GB1511319A - 2,6-methane-3-benzazocine derivatives and their preparation - Google Patents
2,6-methane-3-benzazocine derivatives and their preparationInfo
- Publication number
- GB1511319A GB1511319A GB37887/75A GB3788775A GB1511319A GB 1511319 A GB1511319 A GB 1511319A GB 37887/75 A GB37887/75 A GB 37887/75A GB 3788775 A GB3788775 A GB 3788775A GB 1511319 A GB1511319 A GB 1511319A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compounds
- formula
- reaction
- prepared
- hcl
- 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 13
- -1 iso-butyryl Chemical group 0.000 abstract 8
- 238000006243 chemical reaction Methods 0.000 abstract 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 3
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 abstract 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 abstract 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 abstract 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 abstract 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 abstract 2
- SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical compound CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-UHFFFAOYSA-N 0.000 abstract 2
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 abstract 2
- GPYOGVOBLWYKSF-UHFFFAOYSA-N 1,6-dibenzyl-4,5-diethyl-3,6-dihydro-2h-pyridine Chemical compound C=1C=CC=CC=1CN1CCC(CC)=C(CC)C1CC1=CC=CC=C1 GPYOGVOBLWYKSF-UHFFFAOYSA-N 0.000 abstract 1
- ZJFPQVBARDXZPX-UHFFFAOYSA-N 2,6-methano-3-benzazocine Chemical class C1=CC=C2C(C3)=CC=NC3=CC2=C1 ZJFPQVBARDXZPX-UHFFFAOYSA-N 0.000 abstract 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 abstract 1
- DMGLUDJTJZXMMG-UHFFFAOYSA-N 3-benzazocine Chemical class C1=CN=CC=CC2=CC=CC=C21 DMGLUDJTJZXMMG-UHFFFAOYSA-N 0.000 abstract 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 1
- 229910010082 LiAlH Inorganic materials 0.000 abstract 1
- QXKHYNVANLEOEG-UHFFFAOYSA-N Methoxsalen Chemical group C1=CC(=O)OC2=C1C=C1C=COC1=C2OC QXKHYNVANLEOEG-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 238000007796 conventional method Methods 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 229940079593 drug Drugs 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 abstract 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 abstract 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 abstract 1
- 238000006396 nitration reaction Methods 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D213/16—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing only one pyridine ring
- C07D213/20—Quaternary compounds thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/70—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/80—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D211/82—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- 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
- C07D221/22—Bridged ring systems
-
- 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
- C07D221/22—Bridged ring systems
- C07D221/26—Benzomorphans
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Pyridine Compounds (AREA)
Abstract
1511319 2,6 - Methano - 3 - benzazocine derivatives STERLING DRUG Inc 15 Sept 1975 [20 Sept 1974 (2)] 37887/75 Heading C2C The invention comprises compounds of the general formulµ wherein X is -H, -CH 3 or -C 2 H 5 ; Y is -H, -CH 3 , -C 2 H 5 , -C 3 H 7 , allyl or phenyl; Z is -H, -CH 3 , -C 2 H 5 or -OH; Z<SP>1</SP> is -H, -CH 3 or -C 2 H 5 ; R is -H or -CH 3 ; R<SP>1</SP> is -H, -CH 3 , -C 2 H 5 , -C 3 H 7 , iso - C 3 H 7 , -C 4 H 9 , iso-C 4 H 9 , sec-C 4 H 9 , benzyl, cyclopropylmethyl, formyl, acetyl, propionyl, butyryl, iso-butyryl, benzoyl or cyclopropanecarbonyl; Q<SP>1</SP> is -H (but not in Formula II), benzyl, propyl, iso-butyl, neopentyl, allyl, 