GB1360354A - Chenodeoxycholic acid - Google Patents
Chenodeoxycholic acidInfo
- Publication number
- GB1360354A GB1360354A GB280372A GB280372A GB1360354A GB 1360354 A GB1360354 A GB 1360354A GB 280372 A GB280372 A GB 280372A GB 280372 A GB280372 A GB 280372A GB 1360354 A GB1360354 A GB 1360354A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methyl
- base
- chenodeoxycholic acid
- cholanate
- kishner
- 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
- RUDATBOHQWOJDD-UHFFFAOYSA-N (3beta,5beta,7alpha)-3,7-Dihydroxycholan-24-oic acid Natural products OC1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)CC2 RUDATBOHQWOJDD-UHFFFAOYSA-N 0.000 title abstract 3
- 229960001091 chenodeoxycholic acid Drugs 0.000 title abstract 3
- RUDATBOHQWOJDD-BSWAIDMHSA-N chenodeoxycholic acid Chemical compound C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)CC1 RUDATBOHQWOJDD-BSWAIDMHSA-N 0.000 title abstract 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 abstract 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- 239000002585 base Substances 0.000 abstract 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 2
- 238000005644 Wolff-Kishner reduction reaction Methods 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 abstract 1
- BHQCQFFYRZLCQQ-UHFFFAOYSA-N (3alpha,5alpha,7alpha,12alpha)-3,7,12-trihydroxy-cholan-24-oic acid Natural products OC1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)C(O)C2 BHQCQFFYRZLCQQ-UHFFFAOYSA-N 0.000 abstract 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 abstract 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 1
- 239000004380 Cholic acid Substances 0.000 abstract 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 abstract 1
- 229910002651 NO3 Inorganic materials 0.000 abstract 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 abstract 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 239000000908 ammonium hydroxide Substances 0.000 abstract 1
- -1 chloride or nitrate) Chemical class 0.000 abstract 1
- 229960002471 cholic acid Drugs 0.000 abstract 1
- BHQCQFFYRZLCQQ-OELDTZBJSA-N cholic acid Chemical compound C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)[C@@H](O)C1 BHQCQFFYRZLCQQ-OELDTZBJSA-N 0.000 abstract 1
- 235000019416 cholic acid Nutrition 0.000 abstract 1
- KXGVEGMKQFWNSR-UHFFFAOYSA-N deoxycholic acid Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)C(O)C2 KXGVEGMKQFWNSR-UHFFFAOYSA-N 0.000 abstract 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 abstract 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- 238000006722 reduction reaction Methods 0.000 abstract 1
- PXLIDIMHPNPGMH-UHFFFAOYSA-N sodium chromate Chemical compound [Na+].[Na+].[O-][Cr]([O-])(=O)=O PXLIDIMHPNPGMH-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
1360354 Chenodeoxycholic acid UNION INTERNATIONAL CO Ltd 15 Jan 1973 [20 Jan 1972] 2803/72 Heading C2U Chenodeoxycholic acid (I) is purified by forming a mixture thereof with methanol, a base and a Ca or Sr salt (e.g. chloride or nitrate), separating and acidifying the precipitated Ca or Sr salt of I, and isolating the purified produce. The base may be an alkali metal hydroxides. ammonia, ammonium hydroxide, hydrazine hydrate or an organic nitrogenous base (a list of examples is provided). The preparation of I from cholic acid (II) by the sequence II-(a)#methyl cholate-(b)# methyl - 3α,7α - diacetoxy - 12α - hydroxy - 5#- cholanate-(c)#methyl - 3α,7α - diacetoxy - 12- oxo-5#-cholanate-(d)#I is effected with reactants as follows (a) MeOH/H 2 SO 4 ; (b) Ac 2 O/py in benzene, dioxan, THF, dimethyl sulphoxide or acetonitrile; (c) sodium chromate/H 2 O/ AcOH; (d) Wolff-Kishner, modified Wolff- Kishner or cathodic reduction followed by hydrolysis.
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB280372A GB1360354A (en) | 1972-01-20 | 1972-01-20 | Chenodeoxycholic acid |
| ES410785A ES410785A1 (en) | 1972-01-20 | 1973-01-19 | Chenodeoxycholic acid |
| SE7300810A SE385905B (en) | 1972-01-20 | 1973-01-19 | PROCEDURE FOR PURIFICATION OF CHENODEOXICHOLIC ACID |
| AU51263/73A AU468382B2 (en) | 1972-01-20 | 1973-01-19 | Chenodeoxycholic acid |
| JP910573A JPS4995955A (en) | 1972-01-20 | 1973-01-20 | |
| DE19732302744 DE2302744A1 (en) | 1972-01-20 | 1973-01-20 | METHOD FOR PURIFYING CRUDE CHENODESOXYCHOLIC ACID |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB280372A GB1360354A (en) | 1972-01-20 | 1972-01-20 | Chenodeoxycholic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1360354A true GB1360354A (en) | 1974-07-17 |
Family
ID=9746226
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB280372A Expired GB1360354A (en) | 1972-01-20 | 1972-01-20 | Chenodeoxycholic acid |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS4995955A (en) |
| AU (1) | AU468382B2 (en) |
| DE (1) | DE2302744A1 (en) |
| ES (1) | ES410785A1 (en) |
| GB (1) | GB1360354A (en) |
| SE (1) | SE385905B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US12419897B2 (en) | 2018-12-04 | 2025-09-23 | President And Fellows Of Harvard College | Synthetic derivatives of cholic acid 7-sulfate and uses thereof |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2613346C3 (en) * | 1976-03-29 | 1981-07-23 | Diamalt AG, 8000 München | Monocline crystalline chenodeoxycholic acid and process for its preparation |
| FR2521430A1 (en) * | 1982-02-12 | 1983-08-19 | Pan Medica | AQUEOUS URSODESOXYCHOLIC ACID SOLUTION FOR THERAPEUTIC USES, PROCESS FOR THE PREPARATION THEREOF, AND APPLICATION FOR THE TREATMENT OF BILARY LITHIASES |
| KR20010043558A (en) | 1998-05-13 | 2001-05-25 | 한센 핀 베네드, 안네 제헤르, 웨이콥 마리안느 | Meiosis regulating compounds |
| AU2020274319A1 (en) * | 2019-05-10 | 2021-12-02 | President And Fellows Of Harvard College | Small molecule modulators of gut bacterial bile acid metabolism |
-
1972
- 1972-01-20 GB GB280372A patent/GB1360354A/en not_active Expired
-
1973
- 1973-01-19 ES ES410785A patent/ES410785A1/en not_active Expired
- 1973-01-19 AU AU51263/73A patent/AU468382B2/en not_active Expired
- 1973-01-19 SE SE7300810A patent/SE385905B/en unknown
- 1973-01-20 DE DE19732302744 patent/DE2302744A1/en active Pending
- 1973-01-20 JP JP910573A patent/JPS4995955A/ja active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US12419897B2 (en) | 2018-12-04 | 2025-09-23 | President And Fellows Of Harvard College | Synthetic derivatives of cholic acid 7-sulfate and uses thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| ES410785A1 (en) | 1976-04-01 |
| DE2302744A1 (en) | 1973-07-26 |
| AU468382B2 (en) | 1976-01-08 |
| JPS4995955A (en) | 1974-09-11 |
| AU5126373A (en) | 1974-07-25 |
| SE385905B (en) | 1976-07-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |