CN1013196B - 苯甲酰脲类化合物的制备方法 - Google Patents

苯甲酰脲类化合物的制备方法

Info

Publication number: CN1013196B
Authority: CN; China
Prior art keywords: formula; compound; small white; white mouse; gram
Prior art date: 1985-02-20
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

CN86101087A

Other languages

English (en)

Chinese (zh)

Other versions

CN86101087A (zh

Inventor

芳贺隆弘

山田修逸

杉秀男

小柳徹

近藤伸夫

渡边正弘

横山和正

中岛常隆

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.)

Ishihara Sangyo Kaisha Ltd

Original Assignee

Ishihara Sangyo Kaisha 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.)

1985-02-20

Filing date

1986-02-19

Publication date

1991-07-17

1985-02-20 Priority claimed from JP60032365A external-priority patent/JPS61191623A/ja

1985-03-08 Priority claimed from JP60044737A external-priority patent/JPS61205257A/ja

1986-02-19 Application filed by Ishihara Sangyo Kaisha Ltd filed Critical Ishihara Sangyo Kaisha Ltd

1987-02-25 Publication of CN86101087A publication Critical patent/CN86101087A/zh

1991-07-17 Publication of CN1013196B publication Critical patent/CN1013196B/zh

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 18
HRYILSDLIGTCOP-UHFFFAOYSA-N N-benzoylurea Chemical class NC(=O)NC(=O)C1=CC=CC=C1 HRYILSDLIGTCOP-UHFFFAOYSA-N 0.000 title claims description 4
230000008569 process Effects 0.000 title description 2
238000002360 preparation method Methods 0.000 claims abstract description 24
229910052801 chlorine Inorganic materials 0.000 claims abstract description 8
125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 8
150000001875 compounds Chemical class 0.000 claims description 51
238000006243 chemical reaction Methods 0.000 claims description 20
125000005843 halogen group Chemical group 0.000 claims description 12
125000001246 bromo group Chemical group Br* 0.000 claims description 6
239000003960 organic solvent Substances 0.000 claims description 6
IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 5
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
239000000126 substance Substances 0.000 claims description 2
150000003230 pyrimidines Chemical class 0.000 claims 3
238000010992 reflux Methods 0.000 claims 2
150000007529 inorganic bases Chemical class 0.000 claims 1
AJTDZZVWLFAGOY-UHFFFAOYSA-N n-[(3-chloro-4-hydroxyphenyl)carbamoyl]-2-nitrobenzamide Chemical group C1=C(Cl)C(O)=CC=C1NC(=O)NC(=O)C1=CC=CC=C1[N+]([O-])=O AJTDZZVWLFAGOY-UHFFFAOYSA-N 0.000 claims 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
-1 benzoyl urea compound Chemical class 0.000 abstract description 20
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
241000699666 Mus <mouse, genus> Species 0.000 description 38
239000003814 drug Substances 0.000 description 30
230000004083 survival effect Effects 0.000 description 25
238000011081 inoculation Methods 0.000 description 24
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 20
238000012360 testing method Methods 0.000 description 20
230000000259 anti-tumor effect Effects 0.000 description 18
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OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
238000007912 intraperitoneal administration Methods 0.000 description 14
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HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
238000002425 crystallisation Methods 0.000 description 8
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230000014509 gene expression Effects 0.000 description 8
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125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 6
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PNPCRKVUWYDDST-UHFFFAOYSA-N 3-chloroaniline Chemical compound NC1=CC=CC(Cl)=C1 PNPCRKVUWYDDST-UHFFFAOYSA-N 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
239000003292 glue Substances 0.000 description 4
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125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
238000005406 washing Methods 0.000 description 4
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CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
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VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
239000013543 active substance Substances 0.000 description 3
230000007059 acute toxicity Effects 0.000 description 3
231100000403 acute toxicity Toxicity 0.000 description 3
229940087168 alpha tocopherol Drugs 0.000 description 3
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239000007788 liquid Substances 0.000 description 3
239000000463 material Substances 0.000 description 3
150000003904 phospholipids Chemical class 0.000 description 3
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 3
235000015320 potassium carbonate Nutrition 0.000 description 3
239000004576 sand Substances 0.000 description 3
235000002639 sodium chloride Nutrition 0.000 description 3
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ZEMPKEQAKRGZGQ-AAKVHIHISA-N 2,3-bis[[(z)-12-hydroxyoctadec-9-enoyl]oxy]propyl (z)-12-hydroxyoctadec-9-enoate Chemical compound CCCCCCC(O)C\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CC(O)CCCCCC)COC(=O)CCCCCCC\C=C/CC(O)CCCCCC ZEMPKEQAKRGZGQ-AAKVHIHISA-N 0.000 description 2
