ZA200302516B - Indoline derivatives and their use as 5-HT2 receptor ligands. - Google Patents

Indoline derivatives and their use as 5-HT2 receptor ligands. Download PDF

Info

Publication number: ZA200302516B
Authority: ZA; South Africa
Prior art keywords: composition; substance; diabetes; treatment; disorders
Prior art date: 2000-10-16

Application number

ZA200302516A

Other languages

English (en)

Inventor

Jonathan Mark Bentley

Howard Langham Mansell

James Edward Paul Davidson

Nathaniel Julius Thomas Monck

Original Assignee

Hoffmann La Roche

Vernalis Res Ltd

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.)

2000-10-16

Filing date

2003-03-31

Publication date

2004-06-30

2003-03-31 Application filed by Hoffmann La Roche, Vernalis Res Ltd filed Critical Hoffmann La Roche

2004-06-30 Publication of ZA200302516B publication Critical patent/ZA200302516B/en

Links

125000003387 indolinyl group Chemical class N1(CCC2=CC=CC=C12)* 0.000 title claims description 4
239000003446 ligand Substances 0.000 title description 5
108091005479 5-HT2 receptors Proteins 0.000 title description 2
102000056834 5-HT2 Serotonin Receptors Human genes 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 60
238000000034 method Methods 0.000 claims description 41
238000011282 treatment Methods 0.000 claims description 41
206010012601 diabetes mellitus Diseases 0.000 claims description 28
125000000217 alkyl group Chemical group 0.000 claims description 20
208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 19
229910052739 hydrogen Inorganic materials 0.000 claims description 17
239000001257 hydrogen Substances 0.000 claims description 17
208000008589 Obesity Diseases 0.000 claims description 16
235000020824 obesity Nutrition 0.000 claims description 16
229940086609 Lipase inhibitor Drugs 0.000 claims description 14
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 14
-1 alkylsulfoxyl Chemical group 0.000 claims description 12
125000000753 cycloalkyl group Chemical group 0.000 claims description 11
208000035475 disorder Diseases 0.000 claims description 11
125000003545 alkoxy group Chemical group 0.000 claims description 10
229910052736 halogen Inorganic materials 0.000 claims description 10
150000002367 halogens Chemical group 0.000 claims description 10
230000002265 prevention Effects 0.000 claims description 9
206010067584 Type 1 diabetes mellitus Diseases 0.000 claims description 7
125000003342 alkenyl group Chemical group 0.000 claims description 7
125000006193 alkinyl group Chemical group 0.000 claims description 7
208000002249 Diabetes Complications Diseases 0.000 claims description 6
206010012655 Diabetic complications Diseases 0.000 claims description 6
208000016222 Pancreatic disease Diseases 0.000 claims description 6
125000003118 aryl group Chemical group 0.000 claims description 6
125000001072 heteroaryl group Chemical group 0.000 claims description 6
201000001421 hyperglycemia Diseases 0.000 claims description 6
AHLBNYSZXLDEJQ-FWEHEUNISA-N orlistat Chemical group CCCCCCCCCCC[C@H](OC(=O)[C@H](CC(C)C)NC=O)C[C@@H]1OC(=O)[C@H]1CCCCCC AHLBNYSZXLDEJQ-FWEHEUNISA-N 0.000 claims description 6
150000003431 steroids Chemical class 0.000 claims description 6
208000024172 Cardiovascular disease Diseases 0.000 claims description 5
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
208000015114 central nervous system disease Diseases 0.000 claims description 5
125000004093 cyano group Chemical group *C#N 0.000 claims description 5
229960001243 orlistat Drugs 0.000 claims description 5
229920006395 saturated elastomer Polymers 0.000 claims description 5
238000002560 therapeutic procedure Methods 0.000 claims description 5
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
125000002837 carbocyclic group Chemical group 0.000 claims description 4
125000001153 fluoro group Chemical group F* 0.000 claims description 4
125000001188 haloalkyl group Chemical group 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
125000004414 alkyl thio group Chemical group 0.000 claims description 3
125000004429 atom Chemical group 0.000 claims description 3
125000001309 chloro group Chemical group Cl* 0.000 claims description 3
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
125000005224 heteroarylcarbonylamino group Chemical group 0.000 claims description 3
125000005842 heteroatom Chemical group 0.000 claims description 3
125000000623 heterocyclic group Chemical group 0.000 claims description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 2
125000004658 aryl carbonyl amino group Chemical group 0.000 claims description 2
125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 2
125000004104 aryloxy group Chemical group 0.000 claims description 2
125000000000 cycloalkoxy group Chemical group 0.000 claims description 2
125000004663 dialkyl amino group Chemical group 0.000 claims description 2
150000002148 esters Chemical class 0.000 claims description 2
125000005553 heteroaryloxy group Chemical group 0.000 claims description 2
125000005226 heteroaryloxycarbonyl group Chemical group 0.000 claims description 2
229910052760 oxygen Inorganic materials 0.000 claims description 2
239000008194 pharmaceutical composition Substances 0.000 claims description 2
150000003839 salts Chemical class 0.000 claims description 2
229910052717 sulfur Inorganic materials 0.000 claims description 2
239000000203 mixture Substances 0.000 claims 38
239000000126 substance Substances 0.000 claims 35
239000003814 drug Substances 0.000 claims 10
150000002431 hydrogen Chemical class 0.000 claims 9
238000004519 manufacturing process Methods 0.000 claims 8
210000003169 central nervous system Anatomy 0.000 claims 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 6
238000011321 prophylaxis Methods 0.000 claims 6
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206010000117 Abnormal behaviour Diseases 0.000 claims 4
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206010006550 Bulimia nervosa Diseases 0.000 claims 2
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206010012289 Dementia Diseases 0.000 claims 2
208000026139 Memory disease Diseases 0.000 claims 2
201000009906 Meningitis Diseases 0.000 claims 2
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102100026383 Vasopressin-neurophysin 2-copeptin Human genes 0.000 claims 2
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230000008733 trauma Effects 0.000 claims 2
238000006243 chemical reaction Methods 0.000 claims 1
239000003153 chemical reaction reagent Substances 0.000 claims 1
125000004852 dihydrofuranyl group Chemical group O1C(CC=C1)* 0.000 claims 1
125000005043 dihydropyranyl group Chemical group O1C(CCC=C1)* 0.000 claims 1
239000003937 drug carrier Substances 0.000 claims 1
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
125000001041 indolyl group Chemical group 0.000 claims 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
125000002757 morpholinyl group Chemical group 0.000 claims 1
125000003386 piperidinyl group Chemical group 0.000 claims 1
125000006239 protecting group Chemical group 0.000 claims 1
238000005932 reductive alkylation reaction Methods 0.000 claims 1
125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 1
125000001412 tetrahydropyranyl group Chemical group 0.000 claims 1
QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 18
VHFVKMTVMIZMIK-UHFFFAOYSA-N 1-(3-chlorophenyl)piperazine Chemical compound ClC1=CC=CC(N2CCNCC2)=C1 VHFVKMTVMIZMIK-UHFFFAOYSA-N 0.000 description 6
239000000883 anti-obesity agent Substances 0.000 description 5
229940125710 antiobesity agent Drugs 0.000 description 5
125000004432 carbon atom Chemical group C* 0.000 description 5
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235000012631 food intake Nutrition 0.000 description 5
108020003175 receptors Proteins 0.000 description 5
102000005962 receptors Human genes 0.000 description 5
230000037396 body weight Effects 0.000 description 4
125000004435 hydrogen atom Chemical class [H]* 0.000 description 4
230000007423 decrease Effects 0.000 description 3
201000010099 disease Diseases 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
125000004356 hydroxy functional group Chemical group O* 0.000 description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
239000000018 receptor agonist Substances 0.000 description 3
229940044601 receptor agonist Drugs 0.000 description 3
DBGIVFWFUFKIQN-UHFFFAOYSA-N (+-)-Fenfluramine Chemical compound CCNC(C)CC1=CC=CC(C(F)(F)F)=C1 DBGIVFWFUFKIQN-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
206010033307 Overweight Diseases 0.000 description 2
241000700159 Rattus Species 0.000 description 2
210000000577 adipose tissue Anatomy 0.000 description 2
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125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 2
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
230000003247 decreasing effect Effects 0.000 description 2
229960001582 fenfluramine Drugs 0.000 description 2
125000002541 furyl group Chemical group 0.000 description 2
125000001183 hydrocarbyl group Chemical group 0.000 description 2
NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
125000004076 pyridyl group Chemical group 0.000 description 2
229960004425 sibutramine Drugs 0.000 description 2
UNAANXDKBXWMLN-UHFFFAOYSA-N sibutramine Chemical compound C=1C=C(Cl)C=CC=1C1(C(N(C)C)CC(C)C)CCC1 UNAANXDKBXWMLN-UHFFFAOYSA-N 0.000 description 2
125000001544 thienyl group Chemical group 0.000 description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
DBGIVFWFUFKIQN-VIFPVBQESA-N (+)-Fenfluramine Chemical compound CCN[C@@H](C)CC1=CC=CC(C(F)(F)F)=C1 DBGIVFWFUFKIQN-VIFPVBQESA-N 0.000 description 1
IAZKTAKWBHQCGF-UHFFFAOYSA-N 1,2,3,3a-tetrahydrocyclopenta[b]indole Chemical compound N1=C2C=CC=CC2=C2C1CCC2 IAZKTAKWBHQCGF-UHFFFAOYSA-N 0.000 description 1
HZDXFZHFEASSBM-UHFFFAOYSA-N 1,2,3,4-tetrahydrocyclopenta[b]indole Chemical class N1C2=CC=CC=C2C2=C1CCC2 HZDXFZHFEASSBM-UHFFFAOYSA-N 0.000 description 1
QUERAHCHJWZYJF-UHFFFAOYSA-N 1-(1h-indol-2-yl)ethanamine Chemical class C1=CC=C2NC(C(N)C)=CC2=C1 QUERAHCHJWZYJF-UHFFFAOYSA-N 0.000 description 1
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KKIMDKMETPPURN-UHFFFAOYSA-N 1-(3-(trifluoromethyl)phenyl)piperazine Chemical compound FC(F)(F)C1=CC=CC(N2CCNCC2)=C1 KKIMDKMETPPURN-UHFFFAOYSA-N 0.000 description 1
DGNLGWJZZZOYPT-UHFFFAOYSA-N 1-[3-(trifluoromethyl)phenyl]piperazin-1-ium;chloride Chemical compound [Cl-].FC(F)(F)C1=CC=CC(N2CC[NH2+]CC2)=C1 DGNLGWJZZZOYPT-UHFFFAOYSA-N 0.000 description 1
XKLNOVWDVMWTOB-UHFFFAOYSA-N 2,3,4,9-tetrahydro-1h-carbazole Chemical class N1C2=CC=CC=C2C2=C1CCCC2 XKLNOVWDVMWTOB-UHFFFAOYSA-N 0.000 description 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
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NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
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QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
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125000001246 bromo group Chemical group Br* 0.000 description 1
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125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
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125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
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125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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Classifications

- 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
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/94—[b, c]- or [b, d]-condensed containing carbocyclic rings other than six-membered
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
- 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
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
- 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
- A61P3/00—Drugs for disorders of the metabolism
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- A61P3/00—Drugs for disorders of the metabolism
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- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
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- 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

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ZA200302516A 2000-10-16 2003-03-31 Indoline derivatives and their use as 5-HT2 receptor ligands. ZA200302516B (en)

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EP00122539		2000-10-16

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EP (1)	EP1328515B1 (es)
JP (1)	JP4047723B2 (es)
KR (1)	KR100545435B1 (es)
CN (1)	CN100334076C (es)
AR (1)	AR038762A1 (es)
AT (1)	ATE403647T1 (es)
AU (2)	AU2167002A (es)
BR (1)	BR0114708A (es)
CA (1)	CA2422698C (es)
DE (1)	DE60135239D1 (es)
ES (1)	ES2311563T3 (es)
MX (1)	MXPA03003246A (es)
WO (1)	WO2002044152A1 (es)
ZA (1)	ZA200302516B (es)

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2001
- 2001-10-12 EP EP01998144A patent/EP1328515B1/en not_active Expired - Lifetime
- 2001-10-12 CA CA002422698A patent/CA2422698C/en not_active Expired - Fee Related
- 2001-10-12 AT AT01998144T patent/ATE403647T1/de not_active IP Right Cessation
- 2001-10-12 KR KR1020037005300A patent/KR100545435B1/ko not_active Expired - Fee Related
- 2001-10-12 JP JP2002546522A patent/JP4047723B2/ja not_active Expired - Fee Related
- 2001-10-12 BR BR0114708-0A patent/BR0114708A/pt not_active IP Right Cessation
- 2001-10-12 AU AU2167002A patent/AU2167002A/xx active Pending
- 2001-10-12 ES ES01998144T patent/ES2311563T3/es not_active Expired - Lifetime
- 2001-10-12 DE DE60135239T patent/DE60135239D1/de not_active Expired - Lifetime
- 2001-10-12 AR ARP010104806A patent/AR038762A1/es unknown
- 2001-10-12 AU AU2002221670A patent/AU2002221670B2/en not_active Ceased
- 2001-10-12 CN CNB018174434A patent/CN100334076C/zh not_active Expired - Fee Related
- 2001-10-12 MX MXPA03003246A patent/MXPA03003246A/es active IP Right Grant
- 2001-10-12 WO PCT/EP2001/011814 patent/WO2002044152A1/en active IP Right Grant
- 2001-10-15 US US09/977,783 patent/US6479534B1/en not_active Expired - Fee Related
2003
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Also Published As

Publication number	Publication date
US20020183349A1 (en)	2002-12-05
CN1630636A (zh)	2005-06-22
JP4047723B2 (ja)	2008-02-13
AR038762A1 (es)	2005-01-26
EP1328515A1 (en)	2003-07-23
AU2167002A (en)	2002-06-11
JP2004527467A (ja)	2004-09-09
MXPA03003246A (es)	2003-06-06
BR0114708A (pt)	2003-07-01
EP1328515B1 (en)	2008-08-06
CN100334076C (zh)	2007-08-29
KR100545435B1 (ko)	2006-01-24
CA2422698C (en)	2009-12-15
DE60135239D1 (de)	2008-09-18
ES2311563T3 (es)	2009-02-16
ATE403647T1 (de)	2008-08-15
WO2002044152A1 (en)	2002-06-06
CA2422698A1 (en)	2002-06-06
KR20030048437A (ko)	2003-06-19
US6479534B1 (en)	2002-11-12
AU2002221670B2 (en)	2006-11-02

Publication	Publication Date	Title
ZA200302516B (en)	2004-06-30	Indoline derivatives and their use as 5-HT2 receptor ligands.
US7253281B2 (en)	2007-08-07	Anti-obesity 1,2,3,4,10,10a-hexahydropyrazino[1,2-a]indoles
AU2002228007B8 (en)	2002-07-08	Indole derivatives and their use as 5-HT2b and 5-HT2c receptor ligands
AU2002221670A1 (en)	2002-08-15	Indoline derivatives and their use as 5-HT2 receptor ligands
US7323487B2 (en)	2008-01-29	Condensed indoline derivatives and their use as 5HT, in particular 5HT2C, receptor ligands
US6365598B1 (en)	2002-04-02	Pyrroloquinolines for treatment of obesity
ZA200304346B (en)	2004-09-03	Piperazine derivatives.
US6844345B2 (en)	2005-01-18	Piperazine derivatives
AU2002228007A1 (en)	2003-01-23	Indole derivatives and their use as 5-HT2b and 5-HT2c receptor ligands
AU2002304833A1 (en)	2003-03-20	Tetrahydro-pyrazino (1,2-A) indoles for the treatment of central nervous disorders
WO2000012482A2 (en)	2000-03-09	Indazole derivatives with 5-ht2 receptor activity
ZA200305007B (en)	2004-09-27	Indole derivatives and their use as 5-HT2B and 5-HT2C receptor ligands.