KR900009589A - 신규의 화합물 - Google Patents
신규의 화합물 Download PDFInfo
- Publication number
- KR900009589A KR900009589A KR1019890019763A KR890019763A KR900009589A KR 900009589 A KR900009589 A KR 900009589A KR 1019890019763 A KR1019890019763 A KR 1019890019763A KR 890019763 A KR890019763 A KR 890019763A KR 900009589 A KR900009589 A KR 900009589A
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- KR
- South Korea
- Prior art keywords
- cyano
- dimethyl
- alkyl
- benzopyran
- dihydro
- 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.)
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- 150000001875 compounds Chemical class 0.000 title claims abstract 22
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 28
- 239000001257 hydrogen Substances 0.000 claims abstract 28
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract 18
- -1 hydroxy, amino Chemical group 0.000 claims abstract 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 13
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract 10
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims abstract 6
- 125000001475 halogen functional group Chemical group 0.000 claims abstract 5
- 229910052760 oxygen Inorganic materials 0.000 claims abstract 5
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims abstract 4
- 125000003118 aryl group Chemical group 0.000 claims abstract 4
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims abstract 4
- 229910052736 halogen Inorganic materials 0.000 claims abstract 4
- 150000002367 halogens Chemical group 0.000 claims abstract 4
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract 4
- 150000003839 salts Chemical class 0.000 claims abstract 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract 3
- 125000004423 acyloxy group Chemical group 0.000 claims abstract 3
- 125000004429 atom Chemical group 0.000 claims abstract 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract 3
- 239000001301 oxygen Substances 0.000 claims abstract 3
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims abstract 2
- 125000006625 (C3-C8) cycloalkyloxy group Chemical group 0.000 claims abstract 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract 2
- 125000005236 alkanoylamino group Chemical group 0.000 claims abstract 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract 2
- 239000003814 drug Substances 0.000 claims abstract 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims abstract 2
- 238000000034 method Methods 0.000 claims abstract 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract 2
- 125000000217 alkyl group Chemical group 0.000 claims 16
- 125000003545 alkoxy group Chemical group 0.000 claims 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 6
- 208000014181 Bronchial disease Diseases 0.000 claims 2
- 206010020772 Hypertension Diseases 0.000 claims 2
- 150000001540 azides Chemical class 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 229910052717 sulfur Chemical group 0.000 claims 2
- 239000011593 sulfur Chemical group 0.000 claims 2
- RPGPKVYYPNQWDA-CVEARBPZSA-N (3s,4r)-4-hydroxy-2,2-dimethyl-3-(2-oxopiperidin-1-yl)-3,4-dihydrochromene-6-carbonitrile Chemical compound N1([C@H]2[C@H](O)C3=CC(=CC=C3OC2(C)C)C#N)CCCCC1=O RPGPKVYYPNQWDA-CVEARBPZSA-N 0.000 claims 1
- QASSUNDCRXITHI-SJORKVTESA-N 1-[(3s,4r)-6-cyano-4-hydroxy-2,2-dimethyl-3,4-dihydrochromen-3-yl]-3-cyclohexylurea Chemical compound N([C@H]1[C@H](O)C2=CC(=CC=C2OC1(C)C)C#N)C(=O)NC1CCCCC1 QASSUNDCRXITHI-SJORKVTESA-N 0.000 claims 1
- NTHFQYTXUDYNHH-NEPJUHHUSA-N 1-[(3s,4r)-6-cyano-4-hydroxy-2,2-dimethyl-3,4-dihydrochromen-3-yl]-3-methylurea Chemical compound N#CC1=CC=C2OC(C)(C)[C@@H](NC(=O)NC)[C@H](O)C2=C1 NTHFQYTXUDYNHH-NEPJUHHUSA-N 0.000 claims 1
- IFMVUMNMUOWNLF-KGLIPLIRSA-N 1-[(3s,4r)-6-cyano-4-hydroxy-2,2-dimethyl-3,4-dihydrochromen-3-yl]-3-propan-2-ylthiourea Chemical compound N#CC1=CC=C2OC(C)(C)[C@@H](NC(=S)NC(C)C)[C@H](O)C2=C1 IFMVUMNMUOWNLF-KGLIPLIRSA-N 0.000 claims 1
- RNZQHZJRYWECOU-KGLIPLIRSA-N 1-[(3s,4r)-6-cyano-4-hydroxy-2,2-dimethyl-3,4-dihydrochromen-3-yl]-3-propan-2-ylurea Chemical compound N#CC1=CC=C2OC(C)(C)[C@@H](NC(=O)NC(C)C)[C@H](O)C2=C1 RNZQHZJRYWECOU-KGLIPLIRSA-N 0.000 claims 1
- FAGVORHRDZUMMN-KGLIPLIRSA-N 1-[(3s,4r)-6-cyano-4-hydroxy-2,2-dimethyl-3,4-dihydrochromen-3-yl]-3-propylurea Chemical compound N#CC1=CC=C2OC(C)(C)[C@@H](NC(=O)NCCC)[C@H](O)C2=C1 FAGVORHRDZUMMN-KGLIPLIRSA-N 0.000 claims 1
- AIKUVOULUUHQAG-UHFFFAOYSA-N 1-tert-butyl-3-(6-cyano-2,2-dimethyl-3,4-dihydrochromen-3-yl)urea Chemical compound N#CC1=CC=C2OC(C)(C)C(NC(=O)NC(C)(C)C)CC2=C1 AIKUVOULUUHQAG-UHFFFAOYSA-N 0.000 claims 1
- ACNCDPILCKUBPL-OLZOCXBDSA-N 1-tert-butyl-3-[(3s,4r)-4-hydroxy-2,2-dimethyl-6-(trifluoromethyl)-3,4-dihydrochromen-3-yl]urea Chemical compound FC(F)(F)C1=CC=C2OC(C)(C)[C@@H](NC(=O)NC(C)(C)C)[C@H](O)C2=C1 ACNCDPILCKUBPL-OLZOCXBDSA-N 0.000 claims 1
- LMTGLCIZXMWWQJ-OLZOCXBDSA-N 1-tert-butyl-3-[(3s,4r)-6-chloro-4-hydroxy-2,2-dimethyl-3,4-dihydrochromen-3-yl]urea Chemical compound ClC1=CC=C2OC(C)(C)[C@@H](NC(=O)NC(C)(C)C)[C@H](O)C2=C1 LMTGLCIZXMWWQJ-OLZOCXBDSA-N 0.000 claims 1
- JYSPPCOMVLMJDO-KGLIPLIRSA-N 1-tert-butyl-3-[(3s,4r)-6-cyano-4-hydroxy-2,2-dimethyl-3,4-dihydrochromen-3-yl]urea Chemical compound N#CC1=CC=C2OC(C)(C)[C@@H](NC(=O)NC(C)(C)C)[C@H](O)C2=C1 JYSPPCOMVLMJDO-KGLIPLIRSA-N 0.000 claims 1
- 230000010933 acylation Effects 0.000 claims 1
- 238000005917 acylation reaction Methods 0.000 claims 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 230000018044 dehydration Effects 0.000 claims 1
- 238000006297 dehydration reaction Methods 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 150000002440 hydroxy compounds Chemical class 0.000 claims 1
- GSYSFVSGPABNNL-UHFFFAOYSA-N methyl 2-dimethoxyphosphoryl-2-(phenylmethoxycarbonylamino)acetate Chemical group COC(=O)C(P(=O)(OC)OC)NC(=O)OCC1=CC=CC=C1 GSYSFVSGPABNNL-UHFFFAOYSA-N 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- MONVKDUQFPNXCS-CVEARBPZSA-N n-[(3s,4r)-6-cyano-4-hydroxy-2,2-dimethyl-3,4-dihydrochromen-3-yl]-3,3-dimethylbutanamide Chemical compound N#CC1=CC=C2OC(C)(C)[C@@H](NC(=O)CC(C)(C)C)[C@H](O)C2=C1 MONVKDUQFPNXCS-CVEARBPZSA-N 0.000 claims 1
- APVDFEPMAYEPQK-SJORKVTESA-N n-[(3s,4r)-6-cyano-4-hydroxy-2,2-dimethyl-3,4-dihydrochromen-3-yl]-3,4-difluorobenzamide Chemical compound N([C@H]1[C@H](O)C2=CC(=CC=C2OC1(C)C)C#N)C(=O)C1=CC=C(F)C(F)=C1 APVDFEPMAYEPQK-SJORKVTESA-N 0.000 claims 1
- ZGEUYUSIBPSNRY-SJORKVTESA-N n-[(3s,4r)-6-cyano-4-hydroxy-2,2-dimethyl-3,4-dihydrochromen-3-yl]-4-fluorobenzamide Chemical compound N([C@H]1[C@H](O)C2=CC(=CC=C2OC1(C)C)C#N)C(=O)C1=CC=C(F)C=C1 ZGEUYUSIBPSNRY-SJORKVTESA-N 0.000 claims 1
- XDUVODFCJAFHFK-OLZOCXBDSA-N n-[(3s,4r)-6-cyano-4-hydroxy-2,2-dimethyl-3,4-dihydrochromen-3-yl]acetamide Chemical compound N#CC1=CC=C2OC(C)(C)[C@@H](NC(=O)C)[C@H](O)C2=C1 XDUVODFCJAFHFK-OLZOCXBDSA-N 0.000 claims 1
- RJDKJKROWHBRCO-SJORKVTESA-N n-[(3s,4r)-6-cyano-4-hydroxy-2,2-dimethyl-3,4-dihydrochromen-3-yl]benzamide Chemical compound N([C@H]1[C@H](O)C2=CC(=CC=C2OC1(C)C)C#N)C(=O)C1=CC=CC=C1 RJDKJKROWHBRCO-SJORKVTESA-N 0.000 claims 1
- UCHPIIPVNDCPNC-SJORKVTESA-N n-[(3s,4r)-6-cyano-4-hydroxy-2,2-dimethyl-3,4-dihydrochromen-3-yl]cyclohexanecarboxamide Chemical compound N([C@H]1[C@H](O)C2=CC(=CC=C2OC1(C)C)C#N)C(=O)C1CCCCC1 UCHPIIPVNDCPNC-SJORKVTESA-N 0.000 claims 1
- FMZSLPUUCLLHOT-CVEARBPZSA-N n-[(3s,4r)-6-cyano-4-hydroxy-2,2-dimethyl-3,4-dihydrochromen-3-yl]pyridine-2-carboxamide Chemical compound N([C@H]1[C@H](O)C2=CC(=CC=C2OC1(C)C)C#N)C(=O)C1=CC=CC=N1 FMZSLPUUCLLHOT-CVEARBPZSA-N 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- ORBZUHHZTCLZDD-KGLIPLIRSA-N tert-butyl n-[(3r,4r)-4-chloro-6-cyano-2,2-dimethyl-3,4-dihydrochromen-3-yl]carbamate Chemical compound N#CC1=CC=C2OC(C)(C)[C@@H](NC(=O)OC(C)(C)C)[C@H](Cl)C2=C1 ORBZUHHZTCLZDD-KGLIPLIRSA-N 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 claims 1
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 3
- 125000004356 hydroxy functional group Chemical group O* 0.000 abstract 3
- 125000001589 carboacyl group Chemical group 0.000 abstract 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 1
- FZENGILVLUJGJX-NSCUHMNNSA-N (E)-acetaldehyde oxime Chemical compound C\C=N\O FZENGILVLUJGJX-NSCUHMNNSA-N 0.000 abstract 1
- 239000005864 Sulphur Chemical group 0.000 abstract 1
- 125000006310 cycloalkyl amino group Chemical group 0.000 abstract 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract 1
- 208000035475 disorder Diseases 0.000 abstract 1
