PT99062A - Processo para a preparacao de derivados de xantina - Google Patents

Processo para a preparacao de derivados de xantina Download PDF

Info

Publication number: PT99062A
Authority: PT; Portugal
Prior art keywords: cyclopropylmethyl; group; compound; xanthine; formula
Prior art date: 1990-09-26

Application number

PT99062A

Other languages

English (en)

Portuguese (pt)

Inventor

Derek Richard Buckle

David Glynn Smith

Ashley Edward Fenwick

Original Assignee

Beecham Group Plc

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.)

1990-09-26

Filing date

1991-09-25

Publication date

1992-08-31

1991-09-25 Application filed by Beecham Group Plc filed Critical Beecham Group Plc

1992-08-31 Publication of PT99062A publication Critical patent/PT99062A/pt

Links

238000000034 method Methods 0.000 title claims description 42
230000008569 process Effects 0.000 title claims description 22
238000002360 preparation method Methods 0.000 title claims description 15
150000001875 compounds Chemical class 0.000 claims description 118
150000003839 salts Chemical class 0.000 claims description 36
-1 heterocyclic group unsaturated fatty acid Chemical class 0.000 claims description 34
125000000217 alkyl group Chemical group 0.000 claims description 24
125000005843 halogen group Chemical group 0.000 claims description 24
125000000623 heterocyclic group Chemical group 0.000 claims description 24
238000006243 chemical reaction Methods 0.000 claims description 23
238000011282 treatment Methods 0.000 claims description 22
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 21
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 20
239000012453 solvate Substances 0.000 claims description 16
125000003710 aryl alkyl group Chemical group 0.000 claims description 15
125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 12
229910052739 hydrogen Inorganic materials 0.000 claims description 12
239000001257 hydrogen Substances 0.000 claims description 12
239000003814 drug Substances 0.000 claims description 11
125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims description 9
125000003545 alkoxy group Chemical group 0.000 claims description 9
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
RVZKSGMZJHMLJA-UHFFFAOYSA-N 8-chloro-1,3-bis(cyclopropylmethyl)-7-[(4-methoxyphenyl)methyl]purine-2,6-dione Chemical compound C1=CC(OC)=CC=C1CN1C(C(=O)N(CC2CC2)C(=O)N2CC3CC3)=C2N=C1Cl RVZKSGMZJHMLJA-UHFFFAOYSA-N 0.000 claims description 7
229910052757 nitrogen Inorganic materials 0.000 claims description 7
238000011321 prophylaxis Methods 0.000 claims description 7
208000010668 atopic eczema Diseases 0.000 claims description 6
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
239000003795 chemical substances by application Substances 0.000 claims description 6
125000005647 linker group Chemical group 0.000 claims description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 5
210000003979 eosinophil Anatomy 0.000 claims description 5
XDMFBNUSAATXBH-UHFFFAOYSA-N 8-amino-1,3-bis(cyclopropylmethyl)-7-[(2-nitrophenyl)methyl]purine-2,6-dione Chemical compound O=C1N(CC2CC2)C(=O)C=2N(CC=3C(=CC=CC=3)[N+]([O-])=O)C(N)=NC=2N1CC1CC1 XDMFBNUSAATXBH-UHFFFAOYSA-N 0.000 claims description 4
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239000008194 pharmaceutical composition Substances 0.000 claims description 4
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HUNXERUOBXQHAF-UHFFFAOYSA-N 1,3-bis(cyclopropylmethyl)-7-[(4-methoxyphenyl)methyl]-8-(pyridin-4-ylamino)purine-2,6-dione Chemical compound C1=CC(OC)=CC=C1CN1C(C(=O)N(CC2CC2)C(=O)N2CC3CC3)=C2N=C1NC1=CC=NC=C1 HUNXERUOBXQHAF-UHFFFAOYSA-N 0.000 claims description 3
ZXKJIWBPGNRXKR-BTJKTKAUSA-N 1,3-bis(cyclopropylmethyl)-7-[(4-methoxyphenyl)methyl]-8-piperidin-4-yloxypurine-2,6-dione;(z)-but-2-enedioic acid Chemical compound OC(=O)\C=C/C(O)=O.C1=CC(OC)=CC=C1CN1C(C(=O)N(CC2CC2)C(=O)N2CC3CC3)=C2N=C1OC1CCNCC1 ZXKJIWBPGNRXKR-BTJKTKAUSA-N 0.000 claims description 3
XUIIQCRDOFWKFE-UHFFFAOYSA-N 1,3-bis(cyclopropylmethyl)-7-[(4-methoxyphenyl)methyl]-9h-purine-2,6,8-trione Chemical compound C1=CC(OC)=CC=C1CN1C(=O)NC2=C1C(=O)N(CC1CC1)C(=O)N2CC1CC1 XUIIQCRDOFWKFE-UHFFFAOYSA-N 0.000 claims description 3
MOWDTMLRNMSYSS-UHFFFAOYSA-N 1,3-bis(cyclopropylmethyl)-8-ethoxy-7-[(4-methoxyphenyl)methyl]purine-2,6-dione Chemical compound O=C1N(CC2CC2)C(=O)C=2N(CC=3C=CC(OC)=CC=3)C(OCC)=NC=2N1CC1CC1 MOWDTMLRNMSYSS-UHFFFAOYSA-N 0.000 claims description 3
YBVMJIBEEFLALK-UHFFFAOYSA-N 8-(cyclopropylmethyl)-7-[(4-methoxyphenyl)methyl]-3H-purine-2,6-dione Chemical compound C1=CC(OC)=CC=C1CN1C(C(=O)NC(=O)N2)=C2N=C1CC1CC1 YBVMJIBEEFLALK-UHFFFAOYSA-N 0.000 claims description 3
MSNSVWMURXYFQD-UHFFFAOYSA-N 8-amino-1,3-bis(cyclopropylmethyl)-7-(naphthalen-1-ylmethyl)purine-2,6-dione Chemical compound O=C1N(CC2CC2)C(=O)C=2N(CC=3C4=CC=CC=C4C=CC=3)C(N)=NC=2N1CC1CC1 MSNSVWMURXYFQD-UHFFFAOYSA-N 0.000 claims description 3
TVUCPPTUFFACBD-UHFFFAOYSA-N 8-amino-1,3-bis(cyclopropylmethyl)-7-[(3,4,5-trimethoxyphenyl)methyl]purine-2,6-dione Chemical compound COC1=C(OC)C(OC)=CC(CN2C=3C(=O)N(CC4CC4)C(=O)N(CC4CC4)C=3N=C2N)=C1 TVUCPPTUFFACBD-UHFFFAOYSA-N 0.000 claims description 3
OLQNFXOLYGKUAT-UHFFFAOYSA-N 8-amino-7-benzyl-1,3-bis(cyclopropylmethyl)purine-2,6-dione Chemical compound O=C1N(CC2CC2)C(=O)C=2N(CC=3C=CC=CC=3)C(N)=NC=2N1CC1CC1 OLQNFXOLYGKUAT-UHFFFAOYSA-N 0.000 claims description 3
LNACHJNAXFCTEG-UHFFFAOYSA-N 8-chloro-1,3-bis(cyclopropylmethyl)-7-(naphthalen-1-ylmethyl)purine-2,6-dione Chemical compound O=C1N(CC2CC2)C(=O)C=2N(CC=3C4=CC=CC=C4C=CC=3)C(Cl)=NC=2N1CC1CC1 LNACHJNAXFCTEG-UHFFFAOYSA-N 0.000 claims description 3
VCWUICMKNGMDAT-UHFFFAOYSA-N 8-chloro-1,3-bis(cyclopropylmethyl)-7-(pyridin-3-ylmethyl)purine-2,6-dione;hydrochloride Chemical compound Cl.O=C1N(CC2CC2)C(=O)C=2N(CC=3C=NC=CC=3)C(Cl)=NC=2N1CC1CC1 VCWUICMKNGMDAT-UHFFFAOYSA-N 0.000 claims description 3
JQVJWZAPAPYEPP-UHFFFAOYSA-N 8-chloro-1,3-bis(cyclopropylmethyl)-7-[(4-nitrophenyl)methyl]purine-2,6-dione Chemical compound C1=CC([N+](=O)[O-])=CC=C1CN1C(C(=O)N(CC2CC2)C(=O)N2CC3CC3)=C2N=C1Cl JQVJWZAPAPYEPP-UHFFFAOYSA-N 0.000 claims description 3
OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 claims description 3
229940099471 Phosphodiesterase inhibitor Drugs 0.000 claims description 3
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
150000002431 hydrogen Chemical class 0.000 claims description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 3
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 3
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
239000002571 phosphodiesterase inhibitor Substances 0.000 claims description 3
125000003386 piperidinyl group Chemical group 0.000 claims description 3
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 3
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 2
WRMHPOHHEMATJL-UHFFFAOYSA-N 8-amino-1,3-bis(cyclopropylmethyl)-7-[(4-methoxyphenyl)methyl]purine-2,6-dione Chemical compound C1=CC(OC)=CC=C1CN1C(C(=O)N(CC2CC2)C(=O)N2CC3CC3)=C2N=C1N WRMHPOHHEMATJL-UHFFFAOYSA-N 0.000 claims description 2
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
230000037396 body weight Effects 0.000 claims 2
IVRUCFAKIMUSLL-UHFFFAOYSA-N 1,3-bis(cyclopropylmethyl)-7-[(2-nitrophenyl)methyl]-8-[(2-nitrophenyl)methylamino]purine-2,6-dione Chemical compound [O-][N+](=O)C1=CC=CC=C1CNC(N1CC=2C(=CC=CC=2)[N+]([O-])=O)=NC2=C1C(=O)N(CC1CC1)C(=O)N2CC1CC1 IVRUCFAKIMUSLL-UHFFFAOYSA-N 0.000 claims 1
FQJHNPIRWJZHTM-UHFFFAOYSA-N 8-(cyclopropylmethyl)-7-[(4-nitrophenyl)methyl]-3H-purine-2,6-dione Chemical compound C1(CC1)CC1=NC=2NC(NC(C=2N1CC1=CC=C(C=C1)[N+](=O)[O-])=O)=O FQJHNPIRWJZHTM-UHFFFAOYSA-N 0.000 claims 1
LNXHAVUPXWICFH-UHFFFAOYSA-N COC1=CC=C(CN2C(OCCOCCN3CCNCC3)=NC3=C2C(=O)N(CC2CC2)C(=O)N3CC2CC2)C=C1 Chemical compound COC1=CC=C(CN2C(OCCOCCN3CCNCC3)=NC3=C2C(=O)N(CC2CC2)C(=O)N3CC2CC2)C=C1 LNXHAVUPXWICFH-UHFFFAOYSA-N 0.000 claims 1
235000021122 unsaturated fatty acids Nutrition 0.000 claims 1
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HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 26
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230000001681 protective effect Effects 0.000 description 1
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125000004076 pyridyl group Chemical group 0.000 description 1
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KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
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Classifications

- 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
- 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

Landscapes

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

PT99062A 1990-09-26 1991-09-25 Processo para a preparacao de derivados de xantina PT99062A (pt)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB909020959A GB9020959D0 (en)	1990-09-26	1990-09-26	Novel compounds

Publications (1)

Publication Number	Publication Date
PT99062A true PT99062A (pt)	1992-08-31

Family

ID=10682788

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
PT99062A PT99062A (pt)	1990-09-26	1991-09-25	Processo para a preparacao de derivados de xantina

Country Status (12)

Country	Link
EP (1)	EP0550570A1 (ja)
JP (1)	JPH06501251A (ja)
KR (1)	KR930702351A (ja)
AU (1)	AU653364B2 (ja)
CA (1)	CA2092430A1 (ja)
GB (1)	GB9020959D0 (ja)
IE (1)	IE913350A1 (ja)
MX (1)	MX9101237A (ja)
NZ (1)	NZ239921A (ja)
PT (1)	PT99062A (ja)
WO (1)	WO1992005175A1 (ja)
ZA (1)	ZA917610B (ja)

Families Citing this family (44)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
ATE194345T1 (de) *	1990-12-21	2000-07-15	Beecham Group Plc	Xanthinderivate
GB9210839D0 (en) *	1992-05-21	1992-07-08	Smithkline Beecham Plc	Novel compounds
US5817662A (en) *	1992-11-09	1998-10-06	Cell Therapeutics, Inc.	Substituted amino alkyl compounds
US5646156A (en) *	1994-04-25	1997-07-08	Merck & Co., Inc.	Inhibition of eosinophil activation through A3 adenosine receptor antagonism
EP0814809B1 (en) *	1994-12-13	2003-08-13	Euroceltique S.A.	Aryl thioxanthines
CA2218548A1 (en) *	1995-05-19	1996-11-21	Chiroscience Limited	Xanthines and their therapeutic use
MA24682A1 (fr) *	1997-10-23	1999-07-01	Smithkline Beecham Corp	Formes polymorphes nouvelles de cipamfylline, procede pour leur preparation et compositions les contenant
CZ200319A3 (cs) *	2000-07-04	2003-05-14	Novo Nordisk A/S	Heterocyklické sloučeniny, které jsou inhibitory enzymu DPP-IV
AU6895801A (en) *	2000-07-04	2002-01-14	Novo Nordisk As	Heterocyclic compounds, which are inhibitors of the enzyme dpp-iv
US6821978B2 (en)	2000-09-19	2004-11-23	Schering Corporation	Xanthine phosphodiesterase V inhibitors
MXPA04001891A (es)	2001-08-28	2004-06-15	Schering Corp	Inhibidores policiclicos de guanina fosfodiesterasa v.
WO2003042216A1 (en)	2001-11-09	2003-05-22	Schering Corporation	Polycyclic guanine derivative phosphodiesterase v inhibitors
EP1719772A1 (en)	2002-05-31	2006-11-08	Schering Corporation	Process for preparing xanthine phosphodiesterase v inhibitors and precursors thereof
WO2004009091A1 (en)	2002-06-17	2004-01-29	Glaxo Group Limited	Purine derivatives as liver x receptor agonists
US7407955B2 (en)	2002-08-21	2008-08-05	Boehringer Ingelheim Pharma Gmbh & Co., Kg	8-[3-amino-piperidin-1-yl]-xanthines, the preparation thereof and their use as pharmaceutical compositions
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1990
- 1990-09-26 GB GB909020959A patent/GB9020959D0/en active Pending
1991
- 1991-09-23 JP JP3515543A patent/JPH06501251A/ja active Pending
- 1991-09-23 KR KR1019930700919A patent/KR930702351A/ko not_active Withdrawn
- 1991-09-23 CA CA002092430A patent/CA2092430A1/en not_active Abandoned
- 1991-09-23 EP EP91917224A patent/EP0550570A1/en not_active Withdrawn
- 1991-09-23 WO PCT/GB1991/001633 patent/WO1992005175A1/en not_active Ceased
- 1991-09-23 AU AU85413/91A patent/AU653364B2/en not_active Ceased
- 1991-09-24 IE IE335091A patent/IE913350A1/en unknown
- 1991-09-24 ZA ZA917610A patent/ZA917610B/xx unknown
- 1991-09-24 MX MX9101237A patent/MX9101237A/es not_active IP Right Cessation
- 1991-09-24 NZ NZ239921A patent/NZ239921A/xx unknown
- 1991-09-25 PT PT99062A patent/PT99062A/pt not_active Application Discontinuation

Also Published As

Publication number	Publication date
CA2092430A1 (en)	1992-03-27
AU653364B2 (en)	1994-09-29
GB9020959D0 (en)	1990-11-07
JPH06501251A (ja)	1994-02-10
WO1992005175A1 (en)	1992-04-02
EP0550570A1 (en)	1993-07-14
MX9101237A (es)	1992-05-04
KR930702351A (ko)	1993-09-08
AU8541391A (en)	1992-04-15
ZA917610B (en)	1992-09-30
IE913350A1 (en)	1992-04-08
NZ239921A (en)	1993-12-23

Legal Events

Date	Code	Title	Description
1992-08-31	BB1A	Laying open of patent application	Effective date: 19920408
1999-02-26	FC3A	Refusal	Effective date: 19981117

Publication	Publication Date	Title
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NZ241942A (en)	1992-10-28	Quinoline derivatives
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