DE3119514C2 - - Google Patents
Info
- Publication number
- DE3119514C2 DE3119514C2 DE19813119514 DE3119514A DE3119514C2 DE 3119514 C2 DE3119514 C2 DE 3119514C2 DE 19813119514 DE19813119514 DE 19813119514 DE 3119514 A DE3119514 A DE 3119514A DE 3119514 C2 DE3119514 C2 DE 3119514C2
- Authority
- DE
- Germany
- Prior art keywords
- triacetonamine
- acetone
- solvent
- hydrochloride
- group
- 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 - Fee Related
Links
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 29
- JWUXJYZVKZKLTJ-UHFFFAOYSA-N Triacetonamine Chemical compound CC1(C)CC(=O)CC(C)(C)N1 JWUXJYZVKZKLTJ-UHFFFAOYSA-N 0.000 claims description 16
- 239000002904 solvent Substances 0.000 claims description 15
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 12
- ZXNWYMNKYXUZGM-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidin-1-ium-4-one;chloride Chemical compound Cl.CC1(C)CC(=O)CC(C)(C)N1 ZXNWYMNKYXUZGM-UHFFFAOYSA-N 0.000 claims description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 6
- 229910021529 ammonia Inorganic materials 0.000 claims description 6
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 6
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 6
- 239000011541 reaction mixture Substances 0.000 claims description 6
- 239000002274 desiccant Substances 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 238000004821 distillation Methods 0.000 claims description 3
- 239000012074 organic phase Substances 0.000 claims description 2
- 239000000243 solution Substances 0.000 claims 2
- 239000012670 alkaline solution Substances 0.000 claims 1
- 239000000706 filtrate Substances 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 238000012360 testing method Methods 0.000 description 11
- 241001465754 Metazoa Species 0.000 description 8
- 206010028980 Neoplasm Diseases 0.000 description 8
- 230000000259 anti-tumor effect Effects 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 230000037396 body weight Effects 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 230000005764 inhibitory process Effects 0.000 description 5
- 230000004083 survival effect Effects 0.000 description 5
- IAKHMKGGTNLKSZ-INIZCTEOSA-N (S)-colchicine Chemical compound C1([C@@H](NC(C)=O)CC2)=CC(=O)C(OC)=CC=C1C1=C2C=C(OC)C(OC)=C1OC IAKHMKGGTNLKSZ-INIZCTEOSA-N 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 230000001077 hypotensive effect Effects 0.000 description 4
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 208000001953 Hypotension Diseases 0.000 description 3
- 239000001110 calcium chloride Substances 0.000 description 3
- 229910001628 calcium chloride Inorganic materials 0.000 description 3
- 235000011148 calcium chloride Nutrition 0.000 description 3
- 208000021822 hypotensive Diseases 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000002927 anti-mitotic effect Effects 0.000 description 2
- 229960001338 colchicine Drugs 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 230000002035 prolonged effect Effects 0.000 description 2
- 230000009291 secondary effect Effects 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 239000005418 vegetable material Substances 0.000 description 2
- DNXIKVLOVZVMQF-UHFFFAOYSA-N (3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DNXIKVLOVZVMQF-UHFFFAOYSA-N 0.000 description 1
- FRISOFZUHCOQEC-UHFFFAOYSA-N 1-(6-hydroxy-2,3,4-trimethoxyphenyl)-3-(4-methoxyphenyl)propenone Natural products C1=CC(OC)=CC=C1C=CC(=O)C1=C(O)C=C(OC)C(OC)=C1OC FRISOFZUHCOQEC-UHFFFAOYSA-N 0.000 description 1
- IYLPVORUFDDDFK-UHFFFAOYSA-N 4-methylbenzenesulfonic acid;2,2,6,6-tetramethylpiperidin-4-one Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1.CC1(C)CC(=O)CC(C)(C)N1 IYLPVORUFDDDFK-UHFFFAOYSA-N 0.000 description 1
- BYNYZQQDQIQLSO-UHFFFAOYSA-N 7-hydroxy-3-(3-hydroxy-4-methoxyphenyl)-6-methoxychromen-4-one Chemical compound C1=C(O)C(OC)=CC=C1C1=COC2=CC(O)=C(OC)C=C2C1=O BYNYZQQDQIQLSO-UHFFFAOYSA-N 0.000 description 1
- 208000007848 Alcoholism Diseases 0.000 description 1
- 206010006187 Breast cancer Diseases 0.000 description 1
- 208000002908 Brown-Pearce carcinoma Diseases 0.000 description 1
- 201000009030 Carcinoma Diseases 0.000 description 1
- 206010012218 Delirium Diseases 0.000 description 1
- 208000003098 Ganglion Cysts Diseases 0.000 description 1
- 206010027476 Metastases Diseases 0.000 description 1
- ZVOSNTPXWLRWJG-UHFFFAOYSA-N Odoratin Natural products CC1C2CCC3(C)C(OC(=O)C=C3C2CCC1=O)c4cocc4 ZVOSNTPXWLRWJG-UHFFFAOYSA-N 0.000 description 1