2-methyl- or 2 - chloro - 2 - propenyl, cis - 3 - chloro- 2 - propenyl, cis- or trans - 3 - chloro - 2 - butenyl, propargyl, cyclopropylmethyl or (2,2- dichlorocyclopropyl)methyl and, for compounds of Formula II only, may also be one of the radicals given below for Q; and Q may be a radical Q<SP>1</SP> (but not -H) or may be formyl, acetyl, propionyl, isobutyryl, piraloyl, acryloyl, 2-methyl-, 2-chloro- or cis-3-chloro-acryloyl, cis- or trans-3-chlorocrotonoyl, propiolyl, cyclopropanecarbonyl or 2,2-dichlorocyclopropanecarbonyl; and acid addition salts thereof, particularly with HCl. The compounds of Formula I wherein R<SP>1</SP> is H, alkyl, benzyl or cyclopropylmethyl are prepared by conventional methods including reduction of Formula II compounds with Fe/HCl, reaction of the 8-acylamine compounds with HCl and reaction of Formula IV compounds with (CH 3 CO) 2 O/HCl; compounds wherein Q is -CH 2 -alkyl &c. may be prepared by reduction with LiAlH 4 /THF of the corresponding Q-CO-alkyl compounds. Formula I compounds where R<SP>1</SP> is acyl, benzoyl, &c. are prepared by reaction of 8-amino compounds with H . COOH, (R<SP>1</SP>CO) 2 O or R<SP>1</SP>COCl. The 8-nitro compounds of Formula II are prepared by ring nitration with HNO 3 ; compounds with Q=H may be converted to other Q-substituted compounds by reaction with an appropriate halide. The compounds of Formula III are prepared by treatment of the 8-methoxy analogues with HCl and are themselves converted to compounds of Formula IV by reaction with HONH 2 . HCl/pyridine. The compounds of Formulµ I-IV have pharmaceutical properties. 1,2,3,4,5,6,7,10 - Octahydro - 8 - methoxy- 6(eq), 11(ax) - dimethyl - 2,6 - methano - 3 - benzazocine is prepared from its 1,2,3,4,5,6- hexahydro analogue by reaction with sodium in liquid ammonia. 1,2 - Dibenzyl - 3,4 - diethyl - 1,2,5,6 - tetrahydropyridine is prepared from its 1,2-dihydro analogue by reaction with NaBH 4 ; it is reacted with (1) HBr/acetic acid and (2) NaOH to provide cis - 6,11 - diethyl - 1,2,3,4,5,6 - hexahydro - 3 - benzyl - 2,6 - methano - 3 - benrazocine (hydrochloride) which in turn is hydrogenated over palladium-on-carbon to yield the 3-unsubstituted 3-benzazocine (hydrochloride).
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/507,966 US3968114A (en) | 1974-09-20 | 1974-09-20 | 1,2,3,4,5,6,7,8,9,10-Decahydro-8-oxo-2,6-methano-3-benzazocines |
| US05/507,965 US3957793A (en) | 1974-09-20 | 1974-09-20 | Hydroxyiminobenzazocines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1511319A true GB1511319A (en) | 1978-05-17 |
Family
ID=27056041
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB37887/75A Expired GB1511319A (en) | 1974-09-20 | 1975-09-15 | 2,6-methane-3-benzazocine derivatives and their preparation |
Country Status (12)
| Country | Link |
|---|---|
| JP (1) | JPS5156454A (en) |
| AR (2) | AR212324A1 (en) |
| DE (1) | DE2541859A1 (en) |
| DK (1) | DK418775A (en) |
| FI (1) | FI752615A7 (en) |
| FR (2) | FR2285128A1 (en) |
| GB (1) | GB1511319A (en) |
| IL (1) | IL48140A (en) |
| LU (1) | LU73431A1 (en) |
| NL (1) | NL7511131A (en) |
| NO (1) | NO753165L (en) |
| SE (1) | SE7510550L (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1085231B (en) * | 1977-05-30 | 1985-05-28 | Simonetta Enrico | AUTOMATIC EMBROIDERY MACHINE WITH PROGRAM SELECTION OF ACTIVE AND NON-ACTIVE NEEDLES |
| JP5581211B2 (en) * | 2007-08-09 | 2014-08-27 | レンセラール ポリテクニック インスティチュート | Quaternary opioid carboxamide |
| MA39956A (en) * | 2014-05-06 | 2015-11-12 | Purdue Pharma Lp | Benzomorphan analogs and use thereof |
-
1975
- 1975-09-15 GB GB37887/75A patent/GB1511319A/en not_active Expired
- 1975-09-17 NO NO753165A patent/NO753165L/no unknown
- 1975-09-18 DK DK418775A patent/DK418775A/en unknown
