ZA200206467B - 1,2,3,4-tetrahydroisoquinoline derivatives. - Google Patents

1,2,3,4-tetrahydroisoquinoline derivatives. Download PDF

Info

Publication number: ZA200206467B
Authority: ZA; South Africa
Prior art keywords: benzyl; dimethoxy; acetamide; dihydro; isoquinolin
Prior art date: 2000-03-14

Application number

ZA200206467A

Other languages

English (en)

Inventor

Hamed Aissaoui

Martine Clozel

Ralf Koberstein

Michael Cappi

Walter Fischli

Original Assignee

Actelion Pharmaceuticals 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.)

2000-03-14

Filing date

2002-08-13

Publication date

2003-11-13

2002-08-13 Application filed by Actelion Pharmaceuticals Ltd filed Critical Actelion Pharmaceuticals Ltd

2003-11-13 Publication of ZA200206467B publication Critical patent/ZA200206467B/en

Links

UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical class C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 title description 4
150000001875 compounds Chemical class 0.000 claims description 45
125000000217 alkyl group Chemical group 0.000 claims description 41
125000000623 heterocyclic group Chemical group 0.000 claims description 20
238000000034 method Methods 0.000 claims description 20
239000000203 mixture Substances 0.000 claims description 20
125000003118 aryl group Chemical group 0.000 claims description 19
125000000753 cycloalkyl group Chemical group 0.000 claims description 19
-1 1,2,3,4-tetrahydro-naphthalen-1-yl Chemical group 0.000 claims description 16
125000003342 alkenyl group Chemical group 0.000 claims description 15
125000003710 aryl alkyl group Chemical group 0.000 claims description 15
239000001257 hydrogen Substances 0.000 claims description 15
229910052739 hydrogen Inorganic materials 0.000 claims description 15
102000002512 Orexin Human genes 0.000 claims description 14
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 14
108060005714 orexin Proteins 0.000 claims description 14
150000003839 salts Chemical class 0.000 claims description 13
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 8
125000003545 alkoxy group Chemical group 0.000 claims description 8
208000035475 disorder Diseases 0.000 claims description 8
229910052736 halogen Inorganic materials 0.000 claims description 8
150000002367 halogens Chemical class 0.000 claims description 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
238000002360 preparation method Methods 0.000 claims description 7
125000001424 substituent group Chemical group 0.000 claims description 7
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125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
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201000010099 disease Diseases 0.000 claims description 5
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125000003302 alkenyloxy group Chemical group 0.000 claims description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
125000004430 oxygen atom Chemical group O* 0.000 claims description 4
125000004093 cyano group Chemical group *C#N 0.000 claims description 3
UZJLYRRDVFWSGA-UHFFFAOYSA-N n-benzylacetamide Chemical compound CC(=O)NCC1=CC=CC=C1 UZJLYRRDVFWSGA-UHFFFAOYSA-N 0.000 claims description 3
239000008194 pharmaceutical composition Substances 0.000 claims description 3
JWMZPZFSAXVGMK-UHFFFAOYSA-N 2-[1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl]-n-(6-methoxy-2,3-dihydro-1h-inden-1-yl)acetamide Chemical compound C12=CC(OC)=CC=C2CCC1NC(=O)CN1CCC2=CC(OC)=C(OC)C=C2C1CC1=CC=C(OC)C(OC)=C1 JWMZPZFSAXVGMK-UHFFFAOYSA-N 0.000 claims description 2
BVPKSCZDEKFXBF-UHFFFAOYSA-N 2-[8-(cyclopropylmethoxy)-1-[(3,4-dimethoxyphenyl)methyl]-5-methoxy-3,4-dihydro-1h-isoquinolin-2-yl]-n-(pyridin-2-ylmethyl)acetamide Chemical compound C1=C(OC)C(OC)=CC=C1CC1C2=C(OCC3CC3)C=CC(OC)=C2CCN1CC(=O)NCC1=CC=CC=N1 BVPKSCZDEKFXBF-UHFFFAOYSA-N 0.000 claims description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
125000002102 aryl alkyloxo group Chemical group 0.000 claims description 2
