JPH11506094A - 3(2h)−ピリダジノン誘導体及びその化合物含有の製薬学的組成物 - Google Patents
3(2h)−ピリダジノン誘導体及びその化合物含有の製薬学的組成物Info
- Publication number
- JPH11506094A JPH11506094A JP8536319A JP53631996A JPH11506094A JP H11506094 A JPH11506094 A JP H11506094A JP 8536319 A JP8536319 A JP 8536319A JP 53631996 A JP53631996 A JP 53631996A JP H11506094 A JPH11506094 A JP H11506094A
- Authority
- JP
- Japan
- Prior art keywords
- benzodioxan
- propyl
- pyridazinone
- compounds
- formula
- Prior art date
- Legal status (The legal status 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 status listed.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 54
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 9
- AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical class OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 title claims description 8
- 150000003839 salts Chemical class 0.000 claims abstract description 27
- 239000002253 acid Substances 0.000 claims abstract description 22
- 206010004446 Benign prostatic hyperplasia Diseases 0.000 claims abstract description 14
- 208000004403 Prostatic Hyperplasia Diseases 0.000 claims abstract description 13
- 238000004519 manufacturing process Methods 0.000 claims abstract description 11
- FJNRJBQUOQLUNQ-CYBMUJFWSA-N 2-[3-[[(3r)-2,3-dihydro-1,4-benzodioxin-3-yl]methylamino]propyl]pyridazin-3-one Chemical compound O=C1C=CC=NN1CCCNC[C@H]1OC2=CC=CC=C2OC1 FJNRJBQUOQLUNQ-CYBMUJFWSA-N 0.000 claims abstract description 9
- -1 3-chloro-1-propyl Chemical group 0.000 claims description 25
- 150000001412 amines Chemical class 0.000 claims description 19
- 239000003814 drug Substances 0.000 claims description 11
- 229940079593 drug Drugs 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- FJNRJBQUOQLUNQ-UHFFFAOYSA-N 2-[3-(2,3-dihydro-1,4-benzodioxin-3-ylmethylamino)propyl]pyridazin-3-one Chemical compound O=C1C=CC=NN1CCCNCC1OC2=CC=CC=C2OC1 FJNRJBQUOQLUNQ-UHFFFAOYSA-N 0.000 claims description 3
- 239000000654 additive Substances 0.000 claims description 3
- 230000000996 additive effect Effects 0.000 claims description 2
- 230000008485 antagonism Effects 0.000 abstract description 17
- 239000007858 starting material Substances 0.000 abstract description 3
- 230000000694 effects Effects 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- 238000000034 method Methods 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000002585 base Substances 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 230000003287 optical effect Effects 0.000 description 8
- 238000002474 experimental method Methods 0.000 description 7
- SONNWYBIRXJNDC-VIFPVBQESA-N phenylephrine Chemical compound CNC[C@H](O)C1=CC=CC(O)=C1 SONNWYBIRXJNDC-VIFPVBQESA-N 0.000 description 7
- 229960001802 phenylephrine Drugs 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
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- 230000001242 postsynaptic effect Effects 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
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- AQHHHDLHHXJYJD-UHFFFAOYSA-N propranolol Chemical compound C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 AQHHHDLHHXJYJD-UHFFFAOYSA-N 0.000 description 4
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- YONLFQNRGZXBBF-ZIAGYGMSSA-N (2r,3r)-2,3-dibenzoyloxybutanedioic acid Chemical compound O([C@@H](C(=O)O)[C@@H](OC(=O)C=1C=CC=CC=1)C(O)=O)C(=O)C1=CC=CC=C1 YONLFQNRGZXBBF-ZIAGYGMSSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 241000282326 Felis catus Species 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
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- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 210000003708 urethra Anatomy 0.000 description 3
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- 238000005406 washing Methods 0.000 description 3
- BPICBUSOMSTKRF-UHFFFAOYSA-N xylazine Chemical compound CC1=CC=CC(C)=C1NC1=NCCCS1 BPICBUSOMSTKRF-UHFFFAOYSA-N 0.000 description 3
- 229960001600 xylazine Drugs 0.000 description 3
