DE2449846A1 - N-ersetzte dipropylazetamide und verfahren zu deren herstellung - Google Patents
N-ersetzte dipropylazetamide und verfahren zu deren herstellungInfo
- Publication number
- DE2449846A1 DE2449846A1 DE19742449846 DE2449846A DE2449846A1 DE 2449846 A1 DE2449846 A1 DE 2449846A1 DE 19742449846 DE19742449846 DE 19742449846 DE 2449846 A DE2449846 A DE 2449846A DE 2449846 A1 DE2449846 A1 DE 2449846A1
- Authority
- DE
- Germany
- Prior art keywords
- lot
- acid
- amines
- derivative
- pyridines
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title description 2
- 229940016681 dipropylacetamide Drugs 0.000 title 1
- OMOMUFTZPTXCHP-UHFFFAOYSA-N valpromide Chemical compound CCCC(C(N)=O)CCC OMOMUFTZPTXCHP-UHFFFAOYSA-N 0.000 title 1
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 6
- 150000008064 anhydrides Chemical class 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 4
- 238000002425 crystallisation Methods 0.000 claims description 3
- 230000008025 crystallization Effects 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 150000003222 pyridines Chemical class 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 150000007529 inorganic bases Chemical class 0.000 claims description 2
- 238000002955 isolation Methods 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 150000007530 organic bases Chemical class 0.000 claims description 2
- WONYMNWUJVKVII-UHFFFAOYSA-N 3,5-diiodothyropropionic acid Chemical class IC1=CC(CCC(=O)O)=CC(I)=C1OC1=CC=C(O)C=C1 WONYMNWUJVKVII-UHFFFAOYSA-N 0.000 claims 1
- AKQZEFRALAUBFS-UHFFFAOYSA-N ilamine Natural products COC(C)C(O)(C(=O)OCC1=CCN2CCCC12)C(C)(C)O AKQZEFRALAUBFS-UHFFFAOYSA-N 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- 239000000047 product Substances 0.000 description 12
- 239000007787 solid Substances 0.000 description 11
- 241001465754 Metazoa Species 0.000 description 10
- CWRVKFFCRWGWCS-UHFFFAOYSA-N Pentrazole Chemical compound C1CCCCC2=NN=NN21 CWRVKFFCRWGWCS-UHFFFAOYSA-N 0.000 description 9
- 229960001412 pentobarbital Drugs 0.000 description 9
- 239000000243 solution Substances 0.000 description 8
- WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 208000007101 Muscle Cramp Diseases 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000011521 glass Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- AAOVKJBEBIDNHE-UHFFFAOYSA-N diazepam Chemical compound N=1CC(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 AAOVKJBEBIDNHE-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- 241000699666 Mus <mouse, genus> Species 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000003518 caustics Substances 0.000 description 3
- 239000002826 coolant Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 230000000147 hypnotic effect Effects 0.000 description 3
- 229960005152 pentetrazol Drugs 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- ORRZGUBHBVWWOP-UHFFFAOYSA-N 4-ethyl-4-methylpiperidine-2,6-dione Chemical compound CCC1(C)CC(=O)NC(=O)C1 ORRZGUBHBVWWOP-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- 229920000084 Gum arabic Polymers 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 241000978776 Senegalia senegal Species 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 241001415849 Strigiformes Species 0.000 description 2
- UCUJUFDOQOJLBE-UHFFFAOYSA-N [Cl].[Ca] Chemical compound [Cl].[Ca] UCUJUFDOQOJLBE-UHFFFAOYSA-N 0.000 description 2
- 239000000205 acacia gum Substances 0.000 description 2
- 235000010489 acacia gum Nutrition 0.000 description 2
- 229940125717 barbiturate Drugs 0.000 description 2
- 239000001110 calcium chloride Substances 0.000 description 2
- 229910001628 calcium chloride Inorganic materials 0.000 description 2
- 230000002920 convulsive effect Effects 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000001665 lethal effect Effects 0.000 description 2
