NO309648B1 - Indolderivat og farmasöytisk preparat inneholdende dette - Google Patents

Indolderivat og farmasöytisk preparat inneholdende dette Download PDF

Info

Publication number: NO309648B1
Authority: NO; Norway
Prior art keywords: group; salt; hydrogen atom; formula; ethanol
Prior art date: 1994-11-29

Application number

NO972427A

Other languages

English (en)

Norwegian (no)

Other versions

NO972427D0 (no

NO972427L (no

Inventor

Shiro Kato

Hiroshi Harada

Yoshimi Hirokawa

Naoyuki Yoshida

Hitoshi Kawashima

Original Assignee

Dainippon Pharmaceutical Co

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.)

1994-11-29

Filing date

1997-05-28

Publication date

2001-03-05

1997-05-28 Application filed by Dainippon Pharmaceutical Co filed Critical Dainippon Pharmaceutical Co

1997-05-28 Publication of NO972427D0 publication Critical patent/NO972427D0/no

1997-07-28 Publication of NO972427L publication Critical patent/NO972427L/no

2001-03-05 Publication of NO309648B1 publication Critical patent/NO309648B1/no

Links

150000002475 indoles Chemical class 0.000 title claims abstract description 21
239000000825 pharmaceutical preparation Substances 0.000 title claims description 4
150000001875 compounds Chemical class 0.000 claims abstract description 132
150000003839 salts Chemical class 0.000 claims abstract description 45
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 22
125000003545 alkoxy group Chemical group 0.000 claims abstract description 18
125000000217 alkyl group Chemical group 0.000 claims abstract description 18
238000011282 treatment Methods 0.000 claims abstract description 10
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 9
125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims abstract description 8
206010012601 diabetes mellitus Diseases 0.000 claims abstract description 8
208000008589 Obesity Diseases 0.000 claims abstract description 6
235000020824 obesity Nutrition 0.000 claims abstract description 6
239000002269 analeptic agent Substances 0.000 claims abstract description 5
125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 4
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 3
-1 methoxycarbonylmethoxy group Chemical group 0.000 claims description 22
230000000694 effects Effects 0.000 claims description 21
125000001041 indolyl group Chemical group 0.000 claims description 11
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
YJSBONOKYYPFLW-UHFFFAOYSA-N 1-(3-chlorophenyl)-2-[1-(7-methoxy-1h-indol-3-yl)propan-2-ylamino]ethanol Chemical compound C=1NC=2C(OC)=CC=CC=2C=1CC(C)NCC(O)C1=CC=CC(Cl)=C1 YJSBONOKYYPFLW-UHFFFAOYSA-N 0.000 claims description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
230000003287 optical effect Effects 0.000 claims description 8
JIQLFJFMURQOMY-UHFFFAOYSA-N 1-(3-chlorophenyl)-2-[1-(7-ethoxy-1h-indol-3-yl)propan-2-ylamino]ethanol Chemical compound C=1NC=2C(OCC)=CC=CC=2C=1CC(C)NCC(O)C1=CC=CC(Cl)=C1 JIQLFJFMURQOMY-UHFFFAOYSA-N 0.000 claims description 6
125000002252 acyl group Chemical group 0.000 claims description 4
125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 4
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
239000003085 diluting agent Substances 0.000 claims description 4
239000003814 drug Substances 0.000 claims description 4
239000003937 drug carrier Substances 0.000 claims description 4
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
125000004093 cyano group Chemical group *C#N 0.000 claims description 3
229940079593 drug Drugs 0.000 claims description 3
125000005843 halogen group Chemical group 0.000 claims description 3
GBDSYNHPPHBHMR-UHFFFAOYSA-N methyl 2-[[3-[2-[[2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-1h-indol-7-yl]oxy]acetate Chemical compound C=1NC=2C(OCC(=O)OC)=CC=CC=2C=1CC(C)NCC(O)C1=CC=CC(Cl)=C1 GBDSYNHPPHBHMR-UHFFFAOYSA-N 0.000 claims description 3
FHEYFIGWYQJVDR-UHFFFAOYSA-N 2-[[3-[2-[[2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-1h-indol-7-yl]oxy]acetic acid Chemical compound C=1NC2=C(OCC(O)=O)C=CC=C2C=1CC(C)NCC(O)C1=CC=CC(Cl)=C1 FHEYFIGWYQJVDR-UHFFFAOYSA-N 0.000 claims description 2
125000006263 dimethyl aminosulfonyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])S(*)(=O)=O 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
239000004480 active ingredient Substances 0.000 claims 3
229910052801 chlorine Inorganic materials 0.000 claims 2
125000001309 chloro group Chemical group Cl* 0.000 claims 2
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 2
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims 2
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 1
108060003345 Adrenergic Receptor Proteins 0.000 abstract description 10
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230000003389 potentiating effect Effects 0.000 abstract description 4
229910052739 hydrogen Inorganic materials 0.000 abstract description 3
239000001257 hydrogen Substances 0.000 abstract description 3
238000011321 prophylaxis Methods 0.000 abstract description 3