- XIHBRGWHLXXLNW-UHFFFAOYSA-N 3-chloro-n-(2,3-dihydro-1,4-benzodioxin-3-ylmethyl)propan-1-amine Chemical compound C1=CC=C2OC(CNCCCCl)COC2=C1 XIHBRGWHLXXLNW-UHFFFAOYSA-N 0.000 description 2
- 108060003345 Adrenergic Receptor Proteins 0.000 description 2
- 102000017910 Adrenergic receptor Human genes 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 241000282472 Canis lupus familiaris Species 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 206010020772 Hypertension Diseases 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 206010051482 Prostatomegaly Diseases 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 239000002168 alkylating agent Substances 0.000 description 2
- 229940100198 alkylating agent Drugs 0.000 description 2
- 230000003276 anti-hypertensive effect Effects 0.000 description 2
- 230000036772 blood pressure Effects 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- UBAZGMLMVVQSCD-UHFFFAOYSA-N carbon dioxide;molecular oxygen Chemical compound O=O.O=C=O UBAZGMLMVVQSCD-UHFFFAOYSA-N 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000012258 culturing Methods 0.000 description 2
- 230000035487 diastolic blood pressure Effects 0.000 description 2
- 230000003205 diastolic effect Effects 0.000 description 2
- NTBIYBAYFBNTCD-UHFFFAOYSA-N dibenzoyl 2,3-dihydroxybutanedioate Chemical compound C=1C=CC=CC=1C(=O)OC(=O)C(O)C(O)C(=O)OC(=O)C1=CC=CC=C1 NTBIYBAYFBNTCD-UHFFFAOYSA-N 0.000 description 2
- 230000002526 effect on cardiovascular system Effects 0.000 description 2
- 238000011067 equilibration Methods 0.000 description 2
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- 239000012074 organic phase Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 239000008363 phosphate buffer Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Inorganic materials [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 2
- 229960003712 propranolol Drugs 0.000 description 2
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 2
- 210000003752 saphenous vein Anatomy 0.000 description 2
- 210000002460 smooth muscle Anatomy 0.000 description 2
- 230000001629 suppression Effects 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 2
- 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
- 229930003347 Atropine Natural products 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- RKUNBYITZUJHSG-UHFFFAOYSA-N Hyosciamin-hydrochlorid Natural products CN1C(C2)CCC1CC2OC(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-UHFFFAOYSA-N 0.000 description 1
- 208000001953 Hypotension Diseases 0.000 description 1
- 241001601804 Margites Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 208000001089 Multiple system atrophy Diseases 0.000 description 1
- OPKOKAMJFNKNAS-UHFFFAOYSA-N N-methylethanolamine Chemical compound CNCCO OPKOKAMJFNKNAS-UHFFFAOYSA-N 0.000 description 1
- 206010031127 Orthostatic hypotension Diseases 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 108700043492 SprD Proteins 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000000384 adrenergic alpha-2 receptor agonist Substances 0.000 description 1
- 239000000556 agonist Substances 0.000 description 1
- WNMJYKCGWZFFKR-UHFFFAOYSA-N alfuzosin Chemical compound N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N(C)CCCNC(=O)C1CCCO1 WNMJYKCGWZFFKR-UHFFFAOYSA-N 0.000 description 1
- 229960004607 alfuzosin Drugs 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 230000003113 alkalizing effect Effects 0.000 description 1
- 239000002163 alpha 1-adrenoceptor agonist Substances 0.000 description 1
- 125000004103 aminoalkyl group Chemical group 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 229940030600 antihypertensive agent Drugs 0.000 description 1
- 239000002220 antihypertensive agent Substances 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
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- 230000004872 arterial blood pressure Effects 0.000 description 1
- 210000001367 artery Anatomy 0.000 description 1
- RKUNBYITZUJHSG-SPUOUPEWSA-N atropine Chemical compound O([C@H]1C[C@H]2CC[C@@H](C1)N2C)C(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-SPUOUPEWSA-N 0.000 description 1
- 229960000396 atropine Drugs 0.000 description 1
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- 239000011575 calcium Substances 0.000 description 1
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- 239000002775 capsule Substances 0.000 description 1
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- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 1
- 229940043264 dodecyl sulfate Drugs 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
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- 230000003054 hormonal effect Effects 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 230000036543 hypotension Effects 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
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- 230000030214 innervation Effects 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- IMYZQPCYWPFTAG-IQJOONFLSA-N mecamylamine Chemical compound C1C[C@@H]2C(C)(C)[C@@](NC)(C)[C@H]1C2 IMYZQPCYWPFTAG-IQJOONFLSA-N 0.000 description 1
- 229960002525 mecamylamine Drugs 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000003880 polar aprotic solvent Substances 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 239000003361 porogen Substances 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium 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
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- IENZQIKPVFGBNW-UHFFFAOYSA-N prazosin Chemical compound N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N(CC1)CCN1C(=O)C1=CC=CO1 IENZQIKPVFGBNW-UHFFFAOYSA-N 0.000 description 1
- 229960001289 prazosin Drugs 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000001525 receptor binding assay Methods 0.000 description 1
- 102000005962 receptors Human genes 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
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- 230000002792 vascular Effects 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/50—Pyridazines; Hydrogenated pyridazines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/08—Drugs for disorders of the urinary system of the prostate
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
- C07D319/14—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems
- C07D319/16—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D319/20—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring with substituents attached to the hetero ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Urology & Nephrology (AREA)
- Reproductive Health (AREA)
- Endocrinology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Description
Claims (1)
- 【特許請求の範囲】 1.式(1) のR-2-[3-([1,4]ベンゾジオキサン-2-イルメチルアミノ)-1-プロピル]- 3(2H)-ピリダジノン及びその酸付加塩。 2.式(2) のR-2-[3-([1,4]ベンゾジオキサン-2-イルメチルアミノ)-1-プロピル]- 3(2H)-ピリダジノン及びその酸付加塩。 3.式(6) の3(2H)-ピリダジノン或いはその塩基で形成された塩を、式(4) のR-N-([1,4]ベンゾジオキサン-2-イルメチル)-N-(3-クロロ-1-プロピ ル)アミンと反応せしめ、式(1) のR-2-[3-([1,4]ベンゾジオキサン-2-イルメチルアミノ)-1-プロピル]- 3(2H)-ピリダジノンを得ること、或いは、式(5) のS-N-([1,4]ベンゾジオキサン-2-イルメチル)-N-(3-クロロ-1-プロピ ル)アミンと反応せしめ、式(2) のS-2-[3-([1,4]ベンゾジオキサン-2-イルメチルアミノ)-1-プロピル]- 3(2H)-ピリダジノンを得ること、そして、所望のときは、得られた塩基を、 その酸付加塩に変換せしめ、更に、所望のときは、得られた酸付加塩を、他の酸 付加塩に変換せしめることを特徴とする請求項1或いは2に記載の化合物及びそ の酸付加塩の製造方法。 4.請求項1或いは2に記載の化合物或いはその製薬学的に許容される酸付加塩 を含有し、そして、薬剤製造に通常用いられる添加剤を任意に含有することを特 徴とする良性の前立腺肥大症の処置のための製薬学的組成物。 5.良性の前立腺肥大症の処置のための薬剤の製造のためのR-2[3-([1,4] ベンゾジオキサン-2-イルメチルアミノ)-1-プロピル]-3(2H)-ピリダジノン の用途。 6.良性の前立腺肥大症の処置のための薬剤の製造のためのS-2[3-([1,4] ベンゾジオキサン-2-イルメチルアミノ)-1-プロピル]-3(2H)-ピリダジノン の用途。 7.R-N-([1,4]ベンゾジオキサン-2-イルメチル)-N-(3-クロロ-1-プロ ピル)アミン。 8.S-N-([1,4]ベンゾジオキサン-2-イルメチル)-N-(3-クロロ-1-プロ ピル)アミン。 9.請求項1に記載の化合物の製造のためのR-N-([1,4]ベンゾジオキサン- 2-イルメチル)-N-(3-クロロ-1-プロピル)アミンの用途。 10.請求項2に記載の化合物の製造のためのS-N-([1,4]ベンゾジオキサン -2-イルメチル)-N-(3-クロロ-1-プロピル)アミンの用途。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
HU9501560 | 1995-05-29 | ||
HU9501560A HU224067B1 (hu) | 1995-05-29 | 1995-05-29 | 3(2H)-Piridazinon-származékok és e vegyületeket tartalmazó gyógyszerkészítmények |
PCT/HU1996/000030 WO1996038441A1 (en) | 1995-05-29 | 1996-05-28 | 3(2h)-pyridazinone derivatives and pharmaceutical compositions containing these compounds |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2006153349A Division JP2006316064A (ja) | 1995-05-29 | 2006-06-01 | 3(2h)−ピリダジノン誘導体及びこれら化合物の使用 |
Publications (2)
Publication Number | Publication Date |
---|---|
JPH11506094A true JPH11506094A (ja) | 1999-06-02 |
JP3857313B2 JP3857313B2 (ja) | 2006-12-13 |
Family
ID=10986884
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP53631996A Expired - Fee Related JP3857313B2 (ja) | 1995-05-29 | 1996-05-28 | 3(2h)−ピリダジノン誘導体及びその化合物含有の製薬学的組成物 |
JP2006153349A Pending JP2006316064A (ja) | 1995-05-29 | 2006-06-01 | 3(2h)−ピリダジノン誘導体及びこれら化合物の使用 |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2006153349A Pending JP2006316064A (ja) | 1995-05-29 | 2006-06-01 | 3(2h)−ピリダジノン誘導体及びこれら化合物の使用 |
Country Status (13)
Country | Link |
---|---|
US (2) | US6194411B1 (ja) |
EP (1) | EP0869957B1 (ja) |
JP (2) | JP3857313B2 (ja) |
KR (1) | KR100408364B1 (ja) |
AT (1) | ATE214389T1 (ja) |
AU (1) | AU710265B2 (ja) |
CA (1) | CA2222724C (ja) |
DE (1) | DE69619861T2 (ja) |
DK (1) | DK0869957T3 (ja) |
ES (1) | ES2175100T3 (ja) |
HU (1) | HU224067B1 (ja) |
PT (1) | PT869957E (ja) |
WO (1) | WO1996038441A1 (ja) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
HU227237B1 (en) | 2001-09-27 | 2010-12-28 | Egis Gyogyszergyar Nyilvanosan Muekoedoe Reszvenytarsasag | Substituted alkylpyridazinone derivatives, process for their preparation, pharmaceutical compositions containing them |
CA2597616A1 (en) | 2005-02-17 | 2006-08-24 | Wyeth | Cycloalkylfused indole, benzothiophene, benzofuran and indene derivatives |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
HU195645B (en) * | 1985-10-30 | 1988-06-28 | Gyogyszerkutato Intezet | Process for preparing novel 3(2h)-pyridazinone derivatives and pharmaceutical compositions comprising the same |
-
1995
- 1995-05-29 HU HU9501560A patent/HU224067B1/hu not_active IP Right Cessation
-
1996
- 1996-05-28 US US08/973,584 patent/US6194411B1/en not_active Expired - Fee Related
- 1996-05-28 EP EP96919967A patent/EP0869957B1/en not_active Expired - Lifetime
- 1996-05-28 KR KR1019970708521A patent/KR100408364B1/ko not_active IP Right Cessation
- 1996-05-28 PT PT96919967T patent/PT869957E/pt unknown
- 1996-05-28 CA CA002222724A patent/CA2222724C/en not_active Expired - Fee Related
- 1996-05-28 ES ES96919967T patent/ES2175100T3/es not_active Expired - Lifetime
- 1996-05-28 DK DK96919967T patent/DK0869957T3/da active
- 1996-05-28 JP JP53631996A patent/JP3857313B2/ja not_active Expired - Fee Related
- 1996-05-28 DE DE69619861T patent/DE69619861T2/de not_active Expired - Fee Related
- 1996-05-28 WO PCT/HU1996/000030 patent/WO1996038441A1/en active IP Right Grant
- 1996-05-28 AT AT96919967T patent/ATE214389T1/de not_active IP Right Cessation
- 1996-05-28 AU AU58427/96A patent/AU710265B2/en not_active Ceased
-
2000
- 2000-08-28 US US09/649,077 patent/US6248907B1/en not_active Expired - Fee Related
-
2006
- 2006-06-01 JP JP2006153349A patent/JP2006316064A/ja active Pending
Also Published As
Publication number | Publication date |
---|---|
CA2222724C (en) | 2006-05-23 |
AU710265B2 (en) | 1999-09-16 |
DE69619861D1 (de) | 2002-04-18 |
KR100408364B1 (ko) | 2004-06-14 |
EP0869957A2 (en) | 1998-10-14 |
ES2175100T3 (es) | 2002-11-16 |
JP3857313B2 (ja) | 2006-12-13 |
ATE214389T1 (de) | 2002-03-15 |
WO1996038441A1 (en) | 1996-12-05 |
PT869957E (pt) | 2002-09-30 |
DE69619861T2 (de) | 2002-09-26 |
HU9501560D0 (en) | 1995-07-28 |
HUT75104A (en) | 1997-04-28 |
AU5842796A (en) | 1996-12-18 |
KR19990022042A (ko) | 1999-03-25 |
DK0869957T3 (da) | 2002-07-01 |
EP0869957B1 (en) | 2002-03-13 |
US6194411B1 (en) | 2001-02-27 |
CA2222724A1 (en) | 1996-12-05 |
HU224067B1 (hu) | 2005-05-30 |
JP2006316064A (ja) | 2006-11-24 |
US6248907B1 (en) | 2001-06-19 |
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