GB1239345A - - Google Patents
Info
- Publication number
- GB1239345A GB1239345A GB1239345DA GB1239345A GB 1239345 A GB1239345 A GB 1239345A GB 1239345D A GB1239345D A GB 1239345DA GB 1239345 A GB1239345 A GB 1239345A
- Authority
- GB
- United Kingdom
- Prior art keywords
- groups
- amino
- acid addition
- compound
- 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
Links
- 239000002253 acid Substances 0.000 abstract 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 6
- 150000003839 salts Chemical class 0.000 abstract 6
- 150000001875 compounds Chemical class 0.000 abstract 3
- MWIXENPCUPDSOS-QMMMGPOBSA-N (2s)-2-amino-3-(4-hydroxyphenyl)propanehydrazide Chemical compound NNC(=O)[C@@H](N)CC1=CC=C(O)C=C1 MWIXENPCUPDSOS-QMMMGPOBSA-N 0.000 abstract 2
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 abstract 2
- -1 2,3,4-trihydroxybenzyl Chemical group 0.000 abstract 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- CRPNQSVBEWWHIJ-UHFFFAOYSA-N 2,3,4-trihydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C(O)=C1O CRPNQSVBEWWHIJ-UHFFFAOYSA-N 0.000 abstract 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 abstract 1
- 125000004036 acetal group Chemical group 0.000 abstract 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 abstract 1
- 125000004423 acyloxy group Chemical group 0.000 abstract 1
- 150000003935 benzaldehydes Chemical class 0.000 abstract 1
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzenecarboxaldehyde Natural products O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 abstract 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 abstract 1
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 abstract 1
- 230000003287 optical effect Effects 0.000 abstract 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 abstract 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
-
- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Saccharide Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
1,239,345. Hydrazides. F. HOFFMANNLA ROCHE & CO. A.G. 14 Aug., 1969 [16 Aug., 1968], No. 40605/69. Heading C2C. [Also in Division A5] The invention comprises N<SP>1</SP>-tyrosine-N<SP>2</SP>- (2,3,4-trihydroxybenzyl)-hydrazide (I) and N<SP>1</SP>- tyrosine - N<SP>2</SP> - (2,3,4 - trihydroxybenzylidene)- hydrazide (II) and their acid addition salts. Compound I and its acid addition salts is prepared by (a) hydrogenating compound II or an acid addition salt thereof, or (b) converting by methods known per se the group or groups convertible into the hydroxy group and/or into the α - amino - # - (p - hydroxyphenyl) - ethyl group in a compound of the Formula III in which R 1 , R 2 and R 3 are hydroxy groups or groups convertible into hydroxy groups and R 4 is the α-amino-#-(p-hydroxyphenyl)-ethyl group or a group convertible into the α-amino-#- (p-hydroxyphenyl)-ethyl, at least one of R 1 , R 2 , R 3 , R 4 and R 5 being different from the hydroxy group or from the α-amino-#-(p-hydroxyphenyl)- ethyl group, or in an acid addition salt of such a compound, into the hydroxy group and/or into the α-amino-#-(p-hydroxyphenyl)-ethyl group and, if desired, splitting a racemate obtained into the optical antipodes and, also if desired, converting a base obtained into an acid addition salt. The groups convertible into hydroxy groups are benzyloxy groups, acetal groups which are derived from acetaldehyde, acetone or tetrahydropyran, or acyloxy groups. The groups convertible into the α-amino-#-(phydroxyphenyl)-ethyl group are groups of the formulµ HOOC-C(NH 2 )R 5 , -CHR 5 R 6 and -C(=R 7 )R 5 , in which R 5 is the α-amino-#-(phydroxyphenyl) - ethyl group, R 6 is Compound II is prepared by reacting an acid addition salt of tyrosine hydrazide with 2,3,4- trihydroxybenzaldehyde. Starting materials of Formula III are prepared by reacting a correspondingly substituted tyrosine hydrazide with a correspondingly substituted benzaldehyde and subsequently hydrogenating the benzylidene compound obtained.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1240168A CH554843A (en) | 1968-08-16 | 1968-08-16 | METHOD OF MANUFACTURING A HYDRAZIDE. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1239345A true GB1239345A (en) | 1971-07-14 |
Family
ID=4382650
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1239345D Expired GB1239345A (en) | 1968-08-16 | 1969-08-14 |
Country Status (12)
| Country | Link |
|---|---|
| AT (1) | AT299159B (en) |
| BE (1) | BE737418A (en) |
| CH (1) | CH554843A (en) |
| DE (1) | DE1941240A1 (en) |
| DK (1) | DK126033B (en) |
| ES (1) | ES370502A1 (en) |
| FR (2) | FR2015793B1 (en) |
| GB (1) | GB1239345A (en) |
| IL (1) | IL32766A (en) |
| MY (1) | MY7200065A (en) |
| NL (1) | NL6912381A (en) |
| SE (1) | SE378240B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1988004173A1 (en) * | 1986-12-05 | 1988-06-16 | Serotonin Industries Of Charleston | Method and composition for treating obesity, depression, drug abuse, and narcolepsy |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003008373A1 (en) * | 2001-07-19 | 2003-01-30 | Merck Patent Gmbh | Tyrosine hydrazides |
-
1968
- 1968-08-16 CH CH1240168A patent/CH554843A/en not_active IP Right Cessation
-
1969
- 1969-08-04 SE SE6910876A patent/SE378240B/xx unknown
- 1969-08-04 IL IL32766A patent/IL32766A/en unknown
- 1969-08-13 DE DE19691941240 patent/DE1941240A1/en active Pending
- 1969-08-13 BE BE737418D patent/BE737418A/xx unknown
- 1969-08-14 GB GB1239345D patent/GB1239345A/en not_active Expired
- 1969-08-14 ES ES370502A patent/ES370502A1/en not_active Expired
- 1969-08-14 FR FR696928007A patent/FR2015793B1/fr not_active Expired
- 1969-08-14 AT AT783869A patent/AT299159B/en not_active IP Right Cessation
- 1969-08-14 NL NL6912381A patent/NL6912381A/xx unknown
- 1969-08-14 DK DK436769AA patent/DK126033B/en unknown
-
1971
- 1971-09-09 FR FR7132583A patent/FR2104723B1/fr not_active Expired
-
1972
- 1972-12-30 MY MY65/72A patent/MY7200065A/en unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1988004173A1 (en) * | 1986-12-05 | 1988-06-16 | Serotonin Industries Of Charleston | Method and composition for treating obesity, depression, drug abuse, and narcolepsy |
| US4843071A (en) * | 1986-12-05 | 1989-06-27 | Serotonin Industries Of Charleston | Method and composition for treating obesity, drug abuse, and narcolepsy |
Also Published As
| Publication number | Publication date |
|---|---|
| IL32766A (en) | 1973-02-28 |
| AT299159B (en) | 1972-06-12 |
| DK126033B (en) | 1973-06-04 |
| FR2015793B1 (en) | 1973-08-10 |
| CH554843A (en) | 1974-10-15 |
| MY7200065A (en) | 1972-12-31 |
| BE737418A (en) | 1970-02-13 |
| IL32766A0 (en) | 1969-11-12 |
| FR2104723A1 (en) | 1972-04-21 |
| NL6912381A (en) | 1970-02-18 |
| ES370502A1 (en) | 1971-04-16 |
| SE378240B (en) | 1975-08-25 |
| FR2015793A1 (en) | 1970-04-30 |
| DE1941240A1 (en) | 1970-02-19 |
| FR2104723B1 (en) | 1974-03-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PLNP | Patent lapsed through nonpayment of renewal fees |