GB1360119A - 1-benzoyloxy-2-lower alkylaminobenzocycloalkane derivatives - Google Patents
1-benzoyloxy-2-lower alkylaminobenzocycloalkane derivativesInfo
- Publication number
- GB1360119A GB1360119A GB2660772A GB2660772A GB1360119A GB 1360119 A GB1360119 A GB 1360119A GB 2660772 A GB2660772 A GB 2660772A GB 2660772 A GB2660772 A GB 2660772A GB 1360119 A GB1360119 A GB 1360119A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formula
- compound
- group
- prepared
- amino
- 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
- 150000001875 compounds Chemical class 0.000 abstract 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 3
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 125000003277 amino group Chemical group 0.000 abstract 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- UIZWHUHXZRJJGF-UHFFFAOYSA-N 2-amino-3,4-dihydro-2h-naphthalen-1-one;hydrochloride Chemical compound Cl.C1=CC=C2C(=O)C(N)CCC2=C1 UIZWHUHXZRJJGF-UHFFFAOYSA-N 0.000 abstract 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 abstract 1
- FZYOCWGAGMJUTM-HZPDHXFCSA-N N-[(1R,2R)-1-hydroxy-1,2,3,4-tetrahydronaphthalen-2-yl]benzamide Chemical compound C(C1=CC=CC=C1)(=O)N[C@H]1[C@@H](C2=CC=CC=C2CC1)O FZYOCWGAGMJUTM-HZPDHXFCSA-N 0.000 abstract 1
- 208000025865 Ulcer Diseases 0.000 abstract 1
- 125000004442 acylamino group Chemical group 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000003282 alkyl amino group Chemical group 0.000 abstract 1
- 230000029936 alkylation Effects 0.000 abstract 1
- 238000005804 alkylation reaction Methods 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 230000003444 anaesthetic effect Effects 0.000 abstract 1
- BFAKENXZKHGIGE-UHFFFAOYSA-N bis(2,3,5,6-tetrafluoro-4-iodophenyl)diazene Chemical compound FC1=C(C(=C(C(=C1F)I)F)F)N=NC1=C(C(=C(C(=C1F)F)I)F)F BFAKENXZKHGIGE-UHFFFAOYSA-N 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 235000019253 formic acid Nutrition 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- UNTIIHJWZOCDOS-UHFFFAOYSA-N n-(1-oxo-3,4-dihydro-2h-naphthalen-2-yl)benzamide Chemical compound C1CC2=CC=CC=C2C(=O)C1NC(=O)C1=CC=CC=C1 UNTIIHJWZOCDOS-UHFFFAOYSA-N 0.000 abstract 1
- 150000002828 nitro derivatives Chemical class 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 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
- 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
- 231100000397 ulcer Toxicity 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/60—Naphthoxazoles; Hydrogenated naphthoxazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
1360119 Benzoyloxy alkylamino benzocycloalkane derivatives YAMANOUCHI PHARMACEUTICAL CO Ltd 7 June 1972 [22 June 1971 6 Dec 1971 10 Dec 1971] 26607/72 Heading C2C Novel compounds of Formula IIIa and salts thereof wherein R<SP>1</SP> represents hydrogen atom or a lower alkyl group; R<SP>2</SP> represents a lower alkyl group; R<SP>3</SP>, R<SP>4</SP> and R<SP>5</SP> are same or different from each other and each represents hydrogen atom, a halogen atom, a lower alkyl group, a lower alkoxy group, phenyl group, amino group, a lower alkylamino group, an acylamino group, or nitro group; n is an integer of 1-3; and lower indicates groups of up to 5 carbon atoms are prepared by one of the following methods; (a) a compound of Formula I is reacted with a compound of Formula II or a reactive derivative thereof; (b) a compound of Formula IV is alkylated at the amino group; or (c) a compound of Formula IV above or a compound of Formula V is heated with formaldehyde/formic acid, also amino substituted compounds may be obtained by reduction of the corresponding nitro compound and salts may be formed and compounds separated into their isomers. Intermediates of Formula I above are prepared by alkylation of the free amine or, e.g. 2-methyl-3a,4,5,9b-tetrahydronaphtho-[2, 1d]oxazole obtained by reaction of 2 - acetamide - 1 - hydroxy tetralin with SOCl 2 or of cis - 2 - phenyl - 3,4,5,9b - tetrahydro - [2,1d] oxazole or of 2 - phenyl - 3a,4,5,9b - tetrahydronaphtho-[2,1d]oxazole which is prepared by action of c.nc. H 2 SO 4 on trans-2-benzoylamino- 1-hydroxytetralin obtained by reduction of the 2-benzoylaminotetralone prepared by benzoyation of 2-amino-1-tetralone hydrochloride. Pharmaceutical compositions in conventional forms for oral administration and having local anaesthetic action, e.g. for relief of pain from ulcers, comprises an above novel compound and a carrier therefor.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP46044491A JPS516669B1 (en) | 1971-06-22 | 1971-06-22 | |
| JP9849571A JPS4867274A (en) | 1971-12-06 | 1971-12-06 | |
| JP10004971A JPS4864060A (en) | 1971-12-10 | 1971-12-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1360119A true GB1360119A (en) | 1974-07-17 |
Family
ID=27291920
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2660772A Expired GB1360119A (en) | 1971-06-22 | 1972-06-07 | 1-benzoyloxy-2-lower alkylaminobenzocycloalkane derivatives |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3823181A (en) |
| CA (1) | CA984851A (en) |
| DE (1) | DE2229359A1 (en) |
| ES (1) | ES404115A1 (en) |
| FR (1) | FR2143304B1 (en) |
| GB (1) | GB1360119A (en) |
| SE (1) | SE384854B (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9315566D0 (en) * | 1993-07-28 | 1993-09-08 | Smithkline Beecham Plc | Medicaments |
| GB9315600D0 (en) * | 1993-07-28 | 1993-09-08 | Smithkline Beecham Plc | Compounds |
-
1972
- 1972-06-07 GB GB2660772A patent/GB1360119A/en not_active Expired
- 1972-06-07 CA CA144,068A patent/CA984851A/en not_active Expired
- 1972-06-14 US US00262623A patent/US3823181A/en not_active Expired - Lifetime
- 1972-06-16 DE DE2229359A patent/DE2229359A1/en active Pending
- 1972-06-21 ES ES404115A patent/ES404115A1/en not_active Expired
- 1972-06-21 SE SE7208163A patent/SE384854B/en unknown
- 1972-06-22 FR FR7222597A patent/FR2143304B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| ES404115A1 (en) | 1976-01-01 |
| SE384854B (en) | 1976-05-24 |
| CA984851A (en) | 1976-03-02 |
| FR2143304B1 (en) | 1976-09-17 |
| FR2143304A1 (en) | 1973-02-02 |
| DE2229359A1 (en) | 1973-01-11 |
| US3823181A (en) | 1974-07-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PLNP | Patent lapsed through nonpayment of renewal fees |