SK285715B6 - Soli desloratadínu, spôsob ich prípravy a farmaceutické prípravky s ich obsahom - Google Patents

Soli desloratadínu, spôsob ich prípravy a farmaceutické prípravky s ich obsahom Download PDF

Info

Publication number: SK285715B6
Authority: SK; Slovakia
Prior art keywords: desloratadine; formula; synthesis; hemisulphate; salts
Prior art date: 2000-11-23

Application number

SK566-2003A

Other languages

English (en)

Slovak (sk)

Other versions

SK5662003A3 (en

Inventor

J�Nos Fischer

Tam�S Fodor

Zosnul� Trischler Ferenc

S�Ndor L�Vai

Endr�N� Pet�Nyi

Original Assignee

Richter Gedeon Vegy�Szeti Gy�R 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.)

2000-11-23

Filing date

2001-11-14

Publication date

2007-06-07

2001-11-14 Application filed by Richter Gedeon Vegy�Szeti Gy�R Rt. filed Critical Richter Gedeon Vegy�Szeti Gy�R Rt.

2003-10-07 Publication of SK5662003A3 publication Critical patent/SK5662003A3/sk

2007-06-07 Publication of SK285715B6 publication Critical patent/SK285715B6/sk

Links

JAUOIFJMECXRGI-UHFFFAOYSA-N Neoclaritin Chemical class C=1C(Cl)=CC=C2C=1CCC1=CC=CN=C1C2=C1CCNCC1 JAUOIFJMECXRGI-UHFFFAOYSA-N 0.000 title claims abstract description 41
238000000034 method Methods 0.000 title claims abstract description 15
230000015572 biosynthetic process Effects 0.000 title claims description 7
238000003786 synthesis reaction Methods 0.000 title claims description 6
239000008194 pharmaceutical composition Substances 0.000 title claims description 5
229960001271 desloratadine Drugs 0.000 claims abstract description 36
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical group OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 11
239000002253 acid Substances 0.000 claims abstract description 8
230000003266 anti-allergic effect Effects 0.000 claims abstract description 4
239000000243 solution Substances 0.000 claims description 16
229960003088 loratadine Drugs 0.000 claims description 15
JCCNYMKQOSZNPW-UHFFFAOYSA-N loratadine Chemical compound C1CN(C(=O)OCC)CCC1=C1C2=NC=CC=C2CCC2=CC(Cl)=CC=C21 JCCNYMKQOSZNPW-UHFFFAOYSA-N 0.000 claims description 15
150000003839 salts Chemical class 0.000 claims description 12
BFUKZAZVGNXTDM-UHFFFAOYSA-N 8-chloro-11-piperidin-4-ylidene-5,6-dihydrobenzo[1,2]cyclohepta[2,4-b]pyridine;sulfuric acid Chemical compound OS(O)(=O)=O.C=1C(Cl)=CC=C2C=1CCC1=CC=CN=C1C2=C1CCNCC1.C=1C(Cl)=CC=C2C=1CCC1=CC=CN=C1C2=C1CCNCC1 BFUKZAZVGNXTDM-UHFFFAOYSA-N 0.000 claims description 6
239000000126 substance Substances 0.000 claims description 5
239000004480 active ingredient Substances 0.000 claims description 4
229910052500 inorganic mineral Inorganic materials 0.000 claims description 3
239000011707 mineral Substances 0.000 claims description 3
230000002378 acidificating effect Effects 0.000 claims description 2
239000000654 additive Substances 0.000 claims description 2
239000007864 aqueous solution Chemical group 0.000 claims description 2
239000000969 carrier Substances 0.000 claims 1
239000000203 mixture Substances 0.000 abstract description 11
238000002360 preparation method Methods 0.000 abstract description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
150000001875 compounds Chemical class 0.000 description 6
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
VFNGKCDDZUSWLR-UHFFFAOYSA-L disulfate(2-) Chemical compound [O-]S(=O)(=O)OS([O-])(=O)=O VFNGKCDDZUSWLR-UHFFFAOYSA-L 0.000 description 5
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 4
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
229920002261 Corn starch Polymers 0.000 description 3
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
239000008120 corn starch Substances 0.000 description 3
238000000265 homogenisation Methods 0.000 description 3
239000004615 ingredient Substances 0.000 description 3
239000008101 lactose Substances 0.000 description 3
235000019359 magnesium stearate Nutrition 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
239000000825 pharmaceutical preparation Substances 0.000 description 3
239000000843 powder Substances 0.000 description 3
239000000047 product Substances 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
IUKQLMGVFMDQDP-UHFFFAOYSA-N azane;piperidine Chemical compound N.C1CCNCC1 IUKQLMGVFMDQDP-UHFFFAOYSA-N 0.000 description 2
GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
238000001816 cooling Methods 0.000 description 2
ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 description 2
229910000042 hydrogen bromide Inorganic materials 0.000 description 2
235000010755 mineral Nutrition 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 2
238000004448 titration Methods 0.000 description 2
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 1
206010022998 Irritability Diseases 0.000 description 1
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 description 1
159000000021 acetate salts Chemical class 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
230000001387 anti-histamine Effects 0.000 description 1
239000000043 antiallergic agent Substances 0.000 description 1
239000000739 antihistaminic agent Substances 0.000 description 1
DLGYNVMUCSTYDQ-UHFFFAOYSA-N azane;pyridine Chemical compound N.C1=CC=NC=C1 DLGYNVMUCSTYDQ-UHFFFAOYSA-N 0.000 description 1
-1 bisulfate anions Chemical class 0.000 description 1
238000009835 boiling Methods 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
239000012043 crude product Substances 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
239000013583 drug formulation Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
239000012467 final product Substances 0.000 description 1
238000009472 formulation Methods 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
239000000938 histamine H1 antagonist Substances 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
239000012535 impurity Substances 0.000 description 1
238000002955 isolation Methods 0.000 description 1
239000000463 material Substances 0.000 description 1
239000002207 metabolite Substances 0.000 description 1
229940102396 methyl bromide Drugs 0.000 description 1
125000000896 monocarboxylic acid group Chemical group 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
230000001624 sedative effect Effects 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
238000000954 titration curve Methods 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
238000007039 two-step reaction Methods 0.000 description 1

Classifications

- 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
- C07D401/04—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 directly linked by a ring-member-to-ring-member bond
- 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

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Veterinary Medicine (AREA)
Bioinformatics & Cheminformatics (AREA)
Chemical Kinetics & Catalysis (AREA)
Engineering & Computer Science (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Pulmonology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Immunology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Saccharide Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

SK566-2003A 2000-11-23 2001-11-14 Soli desloratadínu, spôsob ich prípravy a farmaceutické prípravky s ich obsahom SK285715B6 (sk)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
HU0004701A HU226998B1 (en)	2000-11-23	2000-11-23	Desloratadine hemisulphate, process for the preparation thereof and pharmaceutical compositions containing the same
PCT/HU2001/000111 WO2002042290A1 (en)	2000-11-23	2001-11-14	New desloratadine salts, process for their synthesis and pharmaceutical compositions thereof

Publications (2)

Publication Number	Publication Date
SK5662003A3 SK5662003A3 (en)	2003-10-07
SK285715B6 true SK285715B6 (sk)	2007-06-07

Family

ID=89978790

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK566-2003A SK285715B6 (sk)	2000-11-23	2001-11-14	Soli desloratadínu, spôsob ich prípravy a farmaceutické prípravky s ich obsahom

Country Status (19)

Country	Link
US (1)	US7196195B2 (ja)
EP (1)	EP1347965B1 (ja)
JP (1)	JP4427249B2 (ja)
CN (1)	CN1199968C (ja)
AT (1)	ATE316525T1 (ja)
AU (1)	AU2002218422A1 (ja)
CA (1)	CA2425422C (ja)
CY (1)	CY1105595T1 (ja)
CZ (1)	CZ304694B6 (ja)
DE (1)	DE60116902T2 (ja)
DK (1)	DK1347965T3 (ja)
ES (1)	ES2257467T3 (ja)
HU (1)	HU226998B1 (ja)
NO (1)	NO325155B1 (ja)
PL (1)	PL206973B1 (ja)
RU (1)	RU2285001C2 (ja)
SK (1)	SK285715B6 (ja)
UA (1)	UA74858C2 (ja)
WO (1)	WO2002042290A1 (ja)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AU2003262141A1 (en) *	2002-04-15	2003-10-27	Sun Pharmaceutical Industries Limited	Preperation of desloratatine
AU2003251974C1 (en) *	2002-08-05	2006-09-14	Sandoz Ag	Novel salt and polymorphs of desloratadine hemifumarate
JP4501015B2 (ja)	2004-03-17	2010-07-14	味の素株式会社	アミノピリミジン化合物の製造方法
WO2006003479A2 (en) *	2004-07-07	2006-01-12	EGIS Gyógyszergyár Rt.	New pseudopolymorph of desloratadine formed with carbon dioxide
CA2541045A1 (en) *	2006-03-24	2007-09-24	Pharmascience Inc.	A descarbonylethoxyloratadine containing pharmaceutical composition
EP2837631A1 (en) *	2013-08-14	2015-02-18	Merck & Cie	New stable salt of 5,10-methylene-(6R)-tetrahydrofolic acid
KR102567448B1 (ko) *	2019-10-31	2023-08-17	(주)제이디바이오사이언스	삼환식 화합물 및 이의 약학적 용도
CN115785065A (zh) *	2022-12-02	2023-03-14	山东达因海洋生物制药股份有限公司	一种地氯雷他定共晶及其制备方法与应用

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4282233B1 (en) *	1980-06-19	2000-09-05	Schering Corp	Antihistaminic 11-(4-piperidylidene)-5h-benzoÄ5,6Ü-cyclohepta-Ä1,2Ü-pyridines
WO1985003707A1 (en) *	1984-02-15	1985-08-29	Schering Corporation	8-CHLORO-6,11-DIHYDRO-11-(4-PIPERIDYLIDENE)-5H-BENZO AD5,6 BDCYCLOHEPTA AD1,2-b BDPYRIDINE AND ITS SALTS, PROCESSES FOR THE PRODUCTION THEREOF AND PHARMACEUTICAL COMPOSITIONS CONTAINING THESE COMPOUNDS
DE3677842D1 (de) *	1985-05-13	1991-04-11	Schering Corp	Verfahren zur herstellung von piperidyliden-dihydrodibenzo(a,d)zykloheptenen und deren azoderivate, so hergestellte verbindungen und ihre anwendung zur vorbereitung von heilmitteln.
PT656348E (pt) *	1993-12-03	2000-10-31	Hoffmann La Roche	Derivados do acido acetico como medicamentos
GB9709945D0 (en) *	1997-05-17	1997-07-09	Glaxo Group Ltd	A novel salt

2000
- 2000-11-23 HU HU0004701A patent/HU226998B1/hu unknown
2001
- 2001-11-14 SK SK566-2003A patent/SK285715B6/sk not_active IP Right Cessation
- 2001-11-14 CZ CZ2003-1321A patent/CZ304694B6/cs unknown
- 2001-11-14 CA CA002425422A patent/CA2425422C/en not_active Expired - Lifetime
- 2001-11-14 RU RU2003118425/04A patent/RU2285001C2/ru active
- 2001-11-14 DE DE60116902T patent/DE60116902T2/de not_active Expired - Lifetime
- 2001-11-14 AU AU2002218422A patent/AU2002218422A1/en not_active Abandoned
- 2001-11-14 PL PL362126A patent/PL206973B1/pl unknown
- 2001-11-14 CN CNB018193382A patent/CN1199968C/zh not_active Expired - Lifetime
- 2001-11-14 UA UA2003065756A patent/UA74858C2/uk unknown
- 2001-11-14 US US10/432,387 patent/US7196195B2/en not_active Expired - Lifetime
- 2001-11-14 AT AT01997485T patent/ATE316525T1/de active
- 2001-11-14 EP EP01997485A patent/EP1347965B1/en not_active Expired - Lifetime
- 2001-11-14 DK DK01997485T patent/DK1347965T3/da active
- 2001-11-14 WO PCT/HU2001/000111 patent/WO2002042290A1/en active IP Right Grant
- 2001-11-14 JP JP2002544424A patent/JP4427249B2/ja not_active Expired - Lifetime
- 2001-11-14 ES ES01997485T patent/ES2257467T3/es not_active Expired - Lifetime
2003
- 2003-05-22 NO NO20032314A patent/NO325155B1/no not_active IP Right Cessation
2006
- 2006-03-29 CY CY20061100435T patent/CY1105595T1/el unknown

Also Published As

Publication number	Publication date
PL206973B1 (pl)	2010-10-29
US20050203116A1 (en)	2005-09-15
DK1347965T3 (da)	2006-06-06
JP2004514675A (ja)	2004-05-20
US7196195B2 (en)	2007-03-27
CA2425422A1 (en)	2002-05-30
EP1347965B1 (en)	2006-01-25
CZ20031321A3 (cs)	2003-08-13
CZ304694B6 (cs)	2014-09-03
CY1105595T1 (el)	2010-07-28
CN1199968C (zh)	2005-05-04
UA74858C2 (en)	2006-02-15
NO325155B1 (no)	2008-02-11
DE60116902T2 (de)	2006-08-24
PL362126A1 (en)	2004-10-18
NO20032314D0 (no)	2003-05-22
RU2285001C2 (ru)	2006-10-10
NO20032314L (no)	2003-07-18
SK5662003A3 (en)	2003-10-07
DE60116902D1 (de)	2006-04-13
AU2002218422A1 (en)	2002-06-03
WO2002042290A1 (en)	2002-05-30
HU0004701D0 (ja)	2001-02-28
EP1347965A1 (en)	2003-10-01
HUP0004701A2 (hu)	2002-11-28
JP4427249B2 (ja)	2010-03-03
ATE316525T1 (de)	2006-02-15
ES2257467T3 (es)	2006-08-01
CN1476443A (zh)	2004-02-18
CA2425422C (en)	2009-11-10
HU226998B1 (en)	2010-04-28

Legal Events

Date	Code	Title	Description
2021-12-20	MK4A	Patent expired	Expiry date: 20211114

Publication	Publication Date	Title
CZ290496B6 (cs)	2002-08-14	N-Piperidino-5-(4-chlorfenyl)-1-(2,4-dichlorfenyl)-4-methylpyrazol-3-karboxamid, způsob jeho přípravy a farmaceutický přípravek tento karboxamid obsahující
US3639477A (en)	1972-02-01	Novel propoxyguanidine compounds and means of producing the same
EP0769007A1 (en)	1997-04-23	2-ureido-benzamide derivatives
SK285715B6 (sk)	2007-06-07	Soli desloratadínu, spôsob ich prípravy a farmaceutické prípravky s ich obsahom
CA2008610A1 (en)	1990-07-26	Imidazolone derivatives with activity on central nervous system and antihypertensive activity, preparation methods thereof, and pharmaceutical compositions containing them
CA2304879A1 (en)	1999-04-01	New tetracycles, process for their production and pharmaceutical preparations containing these compounds
JPS61254591A (ja)	1986-11-12	新規なチエノ（２、３−ｄ）イミダゾ−ル誘導体、その製法、製剤および使用法
US3299090A (en)	1967-01-17	Nitroimidazoles
US3201406A (en)	1965-08-17	Pyridylcoumarins
US4105777A (en)	1978-08-08	Indoles
US4168313A (en)	1979-09-18	Phthalidyl 2-(3'-trifluoromethyl-anilino)-pyridine-3-carboxylate and its salts
US4794122A (en)	1988-12-27	Novel benzimidazolyl-thiomethyl-benzothiazoles
NO752174L (ja)	1975-12-22
AU619129B2 (en)	1992-01-16	Process for the preparation of methyl-quinoline derivatives
EP0221541A2 (en)	1987-05-13	Quinolonecarboxylic acid derivatives and their preparation
US4782075A (en)	1988-11-01	Hexahydrocarbazole containing alkylaminoamide compounds, pharmaceutical compositions and use
KR890001241B1 (ko)	1989-04-28	4-아세틸 이소퀴놀리논 화합물의 제조방법
US3711505A (en)	1973-01-16	2-(2-imidazolin-2-ylthio)-acetanilides
US4093724A (en)	1978-06-06	Novel-3-(4-quinolylamino)-2-thiophene-carboxylates
JPS5810387B2 (ja)	1983-02-25	４，５，６，７テトラヒドロイミダゾ〔４，５−ｃ〕ピリジン誘導体及びその製法
US3714186A (en)	1973-01-30	7-(1-pyrrolidinyl)-endo-7-norcaranol and its method of preparation
US3549756A (en)	1970-12-22	Antitrichomonal compositions containing 1-substituted - 2 - morpholinyl or thiamorpholinyl-5-nitroimidazoles
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