229910052736 halogen Inorganic materials 0.000 abstract 2
150000002367 halogens Chemical group 0.000 abstract 2
150000002431 hydrogen Chemical group 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
239000000203 mixture Substances 0.000 description 38
238000000034 method Methods 0.000 description 36
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
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238000006243 chemical reaction Methods 0.000 description 19
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125000001424 substituent group Chemical group 0.000 description 16
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108010079452 beta Adrenergic Receptors Proteins 0.000 description 14
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239000007858 starting material Substances 0.000 description 12
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239000002253 acid Substances 0.000 description 10
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229910052799 carbon Inorganic materials 0.000 description 5
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KUHIPKQZKIIHEH-UHFFFAOYSA-N 1-(7-methoxy-1h-indol-3-yl)propan-2-amine Chemical compound COC1=CC=CC2=C1NC=C2CC(C)N KUHIPKQZKIIHEH-UHFFFAOYSA-N 0.000 description 4
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GBDSYNHPPHBHMR-PKDNWHCCSA-N methyl 2-[[3-[2-[[(2r)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-1h-indol-7-yl]oxy]acetate Chemical compound C1([C@@H](O)CNC(C)CC=2C=3C=CC=C(C=3NC=2)OCC(=O)OC)=CC=CC(Cl)=C1 GBDSYNHPPHBHMR-PKDNWHCCSA-N 0.000 description 1
QABLOFMHHSOFRJ-UHFFFAOYSA-N methyl 2-chloroacetate Chemical compound COC(=O)CCl QABLOFMHHSOFRJ-UHFFFAOYSA-N 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
235000010981 methylcellulose Nutrition 0.000 description 1
238000002156 mixing Methods 0.000 description 1
HZAXFHJVJLSVMW-UHFFFAOYSA-N monoethanolamine hydrochloride Natural products NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
230000008693 nausea Effects 0.000 description 1
210000005036 nerve Anatomy 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
MCSAJNNLRCFZED-UHFFFAOYSA-N nitroethane Chemical compound CC[N+]([O-])=O MCSAJNNLRCFZED-UHFFFAOYSA-N 0.000 description 1
239000002736 nonionic surfactant Substances 0.000 description 1
231100000956 nontoxicity Toxicity 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
206010033675 panniculitis Diseases 0.000 description 1
208000011906 peptic ulcer disease Diseases 0.000 description 1
238000009519 pharmacological trial Methods 0.000 description 1
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
229910003446 platinum oxide Inorganic materials 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229960003975 potassium Drugs 0.000 description 1
229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
239000011736 potassium bicarbonate Substances 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
LJCNRYVRMXRIQR-OLXYHTOASA-L potassium sodium L-tartrate Chemical compound [Na+].[K+].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O LJCNRYVRMXRIQR-OLXYHTOASA-L 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
230000002335 preservative effect Effects 0.000 description 1
230000008569 process Effects 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000000611 regression analysis Methods 0.000 description 1
238000001226 reprecipitation Methods 0.000 description 1
230000004044 response Effects 0.000 description 1
210000005245 right atrium Anatomy 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 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
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
239000001476 sodium potassium tartrate Substances 0.000 description 1
235000011006 sodium potassium tartrate Nutrition 0.000 description 1
GWPHPSXTZZEXJK-UHFFFAOYSA-M sodium;2-[[3-[2-[[2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-1h-indol-6-yl]oxy]acetate Chemical compound [Na+].C=1NC2=CC(OCC([O-])=O)=CC=C2C=1CC(C)NCC(O)C1=CC=CC(Cl)=C1 GWPHPSXTZZEXJK-UHFFFAOYSA-M 0.000 description 1
239000007787 solid Substances 0.000 description 1
230000002269 spontaneous effect Effects 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
230000004936 stimulating effect Effects 0.000 description 1
238000003756 stirring Methods 0.000 description 1
210000004304 subcutaneous tissue Anatomy 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
230000002889 sympathetic effect Effects 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 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
230000009466 transformation Effects 0.000 description 1
229910052723 transition metal Inorganic materials 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
208000001072 type 2 diabetes mellitus Diseases 0.000 description 1
239000005526 vasoconstrictor agent Substances 0.000 description 1
210000001835 viscera Anatomy 0.000 description 1
230000008673 vomiting Effects 0.000 description 1
239000001993 wax Substances 0.000 description 1
210000000636 white adipocyte Anatomy 0.000 description 1

