CA1063132A - 4,5-dialkoxy-(6),7-indanaldehyde - Google Patents

4,5-dialkoxy-(6),7-indanaldehyde

Info

Publication number: CA1063132A
Authority: CA; Canada
Prior art keywords: dialkoxy; dimethoxy; indanaldehyde; acid; cyclopentano
Prior art date: 1974-03-28
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.): Expired

Application number

CA303,560A

Other languages

English (en)

Inventor

Raymond H. Jones

William E. Solomons

Ian W. Mathison

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Marion Laboratories Inc

Original Assignee

Marion Laboratories Inc

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.)

1974-03-28

Filing date

1978-05-17

Publication date

1979-09-25

1974-03-28 Priority claimed from US05/455,574 external-priority patent/US3963723A/en

1978-05-17 Application filed by Marion Laboratories Inc filed Critical Marion Laboratories Inc

1978-05-17 Priority to CA303,560A priority Critical patent/CA1063132A/fr

1979-09-25 Application granted granted Critical

1979-09-25 Publication of CA1063132A publication Critical patent/CA1063132A/fr

Status Expired legal-status Critical Current

Links

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150000001299 aldehydes Chemical class 0.000 claims description 12
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KHVRKYOQRGQIRY-UHFFFAOYSA-N 6,7-dimethoxy-2,3-dihydro-1h-indene-4-carbaldehyde Chemical compound COC1=CC(C=O)=C2CCCC2=C1OC KHVRKYOQRGQIRY-UHFFFAOYSA-N 0.000 claims description 5
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239000002253 acid Substances 0.000 abstract description 13
229910052739 hydrogen Inorganic materials 0.000 abstract description 6
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KRTCNRRLJANNSH-UHFFFAOYSA-N n-[1-(6,7-dipropoxy-2,3-dihydro-1h-inden-4-yl)butan-2-yl]methanimine Chemical compound CCCOC1=CC(CC(CC)N=C)=C2CCCC2=C1OCCC KRTCNRRLJANNSH-UHFFFAOYSA-N 0.000 description 1
ORYHODJWDKTVSD-UHFFFAOYSA-N n-[1-(6,7-dipropoxy-2,3-dihydro-1h-inden-5-yl)butan-2-yl]methanimine Chemical compound CCC(N=C)CC1=C(OCCC)C(OCCC)=C2CCCC2=C1 ORYHODJWDKTVSD-UHFFFAOYSA-N 0.000 description 1
WQJWIMOQQFIBOM-UHFFFAOYSA-N n-[2-(6,7-dimethoxy-2,3-dihydro-1h-inden-4-yl)ethyl]methanimine Chemical compound COC1=CC(CCN=C)=C2CCCC2=C1OC WQJWIMOQQFIBOM-UHFFFAOYSA-N 0.000 description 1
230000003472 neutralizing effect Effects 0.000 description 1
239000012457 nonaqueous media Substances 0.000 description 1
238000010899 nucleation Methods 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
235000008390 olive oil Nutrition 0.000 description 1
239000004006 olive oil Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
150000002895 organic esters Chemical class 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
239000002304 perfume Substances 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
239000006187 pill Substances 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000006748 scratching Methods 0.000 description 1
230000002393 scratching effect Effects 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000007909 solid dosage form Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008107 starch Substances 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
229910052719 titanium Inorganic materials 0.000 description 1
239000010936 titanium Substances 0.000 description 1
XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
239000011345 viscous material Substances 0.000 description 1
238000010792 warming Methods 0.000 description 1
238000005406 washing Methods 0.000 description 1
230000003313 weakening effect Effects 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1

Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA303,560A 1974-03-28 1978-05-17 4,5-dialkoxy-(6),7-indanaldehyde Expired CA1063132A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA303,560A CA1063132A (fr)	1974-03-28	1978-05-17	4,5-dialkoxy-(6),7-indanaldehyde

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US05/455,574 US3963723A (en)	1974-03-28	1974-03-28	Cyclopentano (h) or (f) 1,2,3,4-tetrahydroisoquinolines
CA223,273A CA1063117A (fr)	1974-03-28	1975-03-27	Cyclopentano (h) ou (f) 1,2,3,4-tetrahydroisoquinolines
CA303,560A CA1063132A (fr)	1974-03-28	1978-05-17	4,5-dialkoxy-(6),7-indanaldehyde

Publications (1)

Publication Number	Publication Date
CA1063132A true CA1063132A (fr)	1979-09-25

Family

ID=27163879

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA303,560A Expired CA1063132A (fr)	1974-03-28	1978-05-17	4,5-dialkoxy-(6),7-indanaldehyde

Country Status (1)

Country	Link
CA (1)	CA1063132A (fr)

1978
- 1978-05-17 CA CA303,560A patent/CA1063132A/fr not_active Expired

Publication	Publication Date	Title
US3711489A (en)	1973-01-16	Certain 8,9-dihydro(3,4,7,8)cycloocta(1,2-d)imidazoles
Gladiali et al.	1989	Optically active phenanthrolines in asymmetric catalysis: II. Enantioselective transfer hydrogenation of acetophenone by rhodium/alkyl phenanthroline catalysts
US4000197A (en)	1976-12-28	Asymmetric synthesis of phenylisopropylamines
CA1206476A (fr)	1986-06-24	Composes de pyrolidine et de piperidine
EP0028381B1 (fr)	1985-04-10	Azépinoindoles, procédé pour leur préparation et compositions pharmaceutiques les contenant
EP0061149B1 (fr)	1984-11-28	Dérivés du alkylènedioxybenzène et leurs sels d'addition acides et procédé pour leur préparation
PL90293B1 (fr)	1977-01-31
KR840001071B1 (ko)	1984-07-31	9-카바모일-9-(2-시아노에틸)플루오렌유도체의 제조방법
CA1063132A (fr)	1979-09-25	4,5-dialkoxy-(6),7-indanaldehyde
US4010202A (en)	1977-03-01	5,6-Dihydroxy aminotetralol compounds
Reckhow et al.	1952	Hexahydroindolo [2, 3-a] quinolizine1
FR2495470A1 (fr)	1982-06-11	Nouveaux medicaments a base de derives de (quinolyl-4)-1 (piperidyl-4)-2 ethanol ou (quinolyl-4)-1 (piperidyl-4)-3 propanol
IL25953A (en)	1970-10-30	Phenanthridine derivatives and process for the manufacture thereof
CA1063117A (fr)	1979-09-25	Cyclopentano (h) ou (f) 1,2,3,4-tetrahydroisoquinolines
US4705807A (en)	1987-11-10	Amine derivatives
US3997608A (en)	1976-12-14	N-substituted-dihydroxyphenethylamines
US4071562A (en)	1978-01-31	4,5-Dialkoxy-6 or 7-indanaldehydes
US4059586A (en)	1977-11-22	5-Alkoxy-2-alkyl-1,2,3,4-tetrahydroisoquinolene-8-carboxaldehyde and derivatives
JPS5849369A (ja)	1983-03-23	新規のイミダゾール化合物
LEONARD et al.	1957	Synthesis of 2-Hydroxymethylquinolizidine (dl-2-Lupinine)
CA1123826A (fr)	1982-05-18	Cetoamines cycloaliphatiques
CA2011461A1 (fr)	1990-09-20	Derives de tetrahydronaphthalene
CA1061791A (fr)	1979-09-04	7,8-dihydroxy-cyclopentano(f)-1,2,3,4-tetrahydroisoquinolines a substituants en n et ses derives ethers et esters
US3953458A (en)	1976-04-27	1-Substituted amino-2-alkyl-5-hydroxy-7,8-cyclopentano[h]-1,2,3,4-tetrahydroisoquinolines
US3962254A (en)	1976-06-08	N-substituted-5,6-dihydroxycyclopentano[h]-1,2,3,4-tetrahydroisoquinolines and ethers and esters thereof