US3498987A - 9,9-dimethyl-10-amino-alkylacridans - Google Patents
9,9-dimethyl-10-amino-alkylacridans Download PDFInfo
- Publication number
- US3498987A US3498987A US761371*A US3498987DA US3498987A US 3498987 A US3498987 A US 3498987A US 3498987D A US3498987D A US 3498987DA US 3498987 A US3498987 A US 3498987A
- Authority
- US
- United States
- Prior art keywords
- alkylacridans
- dimethyl
- amino
- dimethylacridan
- anilino
- 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.)
- Expired - Lifetime
Links
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- -1 10-{3- [5 chloro 2 (p-chlorophenoxy)anilino]propyl}-9,9- dimethylacridan Chemical compound 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/20—Spiro-condensed ring systems
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
- C07D219/02—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems with only hydrogen, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
- C07D219/14—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems with hydrocarbon radicals, substituted by nitrogen atoms, attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
- C07D219/16—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems with acyl radicals, substituted by nitrogen atoms, attached to the ring nitrogen atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
United States Patent U.S. Cl. 260279 3 Claims ABSTRACT OF THE DISCLOSURE 10 {3 [5 chloro 2 (p-chlorophen0Xy)anilino] propyl}-9,9-dimethylacridan and the corresponding N- lower alkyl compounds have pharmacological activity; e.g., analgesic activity.
CROSS-REFERENCE This is a division of Serial No. 535,684 filed Mar. 21, 1966, now US. Patent No. 3,452,021.
DESCRIPTION OF INVENTION This invention pertains to -{3-[5-chloro-2-(pchlorophenoxy)anilino]propyl}-9,9-dimethylacridan of the formula:
CH3 CH I CHzCHzCHzNH 3,498,987. Patented Mar. 3, 1970 to the N-lower alkyl derivatives thereof, and to the pharmaceutically acceptable non-toxic salts thereof.
The manner and process of making and using this invention is described in US. Patent No. 3,452,021, issued June 24, 1969, the disclosure of which is herein incorporated by reference.
We claim:
1. A compound selected from the group consisting of 10 {3 [5 chloro 2 (pchlorophenoxy)anilino] propyl} 9,9 dimethylacridan and 10-{3-[5-ch10r0-2-(pchlorophenoxy) N lower alkylanilino}-9,9 dimethylacridans.
2. The compound according to claim 1 which is 10-{3- [5 chloro 2 (p-chlorophenoxy)anilino]propyl}-9,9- dimethylacridan.
3. The pharmaceutically acceptable nontoxic acid addition salts of a compound according to claim 1.
References Cited UNITED STATES PATENTS 3,284,454 12/1966 Haring et a1. 260-279 DONALD G. DAUS, Primary Examiner US. Cl. X.R. 424-257 @3 3?" UNITED STATES PATENT OFFICE CERTIFICATE OF CORRECTION Patent No. 3,493,9 7 Dated March 3 1970 Inv nmfl Mex Mp-iqp'lq and Angplo Storni It is certified that error appears in the above-identified patenr and that said Letters Patent are hereby corrected as shown below:
In column 2, line 17, "claim 1" should be claim 2 SIGNED KND SEALED JUL 1 41970 Attest:
Edward M. Fletcher, In mun E. somJYnmR, JI- Attesting Officer t-
Applications Claiming Priority (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH511968A CH455773A (en) | 1965-03-24 | 1965-03-24 | Process for the production of new acridan derivatives |
| CH410065A CH455771A (en) | 1965-03-24 | 1965-03-24 | Process for the production of new acridan derivatives |
| CH527868A CH460009A (en) | 1965-03-24 | 1965-03-24 | Process for the production of new acridan derivatives |
| CH409965A CH455770A (en) | 1965-03-24 | 1965-03-24 | Process for the production of new acridan derivatives |
| CH527768A CH455774A (en) | 1965-03-24 | 1965-03-24 | Process for the production of new acridan derivatives |
| DEG0046536 | 1965-07-06 | ||
| US53568466A | 1966-03-21 | 1966-03-21 | |
| US76137168A | 1968-07-17 | 1968-07-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3498987A true US3498987A (en) | 1970-03-03 |
Family
ID=27570352
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US761371*A Expired - Lifetime US3498987A (en) | 1965-03-24 | 1968-07-17 | 9,9-dimethyl-10-amino-alkylacridans |
Country Status (2)
| Country | Link |
|---|---|
| US (1) | US3498987A (en) |
| NL (1) | NL6603820A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10228132A1 (en) * | 2002-06-24 | 2004-01-22 | Arzneimittelwerk Dresden Gmbh | Amides of cyclic amino acids as PDE 4 inhibitors |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3284454A (en) * | 1961-12-18 | 1966-11-08 | Siegfried Ag | Pharmacologically active acridans and their salts |
-
1966
- 1966-03-23 NL NL6603820A patent/NL6603820A/xx unknown
-
1968
- 1968-07-17 US US761371*A patent/US3498987A/en not_active Expired - Lifetime
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3284454A (en) * | 1961-12-18 | 1966-11-08 | Siegfried Ag | Pharmacologically active acridans and their salts |
Also Published As
| Publication number | Publication date |
|---|---|
| NL6603820A (en) | 1966-09-26 |
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