GB1321424A - N-phenyl-n-disubstituted aminoalkyl-2-amino indanes - Google Patents
N-phenyl-n-disubstituted aminoalkyl-2-amino indanesInfo
- Publication number
- GB1321424A GB1321424A GB6207369A GB1321424DA GB1321424A GB 1321424 A GB1321424 A GB 1321424A GB 6207369 A GB6207369 A GB 6207369A GB 1321424D A GB1321424D A GB 1321424DA GB 1321424 A GB1321424 A GB 1321424A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formula
- reacted
- amine
- compound
- phenyl
- 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
- 150000001412 amines Chemical class 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- 238000000034 method Methods 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- FQSNKGBOFANYSC-UHFFFAOYSA-N 2-oxoindene-1-carbonitrile Chemical compound O=C1C=C2C=CC=CC2=C1C#N FQSNKGBOFANYSC-UHFFFAOYSA-N 0.000 abstract 1
- 238000006820 Bouveault-Blanc reduction reaction Methods 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 230000003444 anaesthetic effect Effects 0.000 abstract 1
- 206010003119 arrhythmia Diseases 0.000 abstract 1
- 230000006793 arrhythmia Effects 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- UMJJFEIKYGFCAT-UHFFFAOYSA-N indan-2-one Chemical compound C1=CC=C2CC(=O)CC2=C1 UMJJFEIKYGFCAT-UHFFFAOYSA-N 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group 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
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
- 230000000699 topical effect Effects 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/44—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring
- C07C211/53—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring having the nitrogen atom of at least one of the amino groups further bound to a hydrocarbon radical substituted by amino groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/13—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
1321424 N-Phenyl-N-disubstituted amino alkyl-2-amino-indanes MANUFACTURE DE PRODUITS PHARMACEUTIQUES A CHRISTIAENS SA 26 Nov 1970 [19 Dec 1969] 62073/69 Heading C2C Novel compounds of formula wherein n is 2 or 3, R 1 and R 2 are C 1 -C 4 alkyl or together with the adjacent nitrogen atom form a heterocyclic ring and R 3 is phenyl optionally substituted by e.g. methyl, methoxy, Cl or CF 3 and acid addition salts thereof, are prepared by reaction of a compound of Formula II with NaNH 2 and Cl(CR 2 ) n N.R 1 .R 2 and optional salt formation. Intermediates of Formula II are prepared by one of the following methods (a) an amine R 3 NH 2 is reacted with a 2-keto-3-cyanoindene and the product reduced by the Bouveault-Blanc method, (b) an amine R 3 NH 2 is reacted with a compound of formula or (c) 2-indanone is reacted with an amine R 3 NH 2 and NaBH 4 is then added to the reaction mixture. Pharmaceutical compositions in conventional forms for topical, parenteral or rectal administration and having local anaesthetic activity or use in treating heart arrhythmia comprise an above novel compound and a suitable carrier or diluent.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB6207369 | 1969-12-19 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1321424A true GB1321424A (en) | 1973-06-27 |
Family
ID=10487848
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB6207369A Expired GB1321424A (en) | 1969-12-19 | 1969-12-19 | N-phenyl-n-disubstituted aminoalkyl-2-amino indanes |
Country Status (9)
Country | Link |
---|---|
AT (1) | AT298478B (en) |
BE (1) | BE760018A (en) |
CH (1) | CH521941A (en) |
ES (1) | ES386586A1 (en) |
FR (1) | FR2081383B1 (en) |
GB (1) | GB1321424A (en) |
LU (1) | LU62232A1 (en) |
NL (1) | NL150099B (en) |
SE (1) | SE372258B (en) |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB2191999A (en) * | 1986-06-19 | 1987-12-31 | Squibb & Sons Inc | p-Aminophenols, derivatives thereof and method of use |
EP1185267A1 (en) * | 1999-06-10 | 2002-03-13 | Bridge Pharma, Inc. | Dermal anesthetic agents |
EP1658847A2 (en) * | 1999-06-10 | 2006-05-24 | Bridge Pharma, Inc. | Indane derivatives as dermal anesthetic agents |
US7592458B2 (en) | 2006-07-21 | 2009-09-22 | Wright George E | Dermal anesthetic compounds and pharmaceutical compositions for inducing local anesthesia and mitigating neuropathic pain |
US7718674B2 (en) | 2004-09-27 | 2010-05-18 | Bridge Pharma, Inc. | Methods of relieving neuropathic pain with the S-isomer of 2-{2[N-(2-indanyl)-N-phenylamino]ethyl}piperidine |
US8865741B2 (en) | 2011-02-18 | 2014-10-21 | Asana Biosciences, Llc | Aminoindane compounds and use thereof in treating pain |
US9044482B2 (en) | 2012-08-15 | 2015-06-02 | Asana Biosciences, Llc | Use of aminoindane compounds in treating overactive bladder and interstitial cystitis |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AR206999A1 (en) * | 1972-11-06 | 1976-09-09 | Christiaens Sa A | PROCEDURE FOR THE PREPARATION OF NEW N-PHENYL-2-AMINOINDANE DERIVATIVES |
GB1468347A (en) * | 1973-03-02 | 1977-03-23 | Christiaens Sa A | Aminoindanes |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2670371A (en) * | 1951-08-01 | 1954-02-23 | Searle & Co | Basic alkyl substitution products of n-indanyl and n-tetrahydronaphthyl-monocarbocyclylamides and their salts |
-
0
- BE BE760018D patent/BE760018A/en not_active IP Right Cessation
-
1969
- 1969-12-19 GB GB6207369A patent/GB1321424A/en not_active Expired
-
1970
- 1970-12-11 LU LU62232D patent/LU62232A1/xx unknown
- 1970-12-14 FR FR7045013A patent/FR2081383B1/fr not_active Expired
- 1970-12-17 CH CH1872070A patent/CH521941A/en not_active IP Right Cessation
- 1970-12-18 ES ES386586A patent/ES386586A1/en not_active Expired
- 1970-12-18 SE SE7017229A patent/SE372258B/xx unknown
- 1970-12-18 AT AT1142870A patent/AT298478B/en not_active IP Right Cessation
- 1970-12-18 NL NL707018508A patent/NL150099B/en not_active IP Right Cessation
Cited By (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB2191999A (en) * | 1986-06-19 | 1987-12-31 | Squibb & Sons Inc | p-Aminophenols, derivatives thereof and method of use |
EP1185267A1 (en) * | 1999-06-10 | 2002-03-13 | Bridge Pharma, Inc. | Dermal anesthetic agents |
US6413987B1 (en) * | 1999-06-10 | 2002-07-02 | Bridge Pharma, Inc. | Dermal anesthetic agents |
EP1185267A4 (en) * | 1999-06-10 | 2003-09-03 | Bridge Pharma Inc | Dermal anesthetic agents |
EP1658847A2 (en) * | 1999-06-10 | 2006-05-24 | Bridge Pharma, Inc. | Indane derivatives as dermal anesthetic agents |
EP1658847A3 (en) * | 1999-06-10 | 2006-07-26 | Bridge Pharma, Inc. | Indane derivatives as dermal anesthetic agents |
US7718674B2 (en) | 2004-09-27 | 2010-05-18 | Bridge Pharma, Inc. | Methods of relieving neuropathic pain with the S-isomer of 2-{2[N-(2-indanyl)-N-phenylamino]ethyl}piperidine |
US7592458B2 (en) | 2006-07-21 | 2009-09-22 | Wright George E | Dermal anesthetic compounds and pharmaceutical compositions for inducing local anesthesia and mitigating neuropathic pain |
US8865741B2 (en) | 2011-02-18 | 2014-10-21 | Asana Biosciences, Llc | Aminoindane compounds and use thereof in treating pain |
US9044482B2 (en) | 2012-08-15 | 2015-06-02 | Asana Biosciences, Llc | Use of aminoindane compounds in treating overactive bladder and interstitial cystitis |
US9375423B2 (en) | 2012-08-15 | 2016-06-28 | Asana Biosciences, Llc | Use of aminoindane compounds in treating overactive bladder and interstitial cystitis |
Also Published As
Publication number | Publication date |
---|---|
FR2081383B1 (en) | 1975-04-18 |
DE2060721A1 (en) | 1971-06-24 |
ES386586A1 (en) | 1973-11-16 |
AT298478B (en) | 1972-05-10 |
SE372258B (en) | 1974-12-16 |
LU62232A1 (en) | 1971-05-11 |
CH521941A (en) | 1972-04-30 |
NL150099B (en) | 1976-07-15 |
DE2060721B2 (en) | 1976-02-26 |
NL7018508A (en) | 1971-06-22 |
BE760018A (en) | 1971-06-08 |
FR2081383A1 (en) | 1971-12-03 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
PS | Patent sealed [section 19, patents act 1949] | ||
PLE | Entries relating assignments, transmissions, licences in the register of patents | ||
PCNP | Patent ceased through non-payment of renewal fee |