CA1058182A - Imides cycliques et procede pour leur fabrication - Google Patents

Imides cycliques et procede pour leur fabrication

Info

Publication number: CA1058182A
Authority: CA; Canada
Prior art keywords: propyl; reaction; compound; phthalimido; formula
Prior art date: 1974-12-20
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

CA241,947A

Other languages

English (en)

Other versions

CA241947S (en

Inventor

Ernst Frankus

Heinrich Muckter

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.)

Gruenenthal GmbH

Original Assignee

Gruenenthal GmbH

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

1975-12-17

Publication date

1979-07-10

1975-12-17 Application filed by Gruenenthal GmbH filed Critical Gruenenthal GmbH

1979-07-10 Application granted granted Critical

1979-07-10 Publication of CA1058182A publication Critical patent/CA1058182A/fr

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims description 10
238000004519 manufacturing process Methods 0.000 title claims description 7
-1 Cyclic imides Chemical class 0.000 title description 4
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims abstract description 30
JNFIIOZEHCYWJM-UHFFFAOYSA-N 2-(2,6-dioxo-1-propylpiperidin-4-yl)isoindole-1,3-dione Chemical compound CCCN1C(=O)CC(CC1=O)N1C(=O)C2=CC=CC=C2C1=O JNFIIOZEHCYWJM-UHFFFAOYSA-N 0.000 claims abstract 2
150000001875 compounds Chemical class 0.000 claims description 34
238000006243 chemical reaction Methods 0.000 claims description 17
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 claims description 5
239000003795 chemical substances by application Substances 0.000 claims description 5
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 4
238000010438 heat treatment Methods 0.000 claims description 4
150000003839 salts Chemical class 0.000 claims description 4
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 3
239000002253 acid Substances 0.000 claims description 3
JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 claims description 3
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 claims description 3
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 claims description 2
230000002378 acidificating effect Effects 0.000 claims description 2
238000009833 condensation Methods 0.000 claims description 2
230000005494 condensation Effects 0.000 claims description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 2
235000017557 sodium bicarbonate Nutrition 0.000 claims description 2
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 description 2
239000011230 binding agent Substances 0.000 claims 1
239000000126 substance Substances 0.000 claims 1
206010028980 Neoplasm Diseases 0.000 abstract description 13
230000002401 inhibitory effect Effects 0.000 abstract description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 7
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
241001465754 Metazoa Species 0.000 description 6
238000007363 ring formation reaction Methods 0.000 description 5
230000000694 effects Effects 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
239000002904 solvent Substances 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
229940086542 triethylamine Drugs 0.000 description 4
241000700159 Rattus Species 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
235000013305 food Nutrition 0.000 description 3
239000007858 starting material Substances 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-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
241000699670 Mus sp. Species 0.000 description 2
239000002671 adjuvant Substances 0.000 description 2
230000000259 anti-tumor effect Effects 0.000 description 2
238000010533 azeotropic distillation Methods 0.000 description 2
230000037396 body weight Effects 0.000 description 2
238000001816 cooling Methods 0.000 description 2
239000008298 dragée Substances 0.000 description 2
230000002349 favourable effect Effects 0.000 description 2
238000007912 intraperitoneal administration Methods 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
239000000203 mixture Substances 0.000 description 2
150000002989 phenols Chemical class 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
AOFUBOWZWQFQJU-SNOJBQEQSA-N (2r,3s,4s,5r)-2,5-bis(hydroxymethyl)oxolane-2,3,4-triol;(2s,3r,4s,5s,6r)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O.OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@@H]1O AOFUBOWZWQFQJU-SNOJBQEQSA-N 0.000 description 1
RFWFOJDAIRDAPK-VKHMYHEASA-N (3s)-3-aminooxane-2,6-dione Chemical compound N[C@H]1CCC(=O)OC1=O RFWFOJDAIRDAPK-VKHMYHEASA-N 0.000 description 1
RXNOYRCWKRFNIM-UHFFFAOYSA-N 2-carbonochloridoylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(Cl)=O RXNOYRCWKRFNIM-UHFFFAOYSA-N 0.000 description 1
RMUICKHCMKLZQP-UHFFFAOYSA-N 4-amino-1-propylpiperidine-2,6-dione Chemical compound CCCN1C(=O)CC(N)CC1=O RMUICKHCMKLZQP-UHFFFAOYSA-N 0.000 description 1
208000023275 Autoimmune disease Diseases 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 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
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 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products 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 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
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
125000001931 aliphatic group Chemical group 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 1
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
201000011510 cancer Diseases 0.000 description 1
235000013877 carbamide Nutrition 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
238000004040 coloring Methods 0.000 description 1
230000002301 combined effect Effects 0.000 description 1
239000013078 crystal Substances 0.000 description 1
229940043279 diisopropylamine Drugs 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
239000003814 drug Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
210000000750 endocrine system Anatomy 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
239000008103 glucose Substances 0.000 description 1
VANNPISTIUFMLH-UHFFFAOYSA-N glutaric anhydride Chemical compound O=C1CCCC(=O)O1 VANNPISTIUFMLH-UHFFFAOYSA-N 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
238000007327 hydrogenolysis reaction Methods 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
238000002955 isolation Methods 0.000 description 1
239000008101 lactose Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
239000000463 material Substances 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
239000008194 pharmaceutical composition Substances 0.000 description 1
239000006187 pill Substances 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
NJSJBTVAKUBCKG-UHFFFAOYSA-N propylazanide Chemical compound CCC[NH-] NJSJBTVAKUBCKG-UHFFFAOYSA-N 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000006798 ring closing metathesis reaction Methods 0.000 description 1
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
229940018038 sodium carbonate decahydrate Drugs 0.000 description 1
238000013223 sprague-dawley female rat Methods 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008107 starch Substances 0.000 description 1
150000005846 sugar alcohols Polymers 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
238000010998 test method Methods 0.000 description 1
150000003585 thioureas Chemical class 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
150000003672 ureas Chemical class 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1
235000019871 vegetable fat Nutrition 0.000 description 1
239000001993 wax 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)