ZYZQSCWSPFLAFM-UHFFFAOYSA-N 4-amino-2-chlorophenol Chemical class NC1=CC=C(O)C(Cl)=C1 ZYZQSCWSPFLAFM-UHFFFAOYSA-N 0.000 description 2
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
208000001382 Experimental Melanoma Diseases 0.000 description 2
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
230000000118 anti-neoplastic effect Effects 0.000 description 2
239000002246 antineoplastic agent Substances 0.000 description 2
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238000005119 centrifugation Methods 0.000 description 2
230000008859 change Effects 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
239000013530 defoamer Substances 0.000 description 2
229910001873 dinitrogen Inorganic materials 0.000 description 2
238000000605 extraction Methods 0.000 description 2
235000013305 food Nutrition 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
210000000936 intestine Anatomy 0.000 description 2
229940043265 methyl isobutyl ketone Drugs 0.000 description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
208000011932 ovarian sarcoma Diseases 0.000 description 2
229920001451 polypropylene glycol Polymers 0.000 description 2
239000000843 powder Substances 0.000 description 2
238000010298 pulverizing process Methods 0.000 description 2
238000000746 purification Methods 0.000 description 2
239000006215 rectal suppository Substances 0.000 description 2
229940100618 rectal suppository Drugs 0.000 description 2
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238000010898 silica gel chromatography Methods 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
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239000000829 suppository Substances 0.000 description 2
238000002525 ultrasonication Methods 0.000 description 2
210000003462 vein Anatomy 0.000 description 2
JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
UTINWYDPJFLMPG-UHFFFAOYSA-N (3-chloro-4-hydroxyphenyl)urea Chemical compound NC(=O)NC1=CC=C(O)C(Cl)=C1 UTINWYDPJFLMPG-UHFFFAOYSA-N 0.000 description 1
JLPULHDHAOZNQI-ZTIMHPMXSA-N 1-hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC JLPULHDHAOZNQI-ZTIMHPMXSA-N 0.000 description 1
FDCJDKXCCYFOCV-UHFFFAOYSA-N 1-hexadecoxyhexadecane Chemical compound CCCCCCCCCCCCCCCCOCCCCCCCCCCCCCCCC FDCJDKXCCYFOCV-UHFFFAOYSA-N 0.000 description 1
CEJAHXLRNZJPQH-UHFFFAOYSA-N 2,5-dichloropyrimidine Chemical compound ClC1=CN=C(Cl)N=C1 CEJAHXLRNZJPQH-UHFFFAOYSA-N 0.000 description 1
ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 description 1
KLGQWSOYKYFBTR-UHFFFAOYSA-N 2-nitrobenzamide Chemical compound NC(=O)C1=CC=CC=C1[N+]([O-])=O KLGQWSOYKYFBTR-UHFFFAOYSA-N 0.000 description 1
QBWKPGNFQQJGFY-QLFBSQMISA-N 3-[(1r)-1-[(2r,6s)-2,6-dimethylmorpholin-4-yl]ethyl]-n-[6-methyl-3-(1h-pyrazol-4-yl)imidazo[1,2-a]pyrazin-8-yl]-1,2-thiazol-5-amine Chemical compound N1([C@H](C)C2=NSC(NC=3C4=NC=C(N4C=C(C)N=3)C3=CNN=C3)=C2)C[C@H](C)O[C@H](C)C1 QBWKPGNFQQJGFY-QLFBSQMISA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
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241000894006 Bacteria Species 0.000 description 1
XEFRGMFWMHZZTG-UHFFFAOYSA-N CCCC(C=CC=C1)=C1OOP(O)(O)=O Chemical compound CCCC(C=CC=C1)=C1OOP(O)(O)=O XEFRGMFWMHZZTG-UHFFFAOYSA-N 0.000 description 1
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
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241000699670 Mus sp. Species 0.000 description 1
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125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000008280 blood Substances 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
230000037396 body weight Effects 0.000 description 1
239000002775 capsule Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
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238000006482 condensation reaction Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
230000006837 decompression Effects 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
239000004205 dimethyl polysiloxane Substances 0.000 description 1
235000013870 dimethyl polysiloxane Nutrition 0.000 description 1
KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
238000003810 ethyl acetate extraction Methods 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
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238000009472 formulation Methods 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
239000008187 granular material Substances 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
239000003701 inert diluent Substances 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
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YFQGSWCVQNRGQX-UHFFFAOYSA-N n-carbamoyl-2-nitrobenzamide Chemical compound NC(=O)NC(=O)C1=CC=CC=C1[N+]([O-])=O YFQGSWCVQNRGQX-UHFFFAOYSA-N 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
239000001814 pectin Substances 0.000 description 1
235000010987 pectin Nutrition 0.000 description 1
229920001277 pectin Polymers 0.000 description 1
DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical class O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
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UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/34—One oxygen atom

