NO315232B1 - 1-(N-fenylaminoalkyl)-piperazin derivater substituert i posisjon 2 på fenylringen, samt anvendelse derav ved fremstilling av et legemiddelfor behandling av nevromuskul¶r dysfunksjon i lavere urinveier i et pattedyr - Google Patents
1-(N-fenylaminoalkyl)-piperazin derivater substituert i posisjon 2 på fenylringen, samt anvendelse derav ved fremstilling av et legemiddelfor behandling av nevromuskul¶r dysfunksjon i lavere urinveier i et pattedyr Download PDFInfo
- Publication number
- NO315232B1 NO315232B1 NO20000521A NO20000521A NO315232B1 NO 315232 B1 NO315232 B1 NO 315232B1 NO 20000521 A NO20000521 A NO 20000521A NO 20000521 A NO20000521 A NO 20000521A NO 315232 B1 NO315232 B1 NO 315232B1
- Authority
- NO
- Norway
- Prior art keywords
- piperazine
- methoxyphenyl
- aminoethyl
- nitrophenyl
- cyclohexylcarbonyl
- Prior art date
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- 238000011282 treatment Methods 0.000 title claims abstract description 20
- 239000003814 drug Substances 0.000 title claims abstract description 13
- 210000001635 urinary tract Anatomy 0.000 title claims abstract description 12
- 230000004064 dysfunction Effects 0.000 title claims abstract description 10
- 230000002232 neuromuscular Effects 0.000 title claims abstract description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 title claims description 16
- 241000124008 Mammalia Species 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 4
- 229940066771 systemic antihistamines piperazine derivative Drugs 0.000 title abstract description 5
- 229940079593 drug Drugs 0.000 title description 10
- 150000001875 compounds Chemical class 0.000 claims abstract description 131
- 125000002950 monocyclic group Chemical group 0.000 claims abstract description 10
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 9
- 125000002252 acyl group Chemical group 0.000 claims abstract description 8
- 125000005843 halogen group Chemical group 0.000 claims abstract description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 6
- 238000004519 manufacturing process Methods 0.000 claims abstract description 5
- -1 phenoxy, nitro, cyano, acetyl Chemical group 0.000 claims description 139
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims description 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
- 125000004442 acylamino group Chemical group 0.000 claims description 7
- 150000002367 halogens Chemical group 0.000 claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 5
- 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims description 5
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 5
- 150000001204 N-oxides Chemical class 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims description 5
- 229910052740 iodine Inorganic materials 0.000 claims description 5
- HVMKWKIPLGPYAR-UHFFFAOYSA-N n-[2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl]-n-(2-nitrophenyl)cyclohexanecarboxamide Chemical compound COC1=CC=CC=C1N1CCN(CCN(C(=O)C2CCCCC2)C=2C(=CC=CC=2)[N+]([O-])=O)CC1 HVMKWKIPLGPYAR-UHFFFAOYSA-N 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 3
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- 125000002541 furyl group Chemical group 0.000 claims description 3
- 125000001041 indolyl group Chemical group 0.000 claims description 3
- PWWWSUGFEGJHDE-UHFFFAOYSA-N n-(2-aminophenyl)-n-[2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl]cyclohexanecarboxamide Chemical compound COC1=CC=CC=C1N1CCN(CCN(C(=O)C2CCCCC2)C=2C(=CC=CC=2)N)CC1 PWWWSUGFEGJHDE-UHFFFAOYSA-N 0.000 claims description 3
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- YBOVYECREWJMDJ-UHFFFAOYSA-N methyl 2-[cyclohexanecarbonyl-[2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl]amino]benzoate Chemical compound COC(=O)C1=CC=CC=C1N(C(=O)C1CCCCC1)CCN1CCN(C=2C(=CC=CC=2)OC)CC1 YBOVYECREWJMDJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
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- KVECKPSOWOJXOI-UHFFFAOYSA-N n-[2-[4-(2-methoxyphenyl)-1,4-dioxidopiperazine-1,4-diium-1-yl]ethyl]-n-(2-nitrophenyl)cyclohexanecarboxamide Chemical compound COC1=CC=CC=C1[N+]1([O-])CC[N+]([O-])(CCN(C(=O)C2CCCCC2)C=2C(=CC=CC=2)[N+]([O-])=O)CC1 KVECKPSOWOJXOI-UHFFFAOYSA-N 0.000 claims description 2
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- ZZXHDQUVDLOZDQ-UHFFFAOYSA-N n-[2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl]-n-[2-(trifluoromethyl)phenyl]cyclohexanecarboxamide Chemical compound COC1=CC=CC=C1N1CCN(CCN(C(=O)C2CCCCC2)C=2C(=CC=CC=2)C(F)(F)F)CC1 ZZXHDQUVDLOZDQ-UHFFFAOYSA-N 0.000 claims description 2
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- 229960003147 reserpine Drugs 0.000 description 1
- MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 230000002295 serotoninergic effect Effects 0.000 description 1
- 230000036299 sexual function Effects 0.000 description 1
- 210000000329 smooth muscle myocyte Anatomy 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 230000009870 specific binding Effects 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000013223 sprague-dawley female rat Methods 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 238000012353 t test Methods 0.000 description 1
- 230000006794 tachycardia Effects 0.000 description 1
- 239000004149 tartrazine Substances 0.000 description 1
- QIQITDHWZYEEPA-UHFFFAOYSA-N thiophene-2-carbonyl chloride Chemical compound ClC(=O)C1=CC=CS1 QIQITDHWZYEEPA-UHFFFAOYSA-N 0.000 description 1
- QTWBEVAYYDZLQL-UHFFFAOYSA-N thiophene-3-carbonyl chloride Chemical compound ClC(=O)C=1C=CSC=1 QTWBEVAYYDZLQL-UHFFFAOYSA-N 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 125000005951 trifluoromethanesulfonyloxy group Chemical group 0.000 description 1
- 210000003708 urethra Anatomy 0.000 description 1
- 206010046494 urge incontinence Diseases 0.000 description 1
- 208000014001 urinary system disease Diseases 0.000 description 1
- 230000002747 voluntary effect Effects 0.000 description 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
- C07D213/02—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 having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—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 having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—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 having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
-
- 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
- A61P25/00—Drugs for disorders of the nervous system
-
- 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
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
-
- 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
- C07D213/02—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 having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—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 having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—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 having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
