DE2559072A1 - Verbindungen und verfahren - Google Patents
Verbindungen und verfahrenInfo
- Publication number
- DE2559072A1 DE2559072A1 DE19752559072 DE2559072A DE2559072A1 DE 2559072 A1 DE2559072 A1 DE 2559072A1 DE 19752559072 DE19752559072 DE 19752559072 DE 2559072 A DE2559072 A DE 2559072A DE 2559072 A1 DE2559072 A1 DE 2559072A1
- Authority
- DE
- Germany
- Prior art keywords
- compound according
- compound
- morpholinyl
- represent
- butyramide
- 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.)
- Ceased
Links
- 150000001875 compounds Chemical class 0.000 title claims description 70
- 238000000034 method Methods 0.000 title claims description 12
- 230000000694 effects Effects 0.000 claims description 36
- -1 4-methylpiperazinyl group Chemical group 0.000 claims description 27
- 239000002253 acid Substances 0.000 claims description 26
- 238000006243 chemical reaction Methods 0.000 claims description 19
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 15
- 210000003169 central nervous system Anatomy 0.000 claims description 15
- 206010039897 Sedation Diseases 0.000 claims description 13
- 230000036280 sedation Effects 0.000 claims description 13
- 150000008065 acid anhydrides Chemical class 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 230000000994 depressogenic effect Effects 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 125000005907 alkyl ester group Chemical group 0.000 claims description 5
- 239000002585 base Substances 0.000 claims description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 150000003512 tertiary amines Chemical class 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 230000001773 anti-convulsant effect Effects 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- JNFXTLLHKZFGFS-UHFFFAOYSA-N n-morpholin-4-yl-4-oxo-4-phenylbutanamide Chemical compound C1COCCN1NC(=O)CCC(=O)C1=CC=CC=C1 JNFXTLLHKZFGFS-UHFFFAOYSA-N 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims 8
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 150000008282 halocarbons Chemical class 0.000 claims 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims 2
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims 1
- PHNMXEPNUDXBBY-UHFFFAOYSA-N 5-(4-methoxyphenyl)-n-morpholin-4-yl-5-oxopentanamide Chemical compound C1=CC(OC)=CC=C1C(=O)CCCC(=O)NN1CCOCC1 PHNMXEPNUDXBBY-UHFFFAOYSA-N 0.000 claims 1
- 229910014033 C-OH Inorganic materials 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 229910014570 C—OH Inorganic materials 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 238000007912 intraperitoneal administration Methods 0.000 description 25
- 241001465754 Metazoa Species 0.000 description 21
- 241000699670 Mus sp. Species 0.000 description 19
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
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- 239000000126 substance Substances 0.000 description 13
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 10
- 150000001412 amines Chemical class 0.000 description 10
- ZPEIMTDSQAKGNT-UHFFFAOYSA-N chlorpromazine Chemical compound C1=C(Cl)C=C2N(CCCN(C)C)C3=CC=CC=C3SC2=C1 ZPEIMTDSQAKGNT-UHFFFAOYSA-N 0.000 description 10
- 229960001076 chlorpromazine Drugs 0.000 description 10
- 230000001143 conditioned effect Effects 0.000 description 10
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- 239000003795 chemical substances by application Substances 0.000 description 7
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- 230000008018 melting Effects 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 5
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 5
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- 229910000039 hydrogen halide Inorganic materials 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
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- 230000007958 sleep Effects 0.000 description 4
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 208000028017 Psychotic disease Diseases 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000003444 anaesthetic effect Effects 0.000 description 3
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- WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 3
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- 238000003786 synthesis reaction Methods 0.000 description 3
