ES397603A1 - Benzobicycloalkane compounds - Google Patents
Benzobicycloalkane compoundsInfo
- Publication number
- ES397603A1 ES397603A1 ES397603A ES397603A ES397603A1 ES 397603 A1 ES397603 A1 ES 397603A1 ES 397603 A ES397603 A ES 397603A ES 397603 A ES397603 A ES 397603A ES 397603 A1 ES397603 A1 ES 397603A1
- Authority
- ES
- Spain
- Prior art keywords
- alkyl
- compound
- lower alkyl
- general formula
- formula
- 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 title abstract 9
- 125000000217 alkyl group Chemical group 0.000 abstract 22
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 6
- 125000003342 alkenyl group Chemical group 0.000 abstract 5
- 229910052739 hydrogen Inorganic materials 0.000 abstract 5
- 239000001257 hydrogen Substances 0.000 abstract 5
- 238000005804 alkylation reaction Methods 0.000 abstract 4
- 150000002431 hydrogen Chemical group 0.000 abstract 4
- 125000003545 alkoxy group Chemical group 0.000 abstract 3
- 230000029936 alkylation Effects 0.000 abstract 3
- 125000000304 alkynyl group Chemical group 0.000 abstract 3
- 238000000034 method Methods 0.000 abstract 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 abstract 1
- 150000001204 N-oxides Chemical class 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000004423 acyloxy group Chemical group 0.000 abstract 1
- 238000005905 alkynylation reaction Methods 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 239000012458 free base Substances 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 150000002466 imines Chemical class 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
A procedure for preparing benzobicycloalkane amines of the general formula (I) **(See formula)** in which Z is (see formula) or **(See formula)** R is hydrogen, lower alkyl, lower alkyloxy, hydroxy, acyloxy, phen-lower alkyloxy, halogen, or trifluoromethyl; R1 is lower alkyl, phen-lower alkyl; and when X is (see formula), hydroxymethyl or alkenyl, R2 is hydrogen, alkyl or phen-lower alkyl; R3 is hydrogen, lower alkyl, phenyl (lower) alkyl, alkenyl, or alkynyl; R4 is lower alkyl; R5 is lower alkyl; m is 0 or 1; and n is an integer valued from 2 to 6, and its pharmaceutically acceptable addition salts, characterized by reducing an imine compound of the general formula (II) **(See formula)** in which R6 is hydroxyl, alkoxy, or R2, except that when R7 is alkoxycarbonyl, R6 is not R2; R7 is alkoxycarbonyl, lower alkyl, lower alkenyl, hydroxymethyl, or phenyl (lower) alkyl; and R, R2, m and n have the same meaning as before, and alternatively, when in the general formula I R1 is lower alkyl, phenyl (lower) alkyl or when X is (see formula), hydroxy-lower alkyl or alkyl; the same type of reduction is carried out on a compound V, of the same structure as compound II, with the formula **(See formula)** in which A is -CH = CH- or -CH (O-tosyl) -CH2; B is (see formula) or **(See formula)** R, R2, R3, R6, R7, m and n have the same meaning attributed to them before, and, if desired, in both cases, undergo lower alkylation, phenyl (lower) alkylation, alkenylation or alkynylation of a compound of the general formula (I) formed in which R3 is hydrogen, resulting in a compound of the general formula (I) wherein R3 is lower alkyl, phen-lower alkyl, alkenyl or alkynyl; and/or undergoing lower alkylation or (lower) phen-alkylation a compound in which R2 is hydrogen and R3 is lower alkyl, phenyl (lower) alkyl, alkenyl or alkynyl, to obtain a respective compound in which R2 is alkyl lower or phenyl (lower) alkyl; and/or oxidizing by a known method a compound in which R2 and R3 are lower alkyl, to obtain the respective N-oxide; and/or converted by known methods a compound of the general formula (I) obtained in which R has some meaning into a compound of the general formula (I) in which R has a different meaning; and/or converting a free base of the general formula (I) to a pharmaceutically acceptable acid addition salt. (Machine-translation by Google Translate, not legally binding)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US9498370A | 1970-12-03 | 1970-12-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES397603A1 true ES397603A1 (en) | 1975-03-16 |
Family
ID=22248330
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES397603A Expired ES397603A1 (en) | 1970-12-03 | 1971-12-02 | Benzobicycloalkane compounds |
Country Status (21)
| Country | Link |
|---|---|
| JP (1) | JPS5747176B1 (en) |
| AR (5) | AR193714A1 (en) |
| AT (2) | AT321265B (en) |
| AU (1) | AU475974B2 (en) |
| BE (1) | BE776173A (en) |
| CA (1) | CA1005822A (en) |
| CH (1) | CH569689A5 (en) |
| CY (1) | CY922A (en) |
| DE (1) | DE2159324C2 (en) |
| DK (1) | DK142984C (en) |
| ES (1) | ES397603A1 (en) |
| FI (1) | FI53967C (en) |
| FR (1) | FR2116509B1 (en) |
| GB (3) | GB1363659A (en) |
| HK (1) | HK12678A (en) |
| KE (1) | KE2770A (en) |
| NL (1) | NL175292C (en) |
| PH (1) | PH13159A (en) |
| SE (1) | SE385471B (en) |
| YU (1) | YU35866B (en) |
| ZA (1) | ZA717697B (en) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1504694A (en) * | 1974-04-08 | 1978-03-22 | Akzo Nv | Benzo-bicyclononene derivatives |
| GB1549172A (en) * | 1975-04-29 | 1979-08-01 | Akzonv | Benzobicyclononene derivatives |
| US5098916A (en) * | 1990-03-29 | 1992-03-24 | G. D. Searle & Co. | Propanobicyclic amine derivatives for cns disorders |
| WO2017118375A1 (en) * | 2016-01-04 | 2017-07-13 | 南京明德新药研发股份有限公司 | Dezocine analogue |
| AU2020214275A1 (en) * | 2019-02-02 | 2021-08-26 | Yangtze River Pharmaceutical Group Co., Ltd. | Dezocine derivative and medical use thereof |
| CN110283085A (en) * | 2019-06-04 | 2019-09-27 | 华润双鹤利民药业（济南）有限公司 | A kind of dezocine fabrication processing |
| CN113979875B (en) * | 2020-07-27 | 2022-11-08 | 扬子江药业集团有限公司 | Dezocine derivative crystal form A and preparation method and application thereof |
-
1971
- 1971-11-16 ZA ZA717697A patent/ZA717697B/en unknown
- 1971-11-29 AT AT1024771A patent/AT321265B/en not_active IP Right Cessation
- 1971-11-29 AT AT10874A patent/AT325597B/en not_active IP Right Cessation
- 1971-11-29 PH PH13059A patent/PH13159A/en unknown
- 1971-11-29 AU AU36248/71A patent/AU475974B2/en not_active Expired
- 1971-11-30 DE DE2159324A patent/DE2159324C2/en not_active Expired
- 1971-12-01 GB GB3538973A patent/GB1363659A/en not_active Expired
- 1971-12-01 GB GB5571771A patent/GB1363658A/en not_active Expired
- 1971-12-01 YU YU3022/71A patent/YU35866B/en unknown
- 1971-12-01 FI FI3437/71A patent/FI53967C/en active
- 1971-12-01 CY CY922A patent/CY922A/en unknown
- 1971-12-01 GB GB3539073A patent/GB1363660A/en not_active Expired
- 1971-12-02 BE BE776173A patent/BE776173A/en not_active IP Right Cessation
- 1971-12-02 FR FR7143351A patent/FR2116509B1/fr not_active Expired
- 1971-12-02 SE SE7115498A patent/SE385471B/en unknown
- 1971-12-02 JP JP46097546A patent/JPS5747176B1/ja active Pending
- 1971-12-02 AR AR239391A patent/AR193714A1/en active
- 1971-12-02 DK DK592071A patent/DK142984C/en active
- 1971-12-02 NL NLAANVRAGE7116567,A patent/NL175292C/en not_active IP Right Cessation
- 1971-12-02 ES ES397603A patent/ES397603A1/en not_active Expired
- 1971-12-03 CH CH1763671A patent/CH569689A5/xx not_active IP Right Cessation
- 1971-12-03 CA CA129,373A patent/CA1005822A/en not_active Expired
-
1972
- 1972-10-26 AR AR244830A patent/AR194020A1/en active
- 1972-10-26 AR AR244831A patent/AR198637A1/en active
- 1972-10-26 AR AR224829A patent/AR197202A1/en active
- 1972-10-26 AR AR244832A patent/AR193903A1/en active
-
1977
- 1977-09-06 KE KE2770A patent/KE2770A/en unknown
-
1978
- 1978-03-09 HK HK126/78A patent/HK12678A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AT321265B (en) | 1975-03-25 |
| NL7116567A (en) | 1972-06-06 |
| YU35866B (en) | 1981-08-31 |
| AU475974B2 (en) | 1976-09-09 |
| AR194020A1 (en) | 1973-06-12 |
| DK142984C (en) | 1981-09-28 |
| CY922A (en) | 1977-12-23 |
| DE2159324C2 (en) | 1984-06-14 |
| FI53967C (en) | 1978-09-11 |
| SE385471B (en) | 1976-07-05 |
| FI53967B (en) | 1978-05-31 |
| AR198637A1 (en) | 1974-07-15 |
| GB1363658A (en) | 1974-08-14 |
| PH13159A (en) | 1980-01-08 |
| AR193903A1 (en) | 1973-05-31 |
| ZA717697B (en) | 1973-06-27 |
| CH569689A5 (en) | 1975-11-28 |
| AT325597B (en) | 1975-10-27 |
| JPS5747176B1 (en) | 1982-10-07 |
| YU302271A (en) | 1981-02-28 |
| BE776173A (en) | 1972-06-02 |
| HK12678A (en) | 1978-03-17 |
| FR2116509B1 (en) | 1975-08-01 |
| DE2159324A1 (en) | 1972-06-15 |
| GB1363660A (en) | 1974-08-14 |
| ATA10874A (en) | 1975-01-15 |
| FR2116509A1 (en) | 1972-07-13 |
| GB1363659A (en) | 1974-08-14 |
| NL175292C (en) | 1984-10-16 |
| DK142984B (en) | 1981-03-09 |
| CA1005822A (en) | 1977-02-22 |
| AR193714A1 (en) | 1973-05-22 |
| KE2770A (en) | 1977-10-21 |
| NL175292B (en) | 1984-05-16 |
| AR197202A1 (en) | 1974-03-22 |
| AU3624871A (en) | 1973-06-07 |
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