CH616671A5 - Process for the preparation of novel cyclic imides - Google Patents

Process for the preparation of novel cyclic imides Download PDF

Info

Publication number: CH616671A5
Authority: CH; Switzerland
Prior art keywords: general formula; phthalimido; compound; preparation; acid
Prior art date: 1974-12-20

Application number

CH1401675A

Other languages

German (de)

English (en)

Inventor

Ernst Frankus

Heinrich Mueckter

Original Assignee

Gruenenthal Chemie

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.)

1974-12-20

Filing date

1975-10-29

Publication date

1980-04-15

1975-10-29 Application filed by Gruenenthal Chemie filed Critical Gruenenthal Chemie

1980-04-15 Publication of CH616671A5 publication Critical patent/CH616671A5/de

Links

238000000034 method Methods 0.000 title claims description 8
238000002360 preparation method Methods 0.000 title claims description 6
-1 cyclic imides Chemical class 0.000 title claims description 5
150000001875 compounds Chemical class 0.000 claims description 28
238000006243 chemical reaction Methods 0.000 claims description 9
150000001412 amines Chemical class 0.000 claims description 7
150000003839 salts Chemical class 0.000 claims description 6
OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical compound [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 claims description 5
239000002253 acid Substances 0.000 claims description 4
239000000126 substance Substances 0.000 claims description 4
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
238000010438 heat treatment Methods 0.000 claims description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
AKTISSCUDMXOBQ-UHFFFAOYSA-N 3-(1,3-dioxoisoindol-2-yl)pentanedioic acid Chemical compound C1=CC=C2C(=O)N(C(CC(O)=O)CC(=O)O)C(=O)C2=C1 AKTISSCUDMXOBQ-UHFFFAOYSA-N 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
206010028980 Neoplasm Diseases 0.000 description 10
238000002844 melting Methods 0.000 description 10
230000008018 melting Effects 0.000 description 10
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
239000002904 solvent Substances 0.000 description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
241001465754 Metazoa Species 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
239000000203 mixture Substances 0.000 description 6
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
239000000243 solution Substances 0.000 description 5
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 4
JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 4
239000003814 drug Substances 0.000 description 4
238000001953 recrystallisation Methods 0.000 description 4
238000003756 stirring Methods 0.000 description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
241000700159 Rattus Species 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000003208 petroleum Substances 0.000 description 3
XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
CWDIBTDSBNWWNE-UHFFFAOYSA-N 2-(2,6-dioxooxan-4-yl)isoindole-1,3-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1C1CC(=O)OC(=O)C1 CWDIBTDSBNWWNE-UHFFFAOYSA-N 0.000 description 2
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 2
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
241000699666 Mus <mouse, genus> Species 0.000 description 2
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-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
239000004480 active ingredient Substances 0.000 description 2
FYXKZNLBZKRYSS-UHFFFAOYSA-N benzene-1,2-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=CC=C1C(Cl)=O FYXKZNLBZKRYSS-UHFFFAOYSA-N 0.000 description 2
230000037396 body weight Effects 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
238000001816 cooling Methods 0.000 description 2
238000004821 distillation Methods 0.000 description 2
229940079593 drug Drugs 0.000 description 2
230000000694 effects Effects 0.000 description 2
VRHAQNTWKSVEEC-UHFFFAOYSA-N ethyl 1,3-dioxoisoindole-2-carboxylate Chemical compound C1=CC=C2C(=O)N(C(=O)OCC)C(=O)C2=C1 VRHAQNTWKSVEEC-UHFFFAOYSA-N 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
BBJIPMIXTXKYLZ-UHFFFAOYSA-N isoglutamic acid Chemical compound OC(=O)CC(N)CC(O)=O BBJIPMIXTXKYLZ-UHFFFAOYSA-N 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