- 1975-09-18 FR FR7528623A patent/FR2285128A1/en not_active Withdrawn
- 1975-09-19 AR AR260450A patent/AR212324A1/en active
- 1975-09-19 SE SE7510550A patent/SE7510550L/en not_active Application Discontinuation
- 1975-09-19 NL NL7511131A patent/NL7511131A/en not_active Application Discontinuation
- 1975-09-19 LU LU73431A patent/LU73431A1/xx unknown
- 1975-09-19 FI FI752615A patent/FI752615A7/fi not_active Application Discontinuation
- 1975-09-19 IL IL48140A patent/IL48140A/en unknown
- 1975-09-19 DE DE19752541859 patent/DE2541859A1/en not_active Withdrawn
- 1975-09-19 JP JP50113551A patent/JPS5156454A/ja active Pending
-
1976
- 1976-03-24 FR FR7608496A patent/FR2296626A1/en not_active Withdrawn
- 1976-09-07 AR AR264608A patent/AR213411A1/en active
Also Published As
| Publication number | Publication date |
|---|---|
| AU8486875A (en) | 1977-03-24 |
| SE7510550L (en) | 1976-03-22 |
| JPS5156454A (en) | 1976-05-18 |
| FR2285128A1 (en) | 1976-04-16 |
| IL48140A (en) | 1979-11-30 |
| DE2541859A1 (en) | 1976-04-08 |
| AR212324A1 (en) | 1978-06-30 |
| LU73431A1 (en) | 1976-08-19 |
| AR213411A1 (en) | 1979-01-31 |
| FR2296626A1 (en) | 1976-07-30 |
| IL48140A0 (en) | 1975-11-25 |
| NL7511131A (en) | 1976-03-23 |
| NO753165L (en) | 1976-03-23 |
| DK418775A (en) | 1976-03-21 |
| FI752615A7 (en) | 1976-03-21 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| ATE83383T1 (en) | HIGH MOLECULAR PRO-DRUG DERIVATIVES OF ANTI-INFLAMMATORY PHARMACEUTICALS. | |
| KR920018062A (en) | Glycyrrhetinic acid derivatives | |
| ES487769A1 (en) | Cycloalkylidenemethylphenylacetic acid derivatives and process for the preparation thereof | |
| US5221692A (en) | Ether linked and relatively nonpungent analogues of N-nonanoyl vanillylamide | |
| ZA793453B (en) | New 3,20-dioxo-4,9-diene-21-hydroxyl steroid derivatives,a process for preparing them,their use as medicaments and the pharmaceutical compositions containing them | |
| GB1511319A (en) | 2,6-methane-3-benzazocine derivatives and their preparation | |
| US4131745A (en) | Aryloxy aminobutanols, their preparation and use thereof | |
| IE40335B1 (en) | Pyrazole derivatives, process for their preparation and their use as medicaments | |
| ES8301219A1 (en) | Substituted phenylamino-2-imidazoline-2 derivatives, their acid addition salts, medicaments containing them and process for their preparation. | |
| US3624094A (en) | Alpha-{8 (phenyl sulfinyl)methyl{9 -alpha-phenyl derivatives of pyridinemethanols | |
| GB1274265A (en) | Dibenzocycloheptene derivatives | |
| SU771093A1 (en) | Method of preparing 1-methyl-3,3-dialkyl-3,4-dihydroisoquinolines | |
| JPS5913765A (en) | 2-(4-quinazolyl)aminobenzoic acid derivative | |
| GB1505633A (en) | 3,5-bis(acylamino)benzamides | |
| JPS55145648A (en) | New derivative of anthranylic acid | |
| JPS55141457A (en) | Novel benzylidene derivative | |
| JPS6337837B2 (en) | ||
| ES8703402A1 (en) | Benzoic-acid derivatives, pharmaceutical preparations comprising them and process for preparing these compounds and pharmaceutical preparations. | |
| ES473689A1 (en) | Novel phloroglucine derivative*its manufacture and use as medicine | |
| JPH0217556B2 (en) | ||
| JPS5692273A (en) | 1-phenylisoquinoline derivative | |
| CH609668A5 (en) | Process for the preparation of acetic acid derivatives | |
| KR960037644A (en) | 2- (4-aminobenzoylamino) benzamide derivative, its preparation method and anti-inflammatory analgesic containing same | |
| JPS5640673A (en) | Aminophenyltetrazole derivative and its salt | |
| KR960041184A (en) | Method for producing 7 - [(2-carboalkoxy-1-methylethenyl) amino] -3-hydroxymethyl-3-cephem-4-carboxylic acid and its intermediates |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |