DD290885A5 - Verfahren zur herstellung neuer piperazinylalkyl-3(2h)-pyridazinone - Google Patents

Verfahren zur herstellung neuer piperazinylalkyl-3(2h)-pyridazinone Download PDF

Info

Publication number: DD290885A5
Authority: DD; German Democratic Republic
Prior art keywords: calc; pyridazinone; amino; piperazinyl; found
Prior art date: 1988-12-06

Application number

DD89335270A

Other languages

German (de)

English (en)

Inventor

Heinz Blaschke

Heimo Stroissning

Harald Fellier

Rita Enzenhofer

Original Assignee

��@��@��k��

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.)

1988-12-06

Filing date

1989-12-05

Publication date

1991-06-13

1989-12-05 Application filed by ��@��@��k�� filed Critical ��@��@��k��

1991-06-13 Publication of DD290885A5 publication Critical patent/DD290885A5/de

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238000004519 manufacturing process Methods 0.000 title abstract 3
-1 PIPERAZINYL Chemical class 0.000 title description 109
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 201
150000003839 salts Chemical class 0.000 claims abstract description 90
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 55
239000001257 hydrogen Substances 0.000 claims abstract description 33
150000002431 hydrogen Chemical class 0.000 claims abstract description 20
229910052736 halogen Inorganic materials 0.000 claims abstract description 18
150000002367 halogens Chemical class 0.000 claims abstract description 18
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 12
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 11
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 9
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 9
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims abstract description 6
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 5
206010020772 Hypertension Diseases 0.000 claims abstract description 4
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims abstract description 4
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 4
239000003814 drug Substances 0.000 claims abstract description 4
230000002093 peripheral effect Effects 0.000 claims abstract description 4
125000001624 naphthyl group Chemical group 0.000 claims abstract description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 3
125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims abstract description 3
125000004076 pyridyl group Chemical group 0.000 claims abstract description 3
125000000335 thiazolyl group Chemical group 0.000 claims abstract description 3
125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 claims abstract description 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 3
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims abstract 4
206010019280 Heart failures Diseases 0.000 claims abstract 3
150000001875 compounds Chemical class 0.000 claims description 44
238000006243 chemical reaction Methods 0.000 claims description 21
239000002253 acid Substances 0.000 claims description 12
PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 9
AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical compound OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 claims description 7
239000003085 diluting agent Substances 0.000 claims description 6
238000002360 preparation method Methods 0.000 claims description 6
150000007513 acids Chemical class 0.000 claims description 5
229910052783 alkali metal Inorganic materials 0.000 claims description 3
150000001340 alkali metals Chemical class 0.000 claims description 3
230000002152 alkylating effect Effects 0.000 claims description 3
239000003153 chemical reaction reagent Substances 0.000 claims description 3
238000005661 deetherification reaction Methods 0.000 claims description 3
238000005695 dehalogenation reaction Methods 0.000 claims description 3
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
239000000969 carrier Substances 0.000 claims description 2
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 1
125000001475 halogen functional group Chemical group 0.000 claims 1
238000000034 method Methods 0.000 abstract description 24
125000002723 alicyclic group Chemical group 0.000 abstract description 4
229940079593 drug Drugs 0.000 abstract 1
125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 404
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 278
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 166
239000000460 chlorine Substances 0.000 description 149
125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 140
239000012453 solvate Substances 0.000 description 88
239000002904 solvent Substances 0.000 description 79
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 75
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 73
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 55
229910052801 chlorine Inorganic materials 0.000 description 44
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 40
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 35
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 28
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229910052757 nitrogen Inorganic materials 0.000 description 24
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 21
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 18
229910052760 oxygen Inorganic materials 0.000 description 18
239000000126 substance Substances 0.000 description 17
125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 14
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 14
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 14
125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 12
235000015497 potassium bicarbonate Nutrition 0.000 description 12
239000011736 potassium bicarbonate Substances 0.000 description 12
229910000028 potassium bicarbonate Inorganic materials 0.000 description 12
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 11
238000010992 reflux Methods 0.000 description 11
ZJEITNHMNVNEEK-UHFFFAOYSA-N 2-aminopyridazin-3-one Chemical compound NN1N=CC=CC1=O ZJEITNHMNVNEEK-UHFFFAOYSA-N 0.000 description 10
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 10
238000001953 recrystallisation Methods 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
239000000203 mixture Substances 0.000 description 9
239000000741 silica gel Substances 0.000 description 9
229910002027 silica gel Inorganic materials 0.000 description 9
229910052938 sodium sulfate Inorganic materials 0.000 description 9
235000011152 sodium sulphate Nutrition 0.000 description 9
238000003756 stirring Methods 0.000 description 9
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 8
239000012074 organic phase Substances 0.000 description 8
239000007858 starting material Substances 0.000 description 8
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 7
230000005764 inhibitory process Effects 0.000 description 7
239000012071 phase Substances 0.000 description 7
238000000039 preparative column chromatography Methods 0.000 description 7
239000000243 solution Substances 0.000 description 7
ACKBTCUMGAHRIE-UHFFFAOYSA-N 4,5-dichloro-2-methylpyridazin-3-one Chemical compound CN1N=CC(Cl)=C(Cl)C1=O ACKBTCUMGAHRIE-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
150000001298 alcohols Chemical class 0.000 description 6
125000000217 alkyl group Chemical group 0.000 description 6
229910052794 bromium Inorganic materials 0.000 description 6
ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 6
239000002244 precipitate Substances 0.000 description 6
239000000377 silicon dioxide Substances 0.000 description 6
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 5
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
239000008346 aqueous phase Substances 0.000 description 5
229910052799 carbon Inorganic materials 0.000 description 5
125000004432 carbon atom Chemical group C* 0.000 description 5
238000004587 chromatography analysis Methods 0.000 description 5
238000010828 elution Methods 0.000 description 5
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230000035484 reaction time Effects 0.000 description 5
238000001226 reprecipitation Methods 0.000 description 5
125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 4
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 4
108060003345 Adrenergic Receptor Proteins 0.000 description 4
102000017910 Adrenergic receptor Human genes 0.000 description 4
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
229960000583 acetic acid Drugs 0.000 description 4
230000002378 acidificating effect Effects 0.000 description 4
230000037396 body weight Effects 0.000 description 4
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MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 4
WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 4
230000007717 exclusion Effects 0.000 description 4
229910052731 fluorine Inorganic materials 0.000 description 4
229940093915 gynecological organic acid Drugs 0.000 description 4
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150000007522 mineralic acids Chemical class 0.000 description 4
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BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
NDVVQPVEUGLAPX-UHFFFAOYSA-N 2-[4-(2-methoxyphenyl)piperazin-1-yl]ethanamine Chemical compound COC1=CC=CC=C1N1CCN(CCN)CC1 NDVVQPVEUGLAPX-UHFFFAOYSA-N 0.000 description 3
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KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
239000003480 eluent Substances 0.000 description 3
MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 3
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HKKFTZWMZXCRRS-UHFFFAOYSA-N 1-[4-(2-methoxyphenyl)piperazin-1-yl]hexan-1-amine Chemical compound C1CN(C(N)CCCCC)CCN1C1=CC=CC=C1OC HKKFTZWMZXCRRS-UHFFFAOYSA-N 0.000 description 2
JZJRVFQLQMGBTI-UHFFFAOYSA-N 1-[4-(2-methoxyphenyl)piperazin-1-yl]propan-1-amine Chemical compound C1CN(C(N)CC)CCN1C1=CC=CC=C1OC JZJRVFQLQMGBTI-UHFFFAOYSA-N 0.000 description 2
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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
- C07D401/12—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 linked by a chain containing hetero atoms as chain links
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D237/22—Nitrogen and oxygen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Cardiology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Medicinal Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Heart & Thoracic Surgery (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Plural Heterocyclic Compounds (AREA)

DD89335270A 1988-12-06 1989-12-05 Verfahren zur herstellung neuer piperazinylalkyl-3(2h)-pyridazinone DD290885A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
AT299188		1988-12-06

Publications (1)

Publication Number	Publication Date
DD290885A5 true DD290885A5 (de)	1991-06-13

Family

ID=3543605

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD89335270A DD290885A5 (de)	1988-12-06	1989-12-05	Verfahren zur herstellung neuer piperazinylalkyl-3(2h)-pyridazinone