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
- C07D209/02—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
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
- 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
- A61P3/04—Anorexiants; Antiobesity agents
- 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
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
- 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

Landscapes

Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Diabetes (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Engineering & Computer Science (AREA)
General Chemical & Material Sciences (AREA)
Veterinary Medicine (AREA)
Bioinformatics & Cheminformatics (AREA)
Hematology (AREA)
Obesity (AREA)
Emergency Medicine (AREA)
Endocrinology (AREA)
Child & Adolescent Psychology (AREA)
Indole Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

NO972427A 1994-11-29 1997-05-28 Indolderivat og farmasöytisk preparat inneholdende dette NO309648B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
JP06321402		1994-11-29
PCT/JP1995/002400 WO1996016938A1 (en)	1994-11-29	1995-11-27	Indole derivative

Publications (3)

Publication Number	Publication Date
NO972427D0 NO972427D0 (no)	1997-05-28
NO972427L NO972427L (no)	1997-07-28
NO309648B1 true NO309648B1 (no)	2001-03-05

Family

ID=18132155

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO972427A NO309648B1 (no)	1994-11-29	1997-05-28	Indolderivat og farmasöytisk preparat inneholdende dette

Country Status (29)

Country	Link
US (1)	US5817689A (cs)
EP (1)	EP0801059B1 (cs)
JP (1)	JP3100165B2 (cs)
KR (1)	KR100388747B1 (cs)
CN (1)	CN1070477C (cs)
AT (1)	ATE202559T1 (cs)
AU (1)	AU688165B2 (cs)
BR (1)	BR9509827A (cs)
CA (1)	CA2206307A1 (cs)
CY (1)	CY2247B1 (cs)
CZ (1)	CZ290871B6 (cs)
DE (1)	DE69521529T2 (cs)
DK (1)	DK0801059T3 (cs)
ES (1)	ES2159648T3 (cs)
FI (1)	FI972275A0 (cs)
GR (1)	GR3036148T3 (cs)
HK (1)	HK1003886A1 (cs)
HU (1)	HUT77308A (cs)
IL (1)	IL116178A (cs)
NO (1)	NO309648B1 (cs)
NZ (1)	NZ295749A (cs)
PL (1)	PL181963B1 (cs)
PT (1)	PT801059E (cs)
RO (1)	RO118426B1 (cs)
RU (1)	RU2137759C1 (cs)
SK (1)	SK281865B6 (cs)
TW (1)	TW349091B (cs)
WO (1)	WO1996016938A1 (cs)
ZA (1)	ZA9510130B (cs)

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PE20010580A1 (es) *	1999-09-03	2001-05-25	Takeda Chemical Industries Ltd	Composicion farmaceutica para tratar la diabetes
WO2001040182A2 (en) *	1999-11-30	2001-06-07	Dainippon Pharmaceutical Co., Ltd.	Solid pharmaceutical preparation
US6458824B1 (en) *	1999-11-30	2002-10-01	Dainippon Pharmaceutical Co., Ltd.	Solid preparation
JP2004331500A (ja) *	2001-02-16	2004-11-25	Dainippon Pharmaceut Co Ltd	血中濃度制御製剤
EP2335700A1 (en) *	2001-07-25	2011-06-22	Boehringer Ingelheim (Canada) Ltd.	Hepatitis C virus polymerase inhibitors with a heterobicylic structure
AU2003225277A1 (en) *	2002-05-02	2003-11-17	Robert Harris	Lipid removal from the body
CA2488699A1 (en) *	2002-06-12	2003-12-24	Sumitomo Pharmaceuticals Co., Ltd.	Indole, indazole, and benzazole derivative
SI1599468T1 (sl) *	2003-01-14	2008-02-29	Arena Pharm Inc	1,2,3-trisubstituirani arilni in heteroarilni derivati kot modulatorji metabolizma ter profilaksa in zdravljenje motenj v zvezi z njim, kot diabetesain hiperglikemije
AU2004205642C1 (en) *	2003-01-14	2012-01-12	Arena Pharmaceuticals, Inc.	1,2,3-trisubstituted aryl and heteroaryl derivatives as modulators of metabolism and the prophylaxis and treatment of disorders related thereto such as diabetes and hyperglycemia
US7098231B2 (en)	2003-01-22	2006-08-29	Boehringer Ingelheim International Gmbh	Viral polymerase inhibitors
US7223785B2 (en)	2003-01-22	2007-05-29	Boehringer Ingelheim International Gmbh	Viral polymerase inhibitors
WO2004089936A1 (ja) *	2003-04-10	2004-10-21	Dainippon Pharmaceutical Co., Ltd.	ヘテロアリールスルホン酸アニリド誘導体及びそれを含有する医薬組成物
AR045047A1 (es)	2003-07-11	2005-10-12	Arena Pharm Inc	Derivados arilo y heteroarilo trisustituidos como moduladores del metabolismo y de la profilaxis y tratamiento de desordenes relacionados con los mismos
CA2553879C (en)	2004-02-20	2011-02-22	Boehringer Ingelheim International Gmbh	Viral polymerase inhibitors
MY148521A (en)	2005-01-10	2013-04-30	Arena Pharm Inc	Substituted pyridinyl and pyrimidinyl derivatives as modulators of metabolism and the treatment of disorders related thereto
DOP2006000010A (es)	2005-01-10	2006-07-31	Arena Pharm Inc	Procedimiento para preparar eteres aromáticos
EP1915378A4 (en) *	2005-08-12	2009-07-22	Boehringer Ingelheim Int	VIRUS POLYMERASE INHIBITORS
SG188548A1 (en)	2010-09-22	2013-04-30	Arena Pharm Inc	Modulators of the gpr119 receptor and the treatment of disorders related thereto
ES2394349B1 (es)	2012-08-29	2013-11-04	Fundación Centro Nacional De Investigaciones Cardiovasculares Carlos Iii	Uso de agonistas selectivos de receptores beta-3 adrenérgicos para el tratamiento de hipertensión pulmonar
JP6660668B2 (ja) *	2014-06-24	2020-03-11	花王株式会社	Ｕｃｐ−１発現促進剤
US10758519B2 (en)	2014-06-24	2020-09-01	Kao Corporation	UCP-1 expression promoter
WO2015199097A1 (ja) *	2014-06-24	2015-12-30	花王株式会社	Ｕｃｐ－１発現促進剤
NZ734220A (en)	2015-01-06	2022-01-28	Arena Pharm Inc	Methods of treating conditions related to the s1p1 receptor
KR102603199B1 (ko)	2015-06-22	2023-11-16	아레나 파마슈티칼스, 인크.	Ｓ1ｐ1 수용체-관련 장애에서의 사용을 위한 (ｒ)-2-(7-(4-시클로펜틸-3-(트리플루오로메틸)벤질옥시)-1,2,3,4-테트라히드로시클로-펜타[ｂ]인돌-3-일)아세트산 (화합물 1)의 결정성 ｌ-아르기닌 염
BR112020024762A2 (pt)	2018-06-06	2021-03-23	Arena Pharmaceuticals, Inc.	métodos de tratamento de condições relacionadas ao receptor s1p1

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GB861428A (en) *	1958-07-14	1961-02-22	Searle & Co	Improvements in or relating to indole derivatives
US4055658A (en) *	1976-05-17	1977-10-25	Mead Johnson & Company	Cyanomethylphenethanolamines
US4338333A (en) *	1979-06-16	1982-07-06	Beecham Group Limited	Ethanamine derivatives their preparation and use in pharmaceutical compositions
FR2541999B1 (fr) *	1983-03-04	1986-09-19	Bristol Myers Co	Phenethanolamines et leurs utilisations
JPH06345731A (ja) *	1992-04-28	1994-12-20	Dainippon Pharmaceut Co Ltd	２−〔２−（インドール−３−イル）エチルアミノ〕−１−フェニルエタノール誘導体
JPH0634531A (ja) *	1992-07-14	1994-02-08	Yokogawa Electric Corp	赤外線水分計

1995
- 1995-11-27 WO PCT/JP1995/002400 patent/WO1996016938A1/ja active IP Right Grant
- 1995-11-27 TW TW084112608A patent/TW349091B/zh not_active IP Right Cessation
- 1995-11-27 NZ NZ295749A patent/NZ295749A/en unknown
- 1995-11-27 PL PL95320461A patent/PL181963B1/pl not_active IP Right Cessation
- 1995-11-27 JP JP08518575A patent/JP3100165B2/ja not_active Expired - Fee Related
- 1995-11-27 DE DE69521529T patent/DE69521529T2/de not_active Expired - Lifetime
- 1995-11-27 AU AU39366/95A patent/AU688165B2/en not_active Ceased
- 1995-11-27 RO RO97-00967A patent/RO118426B1/ro unknown
- 1995-11-27 AT AT95937182T patent/ATE202559T1/de not_active IP Right Cessation
- 1995-11-27 ES ES95937182T patent/ES2159648T3/es not_active Expired - Lifetime
- 1995-11-27 PT PT95937182T patent/PT801059E/pt unknown
- 1995-11-27 SK SK656-97A patent/SK281865B6/sk unknown
- 1995-11-27 HU HU9701807A patent/HUT77308A/hu unknown
- 1995-11-27 DK DK95937182T patent/DK0801059T3/da active
- 1995-11-27 US US08/836,983 patent/US5817689A/en not_active Expired - Lifetime
- 1995-11-27 BR BR9509827A patent/BR9509827A/pt not_active Application Discontinuation
- 1995-11-27 KR KR1019970703537A patent/KR100388747B1/ko not_active Expired - Fee Related
- 1995-11-27 RU RU97110664A patent/RU2137759C1/ru not_active IP Right Cessation
- 1995-11-27 CN CN95197471A patent/CN1070477C/zh not_active Expired - Fee Related
- 1995-11-27 EP EP95937182A patent/EP0801059B1/en not_active Expired - Lifetime
- 1995-11-27 CZ CZ19971655A patent/CZ290871B6/cs not_active IP Right Cessation
- 1995-11-27 CA CA002206307A patent/CA2206307A1/en not_active Abandoned
- 1995-11-28 IL IL11617895A patent/IL116178A/xx not_active IP Right Cessation
- 1995-11-29 ZA ZA9510130A patent/ZA9510130B/xx unknown
1997
- 1997-05-28 NO NO972427A patent/NO309648B1/no not_active IP Right Cessation
- 1997-05-29 FI FI972275A patent/FI972275A0/fi not_active Application Discontinuation
1998
- 1998-04-09 HK HK98103026A patent/HK1003886A1/xx not_active IP Right Cessation
2001
- 2001-06-28 GR GR20010400309T patent/GR3036148T3/el not_active IP Right Cessation
- 2001-11-20 CY CY0100039A patent/CY2247B1/xx unknown

