CA1192904A - Ethers - Google Patents

Ethers

Info

Publication number: CA1192904A
Authority: CA; Canada
Prior art keywords: salt; deoxy; didehydro; compound; iii
Prior art date: 1976-10-20
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

Application number

CA000289017A

Other languages

English (en)

Inventor

Norman Whittaker

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Wellcome Foundation Ltd

Original Assignee

Wellcome Foundation Ltd

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.)

1976-10-20

Filing date

1977-10-19

Publication date

1985-09-03

1977-10-19 Application filed by Wellcome Foundation Ltd filed Critical Wellcome Foundation Ltd

1985-09-03 Application granted granted Critical

1985-09-03 Publication of CA1192904A publication Critical patent/CA1192904A/fr

Status Expired legal-status Critical Current

Links

150000002170 ethers Chemical class 0.000 title 1
230000015572 biosynthetic process Effects 0.000 claims abstract description 20
150000003839 salts Chemical class 0.000 claims description 47
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 45
238000000034 method Methods 0.000 claims description 40
230000008569 process Effects 0.000 claims description 35
230000000903 blocking effect Effects 0.000 claims description 29
150000001875 compounds Chemical class 0.000 claims description 21
230000007062 hydrolysis Effects 0.000 claims description 18
238000006460 hydrolysis reaction Methods 0.000 claims description 18
159000000000 sodium salts Chemical class 0.000 claims description 18
238000006704 dehydrohalogenation reaction Methods 0.000 claims description 17
125000000217 alkyl group Chemical group 0.000 claims description 16
239000002585 base Substances 0.000 claims description 15
229910052739 hydrogen Inorganic materials 0.000 claims description 15
239000001257 hydrogen Substances 0.000 claims description 15
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
125000004432 carbon atom Chemical group C* 0.000 claims description 14
-1 alkali metal alkoxide Chemical class 0.000 claims description 11
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 11
229910052794 bromium Inorganic materials 0.000 claims description 11
125000001246 bromo group Chemical group Br* 0.000 claims description 10
229910052783 alkali metal Inorganic materials 0.000 claims description 9
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 9
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 8
230000003301 hydrolyzing effect Effects 0.000 claims description 6
239000012298 atmosphere Substances 0.000 claims description 4
150000004703 alkoxides Chemical class 0.000 claims description 3
125000004185 ester group Chemical group 0.000 claims description 3
125000004492 methyl ester group Chemical group 0.000 claims description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
229910052740 iodine Inorganic materials 0.000 claims description 2
239000011630 iodine Substances 0.000 claims description 2
125000004356 hydroxy functional group Chemical group O* 0.000 claims 20
101150009274 nhr-1 gene Proteins 0.000 claims 14
238000004519 manufacturing process Methods 0.000 claims 7
150000008044 alkali metal hydroxides Chemical class 0.000 claims 6
239000000126 substance Substances 0.000 claims 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
238000003786 synthesis reaction Methods 0.000 abstract description 3
150000003815 prostacyclins Chemical class 0.000 abstract description 2
239000003814 drug Substances 0.000 abstract 1
239000008194 pharmaceutical composition Substances 0.000 abstract 1
KAQKFAOMNZTLHT-OZUDYXHBSA-N prostaglandin I2 Chemical compound O1\C(=C/CCCC(O)=O)C[C@@H]2[C@@H](/C=C/[C@@H](O)CCCCC)[C@H](O)C[C@@H]21 KAQKFAOMNZTLHT-OZUDYXHBSA-N 0.000 description 15
229960001123 epoprostenol Drugs 0.000 description 14
239000011734 sodium Substances 0.000 description 12
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 9
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
229910052708 sodium Inorganic materials 0.000 description 9
210000001772 blood platelet Anatomy 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 7
238000009472 formulation Methods 0.000 description 7
239000000203 mixture Substances 0.000 description 7
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
150000002148 esters Chemical class 0.000 description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 4
239000004480 active ingredient Substances 0.000 description 4
150000004702 methyl esters Chemical class 0.000 description 4
LMHIPJMTZHDKEW-XQYLJSSYSA-M Epoprostenol sodium Chemical compound [Na+].O1\C(=C/CCCC([O-])=O)C[C@@H]2[C@@H](/C=C/[C@@H](O)CCCCC)[C@H](O)C[C@@H]21 LMHIPJMTZHDKEW-XQYLJSSYSA-M 0.000 description 3
241000700159 Rattus Species 0.000 description 3
QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical group C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 3
210000004369 blood Anatomy 0.000 description 3
239000008280 blood Substances 0.000 description 3
239000000969 carrier Substances 0.000 description 3
230000004087 circulation Effects 0.000 description 3
229910052681 coesite Inorganic materials 0.000 description 3
229910052906 cristobalite Inorganic materials 0.000 description 3
239000013078 crystal Substances 0.000 description 3
229910052751 metal Inorganic materials 0.000 description 3
239000002184 metal Substances 0.000 description 3
231100000252 nontoxic Toxicity 0.000 description 3
230000003000 nontoxic effect Effects 0.000 description 3
238000011321 prophylaxis Methods 0.000 description 3
239000000377 silicon dioxide Substances 0.000 description 3
235000012239 silicon dioxide Nutrition 0.000 description 3
239000007787 solid Substances 0.000 description 3
239000002904 solvent Substances 0.000 description 3
229910052682 stishovite Inorganic materials 0.000 description 3
229910052905 tridymite Inorganic materials 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
241000283973 Oryctolagus cuniculus Species 0.000 description 2
239000002253 acid Substances 0.000 description 2
FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 2
125000004429 atom Chemical group 0.000 description 2
210000004204 blood vessel Anatomy 0.000 description 2
239000012530 fluid Substances 0.000 description 2
230000002496 gastric effect Effects 0.000 description 2
MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 2
210000000056 organ Anatomy 0.000 description 2
230000010412 perfusion Effects 0.000 description 2
230000003389 potentiating effect Effects 0.000 description 2
230000000069 prophylactic effect Effects 0.000 description 2
230000001225 therapeutic effect Effects 0.000 description 2
206010003210 Arteriosclerosis Diseases 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
DCERHCFNWRGHLK-UHFFFAOYSA-N C[Si](C)C Chemical group C[Si](C)C DCERHCFNWRGHLK-UHFFFAOYSA-N 0.000 description 1
241000282472 Canis lupus familiaris Species 0.000 description 1
241000282693 Cercopithecidae Species 0.000 description 1
101000862089 Clarkia lewisii Glucose-6-phosphate isomerase, cytosolic 1A Proteins 0.000 description 1
102000016736 Cyclin Human genes 0.000 description 1
108050006400 Cyclin Proteins 0.000 description 1
241000282326 Felis catus Species 0.000 description 1
206010061459 Gastrointestinal ulcer Diseases 0.000 description 1
206010020772 Hypertension Diseases 0.000 description 1
238000004566 IR spectroscopy Methods 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
101100323108 Mus musculus Amot gene Proteins 0.000 description 1
101100274524 Mus musculus Clec18a gene Proteins 0.000 description 1
241000282320 Panthera leo Species 0.000 description 1
ZTHYODDOHIVTJV-UHFFFAOYSA-N Propyl gallate Chemical compound CCCOC(=O)C1=CC(O)=C(O)C(O)=C1 ZTHYODDOHIVTJV-UHFFFAOYSA-N 0.000 description 1
241000786363 Rhampholeon spectrum Species 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
208000025865 Ulcer Diseases 0.000 description 1
208000027418 Wounds and injury Diseases 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
239000000654 additive Substances 0.000 description 1
239000000853 adhesive Substances 0.000 description 1
230000001070 adhesive effect Effects 0.000 description 1
238000007605 air drying Methods 0.000 description 1
239000003513 alkali Substances 0.000 description 1
239000011717 all-trans-retinol Substances 0.000 description 1
235000019169 all-trans-retinol Nutrition 0.000 description 1
230000003276 anti-hypertensive effect Effects 0.000 description 1
239000003146 anticoagulant agent Substances 0.000 description 1
239000002220 antihypertensive agent Substances 0.000 description 1
229940030600 antihypertensive agent Drugs 0.000 description 1
229960004676 antithrombotic agent Drugs 0.000 description 1
210000000709 aorta Anatomy 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
208000011775 arteriosclerosis disease Diseases 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
239000010836 blood and blood product Substances 0.000 description 1
230000023555 blood coagulation Effects 0.000 description 1
229940125691 blood product Drugs 0.000 description 1
239000003633 blood substitute Substances 0.000 description 1
150000001649 bromium compounds Chemical group 0.000 description 1
150000001768 cations Chemical class 0.000 description 1
210000004027 cell Anatomy 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
210000001072 colon Anatomy 0.000 description 1
238000001816 cooling Methods 0.000 description 1
230000007547 defect Effects 0.000 description 1
230000002939 deleterious effect Effects 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
SEISMQVOJUJKGE-UHFFFAOYSA-M ethyl 1,6-dimethyl-4-oxo-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidin-1-ium-3-carboxylate;methyl sulfate Chemical compound COS([O-])(=O)=O.C1CCC(C)N2C(=O)C(C(=O)OCC)=C[N+](C)=C21 SEISMQVOJUJKGE-UHFFFAOYSA-M 0.000 description 1
210000001035 gastrointestinal tract Anatomy 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
229910000043 hydrogen iodide Inorganic materials 0.000 description 1
239000012535 impurity Substances 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
238000011835 investigation Methods 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
238000002955 isolation Methods 0.000 description 1
150000002632 lipids Chemical class 0.000 description 1
239000007788 liquid Substances 0.000 description 1
208000010125 myocardial infarction Diseases 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
229940094443 oxytocics prostaglandins Drugs 0.000 description 1
230000002093 peripheral effect Effects 0.000 description 1
210000004623 platelet-rich plasma Anatomy 0.000 description 1
230000002980 postoperative effect Effects 0.000 description 1
101150016899 potA gene Proteins 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
150000003180 prostaglandins Chemical class 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000028327 secretion Effects 0.000 description 1
239000008279 sol Substances 0.000 description 1
238000001179 sorption measurement Methods 0.000 description 1
238000003756 stirring Methods 0.000 description 1
229910021653 sulphate ion Inorganic materials 0.000 description 1
238000001356 surgical procedure Methods 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000010409 thin film Substances 0.000 description 1
238000011282 treatment Methods 0.000 description 1
125000004665 trialkylsilyl group Chemical group 0.000 description 1
231100000397 ulcer Toxicity 0.000 description 1
230000024883 vasodilation Effects 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1

Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA000289017A 1976-10-20 1977-10-19 Ethers Expired CA1192904A (fr)

Applications Claiming Priority (6)

Application Number	Priority Date	Filing Date	Title
GB43445/76		1976-10-20
GB4344576		1976-10-20
GB5306076		1976-12-20
GB53060/76		1976-12-20
GB1338977		1977-03-30
GB13389/77		1977-03-30

Publications (1)

Publication Number	Publication Date
CA1192904A true CA1192904A (fr)	1985-09-03

Family

ID=27256988

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000289017A Expired CA1192904A (fr)	1976-10-20	1977-10-19	Ethers

Country Status (3)

Country	Link
AT (1)	AT366382B (fr)
CA (1)	CA1192904A (fr)
HU (1)	HU178137B (fr)

1977
- 1977-05-10 HU HUWE000553 patent/HU178137B/hu unknown
- 1977-05-10 AT AT333177A patent/AT366382B/de not_active IP Right Cessation
- 1977-10-19 CA CA000289017A patent/CA1192904A/fr not_active Expired

Also Published As

Publication number	Publication date
AT366382B (de)	1982-04-13
HU178137B (en)	1982-03-28
ATA333177A (de)	1981-08-15

Legal Events

Date	Code	Title	Description
2002-09-03	MKEX	Expiry

Publication	Publication Date	Title
CA1198118A (fr)	1985-12-17	Derives d'acides pyrrolcarboxyliques alicycliques [c]; methode de preparation, agents a base de ces derives et utilisation; nouveaux acides pyrrolcarboxyliques alicycliques [c] servant comme intermediaires et leur preparation
SU1632371A3 (ru)	1991-02-28	Способ получени @ -циклодекстринового клатрата - аналога карбациклина
US4942166A (en)	1990-07-17	Crystalline purine compounds
US4775751A (en)	1988-10-04	Process for cephalexin hydrochloride alcoholates
IE56488B1 (en)	1991-08-14	Crystalline cephem-acid addition salts and process for their preparation
US4673666A (en)	1987-06-16	2-amino-3-ethoxycarbonylamino-6-(p-fluoro-benzylamino)-pyridine gluconate and pharmaceutical preparations containing it
CA1192904A (fr)	1985-09-03	Ethers
KR870001071B1 (ko)	1987-05-27	고 결정성 나트륨 세포페라존의 제조방법
EP0107693B1 (fr)	1988-07-27	Composes analogues de 2,3,4-trinor-1,5-inter-m-phenylene-prostacycline-i2, leur procede de preparation et compositions pharmaceutiques les contenant
US4054738A (en)	1977-10-18	Sodium cefamandole crystalline forms
US4958046A (en)	1990-09-18	Hydroxypropafenone glycerides
US4321205A (en)	1982-03-23	15-Epi-prostacyclin and analogous prostacyclins
FI62311C (fi)	1982-12-10	Foerfarande foer framstaellning av kristallint natrium- och kaiumcefalexinmonohydrat
US4539333A (en)	1985-09-03	Prostacyclin, methods of using and method of making
US3931285A (en)	1976-01-06	Substituted tolyl esters of PGE1
IL33226A (en)	1973-10-25	Omega-nor and omega-homo pgf2beta derivatives and process for their preparation
US4558053A (en)	1985-12-10	Naphthalene-1,5-disulfonate salts of dimeric indole-dihydroindole alkaloids
SU1467056A1 (ru)	1989-03-23	Производные интерфураниленпростациклина, обладающие гипотензивными свойствами и способностью подавл ть агрегацию тромбоцитов
US4324905A (en)	1982-04-13	Phenacyl-type esters of PGF2α and its 15-methyl analogs
FI67554C (fi)	1985-04-10	Vid framstaellning av kristallinskt natriumcefamandolianhydratsaosom mellanprodukt anvaent kristallinsk metanolsolvat a v atrium-7-(d-2-hydroxi-2-fenylacetamido)-3-(1-metyl-1h-tet raol-5-yltiometyl)-3-cefem-4-karboxylat och foerfarande foe r ess framstaellning
US3988355A (en)	1976-10-26	Substituted phenyl and naphthyl esters of PGE1
US4012427A (en)	1977-03-15	Substituted phenyl esters of PGE1 -type prostaglandins
US4883810A (en)	1989-11-28	Ethers
US6017959A (en)	2000-01-25	Forms of organic salts of N,N'-diacetylcystine
HU180455B (en)	1983-03-28	Process for preparing crystallic methanolate of sodium salt of 7-/d-alpha-formyl-oxy-alpha-phenyl-acetamido/-3-/1-methyl-1h-tetrazol-5-yl-thiomethyl/-3-cefem-4-carboxylic acid