- C07D213/82—Amides; Imides in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-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
- C07D241/24—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/13—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/22—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with hetero atoms directly attached to ring nitrogen atoms
- C07D295/24—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or 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
- C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Urology & Nephrology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Furan Compounds (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
IT97MI001864A IT1293807B1 (it) | 1997-08-01 | 1997-08-01 | Derivati 1- (n-fenilaminoalchil) piperazinici sostituiti alla posizione 2 dell'anello fenilico |
PCT/EP1998/004804 WO1999006384A1 (en) | 1997-08-01 | 1998-07-31 | 1-(n-phenylaminoalkyl)-piperazine derivatives substituted at position 2 of the phenyl ring |
Publications (3)
Publication Number | Publication Date |
---|---|
NO20000521L NO20000521L (no) | 2000-02-01 |
NO20000521D0 NO20000521D0 (no) | 2000-02-01 |
NO315232B1 true NO315232B1 (no) | 2003-08-04 |
Family
ID=11377708
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO20000521A NO315232B1 (no) | 1997-08-01 | 2000-02-01 | 1-(N-fenylaminoalkyl)-piperazin derivater substituert i posisjon 2 på fenylringen, samt anvendelse derav ved fremstilling av et legemiddelfor behandling av nevromuskul¶r dysfunksjon i lavere urinveier i et pattedyr |
Country Status (18)
Country | Link |
---|---|
US (1) | US6071920A (xx) |
EP (1) | EP1000047B1 (xx) |
JP (1) | JP2001512112A (xx) |
KR (1) | KR20010022509A (xx) |
CN (1) | CN1127493C (xx) |
AT (1) | ATE256671T1 (xx) |
AU (1) | AU737456B2 (xx) |
BR (1) | BR9811482A (xx) |
CA (1) | CA2297095A1 (xx) |
DE (1) | DE69820632D1 (xx) |
HU (1) | HUP0004926A3 (xx) |
IL (1) | IL134089A0 (xx) |
IT (1) | IT1293807B1 (xx) |
NO (1) | NO315232B1 (xx) |
NZ (1) | NZ502804A (xx) |
PL (1) | PL338352A1 (xx) |
RU (1) | RU2199533C2 (xx) |
WO (1) | WO1999006384A1 (xx) |
Families Citing this family (31)
Publication number | Priority date | Publication date | Assignee | Title |
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US20020193383A1 (en) * | 1997-08-01 | 2002-12-19 | Recordati S.A., Chemical And Pharmaceutical Comoany | 1-(N-phenylalkylaminoalkyl)piperazine derivatives substituted at position 2 of the phenyl ring |
US6399614B1 (en) * | 1997-08-01 | 2002-06-04 | Recordati S.A. Chemical And Pharmaceutical Company | 1-(N-phenylaminoalkyl)piperazine derivatives substituted at position 2 of the phenyl ring |
IT1293804B1 (it) | 1997-08-01 | 1999-03-10 | Recordati Chem Pharm | Diarilalchilpiperazine attive sulle basse vie urinarie |
EP1004573B1 (en) * | 1997-08-04 | 2002-10-30 | Taisho Pharmaceutical Co., Ltd | Aryloxyaniline derivatives |
UA62015C2 (en) | 1998-12-28 | 2003-12-15 | Pfizer Prod Inc | Benzoizoxazol derivatives, a pharmaceutical composition (variants) based thereon (variants) and a method for treatment (variants) |
IT1313581B1 (it) * | 1999-07-30 | 2002-09-09 | Recordati Chem Pharm | Derivati tienopirancarbossamidici. |
US6387909B1 (en) | 1999-07-30 | 2002-05-14 | Recordati S.A. Chemical And Pharmaceutical Company | Thienopyranecarboxamide derivatives |
