JPH0240079B2 - - Google Patents

Info

Publication number: JPH0240079B2
Authority: JP; Japan
Prior art keywords: androstane; tumor; compounds; chloroethyl; tumors
Prior art date: 1984-06-27
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 - Lifetime

Application number

JP60500685A

Other languages

English (en)

Japanese (ja)

Other versions

JPS61502256A (ja

Inventor

Zoya Petorofuna Sofuiina

Reonido Fuedorobichi Rarionofu

Nina Domitoriefuna Ragoba

Garina Nikoraefuna Puratonoba

Irina Mihairofuna Barueba

Kira Nikoraefuna Kurudoyumoba

Erizabeta Nikora Shakodeinsukaya

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.)

FUSESO ONKOROGICHESUKI NAUCHINO TSUENTORU AKADEMII MEDEITSUINSUKI NAUKU SSSR

Harukofusukii Nauchino Isusuredo Inst Endokurinorogii I Himii Goorumonofu

Original Assignee

FUSESO ONKOROGICHESUKI NAUCHINO TSUENTORU AKADEMII MEDEITSUINSUKI NAUKU SSSR

Harukofusukii Nauchino Isusuredo Inst Endokurinorogii I Himii Goorumonofu

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.)

1984-06-27

Filing date

1984-06-27

Publication date

1990-09-10

1984-06-27 Application filed by FUSESO ONKOROGICHESUKI NAUCHINO TSUENTORU AKADEMII MEDEITSUINSUKI NAUKU SSSR, Harukofusukii Nauchino Isusuredo Inst Endokurinorogii I Himii Goorumonofu filed Critical FUSESO ONKOROGICHESUKI NAUCHINO TSUENTORU AKADEMII MEDEITSUINSUKI NAUKU SSSR

1986-10-09 Publication of JPS61502256A publication Critical patent/JPS61502256A/ja

1990-09-10 Publication of JPH0240079B2 publication Critical patent/JPH0240079B2/ja

Status Granted legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 description 30
206010028980 Neoplasm Diseases 0.000 description 19
230000000259 anti-tumor effect Effects 0.000 description 14
241001465754 Metazoa Species 0.000 description 10
206010061535 Ovarian neoplasm Diseases 0.000 description 10
-1 androstane steroid Chemical class 0.000 description 10
241000699670 Mus sp. Species 0.000 description 9
241000700159 Rattus Species 0.000 description 8
229940088597 hormone Drugs 0.000 description 8
239000005556 hormone Substances 0.000 description 8
UQFHJDVUQSAVOQ-UHFFFAOYSA-N (2-aminophenyl) acetate Chemical compound CC(=O)OC1=CC=CC=C1N UQFHJDVUQSAVOQ-UHFFFAOYSA-N 0.000 description 7
150000003431 steroids Chemical class 0.000 description 7
239000000824 cytostatic agent Substances 0.000 description 5
230000001085 cytostatic effect Effects 0.000 description 5
230000000694 effects Effects 0.000 description 5
230000003054 hormonal effect Effects 0.000 description 5
150000001441 androstanes Chemical class 0.000 description 4
239000000460 chlorine Substances 0.000 description 4
230000035755 proliferation Effects 0.000 description 4
230000002269 spontaneous effect Effects 0.000 description 4
208000024719 uterine cervix neoplasm Diseases 0.000 description 4
208000026310 Breast neoplasm Diseases 0.000 description 3
241000699666 Mus <mouse, genus> Species 0.000 description 3
239000002168 alkylating agent Substances 0.000 description 3
229940100198 alkylating agent Drugs 0.000 description 3
230000002152 alkylating effect Effects 0.000 description 3
FMGSKLZLMKYGDP-USOAJAOKSA-N dehydroepiandrosterone Chemical class C1[C@@H](O)CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CC=C21 FMGSKLZLMKYGDP-USOAJAOKSA-N 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
230000012010 growth Effects 0.000 description 3
231100000508 hormonal effect Toxicity 0.000 description 3
230000005764 inhibitory process Effects 0.000 description 3
229960002847 prasterone Drugs 0.000 description 3
238000011287 therapeutic dose Methods 0.000 description 3
231100000331 toxic Toxicity 0.000 description 3
230000002588 toxic effect Effects 0.000 description 3
230000004614 tumor growth Effects 0.000 description 3
VOXZDWNPVJITMN-ZBRFXRBCSA-N 17β-estradiol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 VOXZDWNPVJITMN-ZBRFXRBCSA-N 0.000 description 2
125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 2
QZLYKIGBANMMBK-UGCZWRCOSA-N 5α-Androstane Chemical compound C([C@@H]1CC2)CCC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CCC[C@@]2(C)CC1 QZLYKIGBANMMBK-UGCZWRCOSA-N 0.000 description 2
206010006187 Breast cancer Diseases 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
201000000274 Carcinosarcoma Diseases 0.000 description 2
FMGSKLZLMKYGDP-UHFFFAOYSA-N Dehydroepiandrosterone Natural products C1C(O)CCC2(C)C3CCC(C)(C(CC4)=O)C4C3CC=C21 FMGSKLZLMKYGDP-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
MUMGGOZAMZWBJJ-DYKIIFRCSA-N Testostosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 MUMGGOZAMZWBJJ-DYKIIFRCSA-N 0.000 description 2
230000001548 androgenic effect Effects 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
125000001309 chloro group Chemical group Cl* 0.000 description 2
230000001419 dependent effect Effects 0.000 description 2
238000011156 evaluation Methods 0.000 description 2
230000002401 inhibitory effect Effects 0.000 description 2
238000001228 spectrum Methods 0.000 description 2
231100000419 toxicity Toxicity 0.000 description 2
230000001988 toxicity Effects 0.000 description 2
NVKAWKQGWWIWPM-ABEVXSGRSA-N 17-β-hydroxy-5-α-Androstan-3-one Chemical compound C1C(=O)CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CC[C@H]21 NVKAWKQGWWIWPM-ABEVXSGRSA-N 0.000 description 1
UIHVAXRVVJJTHU-UHFFFAOYSA-N 2-[bis(2-chloroethyl)amino]acetic acid Chemical group OC(=O)CN(CCCl)CCCl UIHVAXRVVJJTHU-UHFFFAOYSA-N 0.000 description 1
ARSRBNBHOADGJU-UHFFFAOYSA-N 7,12-dimethyltetraphene Chemical compound C1=CC2=CC=CC=C2C2=C1C(C)=C(C=CC=C1)C1=C2C ARSRBNBHOADGJU-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
208000010507 Adenocarcinoma of Lung Diseases 0.000 description 1
FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
201000009030 Carcinoma Diseases 0.000 description 1
VFZRZRDOXPRTSC-UHFFFAOYSA-N DMBA Natural products COC1=CC(OC)=CC(C=O)=C1 VFZRZRDOXPRTSC-UHFFFAOYSA-N 0.000 description 1
208000007093 Leukemia L1210 Diseases 0.000 description 1
206010025327 Lymphopenia Diseases 0.000 description 1
BKAYIFDRRZZKNF-VIFPVBQESA-N N-acetylcarnosine Chemical compound CC(=O)NCCC(=O)N[C@H](C(O)=O)CC1=CN=CN1 BKAYIFDRRZZKNF-VIFPVBQESA-N 0.000 description 1
206010028851 Necrosis Diseases 0.000 description 1
206010029350 Neurotoxicity Diseases 0.000 description 1
BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
PDMMFKSKQVNJMI-BLQWBTBKSA-N Testosterone propionate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](OC(=O)CC)[C@@]1(C)CC2 PDMMFKSKQVNJMI-BLQWBTBKSA-N 0.000 description 1
201000009365 Thymic carcinoma Diseases 0.000 description 1
206010044221 Toxic encephalopathy Diseases 0.000 description 1
230000006978 adaptation Effects 0.000 description 1
125000006295 amino methylene group Chemical group [H]N(*)C([H])([H])* 0.000 description 1
230000001195 anabolic effect Effects 0.000 description 1
239000003098 androgen Substances 0.000 description 1
229960003473 androstanolone Drugs 0.000 description 1
230000003388 anti-hormonal effect Effects 0.000 description 1
230000031018 biological processes and functions Effects 0.000 description 1
230000037396 body weight Effects 0.000 description 1
RSIHSRDYCUFFLA-DYKIIFRCSA-N boldenone Chemical compound O=C1C=C[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 RSIHSRDYCUFFLA-DYKIIFRCSA-N 0.000 description 1
201000008274 breast adenocarcinoma Diseases 0.000 description 1
201000011510 cancer Diseases 0.000 description 1
230000000711 cancerogenic effect Effects 0.000 description 1
231100000357 carcinogen Toxicity 0.000 description 1
239000003183 carcinogenic agent Substances 0.000 description 1
230000010261 cell growth Effects 0.000 description 1
208000019065 cervical carcinoma Diseases 0.000 description 1
229940124558 contraceptive agent Drugs 0.000 description 1
239000003433 contraceptive agent Substances 0.000 description 1
RSIHSRDYCUFFLA-UHFFFAOYSA-N dehydrotestosterone Natural products O=C1C=CC2(C)C3CCC(C)(C(CC4)O)C4C3CCC2=C1 RSIHSRDYCUFFLA-UHFFFAOYSA-N 0.000 description 1
239000003814 drug Substances 0.000 description 1
230000001747 exhibiting effect Effects 0.000 description 1
239000012634 fragment Substances 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
239000011630 iodine Chemical group 0.000 description 1
229910052740 iodine Chemical group 0.000 description 1
210000003734 kidney Anatomy 0.000 description 1
231100001231 less toxic Toxicity 0.000 description 1
210000004185 liver Anatomy 0.000 description 1
230000007774 longterm Effects 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
201000005249 lung adenocarcinoma Diseases 0.000 description 1
230000000527 lymphocytic effect Effects 0.000 description 1
231100001023 lymphopenia Toxicity 0.000 description 1
231100000682 maximum tolerated dose Toxicity 0.000 description 1
230000017074 necrotic cell death Effects 0.000 description 1
230000007135 neurotoxicity Effects 0.000 description 1
231100000228 neurotoxicity Toxicity 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
230000002611 ovarian Effects 0.000 description 1
210000001672 ovary Anatomy 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
229910000162 sodium phosphate Inorganic materials 0.000 description 1
239000001488 sodium phosphate Substances 0.000 description 1
230000000638 stimulation Effects 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
229960003604 testosterone Drugs 0.000 description 1
229960001712 testosterone propionate Drugs 0.000 description 1
150000003515 testosterones Chemical class 0.000 description 1
210000000115 thoracic cavity Anatomy 0.000 description 1
208000008732 thymoma Diseases 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
- C07J41/0033—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
- C07J41/0038—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 with an androstane skeleton, including 18- or 19-substituted derivatives, 18-nor derivatives and also derivatives where position 17-beta is substituted by a carbon atom not directly bonded to a further carbon atom and not being part of an amide group
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Steroid Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

JP60500685A 1984-06-27 1984-06-27 アンドロスタン系ステロイド誘導体 Granted JPS61502256A (ja)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
PCT/SU1984/000033 WO1986000311A1 (en)	1984-06-27	1984-06-27	Derivatives of steroids of androstane series

Publications (2)

Publication Number	Publication Date
JPS61502256A JPS61502256A (ja)	1986-10-09
JPH0240079B2 true JPH0240079B2 (fi)	1990-09-10

Family

ID=21616852

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP60500685A Granted JPS61502256A (ja)	1984-06-27	1984-06-27	アンドロスタン系ステロイド誘導体

Country Status (7)

Country	Link
JP (1)	JPS61502256A (fi)
CH (1)	CH666276A5 (fi)
DE (2)	DE3490728T1 (fi)
FI (1)	FI84834C (fi)
GB (1)	GB2169900B (fi)
SE (1)	SE457535B (fi)
WO (1)	WO1986000311A1 (fi)

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1558472A (en) *	1976-01-22	1980-01-03	Leo Ab	17-esters of 17- hydroxy gestogens
JPS5810393B2 (ja) *	1978-08-14	1983-02-25	呉羽化学工業株式会社	新規なエストラジオ−ル結合体とその製造方法及び抗腫瘍剤

1984
- 1984-06-27 GB GB08602936A patent/GB2169900B/en not_active Expired
- 1984-06-27 DE DE19843490728 patent/DE3490728T1/de active Pending
- 1984-06-27 DE DE19843490728 patent/DE3490728C2/de not_active Expired
- 1984-06-27 WO PCT/SU1984/000033 patent/WO1986000311A1/ru active IP Right Grant
- 1984-06-27 JP JP60500685A patent/JPS61502256A/ja active Granted
- 1984-06-27 CH CH571/86A patent/CH666276A5/de not_active IP Right Cessation
1986
- 1986-02-24 SE SE8600828A patent/SE457535B/sv not_active IP Right Cessation
- 1986-02-25 FI FI860815A patent/FI84834C/fi not_active IP Right Cessation

Also Published As

Publication number	Publication date
FI860815A (fi)	1986-02-25
FI84834C (fi)	1992-01-27
WO1986000311A1 (en)	1986-01-16
FI860815A0 (fi)	1986-02-25
FI84834B (fi)	1991-10-15
SE457535B (sv)	1989-01-09
CH666276A5 (de)	1988-07-15
SE8600828L (sv)	1986-02-24
GB2169900B (en)	1988-02-17
DE3490728C2 (de)	1989-09-14
JPS61502256A (ja)	1986-10-09
DE3490728T1 (de)	1986-06-05
GB8602936D0 (en)	1986-03-12
SE8600828D0 (sv)	1986-02-24
GB2169900A (en)	1986-07-23

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DE3506785A1 (de)	1986-08-28	11ss-n,n-dimethylaminophenyl-estradiene, deren herstellung und diese enthaltende pharmazeutische praeparate
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SE442016B (sv)	1985-11-25	Klorambucilderivat, antitumormedel samt forfarande for framstellning av klorambucilderivat
AU598201B2 (en)	1990-06-21	Steroids useful as anti-cancer, anti-obesity, anti-hyperglycemic, anti-autoimmune and anti-hypercholesterolemic agents
HENDERSON et al.	1951	Methylandrostenediol
US3190880A (en)	1965-06-22	17-tetrahydropyranyl ethers of androstanes
US3432486A (en)	1969-03-11	Synthesis of furan compounds including pharmacologically active furyl steroids
HU198508B (en)	1989-10-30	Process for producing 17beta-/cyclopropyloxy/-androst-5-en-3beta-ol
FI57114B (fi)	1980-02-29	Foerfarande foer framstaellning av nya vid cancerterapi anvaendbara terapeutiskt vaerdefulla enolestrar av steroider
JPH0240079B2 (fi)	1990-09-10
US3164617A (en)	1965-01-05	17alpha-butadiynyl-17beta-hydroxy derivatives of perhydrocyclopentenophenanthrene and process for preparation of same
Giniyatullina et al.	2013	Synthesis of aminopropylamino derivatives of betulinic and oleanolic acids
HU204065B (en)	1991-11-28	Process for producing 10(2-propinyl)-19-norandrost-5-ene-3beta,17beta-diol and pharmaceutical compositins comprising such compound
US3509135A (en)	1970-04-28	3-oxygenated 4'-5 - dihydrospiro(estra-4,9-diene-17,2'(3'h)-furans) and congeners
US3239542A (en)	1966-03-08	19 nor-deta2-androstene-17beta-ol and the esters thereof
DK158741B (da)	1990-07-09	Analogifremgangsmaade til fremstilling af biskvaternaere ammoniumderivater af 2beta,16beta-dipiperidino-5alfa-androstaner
JPH10502088A (ja)	1998-02-24	ブレフェルジンａの新しい誘導体およびがん治療におけるそれらの有用性
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