Country Status (28)

Country	Link
US (1)	US5034391A (ru)
EP (1)	EP0372305B1 (ru)
JP (1)	JPH02200676A (ru)
KR (1)	KR900009626A (ru)
CN (1)	CN1022565C (ru)
AT (1)	ATE92487T1 (ru)
AU (1)	AU622501B2 (ru)
CA (1)	CA2004298A1 (ru)
DD (1)	DD290885A5 (ru)
DE (1)	DE58905151D1 (ru)
DK (1)	DK169102B1 (ru)
ES (1)	ES2058449T3 (ru)
FI (1)	FI93956C (ru)
GR (1)	GR3008659T3 (ru)
HU (1)	HU203748B (ru)
IE (1)	IE62890B1 (ru)
IL (1)	IL92442A0 (ru)
LT (2)	LTIP1615A (ru)
LV (1)	LV10273B (ru)
MD (2)	MD382C2 (ru)
MY (1)	MY106282A (ru)
NO (1)	NO173441C (ru)
NZ (1)	NZ231625A (ru)
PT (1)	PT92488B (ru)
RU (2)	RU1823874C (ru)
UA (1)	UA19756A1 (ru)
YU (1)	YU229289A (ru)
ZA (1)	ZA899320B (ru)

Families Citing this family (16)

* Cited by examiner, † Cited by third party
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US5162321A (en) *	1989-12-20	1992-11-10	Adir Et Compagnie	1-naphthyl piperazines useful as 5-HT1A receptor ligands
ES2149761T3 (es) *	1990-04-25	2000-11-16	Nissan Chemical Ind Ltd	Derivado de piridazinona.
HU214320B (hu) *	1991-12-20	1998-03-02	EGIS Gyógyszergyár Rt.	Eljárás új 3(2H)-piridazinon-származékok és ezeket tartalmazó gyógyszerkészítmények előállítására
US5605896A (en) *	1992-02-25	1997-02-25	Recordati S.A., Chemical And Pharmaceutical Company	Bicyclic heterocyclic derivatives having α1 adrenergic and 5HT1A activities
IT1254469B (it) *	1992-02-25	1995-09-25	Recordati Chem Pharm	Derivati benzopiranici e benzotiopiranici
US5474994A (en) *	1992-05-26	1995-12-12	Recordati S.A., Chemical And Pharmaceutical Company	Bicyclic heterocyclic derivatives having α1 -adrenergic and 5HT1A
IT1258315B (it) *	1992-04-10	1996-02-22	Recordati Chem Pharm	Derivati del flavone
US6960597B2 (en) *	2000-06-30	2005-11-01	Orth-Mcneil Pharmaceutical, Inc.	Aza-bridged-bicyclic amino acid derivatives as α4 integrin antagonists
HU225955B1 (en) *	2001-07-26	2008-01-28	Egis Gyogyszergyar Nyilvanosan	Novel 2h-pyridazin-3-one derivatives, process for their preparation, their use and pharmaceutical compositions containing them
HU227237B1 (en) *	2001-09-27	2010-12-28	Egis Gyogyszergyar Nyilvanosan Muekoedoe Reszvenytarsasag	Substituted alkylpyridazinone derivatives, process for their preparation, pharmaceutical compositions containing them
AU2003209321A1 (en) *	2002-01-18	2003-07-30	Pharmacia Corporation	Substituted pyridazinones as inhibitors of p38
HU227592B1 (en) *	2002-11-13	2011-09-28	Egis Gyogyszergyar Nyilvanosan Muekoedoe Reszvenytarsasag	Use of substituted alkyl-piridazinone derivatives for the treatment of memory decline and learning malfunctions
US20050176755A1 (en) *	2003-10-31	2005-08-11	Dyatkin Alexey B.	Aza-bridged-bicyclic amino acid derivatives as alpha4 integrin antagonists
CA2555594A1 (en) *	2004-02-10	2005-08-25	Janssen Pharmaceutica N.V.	Pyridazinones as antagonists of a4 integrins
ATE371649T1 (de) *	2004-02-10	2007-09-15	Janssen Pharmaceutica Nv	Pyridazinonharnstoffe als antagonisten von a4- integrinen
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1989
- 1989-11-21 IE IE372189A patent/IE62890B1/en not_active IP Right Cessation
- 1989-11-23 ES ES89121681T patent/ES2058449T3/es not_active Expired - Lifetime
- 1989-11-23 AT AT89121681T patent/ATE92487T1/de not_active IP Right Cessation
- 1989-11-23 EP EP89121681A patent/EP0372305B1/de not_active Expired - Lifetime
- 1989-11-23 DE DE8989121681T patent/DE58905151D1/de not_active Expired - Fee Related
- 1989-11-24 IL IL92442A patent/IL92442A0/xx not_active IP Right Cessation
- 1989-11-29 MY MYPI89001659A patent/MY106282A/en unknown
- 1989-11-30 CA CA002004298A patent/CA2004298A1/en not_active Abandoned
- 1989-11-30 US US07/443,166 patent/US5034391A/en not_active Expired - Fee Related
- 1989-12-04 PT PT92488A patent/PT92488B/pt not_active IP Right Cessation
- 1989-12-04 NZ NZ231625A patent/NZ231625A/xx unknown
- 1989-12-04 KR KR1019890017840A patent/KR900009626A/ko not_active Ceased
- 1989-12-04 AU AU45898/89A patent/AU622501B2/en not_active Ceased
- 1989-12-05 NO NO894856A patent/NO173441C/no unknown
- 1989-12-05 HU HU896432A patent/HU203748B/hu not_active IP Right Cessation
- 1989-12-05 DK DK611789A patent/DK169102B1/da not_active IP Right Cessation
- 1989-12-05 FI FI895824A patent/FI93956C/fi not_active IP Right Cessation
- 1989-12-05 UA UA4742661A patent/UA19756A1/ru unknown
- 1989-12-05 JP JP1314490A patent/JPH02200676A/ja active Pending
- 1989-12-05 DD DD89335270A patent/DD290885A5/de not_active IP Right Cessation
- 1989-12-05 RU SU894742661A patent/RU1823874C/ru active
- 1989-12-06 YU YU02292/89A patent/YU229289A/xx unknown
- 1989-12-06 ZA ZA899320A patent/ZA899320B/xx unknown
- 1989-12-06 CN CN89109090A patent/CN1022565C/zh not_active Expired - Fee Related
1990
- 1990-12-24 RU SU904831923A patent/RU2024517C1/ru active
1993
- 1993-08-05 GR GR930400672T patent/GR3008659T3/el unknown
- 1993-11-12 LV LVP-93-1218A patent/LV10273B/xx unknown
- 1993-12-16 LT LTIP1615A patent/LTIP1615A/xx not_active Application Discontinuation
1994
- 1994-01-27 LT LTIP1808A patent/LT3945B/lt not_active IP Right Cessation
- 1994-10-10 MD MD94-0323A patent/MD382C2/ru unknown
- 1994-10-24 MD MD94-0347A patent/MD383C2/ru unknown

Also Published As

Publication number	Publication date
MY106282A (en)	1995-04-29
JPH02200676A (ja)	1990-08-08
US5034391A (en)	1991-07-23
DK169102B1 (da)	1994-08-15
HU203748B (en)	1991-09-30
NO894856D0 (no)	1989-12-05
PT92488A (pt)	1990-06-29
KR900009626A (ko)	1990-07-05
RU2024517C1 (ru)	1994-12-15
FI93956C (fi)	1995-06-26
IL92442A0 (en)	1990-08-31
LTIP1615A (en)	1995-07-25
CN1022565C (zh)	1993-10-27
HUT52094A (en)	1990-06-28
YU229289A (en)	1991-10-31
UA19756A1 (ru)	1997-12-25
CA2004298A1 (en)	1990-06-06
GR3008659T3 (ru)	1993-11-30
AU622501B2 (en)	1992-04-09
RU1823874C (ru)	1993-06-23
LT3945B (en)	1996-05-27
NZ231625A (en)	1991-02-26
LTIP1808A (en)	1995-08-25
NO173441B (no)	1993-09-06
EP0372305B1 (de)	1993-08-04
PT92488B (pt)	1995-08-09
LV10273B (en)	1995-04-20
EP0372305A1 (de)	1990-06-13
LV10273A (lv)	1994-10-20
ES2058449T3 (es)	1994-11-01
DK611789A (da)	1990-06-07
AU4589889A (en)	1990-06-14
CN1043129A (zh)	1990-06-20
IE62890B1 (en)	1995-03-08
ZA899320B (en)	1991-02-27
ATE92487T1 (de)	1993-08-15
FI895824A0 (fi)	1989-12-05
DK611789D0 (da)	1989-12-05
NO894856L (no)	1990-06-07
MD382C2 (ru)	1996-06-30
DE58905151D1 (de)	1993-09-09
NO173441C (no)	1993-12-15
FI93956B (fi)	1995-03-15
IE893721L (en)	1990-06-06
MD383C2 (ru)	1996-06-30

Legal Events

Date	Code	Title	Description
1995-05-24	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
DD290885A5 (de)	1991-06-13	Verfahren zur herstellung neuer piperazinylalkyl-3(2h)-pyridazinone
DE69533057T2 (de)	2005-06-16	Kondensierte pyridazinverbindungen
DD272077A5 (de)	1989-09-27	Verfahren zur herstellung von piperazinyl-heterocyclischen verbindungen
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EP0117403B1 (de)	1988-06-01	6-(Acylaminoaryl)-3(2H)-pyridazinonderivate, ihre Herstellung und Verwendung
DE2847622A1 (de)	1979-05-31	Neue chinazolin-derivate, verfahren zu ihrer herstellung und diese derivate enthaltende arzneimittel
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DE60004671T2 (de)	2004-07-29	Neue piperazinylalkylthiopyrimidine derivate, diese enthaltende pharmazeutische zusammenstellungen und verfahren zu deren herstellung
DE69330090T2 (de)	2001-09-20	Verfahren zur Verwendung von (2-Imitazolin-2-ylamino)-chinoxalindeviraten
DE3622036A1 (de)	1987-01-22	Benzimidazolderivate
DE2164058A1 (de)	1972-07-27	Neue basisch substituierte Benzylphthalazon-Derivate, ihre Salze, Verfahren zu ihrer Herstellung und diese Produkte enthaltende pharmazeutische Präparate
DE3524635A1 (de)	1986-01-23	Isoindolinyl-alkyl-piperazinverbindungen, verfahren zu ihrer herstellung und pharmazeutische mittel
DE2617205A1 (de)	1976-10-28	Anorektische verbindungen
DE3439450A1 (de)	1986-05-07	1,2,4-triazolo-carbamate und ihre saeureadditionssalze, verfahren zu ihrer herstellung und arzneimittel
DE60202970T2 (de)	2006-02-16	Substituierte alkylaminopyridazinonderivate, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische zubereitungen
DD209828A5 (de)	1984-05-23	Verfahren zur herstellung von 2-guanidino-4-(2-subst.-amino-4-imidazolyl)thiazolen
DE3902316A1 (de)	1990-08-02	Neue piperazinylalkyl-3(2h)-pyridazinone, verfahren zu ihrer herstellung und ihre verwendung als blutdrucksenkende mittel
DE2854191A1 (de)	1980-07-03	Dihydropyridazinone, verfahren zu ihrer herstellung und diese verbindungen enthaltende therapeutische mittel
EP1034170A1 (en)	2000-09-13	2-substituted 1,2-benzisothiazole derivatives and their use as serotonin antagonists (5-ht1a, 5-ht1b and 5-ht1d)
DE60207895T2 (de)	2006-08-10	Neue piperidinylalkylaminopyridazinonderivate, ein verfahren zu deren herstellung und pharmazeutische zusammensetzungen, die diese verbindungen enthalten
DE1921049A1 (de)	1969-11-06	Neue organische Verbindungen und Verfahren zu ihrer Herstellung
DD202566A5 (de)	1983-09-21	Verfahren zur herstellung von 1-phenylindazol-3-on-verbindungen
DE2708187A1 (de)	1978-08-31	Neue pyrido-pyridazin-one
DE1595910A1 (de)	1970-02-12	3,6-Disubstituierte Pyridazine und Verfahren zu ihrer Herstellung
HRP940777A2 (en)	1997-06-30	Process for the preparation of new piperazinylalkyl-3(2h)-pyridazinones