US6306861B1 (en) | 1999-07-30 | 2001-10-23 | Recordati S.A. Chemical And Pharmaceutical Company | Thienopyrancecarboxamide derivatives |
IT1314192B1 (it) * | 1999-10-18 | 2002-12-06 | Recordati Chem Pharm | Derivati benzopiranici |
US6403594B1 (en) | 1999-10-18 | 2002-06-11 | Recordati, S.A. Chemical And Pharmaceutical Company | Benzopyran derivatives |
KR100333500B1 (ko) * | 2000-01-19 | 2002-04-25 | 박호군 | 아릴피페라진 화합물 및 그의 제조방법 |
TW200400035A (en) | 2002-03-28 | 2004-01-01 | Glaxo Group Ltd | Novel compounds |
WO2003084541A1 (en) * | 2002-04-08 | 2003-10-16 | Ranbaxy Laboratories Limited | Carboximide derivatives as useful uro-selective alpha-1a adrenoceptor blockers |
US7030122B2 (en) * | 2002-04-12 | 2006-04-18 | Sepracor Inc. | 1,4-disubstituted piperazine ligands for neurotransmitter receptors |
US20040072839A1 (en) * | 2002-06-14 | 2004-04-15 | Amedeo Leonardi | 1-Phenylalkylpiperazines |
US20040058962A1 (en) * | 2002-06-14 | 2004-03-25 | Amedeo Leonardi | Phenylalkylamines and pyridylalkylamines |
US20040215284A1 (en) * | 2003-01-30 | 2004-10-28 | Recordati S.A. | Treatment of neuromuscular dysfunction of the lower urinary tract with selective mGlu5 antagonists |
ITMI20030151A1 (it) * | 2003-01-30 | 2004-07-31 | Recordati Ind Chimica E Farma Ceutica S P A | Uso di antagonisti selettivi del recettore mglu5 per il trattamento di disfunzioni neuromuscolari del tratto urinario inferiore. |
TW200507841A (en) * | 2003-03-27 | 2005-03-01 | Glaxo Group Ltd | Antibacterial agents |
US20050165025A1 (en) * | 2004-01-22 | 2005-07-28 | Recordati Ireland Ltd. | Combination therapy with 5HT 1A and 5HT 1B-receptor antagonists |
TWI391387B (zh) * | 2004-05-12 | 2013-04-01 | Eisai R&D Man Co Ltd | 具有哌啶環之吲哚衍生物 |
JPWO2006082872A1 (ja) * | 2005-02-04 | 2008-06-26 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | 1−(ピペリジン−4−イル)−1h−インドール誘導体 |
KR20080007649A (ko) * | 2005-05-11 | 2008-01-22 | 에자이 알앤드디 매니지먼트 가부시키가이샤 | 피페리딘환을 가지는 인돌 유도체의 결정 및 그의 제조방법 |
US20080227815A1 (en) * | 2005-05-11 | 2008-09-18 | Takahisa Sakaguchi | Crystal of Indole Derivative Having Piperidine Ring and Process for Production Thereof |
CN101175751B (zh) * | 2005-05-11 | 2011-03-23 | 卫材R&D管理有限公司 | 具有哌啶环的吲哚衍生物的晶体和其制备方法 |
JP4932717B2 (ja) * | 2005-05-11 | 2012-05-16 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | ピペリジン環を有するインドール誘導体の製造方法 |
AU2006244916B2 (en) | 2005-05-11 | 2011-04-07 | Eisai R & D Management Co., Ltd. | Method for producing indole derivative having piperidine ring |
US7671221B2 (en) * | 2005-12-28 | 2010-03-02 | Vertex Pharmaceuticals Incorporated | Modulators of ATP-Binding Cassette transporters |
EP2016065B1 (en) * | 2005-12-28 | 2012-09-19 | Vertex Pharmaceuticals Incorporated | 1-(benzo[d][1,3]dioxol-5-yl)-n-(phenyl)cyclopropane-carboxamide derivatives and related compounds as modulators of atp-binding cassette transporters for the treatment of cystic fibrosis |
CN103360342B (zh) * | 2012-04-09 | 2015-12-16 | 江苏恩华药业股份有限公司 | 3-氰基苯胺烷基芳基哌嗪衍生物及在制备药物中的应用 |
CN113402467B (zh) * | 2021-06-18 | 2022-05-13 | 山东汇海医药化工有限公司 | 一种氟班色林的合成方法 |
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US3362956A (en) * | 1965-08-19 | 1968-01-09 | Sterling Drug Inc | 1-[(heterocyclyl)-lower-alkyl]-4-substituted-piperazines |
US3635976A (en) * | 1967-12-20 | 1972-01-18 | Pennwalt Corp | 1 - heterocyclic alkyl-1 2 3 4-tetrahydroquinazolinones and analgesic intermediates thereof |
US4017624A (en) * | 1973-02-05 | 1977-04-12 | Sumitomo Chemical Company, Limited | N-(ω-Amino)alkylaniline derivatives |
JPS49101383A (xx) * | 1973-02-05 | 1974-09-25 | ||
US5008267A (en) * | 1988-10-29 | 1991-04-16 | Mitsui Toatsu Chemicals, Incorporated | Pyrimidinedione compounds, method of producing the same and antiarrythmic agents containing the same |
JPH0413669A (ja) * | 1990-04-27 | 1992-01-17 | Mitsui Toatsu Chem Inc | 新規ピリミジンジオン誘導体及び該化合物を含有する抗不整脈剤 |
EP0598123A4 (en) * | 1991-07-19 | 1995-02-15 | Zeria Pharm Co Ltd | PIPERAZINE DERIVATIVE AND MEDICINAL PRODUCT CONTAINING THE SAME. |
GB9200293D0 (en) * | 1992-01-08 | 1992-02-26 | Wyeth John & Brother Ltd | Piperazine derivatives |
IT1266582B1 (it) * | 1993-07-30 | 1997-01-09 | Recordati Chem Pharm | Derivati (di)azacicloesanici e diazacicloeptanici |
GB9411099D0 (en) * | 1994-06-03 | 1994-07-27 | Wyeth John & Brother Ltd | Piperazine derivatives |
US5688795A (en) * | 1994-11-08 | 1997-11-18 | Syntex (U.S.A.) Inc. | 3-(4-phenylpiperazin-1-yl)propyl-amino, thio and oxy!-pyridine, pyrimidine and benzene derivatives as α1 -adrenoceptor antagonists |
-
1997
- 1997-08-01 IT IT97MI001864A patent/IT1293807B1/it active IP Right Grant
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1998
- 1998-07-31 NZ NZ502804A patent/NZ502804A/xx unknown
- 1998-07-31 RU RU2000105266/04A patent/RU2199533C2/ru not_active IP Right Cessation
- 1998-07-31 CN CN98807820A patent/CN1127493C/zh not_active Expired - Fee Related
- 1998-07-31 US US09/127,057 patent/US6071920A/en not_active Expired - Fee Related
- 1998-07-31 KR KR1020007001096A patent/KR20010022509A/ko not_active Application Discontinuation
- 1998-07-31 PL PL98338352A patent/PL338352A1/xx unknown
- 1998-07-31 DE DE69820632T patent/DE69820632D1/de not_active Expired - Lifetime
- 1998-07-31 HU HU0004926A patent/HUP0004926A3/hu unknown
- 1998-07-31 AT AT98943815T patent/ATE256671T1/de not_active IP Right Cessation
- 1998-07-31 AU AU91578/98A patent/AU737456B2/en not_active Ceased
- 1998-07-31 IL IL13408998A patent/IL134089A0/xx unknown
- 1998-07-31 CA CA002297095A patent/CA2297095A1/en not_active Abandoned
- 1998-07-31 BR BR9811482-4A patent/BR9811482A/pt not_active IP Right Cessation
- 1998-07-31 JP JP2000505143A patent/JP2001512112A/ja active Pending
- 1998-07-31 WO PCT/EP1998/004804 patent/WO1999006384A1/en not_active Application Discontinuation
- 1998-07-31 EP EP98943815A patent/EP1000047B1/en not_active Expired - Lifetime
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2000
- 2000-02-01 NO NO20000521A patent/NO315232B1/no not_active IP Right Cessation
Also Published As
Publication number | Publication date |
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CA2297095A1 (en) | 1999-02-11 |
NO20000521L (no) | 2000-02-01 |
JP2001512112A (ja) | 2001-08-21 |
WO1999006384A1 (en) | 1999-02-11 |
ATE256671T1 (de) | 2004-01-15 |
CN1127493C (zh) | 2003-11-12 |
BR9811482A (pt) | 2002-01-22 |
US6071920A (en) | 2000-06-06 |
PL338352A1 (en) | 2000-10-23 |
HUP0004926A2 (hu) | 2001-11-28 |
AU9157898A (en) | 1999-02-22 |
KR20010022509A (ko) | 2001-03-15 |
CN1265654A (zh) | 2000-09-06 |
IT1293807B1 (it) | 1999-03-10 |
HUP0004926A3 (en) | 2002-01-28 |
RU2199533C2 (ru) | 2003-02-27 |
EP1000047B1 (en) | 2003-12-17 |
DE69820632D1 (de) | 2004-01-29 |
NZ502804A (en) | 2001-02-23 |
AU737456B2 (en) | 2001-08-23 |
NO20000521D0 (no) | 2000-02-01 |
IL134089A0 (en) | 2001-04-30 |
ITMI971864A1 (it) | 1999-02-01 |
EP1000047A1 (en) | 2000-05-17 |
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