- ZFCRHGITKWEXDY-UHFFFAOYSA-N Odoratin I* Natural products CC1CC2OC(=O)C(=C)C2CC2(C)C(O)C(O)CC12 ZFCRHGITKWEXDY-UHFFFAOYSA-N 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- LCQMZZCPPSWADO-UHFFFAOYSA-N Reserpilin Natural products COC(=O)C1COCC2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)C3CC12 LCQMZZCPPSWADO-UHFFFAOYSA-N 0.000 description 1
- QEVHRUUCFGRFIF-SFWBKIHZSA-N Reserpine Natural products O=C(OC)[C@@H]1[C@H](OC)[C@H](OC(=O)c2cc(OC)c(OC)c(OC)c2)C[C@H]2[C@@H]1C[C@H]1N(C2)CCc2c3c([nH]c12)cc(OC)cc3 QEVHRUUCFGRFIF-SFWBKIHZSA-N 0.000 description 1
- 208000005400 Synovial Cyst Diseases 0.000 description 1
- 241000405217 Viola <butterfly> Species 0.000 description 1
- PVQATPQSBYNMGE-UHFFFAOYSA-N [benzhydryloxy(phenyl)methyl]benzene Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)OC(C=1C=CC=CC=1)C1=CC=CC=C1 PVQATPQSBYNMGE-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 201000007930 alcohol dependence Diseases 0.000 description 1
- 229930013930 alkaloid Natural products 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000002220 antihypertensive agent Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 201000008274 breast adenocarcinoma Diseases 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 230000004663 cell proliferation Effects 0.000 description 1
- 150000001793 charged compounds Chemical class 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- -1 cholamine Chemical compound 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 239000000824 cytostatic agent Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 206010073071 hepatocellular carcinoma Diseases 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 201000001441 melanoma Diseases 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000031864 metaphase Effects 0.000 description 1
- 206010061289 metastatic neoplasm Diseases 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 150000002990 phenothiazines Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- BJOIZNZVOZKDIG-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 BJOIZNZVOZKDIG-MDEJGZGSSA-N 0.000 description 1
- 229960003147 reserpine Drugs 0.000 description 1
- MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- FZUJWWOKDIGOKH-UHFFFAOYSA-N sulfuric acid hydrochloride Chemical compound Cl.OS(O)(=O)=O FZUJWWOKDIGOKH-UHFFFAOYSA-N 0.000 description 1
- 238000011477 surgical intervention Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- 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
- C07D211/72—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 hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D211/74—Oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19813119514 DE3119514A1 (de) | 1981-05-15 | 1981-05-15 | Triacetonaminhydrochlorid, verfahren zu seiner herstellung und arzneimittel |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19813119514 DE3119514A1 (de) | 1981-05-15 | 1981-05-15 | Triacetonaminhydrochlorid, verfahren zu seiner herstellung und arzneimittel |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3119514A1 DE3119514A1 (de) | 1983-02-24 |
| DE3119514C2 true DE3119514C2 (enrdf_load_stackoverflow) | 1990-03-29 |
Family
ID=6132475
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19813119514 Granted DE3119514A1 (de) | 1981-05-15 | 1981-05-15 | Triacetonaminhydrochlorid, verfahren zu seiner herstellung und arzneimittel |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE3119514A1 (enrdf_load_stackoverflow) |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK139678B (da) * | 1973-06-25 | 1979-03-26 | Ciba Geigy Ag | Fremgangsmåde til fremstilling af 2,2,6,6-tetramethyl-4-oxopiperidin. |
| FI189774A7 (enrdf_load_stackoverflow) * | 1973-06-26 | 1974-12-27 | Sankyo Co |
-
1981
- 1981-05-15 DE DE19813119514 patent/DE3119514A1/de active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| DE3119514A1 (de) | 1983-02-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| 8172 | Supplementary division/partition in: |
Ref country code: DE Ref document number: 3153609 Format of ref document f/p: P |
|
| Q171 | Divided out to: |
Ref country code: DE Ref document number: 3153609 |
|
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8328 | Change in the person/name/address of the agent |
Free format text: DERZEIT KEIN VERTRETER BESTELLT |
|
| 8328 | Change in the person/name/address of the agent |
Free format text: BLUMBACH, P., DIPL.-ING., 6200 WIESBADEN WESER, W., DIPL.-PHYS. DR.RER.NAT. KRAMER, R., DIPL.-ING.,8000 MUENCHEN ZWIRNER, G., DIPL.-ING. DIPL.-WIRTSCH.-ING., 6200 WIESBADEN HOFFMANN, E., DIPL.-ING., PAT.-ANWAELTE, 8000 MUENCHEN |
|
| 8339 | Ceased/non-payment of the annual fee |