GB1472052A - Preparation of d-penicillamine and substituted 3-pyrazoline- 5-ones - Google Patents
Preparation of d-penicillamine and substituted 3-pyrazoline- 5-onesInfo
- Publication number
- GB1472052A GB1472052A GB458876A GB458876A GB1472052A GB 1472052 A GB1472052 A GB 1472052A GB 458876 A GB458876 A GB 458876A GB 458876 A GB458876 A GB 458876A GB 1472052 A GB1472052 A GB 1472052A
- Authority
- GB
- United Kingdom
- Prior art keywords
- substituted
- formula
- penicillamine
- pyrazoline
- ones
- 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
- XBYRMPXUBGMOJC-UHFFFAOYSA-N 1,2-dihydropyrazol-3-one Chemical class OC=1C=CNN=1 XBYRMPXUBGMOJC-UHFFFAOYSA-N 0.000 title abstract 3
- 229960001639 penicillamine Drugs 0.000 title abstract 3
- VVNCNSJFMMFHPL-VKHMYHEASA-N D-penicillamine Chemical compound CC(C)(S)[C@@H](N)C(O)=O VVNCNSJFMMFHPL-VKHMYHEASA-N 0.000 title abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 abstract 2
- LJRDOKAZOAKLDU-UDXJMMFXSA-N (2s,3s,4r,5r,6r)-5-amino-2-(aminomethyl)-6-[(2r,3s,4r,5s)-5-[(1r,2r,3s,5r,6s)-3,5-diamino-2-[(2s,3r,4r,5s,6r)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-hydroxycyclohexyl]oxy-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]oxyoxane-3,4-diol;sulfuric ac Chemical compound OS(O)(=O)=O.N[C@@H]1[C@@H](O)[C@H](O)[C@H](CN)O[C@@H]1O[C@H]1[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](N)C[C@@H](N)[C@@H]2O)O[C@@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)N)O[C@@H]1CO LJRDOKAZOAKLDU-UDXJMMFXSA-N 0.000 abstract 1
- IYNDLOXRXUOGIU-LQDWTQKMSA-M benzylpenicillin potassium Chemical compound [K+].N([C@H]1[C@H]2SC([C@@H](N2C1=O)C([O-])=O)(C)C)C(=O)CC1=CC=CC=C1 IYNDLOXRXUOGIU-LQDWTQKMSA-M 0.000 abstract 1
- 238000001704 evaporation Methods 0.000 abstract 1
- 230000008020 evaporation Effects 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- QZIQJVCYUQZDIR-UHFFFAOYSA-N mechlorethamine hydrochloride Chemical compound Cl.ClCCN(C)CCCl QZIQJVCYUQZDIR-UHFFFAOYSA-N 0.000 abstract 1
- 239000012452 mother liquor Substances 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 238000001953 recrystallisation Methods 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/44—Oxygen and nitrogen or sulfur and nitrogen atoms
- C07D231/46—Oxygen atom in position 3 or 5 and nitrogen atom in position 4
- C07D231/50—Acylated on said nitrogen atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
1472052 D-penicillamine and substituted 3- pyrazoline-5-ones PLIVA PHARMACEUTICAL & CHEMICAL WORKS 5 Feb 1976 [14 Feb 1975] 04588/76 Heading C2C D-penieillamine and substituted 3-pyrazoline- 5-ones of the formula are prepared by reacting a penicilline of formula with a hydrazine of formula R 2 -NH-NH 2 , in which R 1 represents a radical of the formula and R 2 represents an H atom or a phenyl group, in an organic solvent at a temperature of from 10‹ to 40‹ C., and thereafter heating the reaction mixture in the presence of water for 3 to 10 hours at a temperature of from 50‹ to 100‹ C. The substituted pyrazolone may be filtered off and the penicillamine may be recovered from the mother liquor by evaporation to dryness followed by recrystallization from dilute ethanol.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| YU34575 | 1975-02-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1472052A true GB1472052A (en) | 1977-04-27 |
Family
ID=25549478
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB458876A Expired GB1472052A (en) | 1975-02-14 | 1976-02-05 | Preparation of d-penicillamine and substituted 3-pyrazoline- 5-ones |
Country Status (3)
| Country | Link |
|---|---|
| DE (1) | DE2605563A1 (en) |
| FR (1) | FR2300561A1 (en) |
| GB (1) | GB1472052A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4716232A (en) * | 1985-04-30 | 1987-12-29 | Eli Lilly And Company | 1-(vinyl phosphonate adduct) pyrazolidinones |
| US4767871A (en) * | 1985-04-30 | 1988-08-30 | Eli Lilly And Company | Pyrazolidinium ylides |
| US4826993A (en) * | 1985-04-30 | 1989-05-02 | Eli Lilly And Company | Substituted diazolidinones |
| US6011052A (en) * | 1996-04-30 | 2000-01-04 | Warner-Lambert Company | Pyrazolone derivatives as MCP-1 antagonists |
-
1976
- 1976-02-05 GB GB458876A patent/GB1472052A/en not_active Expired
- 1976-02-12 DE DE19762605563 patent/DE2605563A1/en active Pending
- 1976-02-13 FR FR7603982A patent/FR2300561A1/en not_active Withdrawn
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4716232A (en) * | 1985-04-30 | 1987-12-29 | Eli Lilly And Company | 1-(vinyl phosphonate adduct) pyrazolidinones |
| US4734504A (en) * | 1985-04-30 | 1988-03-29 | Eli Lilly And Company | 1-alkylated diazolidinones |
| US4767871A (en) * | 1985-04-30 | 1988-08-30 | Eli Lilly And Company | Pyrazolidinium ylides |
| US4826993A (en) * | 1985-04-30 | 1989-05-02 | Eli Lilly And Company | Substituted diazolidinones |
| US6011052A (en) * | 1996-04-30 | 2000-01-04 | Warner-Lambert Company | Pyrazolone derivatives as MCP-1 antagonists |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2300561A1 (en) | 1976-09-10 |
| DE2605563A1 (en) | 1976-08-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |