CA2183005A1 - Nouveau conjugue de chlorambucil et d'un derive d'estradiol; methode de preparation, composition pharmaceutique a base de ce conjugue - Google Patents

Nouveau conjugue de chlorambucil et d'un derive d'estradiol; methode de preparation, composition pharmaceutique a base de ce conjugue

Info

Publication number: CA2183005A1
Authority: CA; Canada
Prior art keywords: present; conjugate; cells; estradiol; substance
Prior art date: 1992-06-11
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.): Abandoned

Application number

CA002183005A

Other languages

English (en)

Inventor

Fumio Tamura

Tsuyoshi Saito

Satoshi Mitsuhashi

Tadahiro Matsudaira

Kiro Asano

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.)

Kureha Corp

Original Assignee

Kureha Corp

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.)

1992-06-11

Filing date

1993-05-27

Publication date

1993-12-12

1992-06-11 Priority claimed from JP4177363A external-priority patent/JP2520074B2/ja

1993-05-27 Application filed by Kureha Corp filed Critical Kureha Corp

1993-12-12 Publication of CA2183005A1 publication Critical patent/CA2183005A1/fr

Status Abandoned legal-status Critical Current

Links

229960004630 chlorambucil Drugs 0.000 title abstract description 26
VOXZDWNPVJITMN-ZBRFXRBCSA-N 17β-estradiol Chemical class OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 VOXZDWNPVJITMN-ZBRFXRBCSA-N 0.000 title abstract description 24
229960005309 estradiol Drugs 0.000 title abstract description 19
229930182833 estradiol Natural products 0.000 title abstract description 19
238000004519 manufacturing process Methods 0.000 title abstract description 5
239000008194 pharmaceutical composition Substances 0.000 title abstract description 5
125000000217 alkyl group Chemical group 0.000 claims abstract description 15
125000002252 acyl group Chemical group 0.000 claims abstract description 11
125000004423 acyloxy group Chemical group 0.000 claims abstract description 10
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 10
125000001295 dansyl group Chemical group [H]C1=C([H])C(N(C([H])([H])[H])C([H])([H])[H])=C2C([H])=C([H])C([H])=C(C2=C1[H])S(*)(=O)=O 0.000 claims abstract description 10
229910052736 halogen Inorganic materials 0.000 claims abstract description 10
150000003839 salts Chemical class 0.000 claims abstract description 10
125000003545 alkoxy group Chemical group 0.000 claims abstract description 5
125000005843 halogen group Chemical group 0.000 claims abstract 2
150000001875 compounds Chemical class 0.000 claims description 26
VOXZDWNPVJITMN-WKUFJEKOSA-N estradiol group Chemical group [C@@H]12CCC(O)[C@@]1(C)CC[C@@H]1C3=C(CC[C@@H]21)C=C(O)C=C3 VOXZDWNPVJITMN-WKUFJEKOSA-N 0.000 claims description 4
125000004430 oxygen atom Chemical group O* 0.000 claims 2
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 117
239000000126 substance Substances 0.000 description 84
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CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 39
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 38
238000006243 chemical reaction Methods 0.000 description 38
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238000012360 testing method Methods 0.000 description 35
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XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 26
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 26
239000000243 solution Substances 0.000 description 26
239000002904 solvent Substances 0.000 description 25
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
239000007924 injection Substances 0.000 description 24
238000002347 injection Methods 0.000 description 24
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 23
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 21
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238000004809 thin layer chromatography Methods 0.000 description 20
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 19
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 18
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 18
JCKYGMPEJWAADB-UHFFFAOYSA-N chlorambucil Chemical compound OC(=O)CCCC1=CC=C(N(CCCl)CCCl)C=C1 JCKYGMPEJWAADB-UHFFFAOYSA-N 0.000 description 18
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 17
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HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 17
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230000028327 secretion Effects 0.000 description 9
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CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 8
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239000002994 raw material Substances 0.000 description 8
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HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 7
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LSTRKXWIZZZYAS-UHFFFAOYSA-N 2-bromoacetyl bromide Chemical compound BrCC(Br)=O LSTRKXWIZZZYAS-UHFFFAOYSA-N 0.000 description 5
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XPDXVDYUQZHFPV-UHFFFAOYSA-N Dansyl Chloride Chemical group C1=CC=C2C(N(C)C)=CC=CC2=C1S(Cl)(=O)=O XPDXVDYUQZHFPV-UHFFFAOYSA-N 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
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NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 3
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BBEQQKBWUHCIOU-UHFFFAOYSA-N 5-(dimethylamino)-1-naphthalenesulfonic acid(dansyl acid) Chemical compound C1=CC=C2C(N(C)C)=CC=CC2=C1S(O)(=O)=O BBEQQKBWUHCIOU-UHFFFAOYSA-N 0.000 description 2
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210000003462 vein Anatomy 0.000 description 1

Landscapes

Steroid Compounds (AREA)

