazepin-4-yl)piperazine-1-carbaldehyde Chemical compound S1C(C)=CC2=C1NC1=CC=CC=C1N=C2N1CCN(C=O)CC1 SFWJCBPXQCTXTO-UHFFFAOYSA-N 0.000 abstract 1
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 9
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
238000004519 manufacturing process Methods 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
239000002244 precipitate Substances 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
239000000203 mixture Substances 0.000 description 4
ZVAPWJGRRUHKGP-UHFFFAOYSA-N 1h-1,5-benzodiazepine Chemical compound N1C=CC=NC2=CC=CC=C12 ZVAPWJGRRUHKGP-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
229910021626 Tin(II) chloride Inorganic materials 0.000 description 2
229960000583 acetic acid Drugs 0.000 description 2
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
239000012153 distilled water Substances 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
238000007363 ring formation reaction Methods 0.000 description 2
239000000243 solution Substances 0.000 description 2
239000002904 solvent Substances 0.000 description 2
235000011150 stannous chloride Nutrition 0.000 description 2
239000007858 starting material Substances 0.000 description 2
TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 1
PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 1
ZTTWQKYKGNLCCA-UHFFFAOYSA-N 2-methyl-10H-thieno[2,3-b][1,5]benzodiazepin-4-amine Chemical compound N1C2=CC=CC=C2N=C(N)C2=C1SC(C)=C2 ZTTWQKYKGNLCCA-UHFFFAOYSA-N 0.000 description 1
NPXUFPFFHANGDL-UHFFFAOYSA-N 5-methyl-2-(2-nitroanilino)thiophene-3-carbonitrile Chemical compound S1C(C)=CC(C#N)=C1NC1=CC=CC=C1[N+]([O-])=O NPXUFPFFHANGDL-UHFFFAOYSA-N 0.000 description 1
XBWAZCLHZCFCGK-UHFFFAOYSA-N 7-chloro-1-methyl-5-phenyl-3,4-dihydro-2h-1,4-benzodiazepin-1-ium;chloride Chemical compound [Cl-].C12=CC(Cl)=CC=C2[NH+](C)CCN=C1C1=CC=CC=C1 XBWAZCLHZCFCGK-UHFFFAOYSA-N 0.000 description 1
GSNUFIFRDBKVIE-UHFFFAOYSA-N DMF Natural products CC1=CC=C(C)O1 GSNUFIFRDBKVIE-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
PQLVXDKIJBQVDF-UHFFFAOYSA-N acetic acid;hydrate Chemical compound O.CC(O)=O PQLVXDKIJBQVDF-UHFFFAOYSA-N 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
229940040526 anhydrous sodium acetate Drugs 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
238000009835 boiling Methods 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
210000003169 central nervous system Anatomy 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
230000007812 deficiency Effects 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000003344 environmental pollutant Substances 0.000 description 1
239000012467 final product Substances 0.000 description 1
238000005187 foaming Methods 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
239000012535 impurity Substances 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
ANGDWNBGPBMQHW-UHFFFAOYSA-N methyl cyanoacetate Chemical compound COC(=O)CC#N ANGDWNBGPBMQHW-UHFFFAOYSA-N 0.000 description 1
231100000719 pollutant Toxicity 0.000 description 1
239000000047 product Substances 0.000 description 1
239000000376 reactant Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000006722 reduction reaction Methods 0.000 description 1
238000005932 reductive alkylation reaction Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
239000001119 stannous chloride Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

NO20040658A 2002-06-20 2004-02-13 Fremgansmate for fremstilling av olanzapin. NO328873B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
PL354642A PL199016B1 (pl)	2002-06-20	2002-06-20	Sposób wytwarzania olanzapiny
PCT/IB2003/002181 WO2004000847A1 (en)	2002-06-20	2003-06-10	A process for the preparation of olanzapine and an intermediate therefor

Publications (2)

Publication Number	Publication Date
NO20040658L NO20040658L (no)	2004-02-13
NO328873B1 true NO328873B1 (no)	2010-06-07

Family

ID=29997625

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO20040658A NO328873B1 (no)	2002-06-20	2004-02-13	Fremgansmate for fremstilling av olanzapin.

Country Status (17)

Country	Link
EP (2)	EP1669359B1 (de)
CN (1)	CN100338069C (de)
AT (2)	ATE373664T1 (de)
AU (1)	AU2003240167A1 (de)
BR (1)	BR0305100A (de)
DE (2)	DE60316047T2 (de)
ES (2)	ES2289730T3 (de)
HR (1)	HRP20041075B1 (de)
MX (1)	MXPA04012200A (de)
NO (1)	NO328873B1 (de)
PL (1)	PL199016B1 (de)
PT (2)	PT1669359E (de)
RU (1)	RU2005101324A (de)
SI (2)	SI1513845T2 (de)
TN (1)	TNSN04226A1 (de)
UA (1)	UA76616C2 (de)
WO (1)	WO2004000847A1 (de)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US7323459B2 (en)	2002-12-24	2008-01-29	Teva Pharmaceutical Industries Ltd.	Crystal forms, methods for their preparation and method for preparation of olanzapine
AR047461A1 (es) *	2004-01-27	2006-01-18	Synthon Bv	Formacion, purificacion y uso de n-formilolanzapina
ATE504588T1 (de)	2004-01-27	2011-04-15	Synthon Bv	Stabile salze von olanzapin
AR048272A1 (es) *	2004-03-18	2006-04-12	Lek Pharmaceuticals	Sintesis de 2 metil - 4- (4- metil -1- piperazinil) - 10 h- tieno ( 2,3-b) (1,5) benzodiazepina y sus sales, metodos para su preparacion, composiciones farmaceuticas que la contienen y su uso en la fabricacion de medicamentos para el tratamiento de enfermedades mentales.
US8044196B2 (en)	2004-07-14	2011-10-25	Jubilant Organosys Limited	Process for producing pure form of 2-methyl-4-(4-methyl-1-piperazinyl)-10H-thieno[2,3-b][1,5]benzodiazepine
PL198589B1 (pl)	2004-11-22	2008-06-30	Adamed Sp Z Oo	Sposób wytwarzania N-demetyloolanzapiny
CN100383144C (zh) *	2006-09-11	2008-04-23	杭州盛美医药科技开发有限公司	一种奥氮平的中间体及其制备与应用
EP2292624A1 (de)	2009-07-20	2011-03-09	LEK Pharmaceuticals d.d.	Olanzapinreinigungsverfahren
CN102234285B (zh) *	2010-04-19	2013-06-12	江苏豪森药业股份有限公司	奥氮平的制备方法
CN102924470B (zh) *	2011-08-31	2014-12-03	江苏豪森药业股份有限公司	新颖的奥氮平的制备方法
CN102942573B (zh) *	2011-10-09	2015-03-25	连云港恒运医药科技有限公司	奥氮平的制备方法

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NL7306069A (de) †	1973-05-02	1974-11-05
SU629879A3 (ru) *	1974-11-26	1978-10-25	Лилли Индастриз Лимитед, (Фирма)	Способ получени тиено(1,5) бензодиазепинов или их солей
US4115568A (en) †	1974-11-26	1978-09-19	Lilly Industries Limited	Thieno[3,2-b]-[1,5]benzodiazepines
US5239071A (en) †	1989-11-21	1993-08-24	The B. F. Goodrich Company	Process for methylating a hindered nitrogen atom in an inert non-aqueous solvent
GB9009229D0 (en) *	1990-04-25	1990-06-20	Lilly Industries Ltd	Pharmaceutical compounds
DK55192D0 (da) †	1992-04-28	1992-04-28	Lundbeck & Co As H	1-piperazino-1,2-dihydroindenderivater
PT1133300E (pt)	1998-11-23	2005-04-29	Sepracor Inc	Composicoes de desmetilolanzapina e metodos

2002
- 2002-06-20 PL PL354642A patent/PL199016B1/pl unknown
2003
- 2003-06-10 EP EP06100356A patent/EP1669359B1/de not_active Expired - Lifetime
- 2003-06-10 WO PCT/IB2003/002181 patent/WO2004000847A1/en not_active Ceased
- 2003-06-10 AU AU2003240167A patent/AU2003240167A1/en not_active Abandoned
- 2003-06-10 DE DE60316047T patent/DE60316047T2/de not_active Expired - Fee Related
- 2003-06-10 SI SI200330991T patent/SI1513845T2/sl unknown
- 2003-06-10 DE DE60316439T patent/DE60316439T3/de not_active Expired - Lifetime
- 2003-06-10 AT AT03732782T patent/ATE373664T1/de not_active IP Right Cessation
- 2003-06-10 EP EP03732782A patent/EP1513845B2/de not_active Expired - Lifetime
- 2003-06-10 BR BR0305100-5A patent/BR0305100A/pt not_active IP Right Cessation
- 2003-06-10 SI SI200330985T patent/SI1669359T1/sl unknown
- 2003-06-10 MX MXPA04012200A patent/MXPA04012200A/es not_active Application Discontinuation
- 2003-06-10 AT AT06100356T patent/ATE371660T1/de not_active IP Right Cessation
- 2003-06-10 PT PT06100356T patent/PT1669359E/pt unknown
- 2003-06-10 ES ES06100356T patent/ES2289730T3/es not_active Expired - Lifetime
- 2003-06-10 HR HR20041075A patent/HRP20041075B1/xx not_active IP Right Cessation
- 2003-06-10 PT PT03732782T patent/PT1513845E/pt unknown
- 2003-06-10 CN CNB038141655A patent/CN100338069C/zh not_active Ceased
- 2003-06-10 ES ES03732782T patent/ES2291644T5/es not_active Expired - Lifetime
- 2003-06-10 RU RU2005101324/04A patent/RU2005101324A/ru not_active Application Discontinuation
- 2003-10-06 UA UA20041109317A patent/UA76616C2/uk unknown
2004
- 2004-02-13 NO NO20040658A patent/NO328873B1/no not_active IP Right Cessation
- 2004-11-17 TN TNP2004000226A patent/TNSN04226A1/en unknown

Also Published As

Publication number	Publication date
DE60316439D1 (de)	2007-10-31
EP1513845A1 (de)	2005-03-16
PL354642A1 (en)	2003-12-29
UA76616C2 (en)	2006-08-15
ES2291644T3 (es)	2008-03-01
RU2005101324A (ru)	2005-08-10
HRP20041075B1 (hr)	2008-05-31
SI1513845T2 (sl)	2011-01-31
DE60316439T2 (de)	2008-07-31
ATE371660T1 (de)	2007-09-15
CN1662543A (zh)	2005-08-31
MXPA04012200A (es)	2005-08-26
ATE373664T1 (de)	2007-10-15
AU2003240167A1 (en)	2004-01-06
DE60316439T3 (de)	2011-05-05
PT1513845E (pt)	2007-11-21
EP1669359A1 (de)	2006-06-14
PT1669359E (pt)	2007-10-16
NO20040658L (no)	2004-02-13
EP1513845B1 (de)	2007-09-19
BR0305100A (pt)	2004-09-28
CN100338069C (zh)	2007-09-19
PL199016B1 (pl)	2008-08-29
EP1669359B1 (de)	2007-08-29
WO2004000847A1 (en)	2003-12-31
ES2289730T3 (es)	2008-02-01
DE60316047D1 (de)	2007-10-11
HRP20041075A2 (en)	2005-02-28
EP1513845B2 (de)	2010-11-03
DE60316047T2 (de)	2008-05-21
SI1669359T1 (sl)	2007-12-31
ES2291644T5 (es)	2011-02-15
SI1513845T1 (sl)	2007-12-31
TNSN04226A1 (en)	2007-03-12

Legal Events

Date	Code	Title	Description
2014-02-03	MM1K	Lapsed by not paying the annual fees

Publication	Publication Date	Title
FI66604B (fi)	1984-07-31	Foerfarande foer framstaellning av nya 5h-2,3-bensodiazepinderivat med inverkan pao det centrala nervsystemet
NO328873B1 (no)	2010-06-07	Fremgansmate for fremstilling av olanzapin.
EP1651646B1 (de)	2012-05-09	Neues verfahren zur herstellung von (+)-(s)-clopidogrelbisulfat form-i
NO314304B1 (no)	2003-03-03	Isokinoloner og fremgangsmåte for fremstilling derav
US5196534A (en)	1993-03-23	Process for the preparation of lactam derivatives
SU930902A1 (ru)	1982-10-15	Производные тиено [3,2=в] индола
CA2576862C (en)	2012-09-11	A process for producing pure form of 2-methyl-4-(4-methyl-1-piperazinyl)-10h-thieno[2,3-b][1,5]benzodiazepine
EP1347965B1 (de)	2006-01-25	Neue desloratadinsalze, verfahren zu deren synthese und diese enthaltende pharmazeutische zusammensetzungen
IL148441A (en)	2007-03-08	Intermediates for the production of derivatives of naphthyridine-3-carboxylic acid
CN108250195A (zh)	2018-07-06	帕利哌酮的新合成方法
PL203991B1 (pl)	2009-11-30	Sposoby wytwarzania olanzapiny, nowa pochodna N-demetyloolanzapiny i sposób wytwarzania nowej pochodnej N-demetyloolanzapiny
KR20030005273A (ko)	2003-01-17	벤조 융합된 헤테로사이클의 제조 방법
JPH07121931B2 (ja)	1995-12-25	ベンゾ〔ｂ〕フラン誘導体
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US8106188B2 (en)	2012-01-31	Process for preparing olanzapine form I
Saoud et al.	2001	Convenient Synthesis of 3-(l-carboxyalkyl) pyrido [2, 3-d] pyrimidine-2, 4-diones.
Prashad et al.	1997	Reaction of benzoyleneurea and isatoic anhydride with the Vilsmeier reagent
CN114773341A (zh)	2022-07-22	一种盐酸奥普力农的制备方法
PL198589B1 (pl)	2008-06-30	Sposób wytwarzania N-demetyloolanzapiny
PL203992B1 (pl)	2009-11-30	Sposób wytwarzania olanzapiny
HK1009647B (en)	1999-06-04	Process for the preparation of lactam derivatives
JPS5872583A (ja)	1983-04-30	ピリドピリミジンカルボン酸の製法