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 3
- 239000003981 vehicle Substances 0.000 description 3
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
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- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- JWWCHDITYGYWEI-UHFFFAOYSA-N N-butanoyl-3,4,5-trimethoxybenzamide Chemical compound CCCC(=O)NC(=O)C1=CC(OC)=C(OC)C(OC)=C1 JWWCHDITYGYWEI-UHFFFAOYSA-N 0.000 description 2
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
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- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
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- 238000003756 stirring Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 230000008673 vomiting Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- 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
- C07D295/16—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 acylated on ring nitrogen atoms
- C07D295/18—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 acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
-
- 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
-
- 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
- A61P25/20—Hypnotics; Sedatives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Neurology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Anesthesiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/554,177 US4115570A (en) | 1975-02-28 | 1975-02-28 | Morpholine compounds and methods of use |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2559072A1 true DE2559072A1 (de) | 1976-09-02 |
Family
ID=24212328
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752559072 Ceased DE2559072A1 (de) | 1975-02-28 | 1975-12-30 | Verbindungen und verfahren |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US4115570A (cg-RX-API-DMAC7.html) |
| JP (1) | JPS5725036B2 (cg-RX-API-DMAC7.html) |
| BE (1) | BE838848A (cg-RX-API-DMAC7.html) |
| CA (1) | CA1069897A (cg-RX-API-DMAC7.html) |
| CH (1) | CH621540A5 (cg-RX-API-DMAC7.html) |
| DE (1) | DE2559072A1 (cg-RX-API-DMAC7.html) |
| ES (1) | ES445543A1 (cg-RX-API-DMAC7.html) |
| FR (1) | FR2302086A1 (cg-RX-API-DMAC7.html) |
| GB (1) | GB1536464A (cg-RX-API-DMAC7.html) |
| MX (1) | MX3603E (cg-RX-API-DMAC7.html) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1190601B (it) * | 1986-01-27 | 1988-02-16 | Cometec Srl | Derivati della morfolina,loro uso quali stimolanti di crescita negli animali e procedimento per la loro preparazione |
| DE3881770T2 (de) * | 1987-07-20 | 1993-10-07 | Cometec Srl | Zusammensetzungen zum Fördern der Tierwachstums. |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH83A (fr) * | 1888-11-17 | 1889-01-10 | Fontainemelon Horlogerie | Perfectionnements apportés à la construction des montres de tous calibres |
| US2851494A (en) * | 1955-03-04 | 1958-09-09 | Hoechst Ag | New alpha-amino-beta-hydroxycarboxylic acid amides and a process of preparing them |
| BE758380A (fr) * | 1969-11-04 | 1971-04-16 | Sumitomo Chemical Co | Procede de preparation de derives d'aryl-cetones |
-
1975
- 1975-02-28 US US05/554,177 patent/US4115570A/en not_active Expired - Lifetime
- 1975-12-30 DE DE19752559072 patent/DE2559072A1/de not_active Ceased
-
1976
- 1976-01-19 CH CH58676A patent/CH621540A5/it not_active IP Right Cessation
- 1976-02-03 MX MX761771U patent/MX3603E/es unknown
- 1976-02-18 GB GB6474/76A patent/GB1536464A/en not_active Expired
- 1976-02-23 BE BE164558A patent/BE838848A/xx not_active IP Right Cessation
- 1976-02-25 CA CA246,532A patent/CA1069897A/en not_active Expired
- 1976-02-26 ES ES445543A patent/ES445543A1/es not_active Expired
- 1976-02-27 FR FR7605625A patent/FR2302086A1/fr active Granted
- 1976-02-27 JP JP2204176A patent/JPS5725036B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| AU1090276A (en) | 1977-02-17 |
| FR2302086A1 (fr) | 1976-09-24 |
| ES445543A1 (es) | 1977-11-01 |
| CA1069897A (en) | 1980-01-15 |
| GB1536464A (en) | 1978-12-20 |
| MX3603E (es) | 1981-03-30 |
| JPS5725036B2 (cg-RX-API-DMAC7.html) | 1982-05-27 |
| BE838848A (fr) | 1976-06-16 |
| CH621540A5 (cg-RX-API-DMAC7.html) | 1981-02-13 |
| JPS51110533A (cg-RX-API-DMAC7.html) | 1976-09-30 |
| FR2302086B1 (cg-RX-API-DMAC7.html) | 1979-09-28 |
| US4115570A (en) | 1978-09-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| 8131 | Rejection |