CA002183005A 1992-06-11 1993-05-27 Nouveau conjugue de chlorambucil et d'un derive d'estradiol; methode de preparation, composition pharmaceutique a base de ce conjugue Abandoned CA2183005A1 (fr)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
JP4177363A JP2520074B2 (ja)	1992-06-11	1992-06-11	新規なエストラジオ―ル誘導体−クロラムブチル結合体、その製造方法、及び医薬製剤
JP4-177363		1992-06-11
CA002097137A CA2097137A1 (fr)	1992-06-11	1993-05-27	Nouveau produit de conjugaison d'un derive de l'oestradiol et du chlorambucil, procede de preparation et composition pharmaceutique

Related Parent Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002097137A Division CA2097137A1 (fr)	1992-06-11	1993-05-27	Nouveau produit de conjugaison d'un derive de l'oestradiol et du chlorambucil, procede de preparation et composition pharmaceutique

Publications (1)

Publication Number	Publication Date
CA2183005A1 true CA2183005A1 (fr)	1993-12-12

Family

ID=25676224

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002183005A Abandoned CA2183005A1 (fr)	1992-06-11	1993-05-27	Nouveau conjugue de chlorambucil et d'un derive d'estradiol; methode de preparation, composition pharmaceutique a base de ce conjugue

Country Status (1)

Country	Link
CA (1)	CA2183005A1 (fr)

1993
- 1993-05-27 CA CA002183005A patent/CA2183005A1/fr not_active Abandoned

Publication	Publication Date	Title
US4055641A (en)	1977-10-25	Method of treating benign prostatic hypertrophy
CA2274779A1 (fr)	1998-06-25	Composes aminosterol-esters
JP2813610B2 (ja)	1998-10-22	胆汁酸誘導体、その製造方法およびそれを含有する医薬組成物
CZ113694A3 (en)	1994-11-16	Derivatives of bile acids process of their preparation and their use as medicaments
CZ113594A3 (en)	1994-12-15	Tetrazole derivatives of bile acids, process of their preparation and use of said compounds as medicaments
CZ230798A3 (cs)	1998-11-11	19-Nor-pregnenové deriváty, farmaceutický prostředek obsahující tyto sloučeniny a použití
CA2196694A1 (fr)	1996-02-22	Derives estra-1,3,5(10)-triene, leurs procedes de preparation et compositions pharmaceutiques les contenant
RU2159774C2 (ru)	2000-11-27	Производные сульфамата, способ их получения и фармацевтические составы
AU649180B2 (en)	1994-05-12	Novel estradiol derivative-chlorambucil conjugate, process for preparing the same, and pharmaceutical composition
JP2002518514A (ja)	2002-06-25	テストステロン誘導体
PT728140E (pt)	2002-02-28	Novos esteroides com grupos substituintes com propriedades de captura de radicais, processo para a sua preparacao e medicamentos que contem estes compostos
US4332797A (en)	1982-06-01	Chlorambucil derivatives
ES2255983T3 (es)	2006-07-16	16-hidroxiestratrienos como estrogenos eficaces selectivamente.
US4317818A (en)	1982-03-02	Method of treating prostatic carcinoma
FI57114B (fi)	1980-02-29	Foerfarande foer framstaellning av nya vid cancerterapi anvaendbara terapeutiskt vaerdefulla enolestrar av steroider
CA2171740C (fr)	2005-07-26	Derives de 1,3,5(10)-estratriene, actifs par voie orale
JP3377856B2 (ja)	2003-02-17	骨吸収抑制・骨形成促進化合物
CA2183005A1 (fr)	1993-12-12	Nouveau conjugue de chlorambucil et d'un derive d'estradiol; methode de preparation, composition pharmaceutique a base de ce conjugue
CA2022647A1 (fr)	1991-02-09	Esters d'acides organiques avec des alcools derives de 19-nor steroides et leurs sels, leur procede de preparation et les intermediaires de ce procede, leur application a titre demedicaments et les compositions les renfermant
US4054651A (en)	1977-10-18	Method of contraception
US4938897A (en)	1990-07-03	Chlorambucil derivatives and cell-discriminating agent containing the same
DE102004025966A1 (de)	2005-12-15	Estradiol-Prodrugs
AU601184B2 (en)	1990-09-06	Steroids useful as anti-cancer and anti-obesity agents
RU2099347C1 (ru)	1997-12-20	17 α АЦЕТОКСИ-3 β БУТАНОИЛОКСИ-6-МЕТИЛПРЕГНА-4,6-ДИЕН-20-ОН, ОБЛАДАЮЩИЙ ГЕСТАГЕННОЙ АКТИВНОСТЬЮ
RU2248358C2 (ru)	2005-03-20	3-метиленстероидные производные, фармацевтическая композиция, способ лечения

Legal Events

Date	Code	Title	Description
1996-08-09	EEER	Examination request
2001-05-28	FZDE	Discontinued
2023-05-26	FZDE	Discontinued	Effective date: 20010528