- JKFAIQOWCVVSKC-UHFFFAOYSA-N furazan Chemical compound C=1C=NON=1 JKFAIQOWCVVSKC-UHFFFAOYSA-N 0.000 abstract 1
- 125000000716 hydrazinylidene group Chemical group [*]=NN([H])[H] 0.000 abstract 1
- 125000005004 perfluoroethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 abstract 1
- 239000004036 potassium channel stimulating agent Substances 0.000 abstract 1
- 230000016160 smooth muscle contraction Effects 0.000 abstract 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
-
- 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
- C07D405/04—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 directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
-
- 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
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
- C07D311/70—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with two hydrocarbon radicals attached in position 2 and elements other than carbon and hydrogen in position 6
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Pulmonology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyrane Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Crystals, And After-Treatments Of Crystals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
내용 없음
Description
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Claims (16)
- 하기 일반식(Ⅰ)의 화합물 또는 그의 약학적으로 허용되는 염상기 식에서. a 및 b는 함께 결합 또는 하나의 결합 또는 (R2가 수소인 경우) CH2이고; Y는 N이고 R2는 수소이거나; Y는 C-R1이며; R1및 R2중 하나는 수소이고 다른 하나는 니트로, 시아노, 할로, CF3, C2F5, 포르밀. 알독심. CF3O. NO2-CH=CH-. NC-CH=CH-; 그룹 RxX- [여기서, Rx는 하나, 둘 또는 세개의 C1-4알킬, C1-4알콕시. 니트로. 할로. CF3및 시아노로 임의 치환될 수 있는 C1-6알킬, 아릴 또는 헤테로아릴이고; X는 C=0. 0. C=0. C=0.0, CHOH. S0, S02, 0.S0, 0. SO2, CONH, 0. CONH, 0.S02NH, CO-CH=CH. C=NHOH. C=NNH2이다]; 그룹 RyRzNZ- [여기서, Ry및 Rz는 각각 수소 또는 C1-6알킬이고 Z는 C=O. S0 또는 S02이다]; 또는 그룹 (Rr0)2P(0)W [여기서, Rr는 수소 또는 C1-6알킬이고 W는 0 또는 하나의 결합이다)이거나;R1은 하이드록시. C1-6알콕시. 하나 또는 두개의 C1-6알킬 그룹으로 임의 치환된 아미노. C1-7알카노일아미노. C3-8시클로알킬옥시 또는 C3-8시클로알킬아미노 중 한 그룹으로 임의 치환된 C3-8시클로알킬그룹 또는 C1-6알킬 그룹이고; R2는 수소이거나; R1및 R2중 하나는 니트로, 시아노 또는 C1-3알킬카보닐이고 다른 하나는 니트로. 시아노. 할로, C1-3알킬카보닐. 메록시, 또는 하나 또는 두개의 C1-6알킬 또는 C2-7알킬노일로 임의 치환된 아미노로부터 선택된 상이한 그룹이거나; R1및 R2는 이들의 부착된 탄소 원자와 함께 2.1.3-옥사디아졸을 형성하며; R3및 R4중 하나는 수소 또는 C1-4알킬이고 다른 하나는 C1-4알킬이거나; R5는 수소, 하이드록시, 아미노, C1-6알콕시 또는 C1-7아실옥시이며; E는 수소이거나; R5및 E는 함께 하나의 결합을 형성하고; R6는 수소 또는 C1-6알킬이고 R7은 수소, C3-8시클로알킬, C2-6알케닐; 하이드록시. C1-6알콕시. C1-6알콕시카보닐, 카복시, 할로겐, 또는 하나 또는 두개의 C1-6알킬 그룹으로 임의 치환된 아미노로 임의 치환된 C1-6알킬; C1-6알킬, C1-6알콕시, 하이드록시, 할로겐, 트리플루오로메틸. 니트로, 시아노, C1-12카복실성 아실 중에서 선택된 하나 이상의 그룹 또는 원자로 임의 치환된 아틸 또는 헤테로아릴이거나,R7은 하나 또는 두개의 C1-6알킬 그룹으로 임의 치환된 또는 C3-8시클로알킬로 치환된 아미노 또는 아미노카보닐, 또는 그룹 OR9(여기서, R9는 R7에 대해 상기 정의한 바와같이 임의 치환된 C1-6알킬 또는 벤질이다)이거나; R6및 R7은 함께 결합하여 하나 또는 두개의 C1-6알킬 그룹으로 임의 치환되고하나 또는 두개(C4폴리메틸렌의 경우)의 C=C 이중결합을 임의로 함유하는 C3-4폴리메틸렌을 형성하고; X는 산소 또는 황이다.
- 제1항에 있어서, Y가 C-R1이고 a 및 b가 함께 결합인 화합물.
- 제1 또는 2항에 있어서, R1이니트로, 시아노, 아세틸, CF3, C2F5또는 C1-4알킬이고 R2가 수소인 화합물.
- 제3항에 있어서. R1이시아노인 화합물.
- 제1 내지 4항중 어느 한 항에 있어서, R3및 R4가 모두 메틸 그룹인 화합물.
- 제1 내지 5항 중 어느 한 항에 있어서, R5가 하이드록시이고 E가 수소이며 R6NCXR7잔기가 R5에 대해 트란스인 화합물.
- 제1 내지 6항 중 어느 한 항에 있어서, R6가 수소이고 R7이 임의 치환된 페닐, 측쇄 C1-6알킬, C1-6알콕시, 벤질옥시 또는 임의 치환된 아미노인 화합물.
- 제7항에 있어서, R7이 t-부틸아미노인 화합물.
- 트란스-6-시아노-2,2-디메틸-3,4-디하이드로-3-(t-부톡시카보닐)아미노-2H-1-벤조피란-4-올,트란스-6-시아노-2,2-디메틸-3,4-디하이드로-3-(2-옥소-1-피페리디닐)-2H-1-벤조피란-4-올,트란스-6-시아노-2,2-디메틸-3,4-디하이드로-3-(4-플루오로벤조일아미노)-2H-1-벤조피란-4-올, 2,2-디메틸-3,4-디하이드로-3-(t-부톡시카보닐)아미노-6-시아노-2H-1-벤조피란,트란스-6-시아노-2,2-디메틸-3,4-디하이드로-3-(t-부틸우레이도)-2H-1-벤조피란-4-올,트란스-6-시아노-2,2-디메틸-3,4-디하이드로-3-(3,4-디플루오로-벤조일아미노)-2H-1-벤조피란-4-올,트란스-6-시아노-2,2-디메틸-3,4-디하이드로-3-(메틸-우레이도)-2H-1-벤조피란-4-올,트란스-6-시아노-2,2-디메틸-3,4-디하이드로-3-아세틸아미노-2H-1-벤조피란-4-올,트란스-6-시아노-2,2-디메틸-3,4-디하이드로-3-(2-피리딘-카보닐아미노)-2H-1-벤조피란-4-올,트란스-6-시아노-2,2-디메틸-3,4-디하이드로-3-(t-부틸아세틸아미노)-2H-1-벤조피란-4-올,트란스-6-시아노-2,2-디메틸-3,4-디하이드로-3-(시클로헥산-카보닐아미노)-2H-1-벤조피란-4-올,트란스-6-시아노-2,2-디메틸-3,4-디하이드로-3(시클로헥실-우레이도)-2H-1-벤조피란-4-올),트란스-6-시아노-2,2-디메틸-3,4-디하이드로-3-벤조일아미노-2H-1-벤조피란-4-올,트란스-6-시아노-2,2-디메틸-3,4-디하이드로-3-(이소프로필-우레이도)-2H-1-벤조피란-4-올,트란스-6-시아노-2,2-디메틸-3,4-디하이드로-3-(에틸우레이도-2H-1-벤조피란-4-올,트란스-6-시아노-2,2-디메틸-3,4-디하이드로-3-(n-프로필-우레이도)-2H-1-벤조피란-4-올),트란스-6-클로로-2,2-디메틸-3,4-디하이드로-3-(t-부틸우레이도)-2H-1-벤조피란-4-올,트란스-6-시아노-2,2-디메틸-3,4-디하이드로-3-(디메틸-아미노카보닐아미노)-2H-1-벤조피란-4-올,트란스-6-시아노-2,2-디메틸-3,4-디하이드로-3-(이소프로필-티오우레이도)-2H-1-벤조피란-4-올,트란스-6-트리플루오로메틸-2,2-디메틸-3,4-디하이드로-3-(t-부틸우레이도)-2H-1-벤조피란-4-올,트란스-6-시아노-2,2-디메틸-3,4-디하이드로-3-트리메틸-아세틸아미노-2H-1-벤조피란-4-올,트란스-6-시아노-2,2-디메틸-3,4-디하이드로-3-이소부티릴-아미노-2H-1-벤조피란-4-올,트란스-6-시아노-3,4-디하이드로-2,2-디메틸-3-(벤질옥시카보닐)아미노-2H-1-벤조피란-4-올, 2,2-디메틸-3,4-디하이드로-3- (t-부틸우레이도)-6-시아노-2H-1-벤조피란,트란스-6-시아노-3,4-디하이드로-2,2-디메틸-3-(t-부록시카보닐)아미노-4-메톡시-2H-1-벤조피란 및트란스-6-시아노-3,4-디하이드로-2,2-디메틸-3-(t-부록시카보닐)아미노-4-아미노-2H-1-벤조피란로 이루어진 그룹으로부터 선택된 화합물.
- 하기 일반식(Ⅱ)의 화합물을 a) 하기 일반식(Ⅲ)의 아실화제로 아실화시킨 다음이 R10인 경우에 생성화합물을 폐환시키거나; b) 하기 일반식(Ⅳ)의 화합물로 아실화시킨 다음, 필요시,을 R5로 전환시키고/거나, Y 및/또는를 Y 및/또는 R2로 전환시키고 /거나, 임의로 X가 산소인경우 X가 황인 화합물로 황화시키고 /거나이 하이드록시인 화합물을 탈수시켜 R5및 E가 하나의 결합을 형성하는 일반식(Ⅰ)의 화합물을 생성시키거나, R6NCXR7잔기가 하이드록시인 R5에 대해 트란스인 일반식(Ⅰ)의 화합물을 상응하는 시스 이성체로 전환시키고; 임의로 그의 약학적으로 허용되는 염을 생성시킴을 특징으로 하여, 제1항에 따른 일반식(Ⅰ)의 화합물 또는 그의 약학적으로 허용되는 염을 제조하는 방법.상기식에서, Y' 및 R2'는 각각 Y 및 R2이거나 Y 및 R2로 전환 가능한 그룹 또는 원자이고,은 하이드록시, C1-6알콕시, C1-7아실옥시 또는 아지드이며;은 수소 또는 C1-6알킬이고,그룹은그룹에 대해 트란스위치아지드 이외의 기일 경우이며, Q는 이탈그룹이고,은 R6에 결합되지 않은 경우에 제1항에서 정의한 바와같은 R7또는 R7로 전환가능한 그룹이거나, (이 수소인 경우)은 R10(여기서 R10은 하나 또는 두개의 C1-6 알킬 그룹으로 임의 치환되고 임의로 하나 또는 두개(C4폴리메틸렌의 경우)의 C=C 이중결합(들)을 함유하며 이탈 그룹 L로 말단 치환된 C3-4폴리메틸렌이다)이며, X는 제1항에서 정의한 바와같고 R11은 수소 또는 C1-6알킬이다.
- 하기 일반식(Ⅱ), (Ⅴ) 또는 (Ⅵ)의 화합물 :상기식에서, 각 치환체는 제10항에서 정의한 바와같다.
- 트란스-6-시아노-2,2-디메틸-3,4-디하이드로-3-아미노-2H-1-벤조피란-4-올,트란스-6-클로로-2,2-디메틸-3,4-디하이드로-3-아미노-2H-1-벤조피란-4-올,트란스-트리플루오로메틸-2,2-디메틸-3,4-디하이드로-3-아미노-2H-1-벤조피란-4-올, 6-시아노-3,4-[N-t-부톡시카보닐)아지리이노]-2,2-디메틸-2H-1-벤조피란. 6-클로로-3,4-[N-t-부톡시카보닐)아지리이노]-2,2-디메틸-2H-1-벤조피란, 6-트리플루오로메틸-3,4-[N-t-부톡시카보닐)아지리디노]-2,2-디메틸-2H-1-벤조피란, 6-시아노-3,4-[N-벤질옥시카보닐)아지리디노]-2,2-디메틸-2H-1-벤조피란,트란스-6-시아노-3,4-디하이드로-2,2-디메틸-3-(t-부톡시카보닐아미노)-4-클로로-2H-1-벤조피란,트란스-6-클로로-3,4-디하이드로-2,2-디메틸-3-(t-부톡시카보닐)아미노-4-클로로-2H-1-벤조피란,트란스-6-트리플루오로메틸-3,4-디하이드로-2,2-디메틸-3-(t-부톡시카보닐)아미노-4-클로로-2H-1-벤조피란 및트란스-6-시아노-3,4-디하이드로-2,2-디메틸-3-(벤질옥시카보닐아미노)-4-클로로-2H-1-베조피란으로 이루어진 그룹 중에서 선택된 화합물.