- QMGVPVSNSZLJIA-FVWCLLPLSA-N strychnine Chemical compound O([C@H]1CC(N([C@H]2[C@H]1[C@H]1C3)C=4C5=CC=CC=4)=O)CC=C1CN1[C@@H]3[C@]25CC1 QMGVPVSNSZLJIA-FVWCLLPLSA-N 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- AZLDINFWZADQLF-UHFFFAOYSA-N 3,3-dipropylazetidine Chemical compound CCCC1(CCC)CNC1 AZLDINFWZADQLF-UHFFFAOYSA-N 0.000 description 1
- 241000251730 Chondrichthyes Species 0.000 description 1
- -1 N-substituted dipropylazetamides Chemical class 0.000 description 1
- QMGVPVSNSZLJIA-UHFFFAOYSA-N Nux Vomica Natural products C1C2C3C4N(C=5C6=CC=CC=5)C(=O)CC3OCC=C2CN2C1C46CC2 QMGVPVSNSZLJIA-UHFFFAOYSA-N 0.000 description 1
- 241001279009 Strychnos toxifera Species 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 230000003556 anti-epileptic effect Effects 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 229960000750 bemegride Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- QPMLSUSACCOBDK-UHFFFAOYSA-N diazepane Chemical compound C1CCNNCC1 QPMLSUSACCOBDK-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000001003 psychopharmacologic effect Effects 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 230000008925 spontaneous activity Effects 0.000 description 1
- 229960005453 strychnine Drugs 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 210000002435 tendon Anatomy 0.000 description 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
- C07D213/24—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 with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/40—Acylated substituent nitrogen atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES420074A ES420074A1 (es) | 1973-10-30 | 1973-10-30 | Un metodo para la produccion industrial de dipropilacetami-das n-sustituidas. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2449846A1 true DE2449846A1 (de) | 1975-05-07 |
Family
ID=8465304
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19742449846 Pending DE2449846A1 (de) | 1973-10-30 | 1974-10-19 | N-ersetzte dipropylazetamide und verfahren zu deren herstellung |
Country Status (18)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES479959A1 (es) * | 1979-04-26 | 1979-12-01 | Made Labor Sa | Un procedimiento para la produccion industrial de 1,2-diaci-lamino-1,2-di(4-piridil)etanos. |
| MA20552A1 (fr) * | 1985-10-11 | 1986-07-01 | Pan Medica Sa | Alkylacarboxamides de pyridylalkylamines,leurs preparations et leurs utilisations |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1229064B (de) * | 1962-11-03 | 1966-11-24 | Basf Ag | Verfahren zur kontinuierlichen Herstellung von niedrigmolekularen Carbonsaeureamiden |
| US3367940A (en) * | 1963-01-02 | 1968-02-06 | Chevron Res | Beta-picolinamide derivatives |
| US3528987A (en) * | 1964-07-31 | 1970-09-15 | Geigy Chem Corp | N-(substituted pyridyl)rinolamides and -linolenamides |
-
1973
- 1973-10-30 ES ES420074A patent/ES420074A1/es not_active Expired
-
1974
- 1974-08-30 IN IN1744/CAL/1974A patent/IN141278B/en unknown
- 1974-10-18 FI FI3052/74A patent/FI305274A7/fi unknown
- 1974-10-19 DE DE19742449846 patent/DE2449846A1/de active Pending
- 1974-10-21 SE SE7413213A patent/SE7413213L/xx unknown
- 1974-10-22 IL IL45904A patent/IL45904A0/xx unknown
- 1974-10-23 GB GB4591174A patent/GB1434698A/en not_active Expired
- 1974-10-24 US US05/517,550 patent/US3951995A/en not_active Expired - Lifetime
- 1974-10-24 ZA ZA00746759A patent/ZA746759B/xx unknown
- 1974-10-29 FR FR7436166A patent/FR2248839B1/fr not_active Expired
- 1974-10-29 DK DK563774A patent/DK563774A/da unknown
- 1974-10-29 JP JP49124034A patent/JPS5093977A/ja active Pending
- 1974-10-29 BE BE150020A patent/BE821639A/xx unknown
- 1974-10-29 NO NO743900A patent/NO743900L/no unknown
- 1974-10-29 RO RO7480362A patent/RO70439A/ro unknown
- 1974-10-29 NL NL7414090A patent/NL7414090A/xx unknown
- 1974-10-30 HU HUMA2612A patent/HU168269B/hu unknown
