DD158776A5 - Verfahren zur herstellung von di-oder triesubstituiertenxanthinen - Google Patents

Verfahren zur herstellung von di-oder triesubstituiertenxanthinen Download PDF

Info

Publication number: DD158776A5
Authority: DD; German Democratic Republic
Prior art keywords: deep; formula; compound; allyl; butyl
Prior art date: 1980-05-02

Application number

DD81229559A

Other languages

German (de)

English (en)

Inventor

Georges Philippossian

Marc Enslen

Original Assignee

Nestle Sa

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.)

1980-05-02

Filing date

1981-04-28

Publication date

1983-02-02

1981-04-28 Application filed by Nestle Sa filed Critical Nestle Sa

1983-02-02 Publication of DD158776A5 publication Critical patent/DD158776A5/de

Links

238000000034 method Methods 0.000 title claims abstract description 20
238000002360 preparation method Methods 0.000 title claims abstract description 9
229940065721 systemic for obstructive airway disease xanthines Drugs 0.000 title abstract description 14
150000003839 salts Chemical class 0.000 claims abstract description 11
125000003342 alkenyl group Chemical group 0.000 claims abstract description 10
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims abstract description 8
125000000217 alkyl group Chemical group 0.000 claims abstract description 8
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims abstract description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 3
150000001875 compounds Chemical class 0.000 claims description 47
101000588924 Anthopleura elegantissima Delta-actitoxin-Ael1a Proteins 0.000 claims description 7
239000002168 alkylating agent Substances 0.000 claims description 6
229940100198 alkylating agent Drugs 0.000 claims description 6
238000010438 heat treatment Methods 0.000 claims description 5
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
239000002253 acid Substances 0.000 claims description 4
150000001412 amines Chemical class 0.000 claims description 3
VFNGKCDDZUSWLR-UHFFFAOYSA-L disulfate(2-) Chemical compound [O-]S(=O)(=O)OS([O-])(=O)=O VFNGKCDDZUSWLR-UHFFFAOYSA-L 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
125000005843 halogen group Chemical group 0.000 claims 1
230000000694 effects Effects 0.000 abstract description 27
LRFVTYWOQMYALW-UHFFFAOYSA-N 9H-xanthine Chemical class O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 abstract description 26
208000019901 Anxiety disease Diseases 0.000 abstract description 7
230000000701 neuroleptic effect Effects 0.000 abstract description 5
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239000003814 drug Substances 0.000 abstract description 3
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239000000243 solution Substances 0.000 description 27
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230000033001 locomotion Effects 0.000 description 23
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 16
239000000203 mixture Substances 0.000 description 14
239000002244 precipitate Substances 0.000 description 14
238000006243 chemical reaction Methods 0.000 description 13
239000013078 crystal Substances 0.000 description 13
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IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
239000002904 solvent Substances 0.000 description 11
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 description 8
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239000000126 substance Substances 0.000 description 8
BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 7
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
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229940075420 xanthine Drugs 0.000 description 5
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
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LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 4
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239000000843 powder Substances 0.000 description 3
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
238000012216 screening Methods 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
239000011734 sodium Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
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LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 2
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
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CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
230000007059 acute toxicity Effects 0.000 description 2
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125000000896 monocarboxylic acid group Chemical group 0.000 description 2
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VWKHGJZYMUXTDT-UHFFFAOYSA-N 3-butyl-1,8-diethyl-7h-purine-2,6-dione Chemical compound O=C1N(CC)C(=O)N(CCCC)C2=C1NC(CC)=N2 VWKHGJZYMUXTDT-UHFFFAOYSA-N 0.000 description 1
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LZKYSPPBMXPEBI-UHFFFAOYSA-N 8-methyl-3-(2-methylpropyl)-1-prop-2-enyl-7h-purine-2,6-dione Chemical compound O=C1N(CC=C)C(=O)N(CC(C)C)C2=C1NC(C)=N2 LZKYSPPBMXPEBI-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
ZILBAMAGWHQFHV-UHFFFAOYSA-N CCC(C)N1C(=O)NC=2N=CNC=2C1=O Chemical compound CCC(C)N1C(=O)NC=2N=CNC=2C1=O ZILBAMAGWHQFHV-UHFFFAOYSA-N 0.000 description 1
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238000005684 Liebig rearrangement reaction Methods 0.000 description 1
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241000699670 Mus sp. Species 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
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240000006365 Vitis vinifera Species 0.000 description 1
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239000004480 active ingredient Substances 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
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235000013405 beer Nutrition 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
230000003182 bronchodilatating effect Effects 0.000 description 1
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QYJXDIUNDMRLAO-UHFFFAOYSA-N butyl 4-methylbenzenesulfonate Chemical compound CCCCOS(=O)(=O)C1=CC=C(C)C=C1 QYJXDIUNDMRLAO-UHFFFAOYSA-N 0.000 description 1
CNWSQCLBDWYLAN-UHFFFAOYSA-N butylurea Chemical compound CCCCNC(N)=O CNWSQCLBDWYLAN-UHFFFAOYSA-N 0.000 description 1
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210000003169 central nervous system Anatomy 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000012320 chlorinating reagent Substances 0.000 description 1
230000009194 climbing Effects 0.000 description 1
238000010835 comparative analysis Methods 0.000 description 1
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
239000002934 diuretic Substances 0.000 description 1
230000001882 diuretic effect Effects 0.000 description 1
IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
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239000000546 pharmaceutical excipient Substances 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
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
- C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
- C07D239/545—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other 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
- C07D239/553—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other 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 with halogen atoms or nitro radicals directly attached to ring carbon atoms, e.g. fluorouracil
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/10—Antioedematous agents; Diuretics
- 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
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
- C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
- C07D239/545—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other 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
- 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
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/60—Three or more oxygen or sulfur atoms
- C07D239/62—Barbituric acids
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/04—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms
- C07D473/06—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Engineering & Computer Science (AREA)
Pharmacology & Pharmacy (AREA)
Veterinary Medicine (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Pulmonology (AREA)
Immunology (AREA)
Diabetes (AREA)
Hematology (AREA)
Anesthesiology (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

DD81229559A 1980-05-02 1981-04-28 Verfahren zur herstellung von di-oder triesubstituiertenxanthinen DD158776A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH343180A CH643260A5 (fr)	1980-05-02	1980-05-02	1-allyl-3-butyl-8-methylxanthine, procede de preparation et utilisation dans un medicament.

Publications (1)

Publication Number	Publication Date
DD158776A5 true DD158776A5 (de)	1983-02-02

Family

ID=4255824

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD81229559A DD158776A5 (de)	1980-05-02	1981-04-28	Verfahren zur herstellung von di-oder triesubstituiertenxanthinen

Country Status (21)

Country	Link
US (2)	US4469698A (da)
EP (1)	EP0039780B1 (da)
JP (1)	JPS56169690A (da)
AU (1)	AU539258B2 (da)
CA (1)	CA1155841A (da)
CH (1)	CH643260A5 (da)
CS (1)	CS221829B2 (da)
DD (1)	DD158776A5 (da)
DE (1)	DE3169784D1 (da)
DK (1)	DK149856C (da)
ES (1)	ES8207532A1 (da)
FI (1)	FI68831C (da)
GB (1)	GB2075505B (da)
HK (1)	HK49985A (da)
HU (1)	HU185256B (da)
IL (1)	IL62641A (da)
MX (1)	MX5974E (da)
MY (1)	MY8500517A (da)
PH (2)	PH17137A (da)
PL (1)	PL135383B1 (da)
SG (1)	SG20884G (da)

Families Citing this family (18)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4772607A (en) *	1986-05-20	1988-09-20	Warner-Lambert Company	Dialkenyl derivatives of xanthine, pharmaceutical compositions and methods of use therefor
US4755517A (en) *	1986-07-31	1988-07-05	Warner-Lambert Company	Derivatives of xanthine, pharmaceutical compositions and methods of use therefor
US5338741A (en) *	1986-10-27	1994-08-16	Nestec S.A.	1-hydroxyalkylxanthines and medicaments containing them
US5298508A (en) *	1988-07-19	1994-03-29	The United States Of America As Represented By The Department Of Health And Human Services	Irreversible inhibitors of adenosine receptors
GB8826595D0 (en) *	1988-11-14	1988-12-21	Beecham Wuelfing Gmbh & Co Kg	Active compounds
EP0407651A3 (en) *	1989-07-10	1991-08-07	J. Uriach & Cia. S.A.	Use of 1,3-diisobutyl-8-methylxanthine as a bronchodilator and antiallergy agent
US5939419A (en) *	1993-02-26	1999-08-17	Schering-Plough Corporation	2-benzyl-polycyclic guanine derivatives and process for preparing them
GB9312853D0 (en) *	1993-06-22	1993-08-04	Euro Celtique Sa	Chemical compounds
US5591776A (en) *	1994-06-24	1997-01-07	Euro-Celtique, S.A.	Pheynl or benzyl-substituted rolipram-based compounds for and method of inhibiting phosphodiesterase IV
US5922751A (en) *	1994-06-24	1999-07-13	Euro-Celtique, S.A.	Aryl pyrazole compound for inhibiting phosphodiesterase IV and methods of using same
DE69531506T2 (de) *	1994-12-13	2004-06-24	Euroceltique S.A.	Arylthioxanthine
EP0799040B1 (en) *	1994-12-13	2003-08-20	Euroceltique S.A.	Trisubstituted thioxanthines
US6166041A (en) *	1995-10-11	2000-12-26	Euro-Celtique, S.A.	2-heteroaryl and 2-heterocyclic benzoxazoles as PDE IV inhibitors for the treatment of asthma
FR2741455B1 (fr) *	1995-11-21	1997-12-26	Alcatel Optronics	Procede de formation d'une nappe de fibres optiques inclinees a dioptres de couplage
US6075016A (en) *	1996-04-10	2000-06-13	Euro-Celtique S.A.	6,5-fused aromatic ring systems having enhanced phosphodiesterase IV inhibitory activity
US5864037A (en)	1996-06-06	1999-01-26	Euro-Celtique, S.A.	Methods for the synthesis of chemical compounds having PDE-IV inhibitory activity
DE10018834A1 (de) *	2000-04-15	2001-10-25	Lohmann Therapie Syst Lts	Transdermale oder transmucosale Darreichungsformen mit einer nicotinhaltigen Wirkstoffkombination zur Raucherentwöhnung
US9221821B2 (en) *	2012-06-05	2015-12-29	Forest Laboratories Holdings, Limited	Methods for the synthesis of 1,3-substituted aminouracils and other xanthine-related compounds

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB701242A (en) *	1950-11-28	1953-12-23	Searle & Co	Improvements in or relating to disubstituted 6-amino-1,2,3,4-tetrahydro-2,4-pyrimidinediones and methods of preparing the same
US2673848A (en) *	1951-12-29	1954-03-30	Searle & Co	3-alkenylxanthines and their lower 1-alkyl derivatives
GB759174A (en) *	1952-11-07	1956-10-17	Geigy Ag J R	Improvements in diuretic acting xanthine derivatives
GB766754A (en) *	1954-01-27	1957-01-23	Geigy Ag J R	New derivatives of 1.3-disubstituted and 1.3.8-trisubstituted xanthines and processes for their production
DE1091570B (de) *	1958-10-23	1960-10-27	Albert Ag Chem Werke	Verfahren zur Herstellung von in 8-Stellung substituierten 1, 3-Dialkylxanthinen
GB982079A (en) *	1962-05-01	1965-02-03	Dresden Arzneimittel	Process for the production of xanthine derivatives
US3740433A (en) *	1971-10-01	1973-06-19	Squibb & Sons Inc	Anti-anxiety composition and method of use
US4089959A (en) *	1976-03-31	1978-05-16	Cooper Laboratories, Inc.	Long-acting xanthine bronchodilators and antiallergy agents
CA1077932A (en) *	1976-03-31	1980-05-20	Berlex Laboratories, Inc.	Xanthine compounds and method of treating bronchospastic and allergic diseases
SE7810947L (sv) *	1978-10-20	1980-04-21	Draco Ab	3-alkylxanthines
CH654008A5 (fr) *	1979-05-22	1986-01-31	Nestle Sa	Procede de preparation de 1,3,7-trialkylxanthines.

1980
- 1980-05-02 CH CH343180A patent/CH643260A5/fr not_active IP Right Cessation
1981
- 1981-04-06 DE DE8181102573T patent/DE3169784D1/de not_active Expired
- 1981-04-06 EP EP81102573A patent/EP0039780B1/fr not_active Expired
- 1981-04-07 FI FI811067A patent/FI68831C/fi not_active IP Right Cessation
- 1981-04-08 DK DK158481A patent/DK149856C/da not_active IP Right Cessation
- 1981-04-14 IL IL62641A patent/IL62641A/xx not_active IP Right Cessation
- 1981-04-15 CA CA000375586A patent/CA1155841A/en not_active Expired
- 1981-04-16 AU AU69617/81A patent/AU539258B2/en not_active Ceased
- 1981-04-27 PH PH25561A patent/PH17137A/en unknown
- 1981-04-28 DD DD81229559A patent/DD158776A5/de not_active IP Right Cessation
- 1981-04-30 PL PL1981230936A patent/PL135383B1/pl unknown
- 1981-04-30 MX MX819429U patent/MX5974E/es unknown
- 1981-04-30 CS CS813240A patent/CS221829B2/cs unknown
- 1981-04-30 HU HU811143A patent/HU185256B/hu not_active IP Right Cessation
- 1981-04-30 ES ES502414A patent/ES8207532A1/es not_active Expired
- 1981-04-30 GB GB8113418A patent/GB2075505B/en not_active Expired
- 1981-05-01 JP JP6676681A patent/JPS56169690A/ja active Pending
1982
- 1982-05-25 PH PH27345A patent/PH17660A/en unknown
1983
- 1983-02-28 US US06/470,301 patent/US4469698A/en not_active Expired - Fee Related
1984
- 1984-03-06 SG SG208/84A patent/SG20884G/en unknown
- 1984-06-08 US US06/618,909 patent/US4581451A/en not_active Expired - Fee Related
1985
- 1985-06-27 HK HK499/85A patent/HK49985A/xx unknown
- 1985-12-30 MY MY517/85A patent/MY8500517A/xx unknown

Also Published As

Publication number	Publication date
IL62641A (en)	1985-01-31
SG20884G (en)	1985-01-04
PL230936A1 (da)	1982-06-07
PL135383B1 (en)	1985-10-31
DK149856C (da)	1987-05-25
EP0039780A1 (fr)	1981-11-18
US4581451A (en)	1986-04-08
GB2075505A (en)	1981-11-18
CH643260A5 (fr)	1984-05-30
AU539258B2 (en)	1984-09-20
AU6961781A (en)	1981-11-05
DK158481A (da)	1981-11-03
IL62641A0 (en)	1981-06-29
FI68831B (fi)	1985-07-31
EP0039780B1 (fr)	1985-04-10
PH17137A (en)	1984-06-04
JPS56169690A (en)	1981-12-26
CA1155841A (en)	1983-10-25
CS221829B2 (en)	1983-04-29
MY8500517A (en)	1985-12-31
FI811067L (fi)	1981-11-03
HK49985A (en)	1985-07-05
ES502414A0 (es)	1982-10-01
ES8207532A1 (es)	1982-10-01
DK149856B (da)	1986-10-13
GB2075505B (en)	1984-01-11
HU185256B (en)	1984-12-28
FI68831C (fi)	1985-11-11
DE3169784D1 (en)	1985-05-15
PH17660A (en)	1984-10-25
US4469698A (en)	1984-09-04
MX5974E (es)	1984-09-11

Legal Events

Date	Code	Title	Description
1996-05-23	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
DD158776A5 (de)	1983-02-02	Verfahren zur herstellung von di-oder triesubstituiertenxanthinen
DE3011490C2 (da)	1988-12-22
DE69005248T2 (de)	1994-04-14	2-Aminopyrimidin-3-oxid-Derivate enthaltende Zusammensetzungen zur Verwendung zum Vermindern des Haarausfalles und zum Induzieren und Stimulieren des Haarwuchses und neue von 2-Aminopyrimidin-3-oxid abgeleitete Verbindungen.
DE2264163C2 (de)	1983-09-15	Substituierte 6,7-Dihydro-1-oxo-1H,5H-benzo[ij]chinolizin-2-carbonsäuren
DE2305575C2 (da)	1989-01-12
DD216934A5 (de)	1985-01-02	Verfahren zur herstellung neuer derivate von xanthinen
DD139855A5 (de)	1980-01-23	Verfahren zur herstellung von xanthinderivaten
DE2713389C2 (da)	1992-03-19
EP0130461A2 (de)	1985-01-09	Neue Imidazole, ihre Herstellung und diese Verbindungen enthaltende Arzneimittel
DE60004671T2 (de)	2004-07-29	Neue piperazinylalkylthiopyrimidine derivate, diese enthaltende pharmazeutische zusammenstellungen und verfahren zu deren herstellung
DE1946315C2 (de)	1985-05-15	4,5-Dihydro-5-oxo-s-triazolo-[1,5-a]-pyrimidin-Derivate, Verfahren zu ihrer Herstellung und sie enthaltende pharmazeutische Zusammensetzungen
DE2424334A1 (de)	1974-12-19	Verfahren zur herstellung neuer heterocyclischer verbindungen
DD216014A5 (de)	1984-11-28	Verfahren zur herstellung von verbindungen mit einem heterocyclischen distickstoffkern
DD236928A5 (de)	1986-06-25	Verfahren zur herstellung neuer 1,2,4-triazolo-carbamate
DE1670305C3 (de)	1982-03-25	5-Phenyl-2,4-dioxo-1,2,3,4-tetrahydro-3H-1,5-benzodiazepine und Verfahren zu ihrer Herstellung
DE2804949A1 (de)	1978-08-10	Substituierte tetrazolverbindungen
DE2052719A1 (de)	1971-09-16	Verfahren zur Herstellung von neuen 5 Nitrofuryldenvaten
DE3326724A1 (de)	1985-02-07	In 1-stellung substituierte 4-hydroxymethyl-pyrrolidinone, verfahren zu ihrer herstellung, pharmazeutische zusammensetzungen und zwischenprodukte
DE2038035A1 (de)	1972-02-03	2-Amino-pyrido eckige Klammer auf 2,3-d eckige Klammer zu pyrimidin-4(3H)on-Derivate
DE1695974A1 (de)	1971-05-19	Derivate des Pyrimidins
DE3807084A1 (de)	1989-09-14	Neue benzimidazo(1,2-c)chinazoline, ihre herstellung und verwendung
DD220780A5 (de)	1985-04-10	Verfahren zur herstellung von 5-subst.-(1,2,4) triazolo (1,5-c) pryimidin-2-aminen
DE4325254A1 (de)	1994-02-17	Unsymmetrisch substituierte Xanthine
DE2024049C3 (de)	1978-07-20	a-(3,4-Dihydroxyphenyl)-a- (2-piperidinyl)methanol
DE2253914A1 (de)	1973-05-10	Neue chromonderivate und verfahren zu ihrer herstellung