Also Published As

Publication number	Publication date
HK1003886A1 (en)	1998-11-13
FI972275L (fi)	1997-05-29
IL116178A (en)	2000-07-26
NZ295749A (en)	1998-05-27
GR3036148T3 (en)	2001-09-28
CN1070477C (zh)	2001-09-05
CZ290871B6 (cs)	2002-11-13
BR9509827A (pt)	1997-09-30
MX9703858A (es)	1997-09-30
IL116178A0 (en)	1996-01-31
RO118426B1 (ro)	2003-05-30
CA2206307A1 (en)	1996-06-06
US5817689A (en)	1998-10-06
SK65697A3 (en)	1998-01-14
EP0801059A1 (en)	1997-10-15
DK0801059T3 (da)	2001-09-24
CN1174549A (zh)	1998-02-25
DE69521529D1 (de)	2001-08-02
KR100388747B1 (ko)	2004-03-30
JP3100165B2 (ja)	2000-10-16
ATE202559T1 (de)	2001-07-15
AU688165B2 (en)	1998-03-05
EP0801059B1 (en)	2001-06-27
ES2159648T3 (es)	2001-10-16
FI972275A0 (fi)	1997-05-29
PL181963B1 (pl)	2001-10-31
CY2247B1 (en)	2003-07-04
EP0801059A4 (en)	1998-01-21
RU2137759C1 (ru)	1999-09-20
HUT77308A (hu)	1998-03-30
NO972427D0 (no)	1997-05-28
PL320461A1 (en)	1997-09-29
DE69521529T2 (de)	2001-10-11
CZ165597A3 (en)	1997-11-12
NO972427L (no)	1997-07-28
SK281865B6 (sk)	2001-08-06
AU3936695A (en)	1996-06-19
TW349091B (en)	1999-01-01
WO1996016938A1 (en)	1996-06-06
ZA9510130B (en)	1996-06-11
PT801059E (pt)	2001-10-30

Publication	Publication Date	Title
NO309648B1 (no)	2001-03-05	Indolderivat og farmasöytisk preparat inneholdende dette
EP0593513B1 (en)	1998-10-28	Tryptamine analogues, their synthesis and their use as 5-ht1-like receptors or 5-ht2 receptor agonistes
US4647563A (en)	1987-03-03	Heterocyclic compounds
US5030640A (en)	1991-07-09	Novel β-adrenergic agonists and pharmaceutical compositions thereof
US5036078A (en)	1991-07-30	Piperidinyl indoles for migraine treatment
IE58122B1 (en)	1993-07-14	An indole derivative
EP0775118B1 (en)	2003-06-04	Benzimidazole derivatives having dopaminergic activity
US4604389A (en)	1986-08-05	Benzazepine derivatives
EP0175525A1 (en)	1986-03-26	7-[2-(Dialkylamino)ethyl]-4-hydroxy-1,3-benzimidazol-2-ones
EP1226116A1 (en)	2002-07-31	Processes for the preparation of sumatriptan and related compounds
JPS60158170A (ja)	1985-08-19	エテニルフェノールインドール誘導体及びそれらの塩、これらの製造方法並びにこれらを含有する薬剤
US4505918A (en)	1985-03-19	4-[2-Pyridinylthio(oxy or amino)methyl]-1H-imidazoles and derivatives
CA1243033A (en)	1988-10-11	Process for preparing 4-¬2- (dialkylamino)ethyl\|isatins
JP2003055344A (ja)	2003-02-26	３，７−ジ置換インドール誘導体及びそれを含有する医薬組成物
EP0209275B1 (en)	1988-10-19	Benz-trisubstituted 2-aminotetralins
MXPA97003858A (en)	1998-07-03	Derived from in
US4558061A (en)	1985-12-10	Bronchospasmolytic 1-(3-methanesulfonamido-4-hydroxyphenyl)-2-[(3-(4-acyl-aminophenyl)-imidazolidin-2-one-1-yl)-alkylamino]-ethanols
WO1996016038A1 (fr)	1996-05-30	Derive de 2-[2-(indol-3-yl)ethylamino]-1-phenylethanol
IE63264B1 (en)	1995-04-05	1((4-Morpholinyl)alkyl)-1h-indoles useful as analgesics and preparation thereof
CS200214B2 (cs)	1980-08-29	Způsob přípravy indazolových derivátů
JPH08231504A (ja)	1996-09-10	２−（２−インドリルエチルアミノ）−１−（３−置換フェニル）エタノール誘導体
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