239000000047 product Substances 0.000 description 2
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
238000010992 reflux Methods 0.000 description 2
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
208000023275 Autoimmune disease Diseases 0.000 description 1
208000026310 Breast neoplasm Diseases 0.000 description 1
101100387923 Caenorhabditis elegans dos-1 gene Proteins 0.000 description 1
208000017701 Endocrine disease Diseases 0.000 description 1
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
241001481796 Rattus exulans Species 0.000 description 1
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
XYQRXRFVKUPBQN-UHFFFAOYSA-L Sodium carbonate decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].[O-]C([O-])=O XYQRXRFVKUPBQN-UHFFFAOYSA-L 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
229960000583 acetic acid Drugs 0.000 description 1
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
239000012346 acetyl chloride Substances 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
230000007059 acute toxicity Effects 0.000 description 1
231100000403 acute toxicity Toxicity 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
239000012670 alkaline solution Substances 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
230000000259 anti-tumor effect Effects 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
238000010533 azeotropic distillation Methods 0.000 description 1
HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 1
201000011510 cancer Diseases 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
238000005352 clarification Methods 0.000 description 1
239000003086 colorant Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
239000008298 dragée Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
238000001914 filtration Methods 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
239000008103 glucose Substances 0.000 description 1
229960001031 glucose Drugs 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
238000007912 intraperitoneal administration Methods 0.000 description 1
229960004903 invert sugar Drugs 0.000 description 1
238000002955 isolation Methods 0.000 description 1
239000000787 lecithin Substances 0.000 description 1
235000010445 lecithin Nutrition 0.000 description 1
229940067606 lecithin Drugs 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
238000005259 measurement Methods 0.000 description 1
UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 description 1
235000013336 milk Nutrition 0.000 description 1
239000008267 milk Substances 0.000 description 1
210000004080 milk Anatomy 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
239000003921 oil Substances 0.000 description 1
235000019198 oils Nutrition 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229940001593 sodium carbonate Drugs 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
229940018038 sodium carbonate decahydrate Drugs 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000013223 sprague-dawley female rat Methods 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
229960004793 sucrose Drugs 0.000 description 1
150000005846 sugar alcohols Polymers 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000012730 sustained-release form Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000006188 syrup Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
230000004614 tumor growth Effects 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
239000001993 wax Substances 0.000 description 1
238000005303 weighing Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/22—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/80—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D211/84—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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
- C07D211/86—Oxygen atoms
- C07D211/88—Oxygen atoms attached in positions 2 and 6, e.g. glutarimide
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/32—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Indole Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Hydrogenated Pyridines (AREA)

CH1401675A 1974-12-20 1975-10-29 Process for the preparation of novel cyclic imides CH616671A5 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE2460304A DE2460304C2 (de)	1974-12-20	1974-12-20	1-n-Propyl-4-phthalimido-piperidin-2,6-dion, Verfahren zu seiner Herstellung und dieses enthaltende Arzneimittel

Publications (1)

Publication Number	Publication Date
CH616671A5 true CH616671A5 (en)	1980-04-15

Family

ID=5933927

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
CH1401675A CH616671A5 (en)	1974-12-20	1975-10-29	Process for the preparation of novel cyclic imides
CH636979A CH616672A5 (en)	1974-12-20	1979-07-09	Process for the preparation of novel cyclic imides

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
CH636979A CH616672A5 (en)	1974-12-20	1979-07-09	Process for the preparation of novel cyclic imides

Country Status (14)

Country	Link
JP (1)	JPS5191268A (fr)
AT (1)	AT344696B (fr)
BE (1)	BE836698A (fr)
CA (1)	CA1058182A (fr)
CH (2)	CH616671A5 (fr)
DE (1)	DE2460304C2 (fr)
DK (1)	DK139386C (fr)
ES (1)	ES443648A1 (fr)
FR (1)	FR2294704A1 (fr)
GB (1)	GB1524237A (fr)
IE (1)	IE42363B1 (fr)
NL (1)	NL7514145A (fr)
SE (1)	SE419860B (fr)
ZA (1)	ZA756624B (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP2020506922A (ja)	2017-01-31	2020-03-05	アルビナス・オペレーションズ・インコーポレイテッドＡｒｖｉｎａｓＯｐｅｒａｔｉｏｎｓ，Ｉｎｃ．	セレブロンリガンド、およびセレブロンリガンドを含有する二官能性化合物
PE20221582A1 (es)	2019-12-19	2022-10-06	Arvinas Operations Inc	Compuestos y metodos para la degradacion dirigida de receptor de androgenos

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE1545707A1 (de) *	1965-05-08	1969-06-12	Gruenenthal Chemie	Verfahren zur Herstellung von Dikarbonsaeureimidderivaten
DE1545706A1 (de) *	1965-05-08	1969-10-09	Gruenenthal Chemie	Dicarbonsaeureimidderivate und Verfahren zu ihrer Herstellung
DE1670391A1 (de) *	1965-05-08	1970-11-05	Gruenenthal Chemie	Dikarbonsaeureimidderivate und Verfahren zu ihrer Herstellung
DE1545672B2 (de) *	1965-05-08	1974-11-07	Chemie Gruenenthal Gmbh, 5190 Stolberg	Dikarbonsäureimidderivate und Verfahren zu ihrer Herstellung
AT278739B (de) *	1966-11-08	1970-02-10	Kwizda Fa F Johann	Verfahren zur Herstellung von neuen Anhydriden und Imiden substituierter Dicarbonsäuren

1974
- 1974-12-20 DE DE2460304A patent/DE2460304C2/de not_active Expired
1975
- 1975-10-20 AT AT799575A patent/AT344696B/de not_active IP Right Cessation
- 1975-10-21 ZA ZA00756624A patent/ZA756624B/xx unknown
- 1975-10-29 CH CH1401675A patent/CH616671A5/de not_active IP Right Cessation
- 1975-10-30 SE SE7512191A patent/SE419860B/xx unknown
- 1975-12-01 IE IE2612/75A patent/IE42363B1/en unknown
- 1975-12-03 GB GB49626/75A patent/GB1524237A/en not_active Expired
- 1975-12-04 NL NL7514145A patent/NL7514145A/xx not_active Application Discontinuation
- 1975-12-08 FR FR7537471A patent/FR2294704A1/fr active Granted
- 1975-12-16 BE BE162793A patent/BE836698A/fr not_active IP Right Cessation
- 1975-12-17 CA CA241,947A patent/CA1058182A/fr not_active Expired
- 1975-12-18 ES ES443648A patent/ES443648A1/es not_active Expired
- 1975-12-19 JP JP50150719A patent/JPS5191268A/ja active Pending
- 1975-12-19 DK DK583475A patent/DK139386C/da active
1979
- 1979-07-09 CH CH636979A patent/CH616672A5/de not_active IP Right Cessation

Also Published As

Publication number	Publication date
IE42363L (en)	1976-06-20
BE836698A (fr)	1976-06-16
SE419860B (sv)	1981-08-31
DK583475A (da)	1976-06-21
NL7514145A (nl)	1976-06-22
DE2460304C2 (de)	1983-08-04
FR2294704A1 (fr)	1976-07-16
ZA756624B (en)	1976-09-29
ES443648A1 (es)	1977-05-01
GB1524237A (en)	1978-09-06
IE42363B1 (en)	1980-07-30
CH616672A5 (en)	1980-04-15
CA1058182A (fr)	1979-07-10
FR2294704B1 (fr)	1979-09-21
ATA799575A (de)	1977-12-15
DK139386C (da)	1979-07-23
JPS5191268A (fr)	1976-08-10
SE7512191L (sv)	1976-06-21
AT344696B (de)	1978-08-10
DK139386B (da)	1979-02-12
DE2460304A1 (de)	1976-07-01

Legal Events

Date	Code	Title	Description
1980-08-15	PFA	Name/firm changed	Owner name: GRUENENTHAL GMBH
1985-06-28	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
DE2345064C3 (de)	1979-10-25	4-Amino-2-<l,2r3,4-tetrahydroisochinolin-2 yl)-chinazolinderivate und diese enthaltende Arzneimittel
EP0142739B1 (fr)	1988-01-07	Dérivés d'acides aminés et leur préparation
DE2434911C2 (de)	1984-11-29	Phenyläthylamin-Derivate und pharmazeutische Zusammensetzungen
DE2904445A1 (de)	1979-08-16	Alkylendiaminderivate, ihre herstellung und pharmazeutische mittel
DE2504565A1 (de)	1975-08-14	Neue derivate von 1h-imidazo(4,5-c) pyridin-7-carboxylsaeuren und -saeureestern
WO1980000152A1 (fr)	1980-02-07	Derives d'un 3-aminopropoxy-aryle, leur preparation et utilisation
DE2751181A1 (de)	1978-05-24	Neue therapeutika auf piperidinbasis
DE2723051C3 (de)	1980-07-31	NKAcyO-p-amino-NMn-decyl- und n-tridecyl)-benzamide sowie diese enthaltende Arzneimittel
WO1979000426A1 (fr)	1979-07-12	Diamine cyclique n, n'-disubstituee et procede pour sa preparation
DE3642497A1 (de)	1988-06-23	Substituierte aminopropionsaeureamide, verfahren zu ihrer herstellung, diese enthaltende mittel und ihre verwendung sowie die bei der herstellung anfallenden neuen zwischenprodukte
DE2456098C3 (de)	1979-01-18	Xanthen- und Thioxanthen-Derivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
CH616671A5 (en)	1980-04-15	Process for the preparation of novel cyclic imides
DE2412388A1 (de)	1974-09-19	Dibenzothiophenderivate, verfahren zu deren herstellung und sie enthaltende arzneimittel
DE2735589A1 (de)	1979-02-15	1-phenyl-1-methoxy-2-amino-aethan- derivate und verfahren zu ihrer herstellung
DE2004301A1 (de)	1970-09-03	Phenylserinderivate
DE3245950A1 (de)	1983-07-07	Verfahren zur herstellung substituierter pyridine
DE1007335B (de)	1957-05-02	Verfahren zur Herstellung von neuen chlorierten Benzoesaeurealkaminestern
DE1768505B2 (de)	1973-10-11	Phenathylaminverbindungen und Ver fahren zu ihrer Herstellung
AT234102B (de)	1964-06-10	Verfahren zur Herstellung von neuen, in α-Stellung durch einen 1-Benzylindolyl-(3)-Rest substituierten niedrigen aliphatischen Säuren
DE1768787C3 (de)	1976-04-29	(o-Carboxy-phenyl)-acetamidine, Verfahren zu deren Herstellung und (o-CarboxyphenyO-acetamidine enthaltende Präparate
DE1493567C3 (de)	1976-05-13	Ester von alpha-Alkylthyroxinderivaten und Verfahren zu ihrer Herstellung
AT211001B (de)	1960-09-10	Verfahren zur Herstellung von neuen Scopin-äthern
EP0387677A2 (fr)	1990-09-19	Dérivés de l'acide thiénylacétique, procédé pour leur préparation, leur application ainsi que médicaments les contenant et leur préparation
DE2003840A1 (de)	1970-07-30	3-Phenyl-4-acyloxycarbostyrile,Verfahren zu ihrer Herstellung und ihre Verwendung in Arzneimitteln
DE2022790C3 (de)	1977-07-07	10-Methyl-5-[ (4-Methylpiperazino)-acetyl J-5,10dihydro-llH-dibenzo [b,e ] [1,4 ] diazepin-11-on, ein Verfahren zu dessen Herstellung sowie dieses enthaltende Arzneimittel