DE910562T1 - Verfahren zur herstellung von tertiären aminen, eine in diesem verfahren nützliche verbindung und alpha-2-rezeptor aktive tetrahydroisochinolinderivate - Google Patents
Verfahren zur herstellung von tertiären aminen, eine in diesem verfahren nützliche verbindung und alpha-2-rezeptor aktive tetrahydroisochinolinderivateInfo
- Publication number
- DE910562T1 DE910562T1 DE0910562T DE98936440T DE910562T1 DE 910562 T1 DE910562 T1 DE 910562T1 DE 0910562 T DE0910562 T DE 0910562T DE 98936440 T DE98936440 T DE 98936440T DE 910562 T1 DE910562 T1 DE 910562T1
- Authority
- DE
- Germany
- Prior art keywords
- compound
- alkyl
- group
- formula
- ring
- Prior art date
- Legal status (The legal status 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 status listed.)
- Pending
Links
- 150000001875 compounds Chemical class 0.000 title claims 20
- 238000000034 method Methods 0.000 title claims 5
- 150000001412 amines Chemical class 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- 150000003526 tetrahydroisoquinolines Chemical class 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims 11
- 229910052736 halogen Inorganic materials 0.000 claims 7
- 150000002367 halogens Chemical class 0.000 claims 7
- 125000004122 cyclic group Chemical group 0.000 claims 6
- 125000001033 ether group Chemical group 0.000 claims 5
- 230000015572 biosynthetic process Effects 0.000 claims 4
- 150000003335 secondary amines Chemical class 0.000 claims 4
- 150000003512 tertiary amines Chemical class 0.000 claims 4
- 125000003118 aryl group Chemical group 0.000 claims 3
- 125000000524 functional group Chemical group 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- 239000000758 substrate Substances 0.000 claims 3
- 238000003786 synthesis reaction Methods 0.000 claims 3
- UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 claims 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- 239000004593 Epoxy Substances 0.000 claims 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- -1 hydroxy, amino, thio Chemical group 0.000 claims 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 125000006239 protecting group Chemical group 0.000 claims 2
- 125000001453 quaternary ammonium group Chemical group 0.000 claims 2
- 239000007787 solid Substances 0.000 claims 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 2
- 229920002554 vinyl polymer Polymers 0.000 claims 2
- VDFVNEFVBPFDSB-UHFFFAOYSA-N 1,3-dioxane Chemical compound C1COCOC1 VDFVNEFVBPFDSB-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 150000001350 alkyl halides Chemical class 0.000 claims 1
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 238000003776 cleavage reaction Methods 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 150000002148 esters Chemical group 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
- 125000005113 hydroxyalkoxy group Chemical group 0.000 claims 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims 1
- 238000006140 methanolysis reaction Methods 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- LOTBYPQQWICYBB-UHFFFAOYSA-N methyl n-hexyl-n-[2-(hexylamino)ethyl]carbamate Chemical compound CCCCCCNCCN(C(=O)OC)CCCCCC LOTBYPQQWICYBB-UHFFFAOYSA-N 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 1
- 125000005544 phthalimido group Chemical group 0.000 claims 1
- 238000005956 quaternization reaction Methods 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 230000007017 scission Effects 0.000 claims 1
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 1
Classifications
-
- 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
- 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
-
- 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
- C07D217/02—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
- C07D217/06—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 the ring nitrogen atom acylated by carboxylic or carbonic acids, or with sulfur or nitrogen analogues thereof, e.g. carbamates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/34—Introducing sulfur atoms or sulfur-containing groups
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/00274—Sequential or parallel reactions; Apparatus and devices for combinatorial chemistry or for making arrays; Chemical library technology
- B01J2219/00277—Apparatus
- B01J2219/00497—Features relating to the solid phase supports
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2810/00—Chemical modification of a polymer
- C08F2810/30—Chemical modification of a polymer leading to the formation or introduction of aliphatic or alicyclic unsaturated groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/909,823 US5912342A (en) | 1997-08-12 | 1997-08-12 | Compounds a containing a solid support |
| PCT/FI1998/000602 WO1998051672A2 (en) | 1997-08-12 | 1998-07-22 | A method for the preparation of tertiary amines, a compound useful therefor and alpha-2-receptor active tetrahydroisoquinoline derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE910562T1 true DE910562T1 (de) | 1999-10-07 |
Family
ID=25427886
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE0910562T Pending DE910562T1 (de) | 1997-08-12 | 1998-07-22 | Verfahren zur herstellung von tertiären aminen, eine in diesem verfahren nützliche verbindung und alpha-2-rezeptor aktive tetrahydroisochinolinderivate |
Country Status (8)
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9717173D0 (en) * | 1997-08-13 | 1997-10-22 | Akzo Nobel Nv | Solid phase supports |
| US6824987B1 (en) | 1999-05-11 | 2004-11-30 | President And Fellows Of Harvard College | Small molecule printing |
| US7932213B2 (en) * | 1999-05-11 | 2011-04-26 | President And Fellows Of Harvard College | Small molecule printing |
| JP3398366B2 (ja) * | 2000-08-09 | 2003-04-21 | 富士写真フイルム株式会社 | Ｄｎａ分析用マイクロアレイの製造方法 |
| US20030077598A1 (en) * | 2001-01-04 | 2003-04-24 | Phan Brigitte Chau | Dual bead assays including covalent linkages for improved specificity and related optical analysis discs |
| US20020168663A1 (en) * | 2001-02-27 | 2002-11-14 | Phan Brigitte Chau | Methods for DNA conjugation onto solid phase including related optical biodiscs and disc drive systems |
| WO2008013569A2 (en) * | 2006-01-03 | 2008-01-31 | The President And Fellows Of Harvard College | Small molecule printing |
| US20080186971A1 (en) * | 2007-02-02 | 2008-08-07 | Tarari, Inc. | Systems and methods for processing access control lists (acls) in network switches using regular expression matching logic |
| ES2975689T3 (es) * | 2016-01-29 | 2024-07-11 | Ono Pharmaceutical Co | Derivado de tetrahidronaftaleno |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2054483A1 (en) * | 1969-07-11 | 1971-04-23 | Anvar | Sympatholytic tsoquinoline derivs |
| US3988339A (en) * | 1974-02-08 | 1976-10-26 | Smithkline Corporation | Pharmaceutical compositions and methods of inhibiting phenylethanolamine N-methyltransferase |
| SE470099B (sv) * | 1984-05-17 | 1993-11-08 | Jerker Porath | Sulfonaktiverade tioeteradsorbenter för separation av t ex protein |
| FR2595356B1 (fr) * | 1986-03-05 | 1991-05-24 | Pasteur Strasbourg Universite | Derives des nitro ou aminobenzyltetrahydroisoquinoleines, procedes d'obtention, compositions pharmaceutiques les contenant, proprietes pharmacologiques et applications |
| EP0306375A1 (fr) * | 1987-08-07 | 1989-03-08 | Synthelabo | Dérivés de[(pipéridinyl-4)méthyl]-2 tétrahydro-1,2,3,4 isoquinoléine, leur préparation et leur application en thérapeutique |
| US4963563A (en) * | 1989-10-13 | 1990-10-16 | Abbott Laboratories | 6-substituted-1,2,3,4-tetrahydroisoquinolines |
| US6552170B1 (en) * | 1990-04-06 | 2003-04-22 | Amgen Inc. | PEGylation reagents and compounds formed therewith |
| DK100490D0 (da) * | 1990-04-24 | 1990-04-24 | Novo Nordisk As | Overflademodifikation |
| DK52791D0 (da) * | 1991-03-22 | 1991-03-22 | Kem En Tec As | Adsorptionsmatricer |
| US5246943A (en) * | 1992-05-19 | 1993-09-21 | Warner-Lambert Company | Substituted 1,2,3,4-tetahydroisoquinolines with angiotensin II receptor antagonist properties |
| US5294621A (en) * | 1992-10-07 | 1994-03-15 | Ortho Pharmaceutical Corporation | Thieno tetrahydropyridines useful as class III antiarrhythmic agents |
| US5571937A (en) * | 1994-05-13 | 1996-11-05 | Sloan-Kettering Institute For Cancer Research | Complementary DNA and toxins |
| ES2154470T3 (es) * | 1996-08-14 | 2001-04-01 | Smithkline Beecham Plc | Derivados de tetrahidroisoquinolina y su uso farmaceutico. |
-
1997
- 1997-08-12 US US08/909,823 patent/US5912342A/en not_active Expired - Fee Related
-
1998
- 1998-07-16 ZA ZA986320A patent/ZA986320B/xx unknown
- 1998-07-22 CA CA002300088A patent/CA2300088A1/en not_active Abandoned
- 1998-07-22 DE DE0910562T patent/DE910562T1/de active Pending
- 1998-07-22 WO PCT/FI1998/000602 patent/WO1998051672A2/en not_active Application Discontinuation
- 1998-07-22 AU AU85433/98A patent/AU751185B2/en not_active Ceased
- 1998-07-22 EP EP98936440A patent/EP0910562A2/en not_active Withdrawn
- 1998-07-30 IN IN1697MA1998 patent/IN187838B/en unknown
- 1998-10-07 US US09/167,740 patent/US6096752A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CA2300088A1 (en) | 1998-11-19 |
| ZA986320B (en) | 1999-02-02 |
| AU751185B2 (en) | 2002-08-08 |
| WO1998051672A3 (en) | 1999-03-11 |
| US6096752A (en) | 2000-08-01 |
| IN187838B (US07122603-20061017-C00045.png) | 2002-06-29 |
| EP0910562A2 (en) | 1999-04-28 |
| US5912342A (en) | 1999-06-15 |
| AU8543398A (en) | 1998-12-08 |
| WO1998051672A2 (en) | 1998-11-19 |
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