US4468458A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Two-functional-group-containing terpenoids, processes for the preparation of the same, and anti-ulcer agents containing the same
Assignee: Eisai Co Ltd
•
Filing: 1982-03-22
•
Granted: 1984-08-28
•
Expires: 2002-03-22
Abstract
Abstract A process for the preparation of a two-functional-group-containing terpenoid having the general formula: <IMAGE> in which n is an integer of from 1 to 5, R represents a hydroxymethyl, formyl or carboxyl group, and A represents the hydrogen atom, or a 2-tetrahydropyranyl, benzyl, methoxymethol or methoxyethoxymethyl group comprising the oxidation with a microorganism belonging to the genus Nocardia. Some of the terpenoids are of value as anti-ulcer agents, while others are useful as intermediates.
Inventors
- 👤 Akio Sato
- 👤 Kenji Nakajima
- 👤 Yoshimasa Takahara
- 👤 Shizumasa Kijima
- 👤 Noriaki Kuwana
- 👤 Shinya Abe
- 👤 Kouzi Yamada
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 22:01
CPC Classifications
C; C12; C12P; C12P7/00; C12P7/64; C12P7/6409; C12P7/6427; C12P7/6432; A; A61; A61K; A61K31/00; A61K31/11; C07; C07C; C07C29/00; C07C29/09; C07C29/10; C07C33/00; C07C33/02; C07C47/00; C07C47/20; C07C47/26; C07C47/263; C07C47/277; C07C59/00; C07C59/01; C07C59/40; C07C59/58; C07C59/64; C07C59/66; C07D; C07D309/00; C07D309/02; C07D309/08; C07D309/10; C07D309/12; C12N; C12N1/00; C12N1/20; C12N1/205; C12P17/00; C12P17/02; C12P17/06; C12P7/02; C12P7/24; C12P7/40; C12R; C12R2001/00; C12R2001/01; C12R2001/365; Y; Y02; Y02P; Y02P20/00; Y02P20/50; Y02P20/582; Y10; Y10S; Y10S435/00; Y10S435/8215; Y10S435/822; Y10S435/872
Claims Analysis
Total Claims: 9
Claim 1
Independent Claim
117 words
A process for the preparation of a compound having the formula (I): ##STR28## in which n is an integer of from 1 to 5, A' is 2-tetrahydropyranyl, benzyl, methoxymethyl or methoxyethoxymethyl, and R is hydroxymethyl, formyl or carboxyl, which comprises the steps of: cultivating Nocardia BPM 1613, FERM-P No. 1609, in a nutritive culture medium in the presence of a compound having the formula (II): ##STR29## in which n and A' have the same meanings as defined above, whereby said microorganism utilizes said compound of the general formula (II) as a carbon source and oxidizes said compound (II), thereby converting said compound (II) into said compound (I); and recovering the thus-produced compound having the general formula (I).
Claim 2
Dependent Claim
117 words
A process for the preparation of a compound having the formula (I): ##STR28## in which n is an integer of from 1 to 5, A' is 2-tetrahydropyranyl, benzyl, methoxymethyl or methoxyethoxymethyl, and R is hydroxymethyl, formyl or carboxyl, which comprises the steps of: cultivating Nocardia BPM 1613, FERM-P No. 1609, in a nutritive culture medium in the presence of a compound having the formula (II): ##STR29## in which n and A' have the same meanings as defined above, whereby said microorganism utilizes said compound of the general formula (II) as a carbon source and oxidizes said compound (II), thereby converting said compound (II) into said compound (I); and recovering the thus-produced compound having the general formula (I).
Claim 3
Dependent Claim
20 words
A process as claimed in claim 1, further comprising isolating said compound having the formula (I) after said recovery step.
Claim 4
Dependent Claim
139 words
A process for the preparation of a compound having the formula (I): ##STR30## in which n is an integer of from 1 to 5, and R is hydroxymethyl, formyl or carboxyl, which comprises the steps of: cultivating Nocardia BPM 1613, FERM-P No. 1609, in a nutritive culture medium in the presence of a compound having the formula (II): ##STR31## in which n has the same meaning as defined above, and A' is 2-tetrahydropyranyl, benzyl, methoxymethyl or methoxyethoxymethyl, whereby said microorganism utilizes said compound of the general formula (II) as a carbon source and oxidizes said compound (II), thereby converting said compound (II) into a compound of the formula (III): ##STR32## recovering the thus-produced compound having the general formula (III) from said culture medium; and hydrolyzing said compound (III) to eliminate the group A' therefrom, thereby forming said compound (I).
Claim 5
Dependent Claim
139 words
A process for the preparation of a compound having the formula (I): ##STR30## in which n is an integer of from 1 to 5, and R is hydroxymethyl, formyl or carboxyl, which comprises the steps of: cultivating Nocardia BPM 1613, FERM-P No. 1609, in a nutritive culture medium in the presence of a compound having the formula (II): ##STR31## in which n has the same meaning as defined above, and A' is 2-tetrahydropyranyl, benzyl, methoxymethyl or methoxyethoxymethyl, whereby said microorganism utilizes said compound of the general formula (II) as a carbon source and oxidizes said compound (II), thereby converting said compound (II) into a compound of the formula (III): ##STR32## recovering the thus-produced compound having the general formula (III) from said culture medium; and hydrolyzing said compound (III) to eliminate the group A' therefrom, thereby forming said compound (I).
Claim 6
Dependent Claim
21 words
A process according to claim 1 or claim 3, wherein said medium is maintained at a pH of 7 to 10.
Claim 7
Dependent Claim
31 words
A process according to claim 4, wherein the cultivation is carried out for 3 to 5 days at a temperature in the range of 20° to 40° C. under aerobic conditions.
Claim 8
Dependent Claim
81 words
A process as claimed in claim 1 or claim 3, wherein said culture medium comprises a nitrogen source selected from the group consisting of potassium nitrate, sodium nitrate, ammonium nitrate, ammonium chloride, ammonium sulfate, ammonium phosphate, ammonia and urea, an inorganic salt selected from the group consisting of potassium phosphate, sodium phosphate, magnesium sulfate, ferrous sulfate and magnesium sulfate, and an organic nutrient source selected from the group consisting of vitamins, amino acids, yeast extract, corn steep liquor and malt extract.
Claim 9
Dependent Claim
20 words
A process as claimed in claim 3, further comprising isolating said compound having the formula (I) after said recovery step.
References Cited (Backward Citations)
US3645847A
Cited
US3546073A
Cited
US3748231A
Cited
JPS56113721A
Cited
US4338251A
Cited
GB2076395A
Cited
US4346109A
Cited
JPS5750940A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1987-08-28 | 1988-02-27 | 1988-08-28 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1991-08-28 | 1992-02-27 | 1992-08-28 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1995-08-28 | 1996-02-27 | 1996-08-28 | $7700.00 | Window Closed / Lapsed |