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Medicinal Preparation (AREA)

CN86101087A 1985-02-20 1986-02-19 苯甲酰脲类化合物的制备方法 Expired CN1013196B (zh)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
JP60032365A JPS61191623A (ja)	1985-02-20	1985-02-20	易吸収性医薬組成物
JP32365/85		1985-02-20
JP44737/85		1985-03-08
JP60044737A JPS61205257A (ja)	1985-03-08	1985-03-08	ベンゾイルウレア系化合物、その製法及びそれを含有する抗ガン剤

Publications (2)

Publication Number	Publication Date
CN86101087A CN86101087A (zh)	1987-02-25
CN1013196B true CN1013196B (zh)	1991-07-17

Family

ID=26370920

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CN86101087A Expired CN1013196B (zh)	1985-02-20	1986-02-19	苯甲酰脲类化合物的制备方法

Country Status (7)

Country	Link
KR (1)	KR930004676B1 (es)
CN (1)	CN1013196B (es)
AR (1)	AR240557A1 (es)
DE (2)	DE3667055D1 (es)
DK (1)	DK163124C (es)
ES (1)	ES8707506A1 (es)
NZ (1)	NZ214953A (es)

1986
- 1986-01-28 NZ NZ214953A patent/NZ214953A/xx unknown
- 1986-02-17 AR AR30315286A patent/AR240557A1/es active
- 1986-02-18 DE DE8686102063T patent/DE3667055D1/de not_active Expired
- 1986-02-19 ES ES552191A patent/ES8707506A1/es not_active Expired
- 1986-02-19 KR KR1019860001154A patent/KR930004676B1/ko not_active Expired - Fee Related
- 1986-02-19 CN CN86101087A patent/CN1013196B/zh not_active Expired
- 1986-02-20 DE DE8686102217T patent/DE3686177T2/de not_active Expired - Fee Related
- 1986-02-20 DK DK080286A patent/DK163124C/da not_active IP Right Cessation

Also Published As

Publication number	Publication date
ES8707506A1 (es)	1987-08-01
DE3686177T2 (de)	1993-03-18
KR860006447A (ko)	1986-09-11
DE3667055D1 (en)	1989-12-28
DK163124C (da)	1992-06-09
DE3686177D1 (de)	1992-09-03
DK163124B (da)	1992-01-20
KR930004676B1 (ko)	1993-06-03
ES552191A0 (es)	1987-08-01
NZ214953A (en)	1988-08-30
CN86101087A (zh)	1987-02-25
DK80286A (da)	1986-08-21
DK80286D0 (da)	1986-02-20
AR240557A1 (es)	1990-05-31

Legal Events

Date	Code	Title
1987-02-25	C06	Publication
1987-02-25	PB01	Publication
1988-03-09	C10	Entry into substantive examination
1988-03-09	SE01	Entry into force of request for substantive examination
1991-07-17	C13	Decision
1991-07-17	GR02	Examined patent application
1992-04-08	C14	Grant of patent or utility model
1992-04-08	GR01	Patent grant
1999-04-14	C19	Lapse of patent right due to non-payment of the annual fee
1999-04-14	CF01	Termination of patent right due to non-payment of annual fee

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