GB1436378A - Prostaglandin derivatives - Google Patents
Prostaglandin derivativesInfo
- Publication number
- GB1436378A GB1436378A GB3678573A GB3678573A GB1436378A GB 1436378 A GB1436378 A GB 1436378A GB 3678573 A GB3678573 A GB 3678573A GB 3678573 A GB3678573 A GB 3678573A GB 1436378 A GB1436378 A GB 1436378A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compounds
- prepared
- cooh
- conh
- formula
- 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
- 150000003180 prostaglandins Chemical class 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 30
- 125000000896 monocarboxylic acid group Chemical group 0.000 abstract 9
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 abstract 7
- 150000004702 methyl esters Chemical class 0.000 abstract 3
- -1 amine salts Chemical class 0.000 abstract 2
- 238000006567 deketalization reaction Methods 0.000 abstract 2
- 238000005984 hydrogenation reaction Methods 0.000 abstract 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 abstract 2
- 229920002554 vinyl polymer Polymers 0.000 abstract 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 abstract 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 abstract 1
- 239000007818 Grignard reagent Substances 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 125000005907 alkyl ester group Chemical group 0.000 abstract 1
- 230000003182 bronchodilatating effect Effects 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000003638 chemical reducing agent Substances 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 150000004795 grignard reagents Chemical class 0.000 abstract 1
- 150000004678 hydrides Chemical class 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 238000005907 ketalization reaction Methods 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- 229940094443 oxytocics prostaglandins Drugs 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/72—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 spiro-condensed with carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C405/00—Compounds containing a five-membered ring having two side-chains in ortho position to each other, and having oxygen atoms directly attached to the ring in ortho position to one of the side-chains, one side-chain containing, not directly attached to the ring, a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, and the other side-chain having oxygen atoms attached in gamma-position to the ring, e.g. prostaglandins ; Analogues or derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C405/00—Compounds containing a five-membered ring having two side-chains in ortho position to each other, and having oxygen atoms directly attached to the ring in ortho position to one of the side-chains, one side-chain containing, not directly attached to the ring, a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, and the other side-chain having oxygen atoms attached in gamma-position to the ring, e.g. prostaglandins ; Analogues or derivatives thereof
- C07C405/0008—Analogues having the carboxyl group in the side-chains replaced by other functional groups
- C07C405/0033—Analogues having the carboxyl group in the side-chains replaced by other functional groups containing sulfur
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no 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
- C07D309/10—Oxygen atoms
- C07D309/12—Oxygen atoms only hydrogen atoms and one oxygen atom directly attached to ring carbon atoms, e.g. tetrahydropyranyl ethers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pyrane Compounds (AREA)
Abstract
1436378 Prostaglandins AMERICAN HOME PRODUCTS CORP 2 Aug 1973 [21 Aug 1972] 36785/73 Heading C2C The invention comprises (i) compounds of Formula II in which R<SP>1</SP> = CH 2 NO 2 , vinyl, Ph, Bz, Me, CN, SH, SAlkyl, SPh, CH(CN)COOH, CH(COOAlkyl) 2 , CH(CN) 2 or CH(CN)CONH 2 R<SP>2</SP> = OH, OTHP or OAc and R<SP>3</SP> = H, (ii) compounds of Formula V in which R<SP>1</SP> = CN, COOH, CONH 2 , CHO, CH 2 OH, CH(OH)CH 3 or CH 2 NO 2 , R<SP>2</SP> = OH or OAc and R<SP>3</SP> = H, (iii) compounds of Formula VI in which R<SP>1</SP> = COOH, COCH 3 , CONH 2 , CH 2 OH or CH(OH)CH 3 , (iv)-(vii) compounds of Formulµ VII, VIII, IX and X in which R<SP>1</SP> = CH 2 NO 2 or CN and R<SP>2</SP> = Me or Ph (viii) compounds of Formula IV in which R<SP>1</SP> = CONH 2 , Me, COOH, Bz, CH 2 NO 2 , Ph, CN, CH(CN)COOAlk, CH(COOH) 2 , CH 2 OH, COCH 3 or CH(OH)CH 3 , R<SP>2</SP> = OH, OTHP or OAc, provided that R<SP>2</SP> = OH when R<SP>1</SP> = COOH, COCH 3 , CONH 2 , CH 2 OH or CH(OH)CH 3 , and R<SP>3</SP> = H and (ix) compounds of Formula III in which R<SP>1</SP> = SH, CH 2 NO 2 , vinyl, Ph, Me, Bz, CN, SAlkyl, SPh, CH(CN)COOH, or CH(CN)CONH 2 , R<SP>2</SP> = OH or OTHP and R<SP>3 </SP>= H; and C 1 -C 6 alkyl esters and alkali metal, ammonium and basic amine salts of the said compounds. Compounds II are prepared from compounds I by 1,4-conjugate addition to the α,#-unsaturated ketone system, e.g. by means of Grignard reagents. Compounds III are prepared by treatment of compounds II with a hydride reducing agent. Compounds VI are prepared by deketalization of compounds V. Compounds VII are prepared by oxidation of compounds V. Compounds VIII are prepared by reaction of compounds VII with a methyl or phenyl Grignard reagent. Compounds IX are prepared by deketalization of compounds VIII. Compounds X are prepared by hydrogenation of compounds IX. Compounds IV are prepared by hydrogenation of compounds II or VI. Compounds V in which R<SP>1</SP> = CN or CH 2 NO 2 are prepared from corresponding compounds II by ketalization. Compounds V in which R<SP>1</SP> = COOH, CONH 2 , CHO or COCH 3 are prepared from compounds V in which R<SP>1</SP> = CN. Compounds V in which R<SP>1</SP> = CH 2 OH or CH(OH)CH 3 are prepared by reduction of compounds V in which R<SP>1</SP> = CHO or COCH 3 . Esters and salts may be prepared from compounds containing free OH or COOH groups, and vice versa. Intermediates.-PGA 2 , methyl ester; PGA 2 , 15 - tetrahydropyran - 2 - yl ether, PGA 2 , 15 - tetrahydropyran - 2 - yl ether, methyl ester, 15 - epi - PGA 2 , 15 - tetrahydropyran - 2 - yl ether; and PGA 2 , methyl ester, acetate are prepared in examples. Pharmaceutical compositions having bronchodilating activity for oral, parenteral and oral inhalation activity, comprise a compound of Formula II, III, IV, V, VI, IX or X together with a pharmaceutical carrier.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US28220072A | 1972-08-21 | 1972-08-21 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1436378A true GB1436378A (en) | 1976-05-19 |
Family
ID=23080487
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB3678573A Expired GB1436378A (en) | 1972-08-21 | 1973-08-02 | Prostaglandin derivatives |
Country Status (6)
Country | Link |
---|---|
JP (1) | JPS4962447A (en) |
BE (1) | BE803854A (en) |
DE (1) | DE2342004A1 (en) |
FR (1) | FR2196811B1 (en) |
GB (1) | GB1436378A (en) |
NL (1) | NL7311403A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2608924A1 (en) * | 1986-12-29 | 1988-07-01 | Pasteur Institut | THERAPEUTIC COMPOSITIONS CONTAINING SULFUR DERIVATIVES OF PROSTAGLANDINS, NOVEL SULFUR DERIVATIVES AND THEIR PREPARATION METHOD |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5623984B2 (en) * | 1973-04-19 | 1981-06-03 | ||
US3989744A (en) * | 1973-07-30 | 1976-11-02 | Miles Laboratories, Inc. | 11-Substitute d-11-desoxy-pge analogues |
US3931282A (en) * | 1974-02-21 | 1976-01-06 | Syntex (U.S.A.) Inc. | 11α-Hydroxymethyl prostaglandins |
US3950363A (en) * | 1975-03-10 | 1976-04-13 | The Upjohn Company | Prostaglandin cyclic ethers |
-
1973
- 1973-08-02 GB GB3678573A patent/GB1436378A/en not_active Expired
- 1973-08-17 NL NL7311403A patent/NL7311403A/xx unknown
- 1973-08-20 DE DE19732342004 patent/DE2342004A1/en active Pending
- 1973-08-21 JP JP9380373A patent/JPS4962447A/ja active Pending
- 1973-08-21 FR FR7330374A patent/FR2196811B1/fr not_active Expired
- 1973-08-21 BE BE134799A patent/BE803854A/en unknown
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2608924A1 (en) * | 1986-12-29 | 1988-07-01 | Pasteur Institut | THERAPEUTIC COMPOSITIONS CONTAINING SULFUR DERIVATIVES OF PROSTAGLANDINS, NOVEL SULFUR DERIVATIVES AND THEIR PREPARATION METHOD |
WO1988005042A1 (en) * | 1986-12-29 | 1988-07-14 | Institut Pasteur | Compositions containing sulphur prostaglandines |
Also Published As
Publication number | Publication date |
---|---|
DE2342004A1 (en) | 1974-03-07 |
JPS4962447A (en) | 1974-06-17 |
BE803854A (en) | 1974-02-21 |
FR2196811A1 (en) | 1974-03-22 |
NL7311403A (en) | 1974-02-25 |
FR2196811B1 (en) | 1976-12-24 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
PS | Patent sealed | ||
48S | Specification amended (sect. 8/1949) | ||
SPA | Amended specification published | ||
PCNP | Patent ceased through non-payment of renewal fee |