CA241,947A 1974-12-20 1975-12-17 Imides cycliques et procede pour leur fabrication Expired CA1058182A (fr)

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
CA1058182A true CA1058182A (fr)	1979-07-10

Family

ID=5933927

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA241,947A Expired CA1058182A (fr)	1974-12-20	1975-12-17	Imides cycliques et procede pour leur fabrication

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
BR112019015484A2 (pt)	2017-01-31	2020-04-28	Arvinas Operations Inc	ligantes de cereblon e compostos bifuncionais compreendendo os mesmos
CA3165168A1 (fr)	2019-12-19	2021-06-24	Arvinas Operations, Inc.	Composes et methodes pour la degradation ciblee du recepteur des androgenes

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
DE1545672B2 (de) *	1965-05-08	1974-11-07	Chemie Gruenenthal Gmbh, 5190 Stolberg	Dikarbonsäureimidderivate und Verfahren zu ihrer Herstellung
DE1670391A1 (de) *	1965-05-08	1970-11-05	Gruenenthal Chemie	Dikarbonsaeureimidderivate 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
DK139386B (da)	1979-02-12
SE419860B (sv)	1981-08-31
NL7514145A (nl)	1976-06-22
ZA756624B (en)	1976-09-29
DK139386C (da)	1979-07-23
BE836698A (fr)	1976-06-16
AT344696B (de)	1978-08-10
JPS5191268A (fr)	1976-08-10
ES443648A1 (es)	1977-05-01
GB1524237A (en)	1978-09-06
SE7512191L (sv)	1976-06-21
ATA799575A (de)	1977-12-15
CH616671A5 (en)	1980-04-15
FR2294704B1 (fr)	1979-09-21
IE42363L (en)	1976-06-20
CH616672A5 (en)	1980-04-15
IE42363B1 (en)	1980-07-30
DE2460304A1 (de)	1976-07-01
DE2460304C2 (de)	1983-08-04
FR2294704A1 (fr)	1976-07-16
DK583475A (da)	1976-06-21

Publication	Publication Date	Title
CA1101430A (fr)	1981-05-19	Traduction non-disponible
SU812182A3 (ru)	1981-03-07	Способ получени 7-метокси-1- ОКСАдЕТиАцЕфАлОСпОРиНОВ или иХСОлЕй
FI58494C (fi)	1981-02-10	Menetelmä uusien terapeuttisesti käyttökelpoisten N-(1'-bentsyylipyrrolidin-2'-yylimetyyli) bentsamidien valmistamiseksi
JPS62129280A (ja)	1987-06-11	新規化合物、その製法及びそれを含む医薬組成物
IE60332B1 (en)	1994-06-29	N-(2'aminophenyl)-benzamide-derivatives, process for their preparation and their use in the control of neoplastic diseases
SU1402259A3 (ru)	1988-06-07	Способ получени замещенных 2-фенилгексагидро-1,2,4-триазин-3,5-дионов
CA1081241A (fr)	1980-07-08	Preparation d'acides phosphoneux
CA2109975A1 (fr)	1994-05-28	Derives de l'acide diaminobenzoique
US4324787A (en)	1982-04-13	2-Oxo-1-pyrrolidineacetic acid compounds and their medicinal use
EP0272478B1 (fr)	1993-01-20	Dérivés d'acide glycyrrhétinique et leur utilisation
CA1058182A (fr)	1979-07-10	Imides cycliques et procede pour leur fabrication
EP0314363A2 (fr)	1989-05-03	Agents anti-anxiété
EP0203435B1 (fr)	1990-08-29	Dérivés de pyridine et leur procédé de préparation
CA1116629A (fr)	1982-01-19	Procede d'obtention de derives d'acide troponyl-oxamique
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