FI91634B - Förfarande för framställning av terapeutiskt användbara 1,4-dihydropyridinderivat - Google Patents
Förfarande för framställning av terapeutiskt användbara 1,4-dihydropyridinderivat Download PDFInfo
- Publication number
- FI91634B FI91634B FI873350A FI873350A FI91634B FI 91634 B FI91634 B FI 91634B FI 873350 A FI873350 A FI 873350A FI 873350 A FI873350 A FI 873350A FI 91634 B FI91634 B FI 91634B
- Authority
- FI
- Finland
- Prior art keywords
- phenyl
- formula
- nitro
- dihydro
- dimethyl
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/80—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D211/82—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen 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
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/80—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D211/84—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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 directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/80—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D211/84—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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 directly attached to ring carbon atoms
- C07D211/90—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
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Cardiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Heart & Thoracic Surgery (AREA)
- Hospice & Palliative Care (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Steroid Compounds (AREA)
- Silicates, Zeolites, And Molecular Sieves (AREA)
Claims (8)
1. Förfarande för framställning av nya terapeu-tiskt användbara 1,4-dihydropyridinderivat med formeln I 5 och farmaceutiskt godtagbara salter därav, ^ r1 4— R2 .. V, °2N'^j^\^R5 (I) N^CH3 H 15 i vilken formel R1 är H, C^-C^-alkoxi, nitro, halogen el-ler Cj-C^alkenyl, R2 är trifluormetyl, halogen eller 20 -0(CH2)n -N N- (alk)mAr’ där n är 1 - 12 och Ar' är fenyl, som kan vara substitue-rad med Ci-C^-alkoxi eller tr if luormetyl, eller Ar' är 2-25 pyrimidinyl eller 2-pyridinyl, m är 0 eller 1 och alk är C^-C^-alkylen, eller R2 är -0-CH2-X-CH2-N N-(alk)in-Ar' 30 \_/ där X är -CH=CH-, -CH-CH- eller en epoxid av dessa och alk, m och Ar' betecknar samma som ovan, och R5 är -C02R7, där R7 är « . « II 91634 43 - (CH2) γ-/ N-Ar1 5 -(CH2)2NH(CH2)2-0-Ar’ eller Cj-C^alkyl, varvid r är 1 - 10 och Ar' betecknar samma som ovan, eller R5 är -CONHPh, kännetecknat därav, att a) för framställnlng av föreningar med formeln I, 10 där R2 är -0-CH2-X-CH2-N^_N-(alk)m-Ar' eller 15 -0(CH2)n -N N- (alk)mAr ' 20 brlngas en förenlng med formeln iR1
0-CH2-X-CH2-R1:L -°(CH2)m-Rl1 ;5 eller YY - ' -a3 H3c^ n Ach H 3 I J H 30 (II) (II') varvid R11 är Br, Cl, I, OTs, OMs eller OTf och R1, R5 och X betecknar samma som ovan, i kontakt med en förenlng med formeln 44 91634 H-/ (alk) mAr1 (III) 5 där alk, m och Ar' betecknar sairaita som ovan, eller b) för framställning av föreningar med formeln I, där R5 är -C02R7, där R7 är / \ 10 -(CH2)r-N_^I-Ar' bringas en förenlng med formeln r1 15 Γ — R2 |C-H ° (I if ,IV) H-iC^ N ^CH-, 2° 3 A 3 där R11 är Br, Cl, I, OTs, OMs eller OTf och R1, R2 och r betecknar sairaita som ovan, i kontakt med en förening med formeln 25 H-N Vat' (III·) 30 där Ar' betecknar samma som ovan; och, om sä önskas, omvandlas en erhällen förenlng med formeln I tili ett farmaceutiskt godtagbart sait genom att omsätta förenlngen med en oorganlsk eller organisk syra. 35
2. Förfarande enligt patentkravet 1, känne- t e c k n a t därav, att man framställer 1,4-dihydro- II • 45 y 1634 2.6- dimetyl-5-nitro-4-[3-(trifluormetyl)fenyl]—[2—[4—(2— metoxifenyl-l-piperazinyl]etyl]ester-3-pyridinkarboxylsy-ra.
3. Förfarande enligt patentkravet 1, känne-5 tecknat därav, att man framställer 1,4-dihydro- 2.6- dimetyl-4-[3-(2-(4-(2-metoxifenyl)-l-piperazinyl)eto-xi)fenyl]-5-nitro-metylester-3-pyridinkarboxylsyra.
4. Förfarande enligt patentkravet 1, känne-tecknat därav, att man framställer 1,4-dihydro- 10 2,6-dimetyl-4-[2-(2-(4-(2-metoxifenyl)-l-piperazinyl)eto- xi)fenyl]-5-nitro-metylester-3-pyridinkarboxylsyra.
5. Förfarande enligt patentkravet 1, känne-tecknat därav, att man framställer 1,4-dihydro- 2.6- dimetyl-4-[2-(2-(4-(2-metoxifenyl)-l-piperazinyl)eto- 15 xi)-3-(trifluormetyl)fenyl]-5-nitro-metylester-3-pyridin- karboxylsyra.
6. Förfarande enligt patentkravet 1, känne-tecknat därav, att man framställer 1,4-dihydro- 2.6- dimetyl-4-[2-(3-(4-(2-metoxifenyl)-l-piperazinyl)- 20 propoxi)fenyl]-5-nitro-metylester-3-pyridinkarboxylsyra.
7. Förfarande enligt patentkravet 1, känne-tecknat därav, att man framställer 1,4-dihydro- 2.6- dimetyl-5-nitro-4-[2-(4-(4-(2-pyrimidinyl)-1-piper-azinyl)butoxi)fenyl]-metylester-3-pyridinkarboxylsyra. 25
8. Förfarande enligt patentkravet 1, känne- tecknat därav, att man framställer 1,4-dihydro- 2.6- dimetyl-4-[2-(5-(4-(2-metoxifenyl)-l-piperazinyl)pen-toxyl)fenyl]-5-nitro-metylester-3-pyridinkarboxylsyra.
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US89229386A | 1986-08-04 | 1986-08-04 | |
US89229386 | 1986-08-04 | ||
US07/064,361 US4868181A (en) | 1986-08-04 | 1987-06-30 | 1,4-dihydropyridine derivatives with calcium agonist and alpha1 -antagonist activity |
US6436187 | 1987-06-30 |
Publications (4)
Publication Number | Publication Date |
---|---|
FI873350A0 FI873350A0 (sv) | 1987-08-03 |
FI873350A FI873350A (sv) | 1988-02-05 |
FI91634B true FI91634B (sv) | 1994-04-15 |
FI91634C FI91634C (sv) | 1994-07-25 |
Family
ID=26744430
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
FI873350A FI91634C (sv) | 1986-08-04 | 1987-08-03 | Förfarande för framställning av terapeutiskt användbara 1,4-dihydropyridinderivat |
Country Status (12)
Country | Link |
---|---|
US (1) | US4868181A (sv) |
EP (1) | EP0255710A3 (sv) |
KR (1) | KR930004648B1 (sv) |
AU (1) | AU617650B2 (sv) |
DK (1) | DK403287A (sv) |
FI (1) | FI91634C (sv) |
HU (1) | HU201925B (sv) |
IL (1) | IL83413A0 (sv) |
NO (1) | NO171909C (sv) |
NZ (1) | NZ221284A (sv) |
PT (1) | PT85483B (sv) |
SU (3) | SU1607687A3 (sv) |
Families Citing this family (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5137889A (en) * | 1983-12-02 | 1992-08-11 | Otsuka Pharmaceutical Co., Ltd. | Dihydropyridine derivatives and process for preparing the same |
JPS63112560A (ja) * | 1986-10-29 | 1988-05-17 | Green Cross Corp:The | ジヒドロピリジン誘導体 |
DE3711991A1 (de) * | 1987-04-09 | 1988-10-20 | Bayer Ag | Dihydropyridinamide, verfahren zu ihrer herstellung und ihre verwendung in arzneimitteln |
DE3737340A1 (de) * | 1987-11-04 | 1989-05-24 | Bayer Ag | Neue fluormethoxyphenyl-dihydropyridine, verfahren zur herstellung und ihre verwendung in arzneimitteln |
DE3737341A1 (de) * | 1987-11-04 | 1989-05-18 | Bayer Ag | Neue fluormethoxyphenyl-dihydropyridine, verfahren zur herstellung und ihre verwendung in arzneimitteln |
NZ232396A (en) * | 1989-02-10 | 1991-07-26 | Merrell Dow Pharma | 2-(diphenylalkylamino) -1,3 nn heterocyclic compounds and pharmaceutical compositions |
US5106845A (en) * | 1990-01-10 | 1992-04-21 | Merrell Dow Pharmaceuticals Inc. | Calcium antagonists |
US5166148A (en) * | 1990-07-09 | 1992-11-24 | The Du Pont Merck Pharmaceutical Company | 2-amino-1,4-dihydropyridine derivatives with calcium agonist and alpha1 -antagonist activity |
DE4222770A1 (de) * | 1992-07-10 | 1994-01-13 | Bayer Ag | Lichtaktivierbare 1-(2-Nitrobenzyl)-substituierte 1,4-Dihydropyridine |
US6211198B1 (en) | 1993-04-05 | 2001-04-03 | Synaptic Pharmaceutical Corporation | Dihydropyridines and new uses thereof |
US5767131A (en) * | 1993-04-05 | 1998-06-16 | Synaptic Pharmaceutical Corporation | Dihydropyridines and new uses thereof |
IL109220A0 (en) * | 1993-04-05 | 1994-07-31 | Synaptic Pharma Corp | Dihydropyridines and new uses thereof |
DE4410822A1 (de) * | 1994-03-24 | 1995-09-28 | Schering Ag | Neue Piperidin-Derivate |
US5635503A (en) * | 1995-06-07 | 1997-06-03 | Bristol-Myers Squibb Company | Dihydropyridine npy antagonists: piperazine derivatives |
WO2000024716A1 (fr) * | 1998-10-23 | 2000-05-04 | Ajinomoto Co., Inc. | Derives de dihydropyridine et compositions medicamenteuses contenant ces derives |
EP2925739A4 (en) * | 2012-11-28 | 2016-07-27 | Stichting Dienst Landbouwkundi | SUBSTITUTED DIHYDROPYRTOINS FOR PLANTS WITH SOMATIC EMBRYOGENESIS I |
Family Cites Families (21)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3985758A (en) * | 1973-02-20 | 1976-10-12 | Yamanouchi Pharmaceutical Co., Ltd. | 1,4-Dihydropyridine derivatives |
DE2752820A1 (de) * | 1977-11-26 | 1979-05-31 | Bayer Ag | Neue nitrosubstituierte 1,4-dihydropyridine, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
DE2841667A1 (de) * | 1978-09-25 | 1980-04-10 | Bayer Ag | Fluorhaltige 1,4-dihydropyridine, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
JPS57171968A (en) * | 1981-04-17 | 1982-10-22 | Kyowa Hakko Kogyo Co Ltd | 1,4-dihydropyridine derivative |
NZ201395A (en) * | 1981-07-30 | 1987-02-20 | Bayer Ag | Pharmaceutical compositions containing 1,4-dihydropyridines and certain of these dihydropyridines |
ATE50987T1 (de) * | 1982-05-10 | 1990-03-15 | Takeda Chemical Industries Ltd | Dihydropyridinderivate, deren herstellung und verwendung. |
EP0097821B1 (en) * | 1982-06-03 | 1988-07-13 | Pierrel S.p.A. | Dihydropyridines with an antagonistic activity to calcium, process for their preparation, and pharmaceutical compositions containing them |
WO1985000169A1 (en) * | 1983-06-21 | 1985-01-17 | Sandoz Ag | 1,4-dihydropyridine derivatives, production thereof and pharmaceutical preparations containing them |
DE3326384A1 (de) * | 1983-07-22 | 1985-01-31 | Bayer Ag, 5090 Leverkusen | 1,4-dihydropyridine, verfahren zu ihrer herstellung sowie ihre verwendung in arzneimitteln |
US4603135A (en) * | 1983-10-17 | 1986-07-29 | Takeda Chemical Industries, Ltd. | Substituted piperazinyl alkyl esters of 2-amino-4-aryl-1,4-dihydro-6-alkyl-3,5-pyridinedicarboxylates |
DE3339861A1 (de) * | 1983-11-04 | 1985-05-15 | Bayer Ag, 5090 Leverkusen | Arzneizubereitung enthaltend dihydropyridine |
JPS60156671A (ja) * | 1984-01-25 | 1985-08-16 | Yamanouchi Pharmaceut Co Ltd | ジヒドロピリジン誘導体およびその製造法 |
US4755512A (en) * | 1984-04-11 | 1988-07-05 | Bristol-Myers Company | Pharmaceutically useful dihydropyridinyldicarboxylate amides and esters incorporating arylpiperazinylalkyl moities |
JPS6191185A (ja) * | 1984-10-11 | 1986-05-09 | Sumitomo Seiyaku Kk | 新規なオキサジアゾリル−1,4−ジヒドロピリジン誘導体 |
WO1986003748A1 (en) * | 1984-12-21 | 1986-07-03 | Byk Gulden Lomberg Chemische Fabrik Gesellschaft M | New piperazine derivatives |
GB8503427D0 (en) * | 1985-02-11 | 1985-03-13 | Ici Plc | Basic compounds |
DE3521761A1 (de) * | 1985-06-19 | 1987-01-02 | Bayer Ag | Neue 1,4-dihydropyridine, verfahren zur herstellung und ihre verwendung in arzneimitteln |
EP0222702A3 (de) * | 1985-11-06 | 1988-01-07 | Ciba-Geigy Ag | Basische Carbonylverbindungen |
DE3600596A1 (de) * | 1986-01-11 | 1987-07-16 | Bayer Ag | 4-aminoaryldihydropyridinlactone, verfahren zu ihrer herstellung und ihre verwendung in arzneimitteln |
DE3601397A1 (de) * | 1986-01-18 | 1987-07-23 | Bayer Ag | Substituierte 1,4-dihydropyridin-3-carbonsaeurepiperazide, verfahren zu ihrer herstellung und ihre verwendung in arzneimitteln |
JP2742074B2 (ja) * | 1988-11-30 | 1998-04-22 | マツダ株式会社 | 浸炭炉 |
-
1987
- 1987-06-30 US US07/064,361 patent/US4868181A/en not_active Expired - Fee Related
- 1987-07-31 NZ NZ221284A patent/NZ221284A/xx unknown
- 1987-08-01 EP EP87111142A patent/EP0255710A3/en not_active Withdrawn
- 1987-08-03 HU HU873549A patent/HU201925B/hu not_active IP Right Cessation
- 1987-08-03 FI FI873350A patent/FI91634C/sv not_active IP Right Cessation
- 1987-08-03 IL IL83413A patent/IL83413A0/xx unknown
- 1987-08-03 AU AU76503/87A patent/AU617650B2/en not_active Ceased
- 1987-08-03 NO NO873240A patent/NO171909C/no unknown
- 1987-08-03 KR KR1019870008497A patent/KR930004648B1/ko not_active IP Right Cessation
- 1987-08-03 DK DK403287A patent/DK403287A/da unknown
- 1987-08-03 SU SU874203187A patent/SU1607687A3/ru active
- 1987-08-04 PT PT85483A patent/PT85483B/pt not_active IP Right Cessation
-
1988
- 1988-11-04 SU SU884356767A patent/SU1650011A3/ru active
- 1988-11-04 SU SU884356789A patent/SU1609452A3/ru active
Also Published As
Publication number | Publication date |
---|---|
HUT46907A (en) | 1988-12-28 |
DK403287A (da) | 1988-02-05 |
NO171909B (no) | 1993-02-08 |
EP0255710A2 (en) | 1988-02-10 |
PT85483B (pt) | 1990-06-29 |
NZ221284A (en) | 1989-12-21 |
FI873350A (sv) | 1988-02-05 |
AU7650387A (en) | 1988-02-11 |
EP0255710A3 (en) | 1989-01-04 |
SU1607687A3 (ru) | 1990-11-15 |
US4868181A (en) | 1989-09-19 |
SU1609452A3 (ru) | 1990-11-23 |
HU201925B (en) | 1991-01-28 |
FI91634C (sv) | 1994-07-25 |
KR880002827A (ko) | 1988-05-11 |
DK403287D0 (da) | 1987-08-03 |
IL83413A0 (en) | 1988-01-31 |
PT85483A (en) | 1987-09-01 |
NO873240L (no) | 1988-02-05 |
AU617650B2 (en) | 1991-12-05 |
NO171909C (no) | 1993-05-19 |
KR930004648B1 (ko) | 1993-06-02 |
FI873350A0 (sv) | 1987-08-03 |
SU1650011A3 (ru) | 1991-05-15 |
NO873240D0 (no) | 1987-08-03 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
BB | Publication of examined application | ||
FD | Application lapsed | ||
MM | Patent lapsed | ||
MM | Patent lapsed |
Owner name: THE DU PONT MERCK PHARMACEUTICAL COMPANY |