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UOOXDDHYFFXMJJ-UHFFFAOYSA-N n-(2,3-dihydro-1h-inden-1-yl)acetamide Chemical compound C1=CC=C2C(NC(=O)C)CCC2=C1 UOOXDDHYFFXMJJ-UHFFFAOYSA-N 0.000 claims 2
GEYCZKOLGCILBP-UHFFFAOYSA-N 2-[1-[(3,4-dichlorophenyl)methyl]-6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl]-n-(pyridin-3-ylmethyl)acetamide Chemical compound C=1C=C(Cl)C(Cl)=CC=1CC1C=2C=C(OC)C(OC)=CC=2CCN1CC(=O)NCC1=CC=CN=C1 GEYCZKOLGCILBP-UHFFFAOYSA-N 0.000 claims 1
GCQCVZZGKIKVTL-UHFFFAOYSA-N 2-[1-[(3,4-dimethoxyphenyl)methyl]-5,8-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl]-n-(pyridin-2-ylmethyl)acetamide Chemical compound C1=C(OC)C(OC)=CC=C1CC1C2=C(OC)C=CC(OC)=C2CCN1CC(=O)NCC1=CC=CC=N1 GCQCVZZGKIKVTL-UHFFFAOYSA-N 0.000 claims 1
RTCVKRBTBBZWQK-UHFFFAOYSA-N 2-[1-[(3,4-dimethoxyphenyl)methyl]-5-methoxy-8-propan-2-yloxy-3,4-dihydro-1h-isoquinolin-2-yl]-n-(pyridin-2-ylmethyl)acetamide Chemical compound C1=C(OC)C(OC)=CC=C1CC1C2=C(OC(C)C)C=CC(OC)=C2CCN1CC(=O)NCC1=CC=CC=N1 RTCVKRBTBBZWQK-UHFFFAOYSA-N 0.000 claims 1
SNSUCNJUHNKTRE-UHFFFAOYSA-N 2-[1-[(3,4-dimethoxyphenyl)methyl]-5-methoxy-8-propoxy-3,4-dihydro-1h-isoquinolin-2-yl]-n-(pyridin-2-ylmethyl)acetamide Chemical compound C=1C=C(OC)C(OC)=CC=1CC1C=2C(OCCC)=CC=C(OC)C=2CCN1CC(=O)NCC1=CC=CC=N1 SNSUCNJUHNKTRE-UHFFFAOYSA-N 0.000 claims 1
DBVLOSLXGFOHED-UHFFFAOYSA-N 2-[7-(cyclopropylmethoxy)-1-[(3,4-dimethoxyphenyl)methyl]-6-methoxy-3,4-dihydro-1h-isoquinolin-2-yl]-n-(2,3-dihydro-1h-inden-1-yl)acetamide Chemical compound C1=C(OC)C(OC)=CC=C1CC1C2=CC(OCC3CC3)=C(OC)C=C2CCN1CC(=O)NC1C2=CC=CC=C2CC1 DBVLOSLXGFOHED-UHFFFAOYSA-N 0.000 claims 1
IXIVCTNVUGDCGG-UHFFFAOYSA-N 2-[8-(2,2-difluoroethoxy)-1-[(3,4-dimethoxyphenyl)methyl]-5-methoxy-3,4-dihydro-1h-isoquinolin-2-yl]-n-(pyridin-2-ylmethyl)acetamide Chemical compound C1=C(OC)C(OC)=CC=C1CC1C2=C(OCC(F)F)C=CC(OC)=C2CCN1CC(=O)NCC1=CC=CC=N1 IXIVCTNVUGDCGG-UHFFFAOYSA-N 0.000 claims 1
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241000388430 Tara Species 0.000 claims 1
239000002253 acid Substances 0.000 claims 1
239000012876 carrier material Substances 0.000 claims 1
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150000002148 esters Chemical class 0.000 claims 1
SGHBDLOMRUXKQF-UHFFFAOYSA-N n-(2,3-dihydro-1h-inden-1-yl)-2-[1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl]acetamide Chemical compound C1=C(OC)C(OC)=CC=C1CC1C2=CC(OC)=C(OC)C=C2CCN1CC(=O)NC1C2=CC=CC=C2CC1 SGHBDLOMRUXKQF-UHFFFAOYSA-N 0.000 claims 1
LKVQOJRHCJPELL-UHFFFAOYSA-N n-(5-methoxy-2,3-dihydro-1h-inden-1-yl)acetamide Chemical compound COC1=CC=C2C(NC(C)=O)CCC2=C1 LKVQOJRHCJPELL-UHFFFAOYSA-N 0.000 claims 1
AVKSWJBBMWMGSZ-UHFFFAOYSA-N n-benzyl-2-[1-[(3,4-diethylphenyl)methyl]-6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl]acetamide Chemical compound C1=C(CC)C(CC)=CC=C1CC1C2=CC(OC)=C(OC)C=C2CCN1CC(=O)NCC1=CC=CC=C1 AVKSWJBBMWMGSZ-UHFFFAOYSA-N 0.000 claims 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/472—Non-condensed isoquinolines, e.g. papaverine
- 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
- A61P25/20—Hypnotics; Sedatives
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
- C07D217/04—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
- C07D217/18—Aralkyl radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
- C07D217/18—Aralkyl radicals
- C07D217/20—Aralkyl radicals with oxygen atoms directly attached to the aromatic ring of said aralkyl radical, e.g. papaverine
- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Animal Behavior & Ethology (AREA)
Pharmacology & Pharmacy (AREA)
Medicinal Chemistry (AREA)
Bioinformatics & Cheminformatics (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Engineering & Computer Science (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Hematology (AREA)
Diabetes (AREA)
Obesity (AREA)
Child & Adolescent Psychology (AREA)
Anesthesiology (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Epidemiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Other In-Based Heterocyclic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

ZA200206467A 2000-03-14 2002-08-13 1,2,3,4-tetrahydroisoquinoline derivatives. ZA200206467B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
EP0002245		2000-03-14

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US (1)	US6703392B2 (zh)
JP (1)	JP4009460B2 (zh)
KR (2)	KR100842698B1 (zh)
CN (1)	CN100393703C (zh)
AT (1)	ATE286500T1 (zh)
AU (2)	AU2001260113B2 (zh)
BR (1)	BRPI0109200B8 (zh)
CA (1)	CA2402431C (zh)
DE (1)	DE60108236T2 (zh)
ES (1)	ES2234840T3 (zh)
HU (1)	HU227811B1 (zh)
IL (2)	IL150986A0 (zh)
MX (1)	MXPA02008797A (zh)
NO (1)	NO324932B1 (zh)
NZ (1)	NZ520624A (zh)
PT (1)	PT1274687E (zh)
WO (1)	WO2001068609A1 (zh)
ZA (1)	ZA200206467B (zh)

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JP2006518757A (ja) *	2003-02-24	2006-08-17	メルク　エンド　カムパニー　インコーポレーテッド	ケモカイン受容体活性のアミノシクロペンチル縮合ヘテロ３環アミドモジュレーター
EP1611104B1 (en) *	2003-03-26	2009-07-01	Actelion Pharmaceuticals Ltd.	Tetrahydroisoquinolyl acetamide derivatives for use as orexin receptor antagonists
US7321065B2 (en) *	2003-04-18	2008-01-22	The Regents Of The University Of California	Thyronamine derivatives and analogs and methods of use thereof
JP2007523846A (ja)	2003-04-28	2007-08-23	アクテリオン　ファマシューティカルズ　リミテッド	キノキサリノン誘導体
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EP1814590B2 (en)	2004-11-01	2013-12-11	Amylin Pharmaceuticals, Inc.	Treatment of obesity and related disorders
US20060178307A1 (en) *	2005-01-26	2006-08-10	The Regents Of The University Of California	Modulation of NMDA receptor currents via orexin receptor and/or CRF receptor
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US7501395B2 (en)	2005-04-25	2009-03-10	Eisai R & D Management Co., Ltd.	Method of screening for antianxiety drugs
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CA2609388C (en)	2005-05-30	2013-08-06	Banyu Pharmaceutical Co., Ltd.	Novel piperidine derivative
JPWO2007018248A1 (ja)	2005-08-10	2009-02-19	萬有製薬株式会社	ピリドン化合物
EP2330125A3 (en)	2005-08-11	2012-12-12	Amylin Pharmaceuticals, Inc.	Hybrid polypeptides with selectable properties
WO2007024004A1 (ja)	2005-08-24	2007-03-01	Banyu Pharmaceutical Co., Ltd.	フェニルピリドン誘導体
EP1939194A4 (en)	2005-09-07	2010-12-08	Banyu Pharma Co Ltd	AROMATIC SUBSTITUTED BICYLIC PYRIDONE DERIVATIVE
CN101277960A (zh)	2005-09-29	2008-10-01	默克公司	作为黑皮质素-4受体调节剂的酰化螺哌啶衍生物
RU2008119687A (ru)	2005-10-21	2009-11-27	Новартис АГ (CH)	Комбинации органических соединений
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NZ520624A (en)	2004-02-27
US20030176415A1 (en)	2003-09-18
BRPI0109200B8 (pt)	2021-05-25
HUP0300207A2 (en)	2003-05-28
IL150986A0 (en)	2003-02-12
KR20020080465A (ko)	2002-10-23
NO20024339L (no)	2002-09-11
IL150986A (en)	2007-07-04
HU227811B1 (en)	2012-03-28
MXPA02008797A (es)	2005-09-08
US6703392B2 (en)	2004-03-09
DE60108236T2 (de)	2005-12-22
BRPI0109200B1 (pt)	2015-08-11
ES2234840T3 (es)	2005-07-01
BR0109200A (pt)	2003-06-03
AU6011301A (en)	2001-09-24
NO20024339D0 (no)	2002-09-11
NO324932B1 (no)	2008-01-07
PT1274687E (pt)	2005-04-29
CN1416420A (zh)	2003-05-07
DE60108236D1 (de)	2005-02-10
WO2001068609B1 (en)	2002-02-21
KR100842698B1 (ko)	2008-07-01
KR20070087103A (ko)	2007-08-27
HUP0300207A3 (en)	2005-07-28
ATE286500T1 (de)	2005-01-15
JP4009460B2 (ja)	2007-11-14
JP2003527374A (ja)	2003-09-16
AU2001260113B2 (en)	2006-04-06
WO2001068609A1 (en)	2001-09-20
CN100393703C (zh)	2008-06-11
CA2402431A1 (en)	2001-09-20
CA2402431C (en)	2009-10-06

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