KR987000303A - 신규한 퀴누클리딘 유도체 및 이의 의약 조성물(Novel quinuclidine derivatives and medicinal composition thereof) - Google Patents
신규한 퀴누클리딘 유도체 및 이의 의약 조성물(Novel quinuclidine derivatives and medicinal composition thereof) Download PDFInfo
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- KR987000303A KR987000303A KR1019970703649A KR19970703649A KR987000303A KR 987000303 A KR987000303 A KR 987000303A KR 1019970703649 A KR1019970703649 A KR 1019970703649A KR 19970703649 A KR19970703649 A KR 19970703649A KR 987000303 A KR987000303 A KR 987000303A
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- 150000008584 quinuclidines Chemical class 0.000 title 1
- -1 thiocarbamoyl group Chemical group 0.000 claims abstract 14
- 125000005843 halogen group Chemical group 0.000 claims abstract 12
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 11
- 125000003277 amino group Chemical group 0.000 claims abstract 11
- 150000001204 N-oxides Chemical class 0.000 claims abstract 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 10
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims abstract 10
- 150000003839 salts Chemical class 0.000 claims abstract 10
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract 8
- 125000000217 alkyl group Chemical group 0.000 claims abstract 8
- 125000005842 heteroatom Chemical group 0.000 claims abstract 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract 7
- SBYHFKPVCBCYGV-UHFFFAOYSA-N quinuclidine Chemical class C1CC2CCN1CC2 SBYHFKPVCBCYGV-UHFFFAOYSA-N 0.000 claims abstract 7
- 125000003118 aryl group Chemical group 0.000 claims abstract 6
- 125000000392 cycloalkenyl group Chemical group 0.000 claims abstract 6
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract 6
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract 6
- 229910052717 sulfur Inorganic materials 0.000 claims abstract 6
- 125000004434 sulfur atom Chemical group 0.000 claims abstract 5
- 125000002252 acyl group Chemical group 0.000 claims abstract 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract 4
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims abstract 4
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims abstract 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract 4
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract 4
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract 4
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract 4
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims abstract 4
- 125000000565 sulfonamide group Chemical group 0.000 claims abstract 4
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims abstract 4
- 125000003396 thiol group Chemical group [H]S* 0.000 claims abstract 4
- 150000001875 compounds Chemical class 0.000 claims abstract 3
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims abstract 3
- 125000001424 substituent group Chemical group 0.000 claims abstract 3
- 208000023504 respiratory system disease Diseases 0.000 claims abstract 2
- 208000014001 urinary system disease Diseases 0.000 claims abstract 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 4
- 125000002950 monocyclic group Chemical group 0.000 claims 2
- 239000003681 muscarinic M3 receptor antagonist Substances 0.000 claims 2
- CZCPVZCPLOKBOM-UHFFFAOYSA-N 1-(furan-2-yl)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid Chemical compound OC(=O)N1CCC2=CC=CC=C2C1C1=CC=CO1 CZCPVZCPLOKBOM-UHFFFAOYSA-N 0.000 claims 1
- JJDMEFIXSKMCMK-UHFFFAOYSA-N 1-(furan-3-yl)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid Chemical compound OC(=O)N1CCC2=CC=CC=C2C1C=1C=COC=1 JJDMEFIXSKMCMK-UHFFFAOYSA-N 0.000 claims 1
- OPGPIFMCCIAMNE-UHFFFAOYSA-N 1-azabicyclo[2.2.2]octan-3-yl 1-(4-chlorophenyl)-3,4-dihydro-1h-isoquinoline-2-carboxylate Chemical compound C1=CC(Cl)=CC=C1C1C2=CC=CC=C2CCN1C(=O)OC1C(CC2)CCN2C1 OPGPIFMCCIAMNE-UHFFFAOYSA-N 0.000 claims 1
- CEYITZYIKGLXEN-UHFFFAOYSA-N 1-azabicyclo[2.2.2]octan-3-yl 1-(4-fluorophenyl)-3,4-dihydro-1h-isoquinoline-2-carboxylate Chemical compound C1=CC(F)=CC=C1C1C2=CC=CC=C2CCN1C(=O)OC1C(CC2)CCN2C1 CEYITZYIKGLXEN-UHFFFAOYSA-N 0.000 claims 1
- FCXWHPXCAHMELT-UHFFFAOYSA-N 1-azabicyclo[2.2.2]octan-3-yl 1-cyclohexyl-3,4-dihydro-1h-isoquinoline-2-carboxylate Chemical compound C1N(CC2)CCC2C1OC(=O)N1CCC2=CC=CC=C2C1C1CCCCC1 FCXWHPXCAHMELT-UHFFFAOYSA-N 0.000 claims 1
- FBOUYBDGKBSUES-UHFFFAOYSA-N 1-azabicyclo[2.2.2]octan-3-yl 1-phenyl-3,4-dihydro-1h-isoquinoline-2-carboxylate Chemical compound C1N(CC2)CCC2C1OC(=O)N1CCC2=CC=CC=C2C1C1=CC=CC=C1 FBOUYBDGKBSUES-UHFFFAOYSA-N 0.000 claims 1
- FZSIBWFUOSPJKQ-UHFFFAOYSA-N 1-azabicyclo[2.2.2]octan-3-yl 1-pyridin-4-yl-3,4-dihydro-1h-isoquinoline-2-carboxylate Chemical compound C1N(CC2)CCC2C1OC(=O)N1CCC2=CC=CC=C2C1C1=CC=NC=C1 FZSIBWFUOSPJKQ-UHFFFAOYSA-N 0.000 claims 1
- GVMGFZJINUTVNQ-UHFFFAOYSA-N 1-azabicyclo[2.2.2]octan-3-yl 1-thiophen-2-yl-3,4-dihydro-1h-isoquinoline-2-carboxylate Chemical compound C1N(CC2)CCC2C1OC(=O)N1CCC2=CC=CC=C2C1C1=CC=CS1 GVMGFZJINUTVNQ-UHFFFAOYSA-N 0.000 claims 1
- MIRBPLDKROIBLR-UHFFFAOYSA-N 1-thiophen-3-yl-3,4-dihydro-1h-isoquinoline-2-carboxylic acid Chemical compound OC(=O)N1CCC2=CC=CC=C2C1C=1C=CSC=1 MIRBPLDKROIBLR-UHFFFAOYSA-N 0.000 claims 1
- 206010048994 Bladder spasm Diseases 0.000 claims 1
- 206010006458 Bronchitis chronic Diseases 0.000 claims 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 1
- 239000005977 Ethylene Substances 0.000 claims 1
- 206010020853 Hypertonic bladder Diseases 0.000 claims 1
- 208000000693 Neurogenic Urinary Bladder Diseases 0.000 claims 1
- 206010029279 Neurogenic bladder Diseases 0.000 claims 1
- 206010046543 Urinary incontinence Diseases 0.000 claims 1
- 239000013543 active substance Substances 0.000 claims 1
- 206010006451 bronchitis Diseases 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 208000023819 chronic asthma Diseases 0.000 claims 1
- 208000007451 chronic bronchitis Diseases 0.000 claims 1
- 201000009151 chronic rhinitis Diseases 0.000 claims 1
- 201000003146 cystitis Diseases 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- UANSQQFYKHHDJM-KRWDZBQOSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]naphthalene-1-carboxamide Chemical compound C1=CC=C2C(C(N[C@@H]3C4CCN(CC4)C3)=O)=CC=CC2=C1 UANSQQFYKHHDJM-KRWDZBQOSA-N 0.000 claims 1
- 206010029446 nocturia Diseases 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 206010039083 rhinitis Diseases 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 210000003932 urinary bladder Anatomy 0.000 claims 1
- 230000002485 urinary effect Effects 0.000 claims 1
- 230000003042 antagnostic effect Effects 0.000 abstract 1
- 208000010643 digestive system disease Diseases 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 230000003551 muscarinic effect Effects 0.000 abstract 1
- 230000000069 prophylactic effect Effects 0.000 abstract 1
- 229940124597 therapeutic agent Drugs 0.000 abstract 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
- C07D221/06—Ring systems of three rings
- C07D221/10—Aza-phenanthrenes
- C07D221/12—Phenanthridines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- 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
-
- 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
- A61P13/10—Drugs for disorders of the urinary system of the bladder
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
- C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
- C09K19/3441—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom
- C09K19/3444—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom the heterocyclic ring being a six-membered aromatic ring containing one nitrogen atom, e.g. pyridine
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pulmonology (AREA)
- Materials Engineering (AREA)
- Urology & Nephrology (AREA)
- Crystallography & Structural Chemistry (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Saccharide Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- External Artificial Organs (AREA)
- Tea And Coffee (AREA)
Abstract
Description
Claims (11)
- 화학식 I의 퀴누클리딘 유도체, 이의 염, 이의 N-옥사이드 또는 이의 4급 암모늄염.화학식 I상기 화학식 I에서, A환은 아릴기, 사이클로알킬기, 사이클로알케닐기, 산소원자, 질소원자 및 황원자로 이루어진 헤테로 원자를 1내지 4개 함유하는 헤테로아릴기 또는 5내지 7원 포화 헤테로 환 기이며, 이들 환은 임의의 치환기로 치환될 수 있으며, X는 단일 결합 또는 메틸렌기이며, R은 할로겐 원자, 수산기, 저급 알콕시기, 카복실기, 저급 알콕시카보닐기, 저급 아실기, 머캅토기, 저급 알킬티오기, 설포닐기, 저급 알킬설포닐기, 설피닐기, 저급 알킬설피닐기, 설폰아미드기, 저급 알칸설폰아미드기, 카바모일기, 티오카바모일기, 모노-또는 디-저급 알킬카바모일기, 니트로기, 시아노기, 아미노기, 모노-또는 디-저급 알킬아미노기, 멜틸렌디옥시기 또는 에틸렌디옥시기이거나, 할로겐 원자, 수산기, 저급 알콕시기, 아미노기 또는 모노- 또는 디-저급 알킬아미노로 치환될 수 있는 저급 알킬기이며, 1은 0 또는 1이며, m은 0또는 1 내지 3의 정수이며, n은 1 또는 2의 정수이다.
- 제1항에 있어서, A환이 아릴기, 사이클로알킬기, 사이클로알케닐기, 산소원자, 질소원자 및 황원자로 이루어진 헤테로 원자를 1 내지 4개 함유하는 헤테로아릴기 또는 5원 내지 7원 포화 헤테로 환 기 이며, 이들 환은 할로겐 원자, 수산기, 저급 알콕시기, 카복실기, 저급 알콕시카보닐기, 저급 아실기, 머캅토기, 저급 알킬티오기, 설포닐기, 저급 알킬설포닐기, 설피닐기, 저급 알킬설피날기, 설폰아미드기, 저급 알칸설폰아미드기, 카바모일기, 티오카바모일기, 모노- 또는 디-저급 알킬카바모일기, 니트로기, 시아노기, 아미노기, 모노-또는 디-저급 알킬아미노기, 메틸렌디옥시기 또는 에틸렌디옥시기이거나, 할로겐 원자, 수산기, 저급 알콕시기, 아미노기 또는 모노-또는 디-저급 알킬아미노기로 치환될 수 있는 저급 알킬기로 이루어진 치환기로 치환될 수 있는 퀴누클리딘 유도체, 이의 염, 이의 N-옥사이드 또는 이의 4급 암모늄염.
- 제2항에 있어서, R이 할로겐 원자, 저급 알킬기, 수산기, 저급 알콕시기, 니트로기, 시아노기, 아미노기 또는 모노- 또는 디-저급 알킬아미노기이며, A환이 아릴기, 사이클로알킬기, 사이클로알케닐기, 산소원자, 질소원자 및 황원자로 이루어진 헤테로 원자를 1내지 4개 함유하는 5원 또는 6원의 단환 헤테로아릴기 또는 5원 내지 7원 포화 헤테로 환 기이며, 이들 환은 할로겐 원자, 저급 알킬기, 수산기, 저급 알콕시기, 니트로기, 시아노기, 아미노기, 또는 모노- 또는 디-저급 알킬아미노기로 치환될 수 있는 퀴누클리딘 유도체, 이의 염, 이의 N-옥사이드 또는 이의 4급 암모늄염.
- 제3항에 있어서, m이 0이며 A환이 할로겐 원자, 저급 알킬기, 수산기 또는 저급 알콕시기로 치환될 수 있는 아릴기, 사이클로알킬기 또는 사이클로알케닐기이거나, 산소원자, 질소원자 및 황원자로 이루어진 헤테로 원자를 1내지 4개 함유하는 5원 또는 6원의 단환 헤테로아릴기인 퀴누클리딘 유도체, 이의 염, 이의 N-옥사이드 또는 이의 4급 암모늄염.
- 제4항에 있어서, A환이 할로겐 원자 또는 저급 알킬기로 치환될 수 있는 페닐기, 사이클로알킬기, 피릴딜기, 푸릴기 또는 티에닐기인 퀴누클리딘 유도체, 이의 염, 이의 N-옥사이드 또는 이의 4급 암모늄염.
- 제2항 내지 제5항 중의 어느 한 항에 있어서, X가 단일 결합인 퀴누클리딘 유도체, 이의 염, 이의 N-옥사이드 또는 이의 4급 암모늄염.
- 제2항 내지 제6항 중의 어느 한 항에 있어서, n이 2인 퀴누클리딘 유도체, 이의 염, 이의 N-옥사이드 또는 이의 4급 암모늄염.
- 제1항에 있어서, 3-퀴누클리디닐 1-페닐-1, 2, 3, 4-테트라하이드로-2-이소퀴놀린카복실레이트, 3-퀴누클리디닐 1-(4-피리딜)-1, 2, 3, 4-테트라하이드로-2-이소퀴놀린카복실레이트, 3-퀴누클리디닐 1, 2, 3, 4-테트라하이드로-1-(2-티에닐) -2-이소퀴놀린카복실레이트, 3-퀴누클리디닐 1, 2, 3, 4-테트라하이드로-1-(3-티에닐)-2-이소퀴놀린카복실레이트, 3-퀴누클리디닐 1-(2-푸릴)-1, 2, 3, 4-테트라하이드로-2-이소퀴놀린 카복실레이트, 3-퀴누클리디닐 1-(4-클로로페닐)-1, 2, 3, 4-테트라히아드로-2-이소퀴놀린카복실레이트, 3-퀴누클리디닐 1-(4-플루오로페닐)-1, 2, 3, 4-테트라하이드로-2-이소퀴놀린카복실레이트, 3-퀴누블리디닐 1, 2, 3, 4-데트라하이드로-1-(4-톨릴)-2-이소퀴놀린카복시레이트, 3-퀴누클리디닐 1-사이클로헥실-1, 2, 3, 4-테트라하이드로-2-이소퀴놀린카복실레이트, 3-퀴누클리디닐 1-(3-푸릴)-1, 2, 3, 4-테트라하이드로-2-이소퀴놀린카복실레이트 및 이들의 광학활성체로 이루어진 그룹으로부터 선택된 퀴누클리딘 유도체, 이의 염, 이의 N-옥사이드 또는 이의 4급 암모늄염.
- 화학식 I의 퀴누클리딘 유도체, 이의 염, 이의 N-옥사이드 또는 이의 4급 암모늄염과 약제학적으로 허용되는 담체를 함유하는 의약 조성물.화학식 I상기 화학식 I에서, A환은 아릴기, 사이클로알킬기, 사이클로알케닐기, 산소원자, 질소원자 및 황원자로 이루어진 헤테로 원자를 1내지 4개 함유하는 헤테로아릴기 또는 5 내지 7원 포화 헤테로 환 기이며 이들 환은 임의 치환기로 치환될 수 있으며, X는 단일 결합 또는 메틸렌기이며, R은 할로겐 원자, 수산기, 저급 알콕시기, 카복실기, 저급 알콕시카보닐기, 저급 아실기, 머캅토기, 저급 알킬티오기, 설포닐기, 저급 알킬설포닐기, 설피닐기, 저급 알킬설피닐기, 설폰아미드기, 저급 알칸설폰아미드기, 카바모일기, 티오카바모일기, 모노- 또는 디-저급 알킬카바모일기, 니트로기, 시아노기, 아미노기, 모노-또는 디-저급 알킬아미노기, 메틸렌디옥시기 또는 에틸렌디옥시기이거나, 할로겐 원자, 수산기, 저급 알콕시기, 아미노기 또는 모노- 또는 디-저급 알킬아미노기로 치환될 수 있는 저급 알킬기이며, 1은 0 또는 1이며, m은 0또는 1 내지 3의 정수이며, n은 1 또는 2의 정수이다.
- 제9항에 있어서, 무스카린 M3수용체 길항제인 의약 조성물.
- 제10항에 있어서, 무스카린 M3수용체 길항제가 비뇨기 질환(신경성 빈뇨, 신경 원인성 방광, 야뇨증, 불안정 방광, 방광 경축 및 만성 방광염에서의 요실금과 빈뇨) 또는 호흡기 질환(만성 폐색성 폐질환, 만성 기관지염, 천식 및 비염)의 예방 및 치료제인 의약 조성물.
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| JP94-327045 | 1994-12-28 | ||
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| KR102156441B1 (ko) * | 2012-12-06 | 2020-09-17 | 키에시 파르마슈티시 엣스. 피. 에이. | 무스카린성 수용체 길항제 및 베타2 아드레날린성 수용체 효능제 활성을 가지는 화합물 |
| EP2778167A1 (en) | 2013-03-11 | 2014-09-17 | Abdi Ibrahim Ilac Sanayi Ve Ticaret Anonim Sirketi | Stable pharmaceutical composition comprising amorphous solifenacin or its pharmaceutically acceptable salt |
| EP3023424B1 (en) * | 2013-07-13 | 2019-02-27 | Beijing Shuobai Pharmaceutical Co., Ltd. | Quinine compounds, and optical isomers, preparation method and medical use thereof |
| CA2944714C (en) | 2014-05-06 | 2023-05-16 | Anthony G. Visco | Methods of treating or preventing preterm labor |
| CN104592221A (zh) * | 2015-01-26 | 2015-05-06 | 中山奕安泰医药科技有限公司 | 一种合成索非那新的工艺 |
| KR20160146428A (ko) | 2015-06-12 | 2016-12-21 | 한미정밀화학주식회사 | 솔리페나신 또는 그의 약학적으로 허용되는 염과 락토즈를 포함하는 안정한 무정형 솔리페나신 약학 조성물 및 그의 제조방법 |
| KR102148414B1 (ko) | 2017-05-15 | 2020-08-26 | 주식회사 서울제약 | 솔리페나신을 유효성분으로 하는 구강붕해필름 |
| EP3724188B1 (en) | 2017-12-12 | 2023-06-07 | Arkuda Therapeutics | Progranulin modulators and methods of using the same |
| CA3099655A1 (en) | 2018-05-08 | 2019-11-14 | Nippon Shinyaku Co., Ltd. | Azabenzimidazole compounds and pharmaceutical |
| JP2022545314A (ja) | 2019-06-12 | 2022-10-27 | アルクダ セラピューティクス | プログラニュリンモジュレーターおよびその使用方法 |
| KR20220100627A (ko) | 2019-11-13 | 2022-07-15 | 니뽄 신야쿠 가부시키가이샤 | 아자벤즈이미다졸 화합물 및 의약 |
| CN113200979A (zh) * | 2021-04-13 | 2021-08-03 | 上海予君生物科技发展有限公司 | 一种琥珀酸索非那新的合成工艺 |
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| ES2053451T3 (es) * | 1986-01-07 | 1994-08-01 | Beecham Group Plc | Un procedimiento para la preparacion de un compuesto que tiene propiedades farmacologicas utiles. |
| IT1231238B (it) * | 1987-09-21 | 1991-11-26 | Angeli Inst Spa | Derivati ammidinici |
| IT1228293B (it) * | 1989-02-06 | 1991-06-07 | Angeli Inst Spa | Benzoderivati di composti eterociclici contenenti azoto. |
| IT1230881B (it) * | 1989-06-20 | 1991-11-08 | Angeli Inst Spa | Derivati del r(-) 3-chinuclidinolo |
| GB9023023D0 (en) * | 1990-10-23 | 1990-12-05 | Barlow Richard B | Pharmaceutical compositions |
| GB9202443D0 (en) * | 1992-02-05 | 1992-03-18 | Fujisawa Pharmaceutical Co | A novel substituted-acetamide compound and a process for the preparation thereof |
| JPH076635A (ja) * | 1993-06-18 | 1995-01-10 | Sony Corp | 信号伝送ケーブル |
| AU7545894A (en) * | 1993-09-02 | 1995-03-22 | Yamanouchi Pharmaceutical Co., Ltd. | Carbamate derivative and medicine containing the same |
| JPH07258250A (ja) * | 1994-03-25 | 1995-10-09 | Yamanouchi Pharmaceut Co Ltd | エステル誘導体 |
| EP1424021B1 (en) * | 2002-11-27 | 2006-09-13 | Selmac S.r.l. | Device for positioning and clamping shaped elements and machine equipped with this device |
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