SE7614105L - 4-AMINO-TRANSDEKAYDROKINOLINE DERIVATIVES - Google Patents
4-AMINO-TRANSDEKAYDROKINOLINE DERIVATIVESInfo
- Publication number
- SE7614105L SE7614105L SE7614105A SE7614105A SE7614105L SE 7614105 L SE7614105 L SE 7614105L SE 7614105 A SE7614105 A SE 7614105A SE 7614105 A SE7614105 A SE 7614105A SE 7614105 L SE7614105 L SE 7614105L
- Authority
- SE
- Sweden
- Prior art keywords
- group
- carbonyl
- alkyl
- reacting
- hydrazonomethylene
- Prior art date
Links
- 125000000217 alkyl group Chemical group 0.000 abstract 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 5
- 150000001875 compounds Chemical class 0.000 abstract 5
- 125000000623 heterocyclic group Chemical group 0.000 abstract 5
- 125000004663 dialkyl amino group Chemical group 0.000 abstract 3
- -1 hydroxyiminomethylene Chemical group 0.000 abstract 3
- 229910052757 nitrogen Inorganic materials 0.000 abstract 3
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 3
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 150000001412 amines Chemical class 0.000 abstract 2
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- VZTBFFGJFFYFRT-HTQZYQBOSA-N (4ar,8ar)-2,3,4a,5,6,7,8,8a-octahydro-1h-quinolin-4-one Chemical compound C1CCC[C@H]2C(=O)CCN[C@@H]21 VZTBFFGJFFYFRT-HTQZYQBOSA-N 0.000 abstract 1
- POTIYWUALSJREP-DTWKUNHWSA-N (4as,8ar)-1,2,3,4,4a,5,6,7,8,8a-decahydroquinoline Chemical class N1CCC[C@@H]2CCCC[C@H]21 POTIYWUALSJREP-DTWKUNHWSA-N 0.000 abstract 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 abstract 1
- ATTZFSUZZUNHBP-UHFFFAOYSA-N Piperonyl sulfoxide Chemical compound CCCCCCCCS(=O)C(C)CC1=CC=C2OCOC2=C1 ATTZFSUZZUNHBP-UHFFFAOYSA-N 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 239000005864 Sulphur Chemical group 0.000 abstract 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 abstract 1
- 125000002723 alicyclic group Chemical group 0.000 abstract 1
- 230000000202 analgesic effect Effects 0.000 abstract 1
- 230000003276 anti-hypertensive effect Effects 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 abstract 1
- 125000002541 furyl group Chemical group 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 150000002431 hydrogen Chemical class 0.000 abstract 1
- 150000002466 imines Chemical class 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 229910052740 iodine Inorganic materials 0.000 abstract 1
- 239000011630 iodine Substances 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
- 125000001624 naphthyl group Chemical group 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000000546 pharmaceutical excipient Substances 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
- C07D215/44—Nitrogen atoms attached in position 4 with aryl radicals attached to said nitrogen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Pain & Pain Management (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Quinoline Compounds (AREA)
Abstract
1515540 4 - Amino - trans - decahydroquinoline derivatives LABAZ 24 Nov 1976 [16 Dec 1975] 51507/75 Heading C2C Novel trans decahydroquinoline derivatives of the Formula I and pharmaceutically acceptable acid addition salts thereof, wherein R<SP>1</SP> is alkyl, alkoxy, dialkylamino, a saturated heterocyclic ring attached through a ring nitrogen atom, an unsaturated heterocyclic group or an optionally substituted phenyl, R<SP>2</SP> is alkyl, optionally substituted phenyl, naphthyl, unsaturated heterocyclic optionally substituted by alkyl, aralkyl, aralkenyl or alicyclic and R<SP>3</SP> is alkyl substituted furyl, aralkyl, aralkenyl or a group where A is C 1-4 -alkylene, Y is oxygen, sulphur, carbonyl > C = NOH, >C = NNH 2 or sulphoxide or a group X R<SP>4</SP> and R<SP>5</SP> each are hydrogen, halogen, methyl, methoxy or acetyl and n is zero or 1, with the proviso that when n is zero, Y is carbonyl, where alkyl groups unless otherwise specified have 1 to 4 carbon atoms, may be prepared, when R 1 is other than dialkylamino or saturated heterocyclic group attached by a ring nitrogen atom and when R<SP>3</SP> is a group II, Y is other than hydroxyiminomethylene or hydrazonomethylene by reacting a compound III with R<SP>1</SP>COCl or (R<SP>1</SP>CO) 2 O or when R<SP>1</SP> is dialkylamino or a saturated heterocyclic group attached by a ring nitrogen atom, and when R<SP>3</SP> is a group II, Y is other than hydroxyiminomethylone or hydrazonomethylene by reacting a compound VI with an amine R<SP>1</SP>H, optionally followed by acid addition salt formation and/or reacting a carbonyl at Y with hydroxylamine or hydrazine to form a hydroxylimino methylene or a carbonyl hydrazonomethylene. Intermediates of the Formula III are prepared by reacting 4-oxo-trans-decahydroquinoline with an amine R<SP>2</SP>NH 2 and reducing the imine so formed to produce a compound VIII which is reacted with R<SP>3</SP>-Hal, where Hal is chlorine, bromine or iodine. When R<SP>3</SP> is a group II and Y is carbonyl, the carbonyl group is protected with a group X and thereafter optionally hydrolysed. The isomers of the compound VIII are separated. Pharmaceutical compositions of the compounds I with the usual excipients show analgesic activity when administered orally, parenterally or rectally. The compounds I in which R<SP>1</SP> is alkoxy also show antihypertensive action.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB51507/75A GB1515540A (en) | 1975-12-16 | 1975-12-16 | 4-amino-trans-decahydroquinoline derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SE7614105L true SE7614105L (en) | 1977-06-17 |
| SE434396B SE434396B (en) | 1984-07-23 |
Family
ID=10460296
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE7614105A SE434396B (en) | 1975-12-16 | 1976-12-15 | ANALOGY PROCEDURE FOR PREPARATION OF 4-AMINO-TRANSDEKAH HYDROKINOLINE DERIVATIVES |
Country Status (28)
| Country | Link |
|---|---|
| JP (1) | JPS6022711B2 (en) |
| AR (1) | AR214988A1 (en) |
| AT (1) | AT357535B (en) |
| AU (1) | AU509897B2 (en) |
| BE (1) | BE849431A (en) |
| CA (1) | CA1077040A (en) |
| CH (1) | CH618970A5 (en) |
| DD (1) | DD128709A5 (en) |
| DE (1) | DE2656678C2 (en) |
| DK (1) | DK564876A (en) |
| ES (1) | ES454285A1 (en) |
| FI (1) | FI63023C (en) |
| FR (1) | FR2335224A1 (en) |
| GB (1) | GB1515540A (en) |
| HU (1) | HU175391B (en) |
| IE (1) | IE44355B1 (en) |
| IT (1) | IT1065969B (en) |
| MX (1) | MX5798E (en) |
| NL (1) | NL7613629A (en) |
| NO (1) | NO145916C (en) |
| NZ (1) | NZ182758A (en) |
| OA (1) | OA05515A (en) |
| PL (1) | PL101143B1 (en) |
| PT (1) | PT65970B (en) |
| SE (1) | SE434396B (en) |
| SU (1) | SU633476A3 (en) |
| YU (1) | YU39980B (en) |
| ZA (1) | ZA767112B (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2592879B1 (en) * | 1986-01-13 | 1988-04-29 | Roussel Uclaf | NOVEL DECAHYDROQUINOLEIN DERIVATIVES, PROCESS FOR THEIR PREPARATION, PREPARATION INTERMEDIATES, THEIR APPLICATION AS MEDICAMENTS AND COMPOSITIONS CONTAINING THEM |
| BRPI0508966A (en) * | 2004-03-26 | 2007-08-21 | Lilly Co Eli | compound, pharmaceutical composition, and use of a compound |
-
1975
- 1975-12-16 GB GB51507/75A patent/GB1515540A/en not_active Expired
-
1976
- 1976-11-26 IE IE2613/76A patent/IE44355B1/en unknown
- 1976-11-29 ZA ZA00767112A patent/ZA767112B/en unknown
- 1976-11-29 NZ NZ182758A patent/NZ182758A/en unknown
- 1976-12-07 AU AU20328/76A patent/AU509897B2/en not_active Expired
- 1976-12-08 NL NL7613629A patent/NL7613629A/en not_active Application Discontinuation
- 1976-12-13 CH CH1565976A patent/CH618970A5/en not_active IP Right Cessation
- 1976-12-13 CA CA267,706A patent/CA1077040A/en not_active Expired
- 1976-12-13 AR AR265813A patent/AR214988A1/en active
- 1976-12-14 FR FR7637621A patent/FR2335224A1/en active Granted
- 1976-12-14 MX MX765223A patent/MX5798E/en unknown
- 1976-12-15 SU SU762428755A patent/SU633476A3/en active
- 1976-12-15 IT IT30441/76A patent/IT1065969B/en active
- 1976-12-15 FI FI763603A patent/FI63023C/en not_active IP Right Cessation
- 1976-12-15 DK DK564876A patent/DK564876A/en not_active Application Discontinuation
- 1976-12-15 DD DD7600196381A patent/DD128709A5/en unknown
- 1976-12-15 SE SE7614105A patent/SE434396B/en not_active IP Right Cessation
- 1976-12-15 PT PT65970A patent/PT65970B/en unknown
- 1976-12-15 BE BE173281A patent/BE849431A/en not_active IP Right Cessation
- 1976-12-15 HU HU76LA900A patent/HU175391B/en unknown
- 1976-12-15 OA OA56017A patent/OA05515A/en unknown
- 1976-12-15 NO NO764251A patent/NO145916C/en unknown
- 1976-12-15 DE DE2656678A patent/DE2656678C2/en not_active Expired
- 1976-12-15 JP JP51151456A patent/JPS6022711B2/en not_active Expired
- 1976-12-16 YU YU3071/76A patent/YU39980B/en unknown
- 1976-12-16 PL PL1976194452A patent/PL101143B1/en unknown
- 1976-12-16 ES ES454285A patent/ES454285A1/en not_active Expired
- 1976-12-16 AT AT932076A patent/AT357535B/en not_active IP Right Cessation
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| NUG | Patent has lapsed |
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