PH26179A - Anti-hypertensive sulfonanilides - Google Patents

Anti-hypertensive sulfonanilides Download PDF

Info

Publication number: PH26179A
Authority: PH; Philippines
Prior art keywords: compound; formula; tetrahydro; amino; pharmaceutically acceptable
Prior art date: 1988-04-20

Application number

PH38532A

Other languages

English (en)

Inventor

John Dale Mcdermed

Anjaneyulu Seetharm Tadepalli

Kevin Patrick Hurley

Harold Stanley Freeman

Vincent Huech-Tien Chang

Original Assignee

Wellcome Found

Priority date (The priority date 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 date listed.)

1988-04-20

Filing date

1989-04-19

Publication date

1992-03-18

1989-04-19 Application filed by Wellcome Found filed Critical Wellcome Found

1992-03-18 Publication of PH26179A publication Critical patent/PH26179A/en

Links

230000003276 anti-hypertensive effect Effects 0.000 title description 5
150000001875 compounds Chemical class 0.000 claims description 179
LBTPIFQNEKOAIM-UHFFFAOYSA-N n-phenylmethanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=CC=C1 LBTPIFQNEKOAIM-UHFFFAOYSA-N 0.000 claims description 53
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 38
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 37
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 36
229910052739 hydrogen Inorganic materials 0.000 claims description 31
150000003839 salts Chemical class 0.000 claims description 28
238000000034 method Methods 0.000 claims description 22
239000001257 hydrogen Substances 0.000 claims description 17
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
-1 hydroxymethylene Chemical group 0.000 claims description 15
206010020772 Hypertension Diseases 0.000 claims description 12
125000004356 hydroxy functional group Chemical group O* 0.000 claims description 11
241000124008 Mammalia Species 0.000 claims description 9
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 8
238000011321 prophylaxis Methods 0.000 claims description 6
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 3
239000008194 pharmaceutical composition Substances 0.000 claims description 3
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VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims 1
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XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 40
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CURCMGVZNYCRNY-UHFFFAOYSA-N trimethylazanium;iodide Chemical compound I.CN(C)C CURCMGVZNYCRNY-UHFFFAOYSA-N 0.000 description 11
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HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
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239000002253 acid Substances 0.000 description 3
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208000029078 coronary artery disease Diseases 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000011461 current therapy Methods 0.000 description 1
230000002939 deleterious effect Effects 0.000 description 1
230000003205 diastolic effect Effects 0.000 description 1
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
238000002651 drug therapy Methods 0.000 description 1
238000010828 elution Methods 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
239000002702 enteric coating Substances 0.000 description 1
238000009505 enteric coating Methods 0.000 description 1
210000001105 femoral artery Anatomy 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
238000011010 flushing procedure Methods 0.000 description 1
235000013355 food flavoring agent Nutrition 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
210000001035 gastrointestinal tract Anatomy 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
230000000004 hemodynamic effect Effects 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
239000003701 inert diluent Substances 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
210000003734 kidney Anatomy 0.000 description 1
201000006370 kidney failure Diseases 0.000 description 1
239000012280 lithium aluminium hydride Substances 0.000 description 1
239000007937 lozenge Substances 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
230000014759 maintenance of location Effects 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
PSGAAPLEWMOORI-PEINSRQWSA-N medroxyprogesterone acetate Chemical compound C([C@@]12C)CC(=O)C=C1[C@@H](C)C[C@@H]1[C@@H]2CC[C@]2(C)[C@@](OC(C)=O)(C(C)=O)CC[C@H]21 PSGAAPLEWMOORI-PEINSRQWSA-N 0.000 description 1
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
235000010981 methylcellulose Nutrition 0.000 description 1
239000007932 molded tablet Substances 0.000 description 1
QUSNBJAOOMFDIB-UHFFFAOYSA-N monoethyl amine Natural products CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 1
150000004682 monohydrates Chemical class 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
QFNXQNYBIMKZLS-VIFPVBQESA-N n-[4-[(1r)-2-amino-1-hydroxyethyl]phenyl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=C([C@@H](O)CN)C=C1 QFNXQNYBIMKZLS-VIFPVBQESA-N 0.000 description 1
APOOUNCOSKLROK-UHFFFAOYSA-N n-[4-[2-(dibenzylamino)-1-hydroxyethyl]phenyl]methanesulfonamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1C(O)CN(CC=1C=CC=CC=1)CC1=CC=CC=C1 APOOUNCOSKLROK-UHFFFAOYSA-N 0.000 description 1
KOPMCORITSBDBK-QGZVFWFLSA-N n-[4-[2-[[(2r)-1-oxo-3,4-dihydro-2h-naphthalen-2-yl]methylamino]ethyl]phenyl]methanesulfonamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1CCNC[C@@H]1C(=O)C2=CC=CC=C2CC1 KOPMCORITSBDBK-QGZVFWFLSA-N 0.000 description 1
INKPULPGNNHSHF-UHFFFAOYSA-N n-benzyl-1-(1,2,3,4-tetrahydronaphthalen-2-yl)methanamine Chemical compound C1CC2=CC=CC=C2CC1CNCC1=CC=CC=C1 INKPULPGNNHSHF-UHFFFAOYSA-N 0.000 description 1
WZBCIFZVBDLSDN-UHFFFAOYSA-N n-benzyl-1-phenylmethanamine;hydrobromide Chemical compound Br.C=1C=CC=CC=1CNCC1=CC=CC=C1 WZBCIFZVBDLSDN-UHFFFAOYSA-N 0.000 description 1
UPHOVRVOOJDJEQ-UHFFFAOYSA-N n-phenyl-1,2,3,4-tetrahydronaphthalene-1-sulfonamide Chemical class C1CCC2=CC=CC=C2C1S(=O)(=O)NC1=CC=CC=C1 UPHOVRVOOJDJEQ-UHFFFAOYSA-N 0.000 description 1
229910000069 nitrogen hydride Inorganic materials 0.000 description 1
LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000002245 particle Substances 0.000 description 1
101150101567 pat-2 gene Proteins 0.000 description 1
235000021017 pears Nutrition 0.000 description 1
229960001412 pentobarbital Drugs 0.000 description 1
WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
230000008569 process Effects 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
150000003242 quaternary ammonium salts Chemical class 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000004044 response Effects 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
230000002441 reversible effect Effects 0.000 description 1
125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
238000007493 shaping process Methods 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
230000003595 spectral effect Effects 0.000 description 1
230000002269 spontaneous effect Effects 0.000 description 1
239000007858 starting material Substances 0.000 description 1
210000002784 stomach Anatomy 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
150000005846 sugar alcohols Polymers 0.000 description 1
238000001356 surgical procedure Methods 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
239000003981 vehicle Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
- C07C311/02—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C311/08—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
General Chemical & Material Sciences (AREA)
Cardiology (AREA)
Chemical Kinetics & Catalysis (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Heart & Thoracic Surgery (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Polysaccharides And Polysaccharide Derivatives (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

PH38532A 1988-04-20 1989-04-19 Anti-hypertensive sulfonanilides PH26179A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB888809314A GB8809314D0 (en)	1988-04-20	1988-04-20	Anti-hypertensive sulfonanilides

Publications (1)

Publication Number	Publication Date
PH26179A true PH26179A (en)	1992-03-18

Family

ID=10635507

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
PH38532A PH26179A (en)	1988-04-20	1989-04-19	Anti-hypertensive sulfonanilides

Country Status (22)

Country	Link
US (1)	US5102914A (da)
EP (1)	EP0338793B1 (da)
JP (1)	JPH026461A (da)
KR (1)	KR890016002A (da)
AT (1)	ATE96429T1 (da)
AU (1)	AU626850B2 (da)
CA (1)	CA1332615C (da)
DE (1)	DE68910165T2 (da)
DK (1)	DK189089A (da)
ES (1)	ES2059737T3 (da)
FI (1)	FI91398C (da)
GB (1)	GB8809314D0 (da)
HU (1)	HU204028B (da)
IL (1)	IL90043A (da)
MC (1)	MC2027A1 (da)
MX (1)	MX9203218A (da)
MY (1)	MY105138A (da)
NO (1)	NO173010C (da)
NZ (1)	NZ228803A (da)
PH (1)	PH26179A (da)
PT (1)	PT90307B (da)
ZA (1)	ZA892880B (da)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5194450A (en) *	1988-04-20	1993-03-16	Burroughs Wellcome Co.	Anti-hypertensive sulfonanilides
US5360822A (en) *	1990-02-07	1994-11-01	Nippon Shinyaku Co. Ltd.	Sulfonanilide derivatives and medicine
HUT63827A (en) *	1990-02-07	1993-10-28	Nippon Shinyaku Co Ltd	Process for producing sulfonanilide derivatives and pharmaceutical compositions comprising same
GB9020695D0 (en) *	1990-09-22	1990-11-07	Wellcome Found	Anti-hypertensive tetralins
US5508306A (en) *	1992-11-13	1996-04-16	Synaptic Pharmaceutical Corporation	Aromatic amine derivatives
DE19604191A1 (de) *	1996-02-06	1997-08-07	Hoechst Schering Agrevo Gmbh	2,4-Diamino-1,3,5-triazine, Verfahren zu deren Herstellung und deren Verwendung als Herbizide und Pflanzenwachstumsregulatoren

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE1962497C3 (de) *	1969-12-12	1979-09-20	C.H. Boehringer Sohn, 6507 Ingelheim	Naphthylalkyl- a -hydroxyphenäthyl-amine, ihre Herstellung und diese enthaltende Arzneimittel
US4044150A (en) *	1976-06-18	1977-08-23	Mead Johnson & Company	Antihypertensive 4'-[1-hydroxy-2-[(1-phenoxy ethyl)-amino]ethyl]methanesulfonanilide and salts thereof and therapeutic use
GB2185741B (en) *	1986-01-27	1989-10-25	American Home Prod	Heterocyclic sulphonamides
EG18188A (en) *	1986-05-01	1992-09-30	Pfizer Ltd	Process for preparation anti-arhythmia agents
DE3630903A1 (de) *	1986-09-11	1988-03-24	Thomae Gmbh Dr K	Neue tetrahydronaphthalin- und indanderivate, verfahren zu deren herstellung sowie diese enthaltende arzneimittel
GB8707123D0 (en) *	1987-03-25	1987-04-29	Pfizer Ltd	Antiarrhythmic agents

1988
- 1988-04-20 GB GB888809314A patent/GB8809314D0/en active Pending
1989
- 1989-04-19 AT AT89303862T patent/ATE96429T1/de not_active IP Right Cessation
- 1989-04-19 AU AU33221/89A patent/AU626850B2/en not_active Ceased
- 1989-04-19 NO NO891609A patent/NO173010C/no unknown
- 1989-04-19 PT PT90307A patent/PT90307B/pt not_active IP Right Cessation
- 1989-04-19 NZ NZ228803A patent/NZ228803A/xx unknown
- 1989-04-19 FI FI891866A patent/FI91398C/fi not_active IP Right Cessation
- 1989-04-19 DK DK189089A patent/DK189089A/da not_active Application Discontinuation
- 1989-04-19 MC MC892046A patent/MC2027A1/fr unknown
- 1989-04-19 CA CA000597117A patent/CA1332615C/en not_active Expired - Fee Related
- 1989-04-19 KR KR1019890005237A patent/KR890016002A/ko not_active Ceased
- 1989-04-19 ES ES89303862T patent/ES2059737T3/es not_active Expired - Lifetime
- 1989-04-19 PH PH38532A patent/PH26179A/en unknown
- 1989-04-19 JP JP1097714A patent/JPH026461A/ja active Pending
- 1989-04-19 MY MYPI89000502A patent/MY105138A/en unknown
- 1989-04-19 EP EP89303862A patent/EP0338793B1/en not_active Expired - Lifetime
- 1989-04-19 DE DE89303862T patent/DE68910165T2/de not_active Expired - Fee Related
- 1989-04-19 IL IL9004389A patent/IL90043A/en unknown
- 1989-04-19 HU HU891909A patent/HU204028B/hu not_active IP Right Cessation
- 1989-04-19 ZA ZA892880A patent/ZA892880B/xx unknown
- 1989-12-18 US US07/455,909 patent/US5102914A/en not_active Expired - Fee Related
1992
- 1992-06-24 MX MX9203218A patent/MX9203218A/es unknown

Also Published As

Publication number	Publication date
HU204028B (en)	1991-11-28
ATE96429T1 (de)	1993-11-15
FI91398B (fi)	1994-03-15
AU3322189A (en)	1989-10-26
AU626850B2 (en)	1992-08-13
ZA892880B (en)	1990-12-28
FI891866L (fi)	1989-10-21
DK189089A (da)	1989-10-21
MC2027A1 (fr)	1990-04-25
NZ228803A (en)	1992-01-29
US5102914A (en)	1992-04-07
DK189089D0 (da)	1989-04-19
KR890016002A (ko)	1989-11-27
CA1332615C (en)	1994-10-18
NO173010B (no)	1993-07-05
MY105138A (en)	1994-08-30
NO891609L (no)	1989-10-23
ES2059737T3 (es)	1994-11-16
EP0338793A2 (en)	1989-10-25
PT90307A (pt)	1989-11-10
GB8809314D0 (en)	1988-05-25
DE68910165D1 (de)	1993-12-02
PT90307B (pt)	1994-09-30
HUT51600A (en)	1990-05-28
MX9203218A (es)	1992-07-01
FI91398C (fi)	1994-06-27
EP0338793A3 (en)	1991-01-02
IL90043A0 (en)	1989-12-15
NO173010C (no)	1993-10-13
NO891609D0 (no)	1989-04-19
FI891866A0 (fi)	1989-04-19
JPH026461A (ja)	1990-01-10
EP0338793B1 (en)	1993-10-27
IL90043A (en)	1995-01-24
DE68910165T2 (de)	1994-04-28

Publication	Publication Date	Title
EP0125783B1 (en)	1989-01-04	Dopamine-beta-hydroxylase inhibitors
JPH0261465B2 (da)	1990-12-20
EP0534859A1 (fr)	1993-03-31	3-Benzazépin-zones substituées par un groupe benzocyclobutyl- ou indanyl-alkyl-amino-alkyle, utiles dans le traitement des affections cardiovasculaires
JPS5989625A (ja)	1984-05-23	芳香族置換環状アミジン止瀉剤
PH26179A (en)	1992-03-18	Anti-hypertensive sulfonanilides
US5196454A (en)	1993-03-23	Method of treating disorders of the dopaminergic systems using 2,5-diaminotetralines
US5194450A (en)	1993-03-16	Anti-hypertensive sulfonanilides
JPS58116434A (ja)	1983-07-11	置換されたフエノキシアルカノ−ルアミン類及びフエノキシアルカノ−ル−シクロアルキルアミン類
JPH04266875A (ja)	1992-09-22	新規なイミダゾール化合物、その製造方法およびこれらの化合物を含有する医薬組成物
CA1235417A (en)	1988-04-19	2-(n-pyrrolidino)-3-isobutoxy-n-substituted phenyl-n- benzyl-propylamines, their preparation and pharmaceutical use
US5405872A (en)	1995-04-11	Anti-hypertensive tetralins
JPH04253954A (ja)	1992-09-09	新規な８−スルファミルメチレン−２−アミノテトラリン類
EP0318234A2 (en)	1989-05-31	Improvements in or relating to selective serotonin uptake inhibitors
WO1995000492A1 (en)	1995-01-05	Enantiomers of 4-(5-fluoro-2,3-dihydro-1h-inden-2-yl)-1h-imidazole
KR900005021B1 (ko)	1990-07-18	1-펜옥시-3-히드록시 인돌릴 알킬아미노-3-프로판올류 및 그 제조방법
US4421917A (en)	1983-12-20	Derivatives of 2-ureido-7-phenylhexahydrobenzo[a]quinolizines
EP1131293A1 (fr)	2001-09-12	Derives de 1-aminoethylquinoleine pour le traitement de l'incontinence urinaire
JP2002532481A (ja)	2002-10-02	５−ｈｔ１ａ受容体活性を有するピペラジンエチルアミド誘導体
JPS63303965A (ja)	1988-12-12	モノアミンオキシダーゼ（ＭＡＯ）抑制用前駆薬としてのβ−（フルオロメチレン）−５−ヒドロキシトリプトファン及び誘導体類
JPH07165729A (ja)	1995-06-27	新規なベンゾスピロアルケン誘導体、それらの製造法及びそれら誘導体を含有する製剤組成物