- 1974-10-30 AU AU74878/74A patent/AU7487874A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NO743900L (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-05-26 |
| ZA746759B (en) | 1975-10-29 |
| HU168269B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1976-03-28 |
| FR2248839B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1977-05-20 |
| IN141278B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1977-02-12 |
| JPS5093977A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-07-26 |
| DK563774A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-06-23 |
| RO70439A (ro) | 1981-06-30 |
| AU7487874A (en) | 1976-05-06 |
| ES420074A1 (es) | 1976-07-01 |
| IL45904A0 (en) | 1974-12-31 |
| FR2248839A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-05-23 |
| BE821639A (fr) | 1975-04-29 |
| SE7413213L (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-05-02 |
| NL7414090A (nl) | 1975-05-02 |
| GB1434698A (en) | 1976-05-05 |
| FI305274A7 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-05-01 |
| US3951995A (en) | 1976-04-20 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2635853C2 (de) | Pyrrolidin-2-on-Derivate und diese enthaltende Arzneimittel | |
| DE2005276C3 (de) | 6,7,8,9-Tetrahydro-5-phenyl -IH [1] benzothieno [23-e-] [1,4] diazepin-2(3-H)-on und dessen pharmazeutisch verträgliche Salze | |
| DE2221558C2 (de) | 5-Phenyl-2,3-dihydro-1H-1,4-benzodiazepine und ihre Säureadditionssalze, Verfahren zu deren Herstellung und diese Verbindungen enthaltende Arzneimittel | |
| DE2305575A1 (de) | Neue blutdrucksenkende mittel und verfahren zu deren herstellung | |
| DE2065636A1 (de) | Neue tricyclische verbindungen | |
| DE1770583A1 (de) | Thiazolderivate und ihre Herstellung | |
| DE1134086B (de) | Verfahren zur Herstellung von analeptisch wirksamen alpha-Aminoisobutyrophenonen und deren Säureadditionssalzen | |
| DE1620449B2 (de) | Substituierte benzimidazole und verfahren zu ihrer herstellung | |
| DE1518764B2 (de) | In der 7-SteUung substituierte S-Phenyl^-oxo^-dihydro-lH-M-benzodiazepin-3-carbonsäuresalze und -alkylester | |
| DE2258036A1 (de) | Verfahren zur herstellung von benzo eckige klammer auf b eckige klammer zu thiophen-derivaten | |
| DD216014A5 (de) | Verfahren zur herstellung von verbindungen mit einem heterocyclischen distickstoffkern | |
| DE1014551B (de) | Verfahren zur Herstellung von substituierten 4-Oxycumarinen | |
| DE2449846A1 (de) | N-ersetzte dipropylazetamide und verfahren zu deren herstellung | |
| DE2051962A1 (de) | Benzimidazo eckige Klammer auf l,2d eckige Klammer zu eckige Klammer auf 1,4 eckige Klammer zu benzodiazepin 6 (5H) one und Verfahren zu deren Her stellung | |
| EP0139627B1 (de) | Verfahren zur Herstellung von neuen in 5-Stellung substituierten 5,10-Dihydro-11H-dibenzo(b,e)(1,4)diazepin-11-onen | |
| DE2022694C3 (de) | alpha-(3,4-Dihydro-4-oxo-1H-2,3benzothiazin-S-dioxyd-3-yl)-N,N-dimethylacetamid und Verfahren zur Herstellung desselben | |
| DE2456098B2 (de) | Xanthen- und Thioxanthen-Derivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel | |
| DE2433837C3 (de) | 1-Amidino-3-phenyl-harnstoffe, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende therapeutische Zubereitungen | |
| DE1670378C (de) | Verfahren zur Herstellung des Salzes aus4-n-Butyl-3,5-dioxo-l,2-diphenylpyrazolidin und dem beta-Diäthylamino-äthylamid der p-Chlorphenoxyessigsäure | |
| DE1770187A1 (de) | Neue Chlorchinoline und ein Verfahren zu ihrer Herstellung | |
| DE1190951B (de) | Verfahren zur Herstellung von N-(2, 3-Dimethylphenyl)-anthranilsaeure und deren Salzen | |
| DE1595911C (de) | IH 2,3 Benzoxazin 4(3H) one und Ver fahren zu ihrer Herstellung | |
| DE2163987B2 (de) | 5-(m-Carbäthoxyaminophenyl>5äthylmalonylharnstoff | |
| DE1925607C (de) | Trifluormethyl-chinoline | |
| DE871897C (de) | Verfahren zur Herstellung von heterocyclischen Aminoverbindungen |