DD268247A5 - In der omega-kette modifizierte neue prostaglandin-intermediaere und verfahren zu ihrer herstellung - Google Patents

In der omega-kette modifizierte neue prostaglandin-intermediaere und verfahren zu ihrer herstellung Download PDF

Info

Publication number: DD268247A5
Authority: DD; German Democratic Republic
Prior art keywords: general formula; compounds; alkyl group; compound; cyclopentyl
Prior art date: 1987-03-24

Application number

DD31386588A

Other languages

German (de)

English (en)

Inventor

Istvan Kaldor

Vilmos Simonidesz

Peter Gyoery

Agnes Szabo

Janos Oeri

Original Assignee

Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara Rt.,Hu

Priority date (The priority date 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 date listed.)

1987-03-24

Filing date

1988-03-21

Publication date

1989-05-24

1988-03-21 Application filed by Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara Rt.,Hu filed Critical Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara Rt.,Hu

1989-05-24 Publication of DD268247A5 publication Critical patent/DD268247A5/de

Links

238000000034 method Methods 0.000 title claims abstract description 13
150000003180 prostaglandins Chemical class 0.000 title claims abstract description 4
238000004519 manufacturing process Methods 0.000 title 1
238000002360 preparation method Methods 0.000 claims abstract description 11
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims abstract description 9
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims abstract description 9
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 5
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract 3
150000001875 compounds Chemical class 0.000 claims description 37
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 21
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 15
229910052744 lithium Inorganic materials 0.000 claims description 8
-1 iodo compound Chemical class 0.000 claims description 7
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 claims description 6
HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 claims description 6
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 5
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 5
229910052987 metal hydride Inorganic materials 0.000 claims description 5
150000004681 metal hydrides Chemical class 0.000 claims description 5
150000002497 iodine compounds Chemical class 0.000 claims description 4
229910052751 metal Inorganic materials 0.000 claims description 4
239000002184 metal Substances 0.000 claims description 4
239000011701 zinc Substances 0.000 claims description 4
229910052725 zinc Inorganic materials 0.000 claims description 4
CXLJNMDMFUNLGQ-UHFFFAOYSA-N 1-bromo-3-methylheptan-3-ol Chemical compound CCCCC(C)(O)CCBr CXLJNMDMFUNLGQ-UHFFFAOYSA-N 0.000 claims description 3
239000003960 organic solvent Substances 0.000 claims description 3
229910001516 alkali metal iodide Inorganic materials 0.000 claims description 2
PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 claims description 2
235000009518 sodium iodide Nutrition 0.000 claims description 2
125000000217 alkyl group Chemical group 0.000 claims 4
MEJJUZUMTCTDCF-UHFFFAOYSA-N 3-methylheptane-1,3-diol Chemical compound CCCCC(C)(O)CCO MEJJUZUMTCTDCF-UHFFFAOYSA-N 0.000 claims 1
125000004432 carbon atom Chemical group C* 0.000 claims 1
239000013067 intermediate product Substances 0.000 claims 1
150000004714 phosphonium salts Chemical class 0.000 claims 1
239000000543 intermediate Substances 0.000 abstract description 4
ISCGGGVEXDAQCX-UHFFFAOYSA-N 1-iodo-3-methylheptan-3-ol Chemical compound CCCCC(C)(O)CCI ISCGGGVEXDAQCX-UHFFFAOYSA-N 0.000 abstract description 3
125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
238000006243 chemical reaction Methods 0.000 description 16
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 7
238000004587 chromatography analysis Methods 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
239000012280 lithium aluminium hydride Substances 0.000 description 5
239000000203 mixture Substances 0.000 description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 4
239000002904 solvent Substances 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
229910052740 iodine Inorganic materials 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
238000005160 1H NMR spectroscopy Methods 0.000 description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
238000005481 NMR spectroscopy Methods 0.000 description 2
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
239000003480 eluent Substances 0.000 description 2
125000004494 ethyl ester group Chemical group 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
HSZCZNFXUDYRKD-UHFFFAOYSA-M lithium iodide Chemical compound [Li+].[I-] HSZCZNFXUDYRKD-UHFFFAOYSA-M 0.000 description 2
239000012452 mother liquor Substances 0.000 description 2
XVDBWWRIXBMVJV-UHFFFAOYSA-N n-[bis(dimethylamino)phosphanyl]-n-methylmethanamine Chemical compound CN(C)P(N(C)C)N(C)C XVDBWWRIXBMVJV-UHFFFAOYSA-N 0.000 description 2
239000012071 phase Substances 0.000 description 2
238000000746 purification Methods 0.000 description 2
239000007858 starting material Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 1
LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 1
GKUCVIBSNKXKPF-UHFFFAOYSA-N CCCCC(C)(CCP(c1ccccc1)(c1ccccc1)c1ccccc1)[IH]O Chemical compound CCCCC(C)(CCP(c1ccccc1)(c1ccccc1)c1ccccc1)[IH]O GKUCVIBSNKXKPF-UHFFFAOYSA-N 0.000 description 1
VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical compound [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 description 1
238000003747 Grignard reaction Methods 0.000 description 1
238000005684 Liebig rearrangement reaction Methods 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
238000007239 Wittig reaction Methods 0.000 description 1
238000007259 addition reaction Methods 0.000 description 1
125000005907 alkyl ester group Chemical group 0.000 description 1
AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
230000002051 biphasic effect Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
230000001120 cytoprotective effect Effects 0.000 description 1
238000004821 distillation Methods 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
WBJINCZRORDGAQ-UHFFFAOYSA-N ethyl formate Chemical compound CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
238000011049 filling Methods 0.000 description 1
230000027119 gastric acid secretion Effects 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
239000011630 iodine Substances 0.000 description 1
YLERVAXAQFOFRI-UHFFFAOYSA-M magnesium;propa-1,2-diene;bromide Chemical compound [Mg+2].[Br-].[CH2-]C#C YLERVAXAQFOFRI-UHFFFAOYSA-M 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
OJLOPKGSLYJEMD-URPKTTJQSA-N methyl 7-[(1r,2r,3r)-3-hydroxy-2-[(1e)-4-hydroxy-4-methyloct-1-en-1-yl]-5-oxocyclopentyl]heptanoate Chemical compound CCCCC(C)(O)C\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(=O)OC OJLOPKGSLYJEMD-URPKTTJQSA-N 0.000 description 1
229960005249 misoprostol Drugs 0.000 description 1
238000002156 mixing Methods 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
230000037361 pathway Effects 0.000 description 1
150000003017 phosphorus Chemical class 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
230000007017 scission Effects 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
230000000707 stereoselective effect Effects 0.000 description 1
125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
238000006227 trimethylsilylation reaction Methods 0.000 description 1
PGOLTJPQCISRTO-UHFFFAOYSA-N vinyllithium Chemical compound [Li]C=C PGOLTJPQCISRTO-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/535—Organo-phosphoranes
- C07F9/5352—Phosphoranes containing the structure P=C-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/18—Polyhydroxylic acyclic alcohols
- C07C31/20—Dihydroxylic alcohols
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/34—Halogenated alcohols
- C07C31/36—Halogenated alcohols the halogen not being fluorine
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/54—Quaternary phosphonium compounds
- C07F9/5407—Acyclic saturated phosphonium compounds

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Biochemistry (AREA)
General Health & Medical Sciences (AREA)
Molecular Biology (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

DD31386588A 1987-03-24 1988-03-21 In der omega-kette modifizierte neue prostaglandin-intermediaere und verfahren zu ihrer herstellung DD268247A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
HU128187A HU198503B (en)	1987-03-24	1987-03-24	Process for producing triphenyl phosphonium salts

Publications (1)

Publication Number	Publication Date
DD268247A5 true DD268247A5 (de)	1989-05-24

Family

ID=10953674

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD31386588A DD268247A5 (de)	1987-03-24	1988-03-21	In der omega-kette modifizierte neue prostaglandin-intermediaere und verfahren zu ihrer herstellung

Country Status (5)

Country	Link
CS (1)	CS266349B2 (cs)
DD (1)	DD268247A5 (cs)
HU (1)	HU198503B (cs)
PL (1)	PL153699B1 (cs)
WO (1)	WO1988007537A1 (cs)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
ATE394372T1 (de)	2003-03-03	2008-05-15	Serono Lab	G-lactamderivate als prostaglandinagonisten
WO2005097812A1 (en)	2004-04-09	2005-10-20	Valorisation-Recherche, Société en Commandite	Phosphonium salts derivatives and their use as solubility controlling auxiliaries

1987
- 1987-03-24 HU HU128187A patent/HU198503B/hu not_active IP Right Cessation
1988
- 1988-03-21 DD DD31386588A patent/DD268247A5/de not_active IP Right Cessation
- 1988-03-23 WO PCT/HU1988/000016 patent/WO1988007537A1/en not_active Ceased
- 1988-03-23 CS CS881898A patent/CS266349B2/cs unknown
- 1988-03-24 PL PL27141388A patent/PL153699B1/pl unknown

Also Published As

Publication number	Publication date
CS266349B2 (en)	1989-12-13
HUT46333A (en)	1988-10-28
CS189888A2 (en)	1989-02-10
WO1988007537A1 (en)	1988-10-06
HU198503B (en)	1989-10-30
PL153699B1 (en)	1991-05-31
PL271413A1 (en)	1989-03-06

Legal Events

Date	Code	Title	Description
1997-11-06	ENJ	Ceased due to non-payment of renewal fee

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