JPH11508536A - アドレナリン性α▲下1a▼受容体アンタゴニスト - Google Patents
アドレナリン性α▲下1a▼受容体アンタゴニストInfo
- Publication number
- JPH11508536A JPH11508536A JP8525855A JP52585596A JPH11508536A JP H11508536 A JPH11508536 A JP H11508536A JP 8525855 A JP8525855 A JP 8525855A JP 52585596 A JP52585596 A JP 52585596A JP H11508536 A JPH11508536 A JP H11508536A
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- dioxide
- mono
- oxo
- piperidin
- 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.)
- Pending
Links
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- 208000004403 Prostatic Hyperplasia Diseases 0.000 claims abstract description 31
- 239000002677 5-alpha reductase inhibitor Substances 0.000 claims abstract description 22
- 238000011282 treatment Methods 0.000 claims abstract description 22
- 229940113178 5 Alpha reductase inhibitor Drugs 0.000 claims abstract description 17
- 210000002460 smooth muscle Anatomy 0.000 claims abstract description 16
- 230000001939 inductive effect Effects 0.000 claims abstract description 7
- -1 C1-4Alkoxy Chemical group 0.000 claims description 132
- 229910052739 hydrogen Inorganic materials 0.000 claims description 101
- 239000001257 hydrogen Substances 0.000 claims description 101
- 150000002431 hydrogen Chemical class 0.000 claims description 94
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- 125000001424 substituent group Chemical group 0.000 claims description 70
- 150000003839 salts Chemical class 0.000 claims description 62
- 125000000217 alkyl group Chemical group 0.000 claims description 61
- 239000000203 mixture Substances 0.000 claims description 50
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- 125000003118 aryl group Chemical group 0.000 claims description 29
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- 125000004093 cyano group Chemical group *C#N 0.000 claims description 26
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 21
- RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical group C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 claims description 19
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- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 17
- 125000003342 alkenyl group Chemical group 0.000 claims description 17
- 229910052801 chlorine Inorganic materials 0.000 claims description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
- MUMGGOZAMZWBJJ-DYKIIFRCSA-N Testostosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 MUMGGOZAMZWBJJ-DYKIIFRCSA-N 0.000 claims description 16
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- 125000003784 fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims description 10
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- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 9
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 230000005764 inhibitory process Effects 0.000 claims description 5
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 5
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 5
- ICTZOWVELHATOU-UHFFFAOYSA-N 3-piperidin-1-yl-1h-benzimidazol-2-one Chemical group O=C1NC2=CC=CC=C2N1N1CCCCC1 ICTZOWVELHATOU-UHFFFAOYSA-N 0.000 claims description 4
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- 238000006467 substitution reaction Methods 0.000 claims description 4
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- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 3
- 230000036772 blood pressure Effects 0.000 claims description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 3
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 2
- OVHVVWXDKDMZQA-UHFFFAOYSA-N 2-butyl-1,1-dioxo-1,2-benzothiazol-3-one Chemical group C1=CC=C2S(=O)(=O)N(CCCC)C(=O)C2=C1 OVHVVWXDKDMZQA-UHFFFAOYSA-N 0.000 claims description 2
- 241000790917 Dioxys <bee> Species 0.000 claims description 2
- 125000004965 chloroalkyl group Chemical group 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
- QUJXIMWUJGTUEG-CLKUPZDLSA-N 2-[2-[[[(2s,6s,9e,13s)-13-amino-2-[(4-hydroxyphenyl)methyl]-4,14-dioxo-1,5-diazacyclotetradec-9-ene-6-carbonyl]amino]methyl]phenyl]acetic acid Chemical compound C([C@H]1CC(=O)N[C@@H](CC/C=C/CC[C@@H](C(N1)=O)N)C(=O)NCC=1C(=CC=CC=1)CC(O)=O)C1=CC=C(O)C=C1 QUJXIMWUJGTUEG-CLKUPZDLSA-N 0.000 claims 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 1
- 241000255925 Diptera Species 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 150000001993 dienes Chemical class 0.000 claims 1
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- 125000001475 halogen functional group Chemical group 0.000 claims 1
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- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 59
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 46
- 239000000243 solution Substances 0.000 description 45
