CA1098125A - Procede de preparation de nouveaux analogues de la prostaglandine - Google Patents

Procede de preparation de nouveaux analogues de la prostaglandine

Info

Publication number: CA1098125A
Authority: CA; Canada
Prior art keywords: compound; general formula; group; trans; formula
Prior art date: 1976-04-20
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

CA276,100A

Other languages

English (en)

Inventor

Masaki Hayashi

Seiji Kori

Hirohisa Wakatsuka

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.)

Ono Pharmaceutical Co Ltd

Original Assignee

Ono Pharmaceutical Co 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.)

1976-04-20

Filing date

1977-04-13

Publication date

1981-03-24

1976-04-20 Priority claimed from GB1598276A external-priority patent/GB1540427A/en

1977-04-13 Application filed by Ono Pharmaceutical Co Ltd filed Critical Ono Pharmaceutical Co Ltd

1981-03-24 Application granted granted Critical

1981-03-24 Publication of CA1098125A publication Critical patent/CA1098125A/fr

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 21
229940006138 antiglaucoma drug and miotics prostaglandin analogues Drugs 0.000 title claims abstract description 12
238000002360 preparation method Methods 0.000 title claims abstract description 8
150000001875 compounds Chemical class 0.000 claims abstract description 113
-1 1,1-dimethylpentyl Chemical group 0.000 claims abstract description 48
150000004702 methyl esters Chemical class 0.000 claims abstract description 28
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 26
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 19
125000000217 alkyl group Chemical group 0.000 claims abstract description 11
FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 claims abstract description 10
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 10
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical class [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims abstract description 9
230000003301 hydrolyzing effect Effects 0.000 claims abstract description 8
UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims abstract description 8
BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 claims abstract description 7
JKTCBAGSMQIFNL-UHFFFAOYSA-N 2,3-dihydrofuran Chemical compound C1CC=CO1 JKTCBAGSMQIFNL-UHFFFAOYSA-N 0.000 claims abstract description 5
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims abstract description 4
125000004043 oxo group Chemical group O=* 0.000 claims abstract description 4
125000004448 alkyl carbonyl group Chemical group 0.000 claims abstract description 3
239000002253 acid Substances 0.000 claims description 18
150000003839 salts Chemical class 0.000 claims description 16
229920000858 Cyclodextrin Polymers 0.000 claims description 14
HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 claims description 14
150000007513 acids Chemical class 0.000 claims description 13
231100000252 nontoxic Toxicity 0.000 claims description 12
230000003000 nontoxic effect Effects 0.000 claims description 12
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150000001412 amines Chemical class 0.000 description 5
239000012298 atmosphere Substances 0.000 description 5
238000004440 column chromatography Methods 0.000 description 5
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 5
239000000284 extract Substances 0.000 description 5
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QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
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 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
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CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 4
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230000035935 pregnancy Effects 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
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239000011734 sodium Substances 0.000 description 4
JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 4
150000003512 tertiary amines Chemical class 0.000 description 4
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 3
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206010020772 Hypertension Diseases 0.000 description 3
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
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229910052783 alkali metal Inorganic materials 0.000 description 3
150000001340 alkali metals Chemical class 0.000 description 3
229960000711 alprostadil Drugs 0.000 description 3
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230000033228 biological regulation Effects 0.000 description 3
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239000002775 capsule Substances 0.000 description 3
KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 3
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XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
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QPNOPWWAMGQISP-UHFFFAOYSA-N n,n'-dicyclohexylmethanediimine;methylsulfinylmethane Chemical compound CS(C)=O.C1CCCCC1N=C=NC1CCCCC1 QPNOPWWAMGQISP-UHFFFAOYSA-N 0.000 description 1
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
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239000008158 vegetable oil Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 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
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/02—Lithium compounds
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C391/00—Compounds containing selenium
- C07C391/02—Compounds containing selenium having selenium atoms bound to carbon atoms of six-membered aromatic 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
- C07C405/0025—Analogues having the carboxyl group in the side-chains replaced by other functional groups containing keto groups
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Materials Engineering (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA276,100A 1976-04-20 1977-04-13 Procede de preparation de nouveaux analogues de la prostaglandine Expired CA1098125A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB1598276A GB1540427A (en)	1972-12-29	1976-04-20	Prostaglandin analogues
GB15982/76		1976-04-20

Publications (1)

Publication Number	Publication Date
CA1098125A true CA1098125A (fr)	1981-03-24

Family

ID=10069096

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA276,100A Expired CA1098125A (fr)	1976-04-20	1977-04-13	Procede de preparation de nouveaux analogues de la prostaglandine

Country Status (4)

Country	Link
CA (1)	CA1098125A (fr)
CH (1)	CH624669A5 (fr)
HU (1)	HU179560B (fr)
SE (2)	SE423093B (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2014040457A1 (fr) *	2012-09-13	2014-03-20	上海源力生物技术有限公司	Intermédiaire de limaprost, son procédé de préparation et procédé de préparation de limaprost à partir de celui-ci

1977
- 1977-04-13 CA CA276,100A patent/CA1098125A/fr not_active Expired
- 1977-04-13 HU HU77OO239A patent/HU179560B/hu unknown
- 1977-04-13 SE SE7704248A patent/SE423093B/xx not_active IP Right Cessation
- 1977-04-19 CH CH482577A patent/CH624669A5/fr not_active IP Right Cessation
1981
- 1981-10-13 SE SE8106061A patent/SE442746B/sv not_active IP Right Cessation

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2014040457A1 (fr) *	2012-09-13	2014-03-20	上海源力生物技术有限公司	Intermédiaire de limaprost, son procédé de préparation et procédé de préparation de limaprost à partir de celui-ci
CN104284886A (zh) *	2012-09-13	2015-01-14	上海源力生物技术有限公司	一种制备利马前列素的中间体、其制备方法以及通过其制备利马前列素的方法
CN104284886B (zh) *	2012-09-13	2016-08-24	上海源力生物技术有限公司	一种制备利马前列素的中间体、其制备方法以及通过其制备利马前列素的方法
TWI623521B (zh) *	2012-09-13	2018-05-11	江蘇盛迪醫藥有限公司	一種製備利馬前列素的中間體、其製備方法以及藉由其製備利馬前列素的方法

Also Published As

Publication number	Publication date
HU179560B (en)	1982-11-29
SE7704248L (sv)	1977-10-21
SE442746B (sv)	1986-01-27
CH624669A5 (en)	1981-08-14
SE8106061L (sv)	1981-10-13
SE423093B (sv)	1982-04-13

Legal Events

Date	Code	Title	Description
1998-03-24	MKEX	Expiry

Publication	Publication Date	Title
US4128720A (en)	1978-12-05	Prostaglandin analogues
US3966792A (en)	1976-06-29	Prostaglandin compounds
CA1119169A (fr)	1982-03-02	Analogues de la prostaglandine
US4018812A (en)	1977-04-19	16-methylene-prostaglandin compounds
US4140712A (en)	1979-02-20	20-Hydroxy-prostaglandins
CA1066699A (fr)	1979-11-20	Analogues de la prostaglandine
US4087620A (en)	1978-05-02	15-Cycloalkyl-prostaglandin derivatives
US4034003A (en)	1977-07-05	15-Cycloalkyl-prostaglandins
GB2038815A (en)	1980-07-30	Prostacyclin analogues
CA1098125A (fr)	1981-03-24	Procede de preparation de nouveaux analogues de la prostaglandine
US3953435A (en)	1976-04-27	Aldehyde derivatives of prostaglandins
US4399147A (en)	1983-08-16	Prostaglandin 12 analogues and their pharmaceutical compositions
US4052512A (en)	1977-10-04	Prostaglandin analogues
US4208428A (en)	1980-06-17	Prostaglandin analogues
US4195182A (en)	1980-03-25	Trans-Δ2 -prostaglandin analogues
US4275075A (en)	1981-06-23	15-cylobutyl-trans-Δ2 -prostaglandin analogues
US4065632A (en)	1977-12-27	16-Phenoxy and phenylthio prostaglandin derivatives
US4069387A (en)	1978-01-17	16-Chloro-substituted prostaglandins and derivatives thereof
US4045465A (en)	1977-08-30	Cyanoprostaglandins
US4180675A (en)	1979-12-25	15-Cycloalkyl-prostaglandin derivatives
GB2075015A (en)	1981-11-11	Trans-2-pge alkylsulphonyl amides
US4165437A (en)	1979-08-21	Δ3 -Prostaglandin analogs
US4145555A (en)	1979-03-20	Δ3 -Prostaglandin analogs
US4070537A (en)	1978-01-24	17-Oxo-17-phenyl-prostaglandins
US4113766A (en)	1978-09-12	Oxaprostaglandins