GB1329447A - 4-adamantylaminoalkylamino-2-styryl-quinolines salts and derivatives thereof - Google Patents
4-adamantylaminoalkylamino-2-styryl-quinolines salts and derivatives thereofInfo
- Publication number
- GB1329447A GB1329447A GB4818670A GB4818670A GB1329447A GB 1329447 A GB1329447 A GB 1329447A GB 4818670 A GB4818670 A GB 4818670A GB 4818670 A GB4818670 A GB 4818670A GB 1329447 A GB1329447 A GB 1329447A
- Authority
- GB
- United Kingdom
- Prior art keywords
- general formula
- adamantylaminoalkylamino
- reaction
- resulting
- ethyl
- 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
Links
- 229940111121 antirheumatic drug quinolines Drugs 0.000 title abstract 2
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 abstract 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 2
- 125000005843 halogen group Chemical group 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 239000012280 lithium aluminium hydride Substances 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 abstract 1
- DRROTNRHCXFLBA-UHFFFAOYSA-N 3-(1-adamantylamino)propanenitrile Chemical compound C1C(C2)CC3CC2CC1(NCCC#N)C3 DRROTNRHCXFLBA-UHFFFAOYSA-N 0.000 abstract 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 abstract 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 abstract 1
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- DKNWSYNQZKUICI-UHFFFAOYSA-N amantadine Chemical compound C1C(C2)CC3CC2CC1(N)C3 DKNWSYNQZKUICI-UHFFFAOYSA-N 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 230000000844 anti-bacterial effect Effects 0.000 abstract 1
- 230000000843 anti-fungal effect Effects 0.000 abstract 1
- 230000000842 anti-protozoal effect Effects 0.000 abstract 1
- 230000000840 anti-viral effect Effects 0.000 abstract 1
- 229940121375 antifungal agent Drugs 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 238000009472 formulation Methods 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 229910052740 iodine Chemical group 0.000 abstract 1
- ZKTAQLUVESNSMW-UHFFFAOYSA-N n'-(1-adamantyl)-n'-ethylethane-1,2-diamine Chemical compound C1C(C2)CC3CC2CC1(N(CCN)CC)C3 ZKTAQLUVESNSMW-UHFFFAOYSA-N 0.000 abstract 1
- PEISMEIIGOUEOP-UHFFFAOYSA-N n'-(1-adamantyl)propane-1,3-diamine Chemical compound C1C(C2)CC3CC2CC1(NCCCN)C3 PEISMEIIGOUEOP-UHFFFAOYSA-N 0.000 abstract 1
- BCVXYGJCDZPKGV-UHFFFAOYSA-N n-(1-adamantyl)acetamide Chemical compound C1C(C2)CC3CC2CC1(NC(=O)C)C3 BCVXYGJCDZPKGV-UHFFFAOYSA-N 0.000 abstract 1
- VXGGWVBRICYCGO-UHFFFAOYSA-N n-ethyladamantan-1-amine Chemical compound C1C(C2)CC3CC2CC1(NCC)C3 VXGGWVBRICYCGO-UHFFFAOYSA-N 0.000 abstract 1
- -1 nitro, hydroxyl Chemical group 0.000 abstract 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/38—Nitrogen atoms
- C07D215/42—Nitrogen atoms attached in position 4
- C07D215/46—Nitrogen atoms attached in position 4 with hydrocarbon radicals, substituted by nitrogen atoms, attached to said nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
1329447 4-(Adamantylaminoalkylamino)-2- styrylquinolines E R SQUIBB & SONS Inc 9 Oct 1970 [27 Oct 1969] 48186/70 Heading C2C Novel 4-(adamantylaminoalkylamino)-2-styryl-quinolines of the general formula wherein each of R and R<SP>1</SP> is a hydrogen or halogen atom or a nitro, hydroxyl or alkoxy group, R<SP>2</SP> is a hydrogen atom or a C 1-8 alkyl group, each of R<SP>3</SP> and R<SP>4</SP> is a hydrogen or halogen atom or an alkyl, hydroxyl, alkoxy or phenyl group, R<SP>5</SP> is a hydrogen atom or a C 1-8 alkyl, C 2-8 alkenyl or phenyl-C 1-8 alkyl group and n is 2,3 or 4, and pharmaecutically acceptable acid addition salts thereof are prepared by reaction of a 4-halo-2-methylquinoline of the general formula wherein X is a chlorine, bromine or iodine atom, with an adamantylaminoalkylamine of the general formula and reaction of the resulting 4-(adamantylaminoalkylamino)-2-methylquinoline of the general formula with a benzaldehyde of the general formula followed optionally by salification of the product. N-(1-Adamantyl)-1,3-propanediamine is prepared by reaction of 1-adamantylamine with acrylonitrile and reduction of the resulting 3-(1- adamantylamino)propionitrile with lithium aluminium hydride. N-(1-Adamantyl)-N-ethyl-ethylenediamine is prepared by reduction of 1-acetamidoadamantane with lithium aluminium hydride, reaction of the resulting N-ethyl-1- adamantylamine with ethyleneimine and tosyl chloride and reaction of the resulting-N-}2-[N<SP>1</SP>- (1-adamanytl)-N<SP>1</SP>-ethylamino]ethyl}-p-toluenesulphonamide with ammonia. Pharmaceutical compositions having antiviral, antibacterial, antifungal and antiprotozoal activity comprise, as active ingredient, a 4- (adamantylaminoalkylamino) -2 -styrylquinoline of the first general formula above or a physiologically acceptable acid addition salt thereof, together with a suitable carrier, and may be administered orally or parenterally.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US86985269A | 1969-10-27 | 1969-10-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1329447A true GB1329447A (en) | 1973-09-05 |
Family
ID=25354374
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4818670A Expired GB1329447A (en) | 1969-10-27 | 1970-10-09 | 4-adamantylaminoalkylamino-2-styryl-quinolines salts and derivatives thereof |
Country Status (4)
| Country | Link |
|---|---|
| CH (2) | CH530400A (en) |
| DE (1) | DE2050074A1 (en) |
| FR (1) | FR2070165B1 (en) |
| GB (1) | GB1329447A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000073283A1 (en) * | 1999-06-02 | 2000-12-07 | Nps Pharmaceuticals, Inc. | Metabotropic glutamate receptor antagonists and their use for treating central nervous system diseases |
| AU2004202776B2 (en) * | 1997-11-21 | 2008-06-19 | Astrazeneca Ab | Metabotropic glutamate receptor antagonists for treating central nervous system diseases |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6429207B1 (en) | 1997-11-21 | 2002-08-06 | Nps Pharmaceuticals, Inc. | Metabotropic glutamate receptor antagonists and their use for treating central nervous system diseases |
-
1970
- 1970-10-09 GB GB4818670A patent/GB1329447A/en not_active Expired
- 1970-10-12 DE DE19702050074 patent/DE2050074A1/en active Pending
- 1970-10-19 FR FR7037661A patent/FR2070165B1/fr not_active Expired
- 1970-10-23 CH CH1569170A patent/CH530400A/en not_active IP Right Cessation
- 1970-10-27 CH CH1587670A patent/CH525888A/en not_active IP Right Cessation
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2004202776B2 (en) * | 1997-11-21 | 2008-06-19 | Astrazeneca Ab | Metabotropic glutamate receptor antagonists for treating central nervous system diseases |
| WO2000073283A1 (en) * | 1999-06-02 | 2000-12-07 | Nps Pharmaceuticals, Inc. | Metabotropic glutamate receptor antagonists and their use for treating central nervous system diseases |
| EP1595871A3 (en) * | 1999-06-02 | 2005-11-30 | Nps Pharmaceuticals, Inc. | Metabotropic glutamate receptor antagonists and their use for treating central nervous system diseases |
Also Published As
| Publication number | Publication date |
|---|---|
| CH525888A (en) | 1972-07-31 |
| FR2070165A1 (en) | 1971-09-10 |
| FR2070165B1 (en) | 1975-10-10 |
| DE2050074A1 (en) | 1971-05-06 |
| CH530400A (en) | 1972-11-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PLNP | Patent lapsed through nonpayment of renewal fees |