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- 239000007787 solid Substances 0.000 description 39
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- 229940005550 sodium alginate Drugs 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 238000000935 solvent evaporation Methods 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 230000009870 specific binding Effects 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 238000005556 structure-activity relationship Methods 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical class ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 230000002889 sympathetic effect Effects 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000007910 systemic administration Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 230000008685 targeting Effects 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 1
- HJKUNABSNYEGJB-UHFFFAOYSA-N tert-butyl 4-(2-hydroxyanilino)piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1NC1=CC=CC=C1O HJKUNABSNYEGJB-UHFFFAOYSA-N 0.000 description 1
- STEAYGPTLHZMJU-UHFFFAOYSA-N tert-butyl 4-(2-oxo-3h-benzimidazol-1-yl)piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1N1C(=O)NC2=CC=CC=C21 STEAYGPTLHZMJU-UHFFFAOYSA-N 0.000 description 1
- KAXDRALMRYZRCT-UHFFFAOYSA-N tert-butyl 4-(5-fluoro-2-oxo-3h-benzimidazol-1-yl)piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1N1C(=O)NC2=CC(F)=CC=C21 KAXDRALMRYZRCT-UHFFFAOYSA-N 0.000 description 1
- ROUYFJUVMYHXFJ-UHFFFAOYSA-N tert-butyl 4-oxopiperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(=O)CC1 ROUYFJUVMYHXFJ-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- IXZDIALLLMRYOU-UHFFFAOYSA-N tert-butyl hypochlorite Chemical compound CC(C)(C)OCl IXZDIALLLMRYOU-UHFFFAOYSA-N 0.000 description 1
- 210000001550 testis Anatomy 0.000 description 1
- 229940095585 testosterone-5-alpha reductase inhibitors for benign prostatic hypertrophy Drugs 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- DPJRMOMPQZCRJU-UHFFFAOYSA-M thiamine hydrochloride Chemical compound Cl.[Cl-].CC1=C(CCO)SC=[N+]1CC1=CN=C(C)N=C1N DPJRMOMPQZCRJU-UHFFFAOYSA-M 0.000 description 1
- 125000006089 thiamorpholinyl sulfoxide group Chemical group 0.000 description 1
- 125000001984 thiazolidinyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 1
- 229940125725 tranquilizer Drugs 0.000 description 1
- 239000003204 tranquilizing agent Substances 0.000 description 1
- 230000002936 tranquilizing effect Effects 0.000 description 1
- 230000037317 transdermal delivery Effects 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 239000002753 trypsin inhibitor Substances 0.000 description 1
- 210000003954 umbilical cord Anatomy 0.000 description 1
- 201000002327 urinary tract obstruction Diseases 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 229940070710 valerate Drugs 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 230000003442 weekly effect Effects 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 229930195724 β-lactose Natural products 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US39269995A | 1995-02-23 | 1995-02-23 | |
| US253495P | 1995-08-18 | 1995-08-18 | |
| GB08/392,699 | 1996-02-19 | ||
| GBGB9603457.4A GB9603457D0 (fr) | 1996-02-19 | 1996-02-19 | |
| GB60/002,534 | 1996-02-19 | ||
| GB9603457.4 | 1996-02-19 | ||
| PCT/US1996/002534 WO1996025934A1 (fr) | 1995-02-23 | 1996-02-23 | ANTAGONISTES DU RECEPTEUR ALPHA-1a-ADRENERGIQUE |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH11508536A true JPH11508536A (ja) | 1999-07-27 |
Family
ID=26308756
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP8525855A Pending JPH11508536A (ja) | 1995-02-23 | 1996-02-23 | アドレナリン性α▲下1a▼受容体アンタゴニスト |
Country Status (4)
| Country | Link |
|---|---|
| EP (1) | EP0812196A4 (fr) |
| JP (1) | JPH11508536A (fr) |
| AU (1) | AU700559B2 (fr) |
| CA (1) | CA2213192A1 (fr) |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4110449A (en) * | 1977-05-23 | 1978-08-29 | E. R. Squibb & Sons, Inc. | 2-substituted benzisothiazol-3-ones |
| RU2118322C1 (ru) * | 1993-07-05 | 1998-08-27 | Дюфар Интернэшнл Рисерч Б.В. | 2,3-дигидро-1,4-бензодиокси-5-ил-пиперазиновые производные или их соли |
| CA2187767A1 (fr) * | 1994-04-14 | 1995-10-26 | Joel R. Huff | Antagonistes du recepteur adrenergique alpha1c |
-
1996
- 1996-02-23 CA CA002213192A patent/CA2213192A1/fr not_active Abandoned
- 1996-02-23 AU AU49301/96A patent/AU700559B2/en not_active Ceased
- 1996-02-23 JP JP8525855A patent/JPH11508536A/ja active Pending
- 1996-02-23 EP EP96905575A patent/EP0812196A4/fr not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| CA2213192A1 (fr) | 1996-08-29 |
| EP0812196A4 (fr) | 1998-05-20 |
| EP0812196A1 (fr) | 1997-12-17 |
| AU4930196A (en) | 1996-09-11 |
| AU700559B2 (en) | 1999-01-07 |
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