DD268937A5 - Verfahren zur herstellung bestimmter sulfonamide und ihre verwendung als antiarrhythmische mittel - Google Patents

Verfahren zur herstellung bestimmter sulfonamide und ihre verwendung als antiarrhythmische mittel Download PDF

Info

Publication number: DD268937A5
Authority: DD; German Democratic Republic
Prior art keywords: formula; group; alk; alkyl; item
Prior art date: 1986-05-01

Application number

DD87302295A

Other languages

German (de)

English (en)

Inventor

Edmund J Arrowsmith

Peter E Cross

Geoffrey N Thomas

Original Assignee

Pfizer Limited,Gb

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.)

1986-05-01

Filing date

1987-04-30

Publication date

1989-06-14

1987-04-30 Application filed by Pfizer Limited,Gb filed Critical Pfizer Limited,Gb

1989-06-14 Publication of DD268937A5 publication Critical patent/DD268937A5/de

Links

238000000034 method Methods 0.000 title claims abstract description 26
229940124530 sulfonamide Drugs 0.000 title claims abstract description 8
150000003456 sulfonamides Chemical class 0.000 title claims abstract description 8
239000003416 antiarrhythmic agent Substances 0.000 title abstract description 11
238000004519 manufacturing process Methods 0.000 title description 10
150000001875 compounds Chemical class 0.000 claims abstract description 92
-1 piperidino, morpholino Chemical group 0.000 claims abstract description 40
238000002360 preparation method Methods 0.000 claims abstract description 21
150000003839 salts Chemical class 0.000 claims abstract description 16
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 11
125000000217 alkyl group Chemical group 0.000 claims abstract description 8
230000008569 process Effects 0.000 claims abstract description 7
125000001424 substituent group Chemical group 0.000 claims abstract description 6
229910052717 sulfur Inorganic materials 0.000 claims abstract description 6
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 5
229910052760 oxygen Inorganic materials 0.000 claims abstract description 5
125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims abstract description 4
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims abstract description 4
125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 4
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims abstract description 3
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 32
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 32
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 22
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 18
229910000027 potassium carbonate Inorganic materials 0.000 claims description 16
235000017557 sodium bicarbonate Nutrition 0.000 claims description 16
229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 16
239000002253 acid Substances 0.000 claims description 14
239000000460 chlorine Substances 0.000 claims description 13
OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims description 12
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 11
238000006243 chemical reaction Methods 0.000 claims description 10
IZDROVVXIHRYMH-UHFFFAOYSA-N methanesulfonic anhydride Chemical compound CS(=O)(=O)OS(C)(=O)=O IZDROVVXIHRYMH-UHFFFAOYSA-N 0.000 claims description 10
239000012359 Methanesulfonyl chloride Substances 0.000 claims description 8
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 claims description 8
LBTPIFQNEKOAIM-UHFFFAOYSA-N n-phenylmethanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=CC=C1 LBTPIFQNEKOAIM-UHFFFAOYSA-N 0.000 claims description 6
230000010933 acylation Effects 0.000 claims description 4
238000005917 acylation reaction Methods 0.000 claims description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
229910052736 halogen Inorganic materials 0.000 claims description 4
150000002367 halogens Chemical class 0.000 claims description 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 3
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
229910052794 bromium Inorganic materials 0.000 claims description 2
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 2
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
229910052801 chlorine Inorganic materials 0.000 claims 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 1
ITYJDNHFRZSTJY-UHFFFAOYSA-N methanesulfonyl bromide Chemical compound CS(Br)(=O)=O ITYJDNHFRZSTJY-UHFFFAOYSA-N 0.000 claims 1
125000005948 methanesulfonyloxy group Chemical group 0.000 claims 1
239000000546 pharmaceutical excipient Substances 0.000 claims 1
NBNBICNWNFQDDD-UHFFFAOYSA-N sulfuryl dibromide Chemical compound BrS(Br)(=O)=O NBNBICNWNFQDDD-UHFFFAOYSA-N 0.000 claims 1
239000000543 intermediate Substances 0.000 abstract description 10
125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract description 5
230000003288 anthiarrhythmic effect Effects 0.000 abstract description 3
125000005843 halogen group Chemical group 0.000 abstract description 2
239000002371 cardiac agent Substances 0.000 abstract 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 126
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 113
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 66
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 59
239000000243 solution Substances 0.000 description 51
235000019439 ethyl acetate Nutrition 0.000 description 39
239000007787 solid Substances 0.000 description 37
238000004458 analytical method Methods 0.000 description 36
239000003921 oil Substances 0.000 description 30
235000019198 oils Nutrition 0.000 description 30
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 27
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 27
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 27
239000000203 mixture Substances 0.000 description 19
238000010992 reflux Methods 0.000 description 18
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 18
238000005481 NMR spectroscopy Methods 0.000 description 17
239000000741 silica gel Substances 0.000 description 17
229910002027 silica gel Inorganic materials 0.000 description 17
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 16
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 14
239000000047 product Substances 0.000 description 14
239000007858 starting material Substances 0.000 description 14
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 13
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 13
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
239000012267 brine Substances 0.000 description 12
238000000605 extraction Methods 0.000 description 12
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 11
239000002904 solvent Substances 0.000 description 11
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 10
229910052943 magnesium sulfate Inorganic materials 0.000 description 10
235000019341 magnesium sulphate Nutrition 0.000 description 10
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
238000002425 crystallisation Methods 0.000 description 9
230000008025 crystallization Effects 0.000 description 9
229910052739 hydrogen Inorganic materials 0.000 description 9
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 9
229910000041 hydrogen chloride Inorganic materials 0.000 description 9
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 8
238000001816 cooling Methods 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 8
230000037024 effective refractory period Effects 0.000 description 7
238000003756 stirring Methods 0.000 description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
239000007868 Raney catalyst Substances 0.000 description 6
229910000564 Raney nickel Inorganic materials 0.000 description 6
206010003119 arrhythmia Diseases 0.000 description 6
238000004587 chromatography analysis Methods 0.000 description 6
239000001257 hydrogen Substances 0.000 description 6
239000012044 organic layer Substances 0.000 description 6
235000009518 sodium iodide Nutrition 0.000 description 6
239000000725 suspension Substances 0.000 description 6
125000001309 chloro group Chemical group Cl* 0.000 description 5
239000012458 free base Substances 0.000 description 5
NTURQZFFJDCTMZ-UHFFFAOYSA-N 1-(2-bromoethyl)-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(CCBr)C=C1 NTURQZFFJDCTMZ-UHFFFAOYSA-N 0.000 description 4
235000019502 Orange oil Nutrition 0.000 description 4
230000001746 atrial effect Effects 0.000 description 4
PTPPVTUXJDJAGY-UHFFFAOYSA-N n-methyl-2-(4-nitrophenyl)ethanamine Chemical compound CNCCC1=CC=C([N+]([O-])=O)C=C1 PTPPVTUXJDJAGY-UHFFFAOYSA-N 0.000 description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
239000010502 orange oil Substances 0.000 description 4
238000000746 purification Methods 0.000 description 4
229920006395 saturated elastomer Polymers 0.000 description 4
239000011734 sodium Substances 0.000 description 4
229910000029 sodium carbonate Inorganic materials 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
CIIGWOXXOUVEAD-UHFFFAOYSA-N 2-chloroethyl benzenesulfonate Chemical compound ClCCOS(=O)(=O)C1=CC=CC=C1 CIIGWOXXOUVEAD-UHFFFAOYSA-N 0.000 description 3
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
230000006793 arrhythmia Effects 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
238000004440 column chromatography Methods 0.000 description 3
238000007796 conventional method Methods 0.000 description 3
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239000003814 drug Substances 0.000 description 3
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QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 2
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BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 description 2
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241000700199 Cavia porcellus Species 0.000 description 2
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150000003840 hydrochlorides Chemical class 0.000 description 2
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229910052708 sodium Inorganic materials 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
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KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
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SRSRGGYRIOZFAT-UHFFFAOYSA-N methyl 4-(2-chloroethoxy)benzoate Chemical compound COC(=O)C1=CC=C(OCCCl)C=C1 SRSRGGYRIOZFAT-UHFFFAOYSA-N 0.000 description 1
210000004165 myocardium Anatomy 0.000 description 1
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210000003540 papillary muscle Anatomy 0.000 description 1
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NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
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230000009090 positive inotropic effect Effects 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
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230000004044 response Effects 0.000 description 1
230000033764 rhythmic process Effects 0.000 description 1
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210000001519 tissue Anatomy 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

DD87302295A 1986-05-01 1987-04-30 Verfahren zur herstellung bestimmter sulfonamide und ihre verwendung als antiarrhythmische mittel DD268937A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB868610668A GB8610668D0 (en)	1986-05-01	1986-05-01	Anti-arrhythmia agents

Publications (1)

Publication Number	Publication Date
DD268937A5 true DD268937A5 (de)	1989-06-14

Family

ID=10597176

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD87302295A DD268937A5 (de)	1986-05-01	1987-04-30	Verfahren zur herstellung bestimmter sulfonamide und ihre verwendung als antiarrhythmische mittel

Country Status (8)

Country	Link
JP (1)	JPS62267250A (pt)
DD (1)	DD268937A5 (pt)
GB (1)	GB8610668D0 (pt)
LV (1)	LV5466A3 (pt)
MX (1)	MX6311A (pt)
SU (1)	SU1591805A3 (pt)
UA (1)	UA6154A1 (pt)
ZA (1)	ZA873078B (pt)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
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WO1996004231A1 (en) *	1994-08-04	1996-02-15	C & C Research Labs.	Novel amine derivative, process for producing the same, and use thereof as antiarrhythmic
HUE028976T2 (en) *	2003-06-17	2017-02-28	Arena Pharm Inc	8-Chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine hydrochloride
SG158168A1 (en)	2004-12-23	2010-01-29	Arena Pharm Inc	5ht2c receptor modulator compositions and methods of use
EP2471779A1 (en)	2006-04-03	2012-07-04	Arena Pharmaceuticals, Inc.	Process for the resolution of a mixture of (R)- and (S)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine
KR20100045983A (ko) *	2007-06-29	2010-05-04	에모리 유니버시티	신경보호를 위한 ｎｍｄａ 수용체 길항물질
US8952197B2 (en)	2009-06-18	2015-02-10	Arena Pharmaceuticals, Inc.	Processes for the preparation of 5-HT2C receptor agonists
KR20130112848A (ko)	2010-06-02	2013-10-14	아레나 파마슈티칼스, 인크.	5-ｈｔ2ｃ 수용체 아고니스트의 제조 방법
KR20130138770A (ko)	2010-09-01	2013-12-19	아레나 파마슈티칼스, 인크.	광학적으로 활성 산을 갖는 로르카세린의 염
EP3485878A1 (en)	2010-09-01	2019-05-22	Arena Pharmaceuticals, Inc.	Modified-release dosage forms of 5-ht2c agonists useful for weight management
KR20140091458A (ko)	2010-09-01	2014-07-21	아레나 파마슈티칼스, 인크.	신장 손상을 갖는 개체에 대한 로카세린의 투여
JP2013536859A (ja)	2010-09-01	2013-09-26	アリーナファーマシューティカルズ，インコーポレイテッド	５−ｈｔ２ｃアゴニストの非吸湿性塩
WO2014058441A1 (en)	2012-10-09	2014-04-17	Arena Pharmaceuticals, Inc.	Method of weight management

1986
- 1986-05-01 GB GB868610668A patent/GB8610668D0/en active Pending
1987
- 1987-04-29 ZA ZA873078A patent/ZA873078B/xx unknown
- 1987-04-30 SU SU874202474A patent/SU1591805A3/ru active
- 1987-04-30 DD DD87302295A patent/DD268937A5/de not_active IP Right Cessation
- 1987-04-30 MX MX631187A patent/MX6311A/es unknown
- 1987-04-30 UA UA4202474A patent/UA6154A1/uk unknown
- 1987-05-01 JP JP62108720A patent/JPS62267250A/ja active Granted
1993
- 1993-12-03 LV LV931305A patent/LV5466A3/xx unknown

Also Published As

Publication number	Publication date
UA6154A1 (uk)	1994-12-29
LV5466A3 (lv)	1994-03-10
JPS62267250A (ja)	1987-11-19
MX6311A (es)	1993-08-01
GB8610668D0 (en)	1986-06-04
JPH0360814B2 (pt)	1991-09-17
ZA873078B (en)	1988-12-28
SU1591805A3 (ru)	1990-09-07

Legal Events

Date	Code	Title	Description
1994-04-14	NPV	Change in the person, the name or the address of the representative (addendum to changes before extension act)
1994-05-05	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
AT363096B (de)	1981-07-10	Verfahren zur herstellung von neuen phthalazinderivaten und deren salzen
FI95245C (fi)	1996-01-10	Menetelmä rytmihäiriöiden vastaisten pyrimidiinidionijohdannaisten valmistamiseksi
US5079248A (en)	1992-01-07	Anti-arrhythmic agents
DE69013959T2 (de)	1995-03-16	Aminobenzolsulfonsäurederivate.
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DE3248138C2 (pt)	1992-12-10
DE3875600T2 (de)	1993-03-11	Antiarrythmische derivate 2.
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DE2505297A1 (de)	1975-10-09	Neue 2-arylamino-2-imidazolinderivate und ein verfahren zu deren herstellung
DE2434951C3 (de)	1977-05-18	In 3-stellung basisch substituierte diphenylhydantoine
DE2112249A1 (de)	1972-09-14	Pharmakologisch wirksame Derivate von Phenylalkylaminen
DD280965A5 (de)	1990-07-25	Verfahren zur herstellung von antiarrhythmisch wirkenden mitteln
DE2720545B2 (de)	1980-01-10	Derivate des 2,4-Diamino-6,7-dimethoxychinazolins, ihre Herstellung und pharmazeutische Mittel
DE69221106T2 (de)	1997-12-11	Antitumorzusammensetzung und Verfahren zur Behandlung
EP0018360B1 (de)	1981-09-30	N-(5-Methoxybentofuran-2-ylcarbonyl)-N'-benzylpiperazin und Verfahren zu dessen Herstellung
DE60025270T2 (de)	2006-08-17	N-substituierte benzyl oder phenyl arylsulfamide und ihre verwendung
DE69512104T2 (de)	2000-04-20	Substituierte Sulfonamide, Verfahren zu deren Herstellung und sie enthaltende pharmazeutische Zusammensetzungen
DE69713128T2 (de)	2003-03-20	4-(1-piperazinyl)benzosäurederivate, verfahren zu ihrer herstellung und ihre therapeutischen verwendungen
DD296913A5 (de)	1991-12-19	Substituierte (chinolin-2-yl-methoxy)phenyl-n,n'-sulfonylharnstoffe, verfahren zu ihrer herstellung und ihre verwendung in arzneimitteln
DE3715763A1 (de)	1988-11-24	Diarylalkyl-substituierte alkylamine, verfahren zu ihrer herstellung, ihre verwendung sowie sie enthaltende arzneimittel
DE69008019T2 (de)	1994-08-25	Benzothiazol-Derivate.