DE1966821C3 - Ni.i^»>i-N2 -(23.4- trihydroxy-benzyliden)-hydrazid und dessen Säureadditionssalze - Google Patents
Ni.i^»>i-N2 -(23.4- trihydroxy-benzyliden)-hydrazid und dessen SäureadditionssalzeInfo
- Publication number
- DE1966821C3 DE1966821C3 DE1966821A DE1966821A DE1966821C3 DE 1966821 C3 DE1966821 C3 DE 1966821C3 DE 1966821 A DE1966821 A DE 1966821A DE 1966821 A DE1966821 A DE 1966821A DE 1966821 C3 DE1966821 C3 DE 1966821C3
- Authority
- DE
- Germany
- Prior art keywords
- hydrazide
- trihydroxy
- acid addition
- addition salts
- benzylidene
- 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
- 150000003839 salts Chemical class 0.000 title claims description 6
- 239000002253 acid Substances 0.000 title claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 9
- 229960001153 serine Drugs 0.000 claims description 2
- 150000003841 chloride salts Chemical class 0.000 claims 1
- -1 2,3,4-trihydroxy-benzyl Chemical group 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 150000003943 catecholamines Chemical class 0.000 description 3
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 description 2
- CRPNQSVBEWWHIJ-UHFFFAOYSA-N 2,3,4-trihydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C(O)=C1O CRPNQSVBEWWHIJ-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- ULFCBIUXQQYDEI-RGMNGODLSA-N (2s)-2-amino-3-hydroxy-n'-[(2,3,4-trihydroxyphenyl)methyl]propanehydrazide;hydrochloride Chemical compound Cl.OC[C@H](N)C(=O)NNCC1=CC=C(O)C(O)=C1O ULFCBIUXQQYDEI-RGMNGODLSA-N 0.000 description 1
- YTHVXUGXVASXJZ-REOHCLBHSA-N (2s)-2-amino-3-hydroxypropanehydrazide Chemical compound NNC(=O)[C@@H](N)CO YTHVXUGXVASXJZ-REOHCLBHSA-N 0.000 description 1
- JNWGUZKRVDKZBI-DKWTVANSSA-N (2s)-2-amino-3-hydroxypropanehydrazide;hydrochloride Chemical compound Cl.NNC(=O)[C@@H](N)CO JNWGUZKRVDKZBI-DKWTVANSSA-N 0.000 description 1
- WTDRDQBEARUVNC-UHFFFAOYSA-N L-Dopa Natural products OC(=O)C(N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-UHFFFAOYSA-N 0.000 description 1
- 208000027089 Parkinsonian disease Diseases 0.000 description 1
- 206010034010 Parkinsonism Diseases 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 230000001430 anti-depressive effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- JNGZXGGOCLZBFB-IVCQMTBJSA-N compound E Chemical compound N([C@@H](C)C(=O)N[C@@H]1C(N(C)C2=CC=CC=C2C(C=2C=CC=CC=2)=N1)=O)C(=O)CC1=CC(F)=CC(F)=C1 JNGZXGGOCLZBFB-IVCQMTBJSA-N 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/72—Hydrazones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
- C07C243/24—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids
- C07C243/26—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids with acylating carboxyl groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C243/34—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids with acylating carboxyl groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of a carbon skeleton further substituted by nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1240368A CH554844A (de) | 1968-08-16 | 1968-08-16 | Verfahren zur herstellung eines hydrazids. |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1966821A1 DE1966821A1 (de) | 1974-07-11 |
| DE1966821B2 DE1966821B2 (de) | 1978-03-16 |
| DE1966821C3 true DE1966821C3 (de) | 1978-11-23 |
Family
ID=4382677
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1966821A Expired DE1966821C3 (de) | 1968-08-16 | 1969-08-13 | Ni.i^»>i-N2 -(23.4- trihydroxy-benzyliden)-hydrazid und dessen Säureadditionssalze |
