DK174543B1 - Fremgangsmåde til fremstilling af 2-[2-[4-[[(4-chlorphenyl)phenylmethyl)]-1-piperazinyl]ethoxy]eddikesyre og dens dihydrochlorid og udgangsforbindelse til anvendelse ved fremgangsmåden - Google Patents

Fremgangsmåde til fremstilling af 2-[2-[4-[[(4-chlorphenyl)phenylmethyl)]-1-piperazinyl]ethoxy]eddikesyre og dens dihydrochlorid og udgangsforbindelse til anvendelse ved fremgangsmåden Download PDF

Info

Publication number: DK174543B1
Authority: DK; Denmark
Prior art keywords: phenylmethyl; chlorophenyl; piperazinyl; ethoxy; dihydrochloride
Prior art date: 1988-11-23

Application number

DK198905867A

Other languages

Danish (da)

English (en)

Other versions

DK586789D0 (da

DK586789A (da

Inventor

Jean Gobert

Guy Bodson

Eric Cossement

Genevieve Motte

Original Assignee

Ucb Sa

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.)

1988-11-23

Filing date

1989-11-22

Publication date

2003-05-19

1989-11-22 Application filed by Ucb Sa filed Critical Ucb Sa

1989-11-22 Publication of DK586789D0 publication Critical patent/DK586789D0/da

1990-05-24 Publication of DK586789A publication Critical patent/DK586789A/da

2003-05-19 Application granted granted Critical

2003-05-19 Publication of DK174543B1 publication Critical patent/DK174543B1/da

Links

238000000034 method Methods 0.000 title claims description 20
238000002360 preparation method Methods 0.000 title claims description 7
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 title description 8
-1 (4-chlorophenyl) phenylmethyl Chemical group 0.000 title description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 title description 6
239000007858 starting material Substances 0.000 title description 3
239000002253 acid Substances 0.000 claims description 20
239000011541 reaction mixture Substances 0.000 claims description 17
239000000203 mixture Substances 0.000 claims description 13
ZKLPARSLTMPFCP-UHFFFAOYSA-N Cetirizine Chemical compound C1CN(CCOCC(=O)O)CCN1C(C=1C=CC(Cl)=CC=1)C1=CC=CC=C1 ZKLPARSLTMPFCP-UHFFFAOYSA-N 0.000 claims description 10
230000007062 hydrolysis Effects 0.000 claims description 9
238000006460 hydrolysis reaction Methods 0.000 claims description 9
239000002609 medium Substances 0.000 claims description 9
SBAKHIDRFYZRKO-UHFFFAOYSA-N 2-[2-[4-[(4-chlorophenyl)-phenylmethyl]piperazin-1-yl]ethoxy]acetonitrile Chemical compound C1=CC(Cl)=CC=C1C(C=1C=CC=CC=1)N1CCN(CCOCC#N)CC1 SBAKHIDRFYZRKO-UHFFFAOYSA-N 0.000 claims description 7
238000010992 reflux Methods 0.000 claims description 5
230000001476 alcoholic effect Effects 0.000 claims description 3
239000012736 aqueous medium Substances 0.000 claims description 2
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 15
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 14
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
UZKBSZSTDQSMDR-UHFFFAOYSA-N 1-[(4-chlorophenyl)-phenylmethyl]piperazine Chemical compound C1=CC(Cl)=CC=C1C(C=1C=CC=CC=1)N1CCNCC1 UZKBSZSTDQSMDR-UHFFFAOYSA-N 0.000 description 11
WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Substances CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 11
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 11
238000003756 stirring Methods 0.000 description 9
239000000243 solution Substances 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
150000001875 compounds Chemical class 0.000 description 5
150000002825 nitriles Chemical class 0.000 description 5
PGLIUCLTXOYQMV-UHFFFAOYSA-N Cetirizine hydrochloride Chemical compound Cl.Cl.C1CN(CCOCC(=O)O)CCN1C(C=1C=CC(Cl)=CC=1)C1=CC=CC=C1 PGLIUCLTXOYQMV-UHFFFAOYSA-N 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
239000013078 crystal Substances 0.000 description 4
239000012074 organic phase Substances 0.000 description 4
GQFCLJZQECVTDO-UHFFFAOYSA-N 2-(2-chloroethoxy)acetonitrile Chemical compound ClCCOCC#N GQFCLJZQECVTDO-UHFFFAOYSA-N 0.000 description 3
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
230000002378 acidificating effect Effects 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
229960001803 cetirizine Drugs 0.000 description 3
238000002425 crystallisation Methods 0.000 description 3
230000008025 crystallization Effects 0.000 description 3
238000000354 decomposition reaction Methods 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
239000002904 solvent Substances 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
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 description 2
241000965606 Saccopharyngidae Species 0.000 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 description 2
IHTYTYHXCRAMAV-UHFFFAOYSA-N acetic acid;dihydrochloride Chemical compound Cl.Cl.CC(O)=O IHTYTYHXCRAMAV-UHFFFAOYSA-N 0.000 description 2
125000000068 chlorophenyl group Chemical group 0.000 description 2
238000001035 drying Methods 0.000 description 2
238000001914 filtration Methods 0.000 description 2
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
229910000041 hydrogen chloride Inorganic materials 0.000 description 2
150000007529 inorganic bases Chemical class 0.000 description 2
150000007522 mineralic acids Chemical class 0.000 description 2
239000000377 silicon dioxide Substances 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
235000002906 tartaric acid Nutrition 0.000 description 2
239000011975 tartaric acid Substances 0.000 description 2
HBIIDJDBPRTHCQ-UHFFFAOYSA-N 2-[2-[2-[[4-(4-chlorophenyl)phenyl]methyl]piperazin-1-yl]ethoxy]acetic acid Chemical compound OC(=O)COCCN1CCNCC1CC1=CC=C(C=2C=CC(Cl)=CC=2)C=C1 HBIIDJDBPRTHCQ-UHFFFAOYSA-N 0.000 description 1
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
206010010744 Conjunctivitis allergic Diseases 0.000 description 1
230000005526 G1 to G0 transition Effects 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-L L-tartrate(2-) Chemical compound [O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O FEWJPZIEWOKRBE-JCYAYHJZSA-L 0.000 description 1
208000003251 Pruritus Diseases 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
208000024780 Urticaria Diseases 0.000 description 1
238000005903 acid hydrolysis reaction Methods 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000001154 acute effect Effects 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
229910001516 alkali metal iodide Inorganic materials 0.000 description 1
208000002205 allergic conjunctivitis Diseases 0.000 description 1
230000000172 allergic effect Effects 0.000 description 1
208000024998 atopic conjunctivitis Diseases 0.000 description 1
208000010668 atopic eczema Diseases 0.000 description 1
239000002585 base Substances 0.000 description 1
230000001684 chronic effect Effects 0.000 description 1
238000007598 dipping method Methods 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
QYRFJLLXPINATB-UHFFFAOYSA-N hydron;2,4,5,6-tetrafluorobenzene-1,3-diamine;dichloride Chemical compound Cl.Cl.NC1=C(F)C(N)=C(F)C(F)=C1F QYRFJLLXPINATB-UHFFFAOYSA-N 0.000 description 1
238000002955 isolation Methods 0.000 description 1
RDFIZBYHUOHTQI-UHFFFAOYSA-N methyl 2-(2-chloroethoxy)acetate Chemical compound COC(=O)COCCCl RDFIZBYHUOHTQI-UHFFFAOYSA-N 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
201000009240 nasopharyngitis Diseases 0.000 description 1
239000002547 new drug Substances 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
239000012071 phase Substances 0.000 description 1
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
YLLIGHVCTUPGEH-UHFFFAOYSA-M potassium;ethanol;hydroxide Chemical compound [OH-].[K+].CCO YLLIGHVCTUPGEH-UHFFFAOYSA-M 0.000 description 1
FJWLWIRHZOHPIY-UHFFFAOYSA-N potassium;hydroiodide Chemical compound [K].I FJWLWIRHZOHPIY-UHFFFAOYSA-N 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
206010039083 rhinitis Diseases 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000007787 solid Substances 0.000 description 1
208000011580 syndromic disease Diseases 0.000 description 1

Classifications

- 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

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

DK198905867A 1988-11-23 1989-11-22 Fremgangsmåde til fremstilling af 2-[2-[4-[[(4-chlorphenyl)phenylmethyl)]-1-piperazinyl]ethoxy]eddikesyre og dens dihydrochlorid og udgangsforbindelse til anvendelse ved fremgangsmåden DK174543B1 (da)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB888827391A GB8827391D0 (en)	1988-11-23	1988-11-23	Process for preparation of 2-(2-(4-((4-chlorophenyl)phenylmethyl)-1-pipera-zinyl)ethoxy)-acetic acid & its dihydrochloride
GB8827391		1988-11-23

Publications (3)

Publication Number	Publication Date
DK586789D0 DK586789D0 (da)	1989-11-22
DK586789A DK586789A (da)	1990-05-24
DK174543B1 true DK174543B1 (da)	2003-05-19

Family

ID=10647347

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DK198905867A DK174543B1 (da)	1988-11-23	1989-11-22	Fremgangsmåde til fremstilling af 2-[2-[4-[[(4-chlorphenyl)phenylmethyl)]-1-piperazinyl]ethoxy]eddikesyre og dens dihydrochlorid og udgangsforbindelse til anvendelse ved fremgangsmåden

Country Status (16)

Country	Link
KR (1)	KR970009728B1 (de)
AT (1)	AT398971B (de)
CA (1)	CA1317300C (de)
CY (1)	CY1671A (de)
DK (1)	DK174543B1 (de)
ES (1)	ES2021907A6 (de)
FI (1)	FI91862C (de)
GB (2)	GB8827391D0 (de)
GR (1)	GR1000553B (de)
HK (1)	HK95892A (de)
HU (1)	HU205094B (de)
NO (1)	NO172342C (de)
PH (1)	PH25982A (de)
PL (1)	PL161379B1 (de)
PT (1)	PT92364B (de)
SG (1)	SG89492G (de)

Families Citing this family (38)

* Cited by examiner, † Cited by third party
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GB9305282D0 (en) *	1993-03-15	1993-05-05	Ucb Sa	Enantiomers of 1-(4-chlorophenyl)phenylmethyl)-4-(4-methylphenyl)sulphonyl)piperazine
US6469009B1 (en)	1996-04-08	2002-10-22	Ucb, S.A.	Pharmaceutical compositions for the treatment of rhinitis
BE1010094A3 (fr) *	1996-04-10	1997-12-02	Ucb Sa	Nouveaux [2-(1-piperazinyl)ethoxy] methyle substitues.
BE1010095A3 (fr) *	1996-04-10	1997-12-02	Ucb Sa	Procede de preparation de l'acide 2-[2-[4-[(4-chlorophenyl)phenylmethyl]-1-piperazinyl] ethoxy]-acetique et de ses sels.
JP3476475B2 (ja)	1997-06-04	2003-12-10	株式会社アズウェル	ピペラジンスルホンアミド誘導体およびその塩の製造方法
EP0919550A1 (de) *	1997-11-26	1999-06-02	Ucb, S.A.	Pseudopolymorphische Formen der 2-2-4-Bis(4-fluorophenyl)methyl-1-piperazinyl-ethoxyessigsäure Dihydrochloride
IL124195A (en) *	1998-04-23	2000-08-31	Chemagis Ltd	Process for the preparation of esters of 2-¬4-¬4-chlorophenyl¾phenylmethyl¾-1-piperazinyl¬ethoxy¾acetic acid
GR990100135A (el) *	1999-04-22	2000-12-29	Genepharm �.�.	Μεθοδος παρασκευης του 2-(2-[4-[4-χλωροφαινυλο)(φαινυλο)μεθυλο]πιπεραζινο]αιθοξυ) οξικου οξεος και του διυδροχλωρικου αλατος αυτου
JP2002249487A (ja)	2001-02-22	2002-09-06	Sumitomo Chem Co Ltd	４−（ｔｅｒｔ−ブトキシカルボニル）ピペラジン誘導体、その光学活性な酸付加塩、それらの製造法、およびそれらを用いる光学活性な１−［（置換フェニル）フェニルメチル］ピペラジンの製造法。
US6977301B1 (en)	2001-05-29	2005-12-20	Ucb, S.A.	Process for preparing (S) and (R)—2-[4-(4-chlorobenzhydryl)piperazin-1-yl]-ethoxyacetamide
US7199241B1 (en)	2001-05-29	2007-04-03	Ucb, S.A.	Process for preparing (S) and (R)-2-[4-(4-chlorobenzhydryl)piperazin-1-yl]-ethoxyacetamide
US7381821B2 (en)	2003-01-23	2008-06-03	Ucb, S.A.	Piperazine derivatives and their use as synthesis intermediates
KR100503443B1 (ko)	2004-02-02	2005-07-22	한림제약(주)	광학적으로 활성인 세티리진 또는 그의 염의 제조방법
AU2006222298B2 (en) *	2005-03-03	2011-02-24	Ucb Farchim Sa	Pyroglutamate salts and their use in the optical resolution of intermediates for the synthesis of dextrocetirizine and levocetirizine
HU227325B1 (en) *	2005-12-08	2011-03-28	Egis Gyogyszergyar Nyrt	Process for the production of an intermediate of (dextro- and levo)- cetirizine
US8049011B2 (en)	2007-03-12	2011-11-01	Krka, Tovarna Zdravil, D.D., Novo Mesto	Process for the preparation of levocetirizine and intermediates thereof
SI22489A (sl) *	2007-03-12	2008-10-31	Krka, Tovarna Zdravil, D.D., Novo Mesto	Nov postopek za pripravo levocetirizina in njegovih intermediatov
WO2008152650A1 (en)	2007-06-15	2008-12-18	Symed Labs Limited	Process for preparation of substantially optically pure levorotatory and dextrorotatory enantiomers of cetirizine using novel intermediates
WO2009062036A2 (en) *	2007-11-09	2009-05-14	Dr. Reddy's Laboratories Ltd.	Processes for preparing levocetirizine and pharmaceutically acceptable salts thereof
US7989623B2 (en)	2007-11-21	2011-08-02	Synthon Bv	Process for making n-(diphenylmethyl)piperazines
ES2361343T3 (es)	2007-11-21	2011-06-16	Synthon B.V.	Procedimiento para obtener n-(difenilmetil)piperazinas.
WO2009147389A2 (en)	2008-06-02	2009-12-10	Cipla Limited	Processes for the synthesis of levocetirizine and intermediates for use therein
WO2009150147A1 (en) *	2008-06-11	2009-12-17	Krka, Tovarna Zdravil, D.D., Novo Mesto	New process for the preparation of levocetirizine and intermediates thereof
KR100998067B1 (ko)	2008-09-08	2010-12-03	주식회사 삼오제약	비스(1-[(4-클로로페닐)페닐메틸]피페라진)-2,3-디벤조일 타르타르산 신규 중간체 염 및 이를 이용한 광학 활성적으로 순수한 1-[(4-클로로페닐)페닐메틸]피페라진을 분리하는 분리방법
WO2010046908A2 (en)	2008-09-17	2010-04-29	Calyx Chemicals And Pharmaceuticals Pvt. Ltd.	Novel water based process for the preparation of substituted diphenylmethyl piperazines
WO2010107404A1 (en)	2009-03-16	2010-09-23	Mahmut Bilgic	Stable pharmaceutical combinations
TR201007652A2 (tr)	2010-09-20	2012-04-24	Bi̇lgi̇ç Mahmut	Sinerjik etki.
TR201009398A2 (tr)	2010-11-11	2012-05-21	Bi̇lgi̇ç Mahmut	Fiziksel özellikleri geliştirilmiş tablet formülasyonları
WO2012101475A1 (en)	2011-01-27	2012-08-02	Jubilant Life Sciences Limited	An improved process for the preparation of antihistaminic drugs via a novel carbamate intermediate
CN103044355A (zh) *	2011-10-13	2013-04-17	湖南九典制药有限公司	合成左西替利嗪的关键中间体及其制备方法
KR101418404B1 (ko)	2012-01-06	2014-07-10	한미약품 주식회사	레보세티리진 또는 이의 약학적으로 허용가능한 염 및 몬테루카스트 또는 이의 약학적으로 허용가능한 염을 함유하는 안정한 경구투여용 약학 제제
KR102226833B1 (ko)	2013-06-28	2021-03-12	한미약품 주식회사	레보세티리진 및 몬테루카스트를 포함하는 안정성이 개선된 복합 과립 제형
CN104045607B (zh) *	2014-05-21	2016-04-13	丽珠医药集团股份有限公司	一种盐酸西替利嗪的纯化方法
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FI75816C (fi) *	1981-02-06	1988-08-08	Ucb Sa	Foerfarande foer framstaellning av terapeutiskt aktiv 2-/4-(difenylmetyl)-1-piperazinyl/-aettiksyror eller dess amid.

1988
- 1988-11-23 GB GB888827391A patent/GB8827391D0/en active Pending
1989
- 1989-09-29 CA CA000614709A patent/CA1317300C/en not_active Expired - Fee Related
- 1989-11-20 GR GR890100770A patent/GR1000553B/el not_active IP Right Cessation
- 1989-11-21 PT PT92364A patent/PT92364B/pt not_active IP Right Cessation
- 1989-11-21 GB GB8926243A patent/GB2225321B/en not_active Expired - Lifetime
- 1989-11-22 DK DK198905867A patent/DK174543B1/da not_active IP Right Cessation
- 1989-11-22 ES ES8903975A patent/ES2021907A6/es not_active Expired - Lifetime
- 1989-11-22 HU HU896131A patent/HU205094B/hu not_active IP Right Cessation
- 1989-11-22 AT AT0266589A patent/AT398971B/de not_active IP Right Cessation
- 1989-11-22 NO NO894651A patent/NO172342C/no not_active IP Right Cessation
- 1989-11-22 PL PL1989282410A patent/PL161379B1/pl unknown
- 1989-11-22 FI FI895564A patent/FI91862C/fi not_active IP Right Cessation
- 1989-11-23 PH PH39570A patent/PH25982A/en unknown
- 1989-11-23 KR KR1019890017040A patent/KR970009728B1/ko not_active Expired - Fee Related
1992
- 1992-09-05 SG SG894/92A patent/SG89492G/en unknown
- 1992-12-03 HK HK958/92A patent/HK95892A/xx not_active IP Right Cessation
1993
- 1993-05-14 CY CY1671A patent/CY1671A/en unknown

Also Published As

Publication number	Publication date
FI91862C (fi)	1994-08-25
GB2225321A (en)	1990-05-30
PT92364B (pt)	1995-07-18
GB2225321B (en)	1992-04-08
ATA266589A (de)	1994-07-15
CA1317300C (en)	1993-05-04
AT398971B (de)	1995-02-27
KR900007825A (ko)	1990-06-02
HUT53627A (en)	1990-11-28
NO894651D0 (no)	1989-11-22
HK95892A (en)	1992-12-11
GB8926243D0 (en)	1990-01-10
DK586789D0 (da)	1989-11-22
FI91862B (fi)	1994-05-13
NO172342C (no)	1993-07-07
ES2021907A6 (es)	1991-11-16
HU205094B (en)	1992-03-30
NO894651L (no)	1990-05-25
NO172342B (no)	1993-03-29
FI895564A0 (fi)	1989-11-22
GR890100770A (en)	1990-12-31
KR970009728B1 (ko)	1997-06-17
CY1671A (en)	1993-05-14
PL161379B1 (pl)	1993-06-30
HU896131D0 (en)	1990-02-28
GB8827391D0 (en)	1988-12-29
SG89492G (en)	1992-12-04
DK586789A (da)	1990-05-24
PH25982A (en)	1992-01-13
PT92364A (pt)	1990-05-31
GR1000553B (el)	1992-08-26

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Publication	Publication Date	Title
DK174543B1 (da)	2003-05-19	Fremgangsmåde til fremstilling af 2-[2-[4-[[(4-chlorphenyl)phenylmethyl)]-1-piperazinyl]ethoxy]eddikesyre og dens dihydrochlorid og udgangsforbindelse til anvendelse ved fremgangsmåden
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HU195806B (en)	1988-07-28	Process for producing new piperazinyl-benzisothiazol- and piperazinyl-benzisoxasol-derivatives
HU211256A9 (en)	1995-11-28	New benzimidazolone derivatives
NO155805B (no)	1987-02-23	Analogifremgangsmaate for fremstilling av terapeutisk virksomme 2-(4-(difenylmethyl)-1-piperazinyl)-eddiksyrer og deres amider og ikke-toksiske salter.
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HU190827B (en)	1986-11-28	Process for preparing 2-/4/-/4,4-dialkyl-1,2,6-piperidindion-1-yl/-butyl/-1-piperazinyl/-pyridines
DK174289B1 (da)	2002-11-18	Fremgangsmåde til fremstilling af 2-[2-[4-[(4-chlorphenyl)phenylmethyl]-1-piperazinyl]ethoxy]eddikesyre og dens dihydrochlorid
SU545256A3 (ru)	1977-01-30	Способ получени производных изохинолина или их солей
JPWO1993002062A1 (ja)	1993-08-05	ピペラジン誘導体及びこれを含有する医薬
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US20110172425A1 (en)	2011-07-14	Novel water based process for the preparation of substituted diphenylmethyl piperazines
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PL78185B2 (de)	1975-04-30