- 제1 내지 9항 중 어느 한 항에 따른 화합물 및 약학적으로 허용되는 담체로 이루어진 약학 조성물.
- 활성적인 치료 물질로서 사용되는 제1 내지 9항 중 어느 한 항에 따른 화합물.
- 고혈압 및/또는 기관지 질환의 치료에 사용되는 제1 내지 9항 중 어느 한 항에 따른 화합물.
- 고혈압 및/또는 기관지 질환의 치료에 사용하기 위한 약제 제조에 있어서의 제1 내지 9항 중 어느 한 항에 따른 화합물의 용도.※ 참고사항 ; 최초출원 내용에 의하여 공개하는 것임.
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| AT330774B (de) * | 1974-05-28 | 1976-07-26 | Takeda Chemical Industries Ltd | Verfahren zur herstellung von neuen bicyclischen verbindungen |
| US4203895A (en) * | 1978-04-14 | 1980-05-20 | Warner-Lambert Company | Process for the preparation of cis-(±)-3,4-dihydro-N,N,2-trimethyl-2H-1-benzopyran-3-amine and intermediates produced thereby |
| GB8521857D0 (en) * | 1985-09-03 | 1985-10-09 | Beecham Group Plc | Active compounds |
| PH22522A (en) * | 1985-09-03 | 1988-10-17 | Ciba Geigy Ag | 3-amino-dihydro-1-benzopyrans and benzothiopyrans, their pharmaceutical compositions and method of using said compounds |
| CA2015296C (en) * | 1989-05-31 | 2001-08-07 | Karnail Atwal | Pyranyl cyanoguanidine derivatives |
-
1989
- 1989-12-21 NZ NZ231969A patent/NZ231969A/en unknown
- 1989-12-21 DK DK657389A patent/DK657389A/da not_active Application Discontinuation
- 1989-12-21 PT PT92669A patent/PT92669B/pt not_active IP Right Cessation
- 1989-12-21 EP EP89313490A patent/EP0375449B1/en not_active Expired - Lifetime
- 1989-12-21 CA CA002006429A patent/CA2006429A1/en not_active Abandoned
- 1989-12-21 DE DE68921175T patent/DE68921175T2/de not_active Expired - Fee Related
- 1989-12-21 AT AT89313490T patent/ATE118492T1/de not_active IP Right Cessation
- 1989-12-21 AU AU47172/89A patent/AU631588B2/en not_active Ceased
- 1989-12-22 KR KR1019890019763A patent/KR900009589A/ko not_active Withdrawn
- 1989-12-25 JP JP1333005A patent/JPH02262576A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| DE68921175D1 (de) | 1995-03-23 |
| NZ231969A (en) | 1992-09-25 |
| DE68921175T2 (de) | 1995-06-14 |
| EP0375449A3 (en) | 1990-08-29 |
| DK657389A (da) | 1990-06-24 |
| DK657389D0 (da) | 1989-12-21 |
| ATE118492T1 (de) | 1995-03-15 |
| JPH02262576A (ja) | 1990-10-25 |
| PT92669B (pt) | 1995-09-12 |
| CA2006429A1 (en) | 1990-06-23 |
| AU4717289A (en) | 1990-06-28 |
| EP0375449A2 (en) | 1990-06-27 |
| EP0375449B1 (en) | 1995-02-15 |
| PT92669A (pt) | 1990-06-29 |
| AU631588B2 (en) | 1992-12-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PA0109 | Patent application |
Patent event code: PA01091R01D Comment text: Patent Application Patent event date: 19891222 |
|
| PG1501 | Laying open of application | ||
| PC1203 | Withdrawal of no request for examination | ||
| WITN | Application deemed withdrawn, e.g. because no request for examination was filed or no examination fee was paid |