| DE1941284A Expired DE1941284C3 (de) | 1968-08-16 | 1969-08-13 | N hoch 1-L-Seryl-N hoch 2-(2,3,4trihydroxybenzyl)-hydrazld, Verfahren zu dessen Herstellung sowie dessen Säureadditionssalze und dieses enthaltende Arzneimittel |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1941284A Expired DE1941284C3 (de) | 1968-08-16 | 1969-08-13 | N hoch 1-L-Seryl-N hoch 2-(2,3,4trihydroxybenzyl)-hydrazld, Verfahren zu dessen Herstellung sowie dessen Säureadditionssalze und dieses enthaltende Arzneimittel |
Country Status (16)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103951587A (zh) * | 2014-04-11 | 2014-07-30 | 浙江耐司康药业有限公司 | 盐酸苄丝肼的中间体的合成方法 |
| WO2015197909A1 (en) | 2014-06-27 | 2015-12-30 | Fermion Oy | Process for the preparation of a crystalline polymorph of 2-amino-3-hydroxy-n'-(2,3,4-trihydroxybenzyl)propanehydrazide (benserazide) hydrochloride |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3065265A (en) * | 1957-07-04 | 1962-11-20 | Hoffmann La Roche | Amino acid hydrazides |
-
1968
- 1968-08-16 CH CH1240368A patent/CH554844A/xx not_active IP Right Cessation
-
1969
- 1969-08-04 IL IL32767A patent/IL32767A/en unknown
- 1969-08-04 SE SE6910878A patent/SE378242B/xx unknown
- 1969-08-11 IE IE1125/69A patent/IE33519B1/xx unknown
- 1969-08-13 DE DE1966821A patent/DE1966821C3/de not_active Expired
- 1969-08-13 NL NL6912320A patent/NL6912320A/xx unknown
- 1969-08-13 CS CS5600A patent/CS162689B2/cs unknown
- 1969-08-13 DE DE1941284A patent/DE1941284C3/de not_active Expired
- 1969-08-13 BE BE737420D patent/BE737420A/xx unknown
- 1969-08-14 DK DK436569AA patent/DK126776B/da unknown
- 1969-08-14 AT AT534671A patent/AT299160B/de not_active IP Right Cessation
- 1969-08-14 GB GB1250279D patent/GB1250279A/en not_active Expired
- 1969-08-14 FR FR696928006A patent/FR2015792B1/fr not_active Expired
- 1969-08-14 AT AT783669A patent/AT299158B/de not_active IP Right Cessation
- 1969-08-14 ES ES370500A patent/ES370500A1/es not_active Expired
- 1969-08-15 JP JP44064663A patent/JPS5114501B1/ja active Pending
- 1969-08-15 CA CA059,620A patent/CA958418A/en not_active Expired
-
1971
- 1971-09-09 FR FR7132582A patent/FR2104722B1/fr not_active Expired
-
1973
- 1973-12-30 MY MY18/73A patent/MY7300018A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SE378242B (enrdf_load_stackoverflow) | 1975-08-25 |
| FR2104722B1 (enrdf_load_stackoverflow) | 1974-03-22 |
| CH554844A (de) | 1974-10-15 |
| GB1250279A (enrdf_load_stackoverflow) | 1971-10-20 |
| FR2015792A1 (enrdf_load_stackoverflow) | 1970-04-30 |
| FR2104722A1 (enrdf_load_stackoverflow) | 1972-04-21 |
| DE1941284B2 (de) | 1974-05-30 |
| IE33519L (en) | 1970-02-16 |
| IL32767A (en) | 1973-01-30 |
| CA958418A (en) | 1974-11-26 |
| JPS5114501B1 (enrdf_load_stackoverflow) | 1976-05-10 |
| IL32767A0 (en) | 1969-11-12 |
| BE737420A (enrdf_load_stackoverflow) | 1970-02-13 |
| MY7300018A (en) | 1973-12-31 |
| AT299158B (de) | 1972-06-12 |
| DE1941284A1 (de) | 1970-02-19 |
| DE1941284C3 (de) | 1975-01-30 |
| DE1966821A1 (de) | 1974-07-11 |
| DK126776B (da) | 1973-08-20 |
| FR2015792B1 (enrdf_load_stackoverflow) | 1973-08-10 |
| DE1966821B2 (de) | 1978-03-16 |
| IE33519B1 (en) | 1974-07-24 |
| AT299160B (de) | 1972-06-12 |
| NL6912320A (enrdf_load_stackoverflow) | 1970-02-18 |
| CS162689B2 (enrdf_load_stackoverflow) | 1975-07-15 |
| ES370500A1 (es) | 1971-04-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |