FI112227B - Menetelmä farmakologisesti aktiivisten pyridiinijohdannaisten valmistamiseksi - Google Patents

Menetelmä farmakologisesti aktiivisten pyridiinijohdannaisten valmistamiseksi Download PDF

Info

Publication number: FI112227B
Authority: FI; Finland
Prior art keywords: pyridyl; formula; pyrimidinamine; compound; amino
Prior art date: 1993-10-01

Application number

FI952607A

Other languages

English (en)

Finnish (fi)

Swedish (sv)

Other versions

FI952607A7 (fi

FI952607A0 (fi

Inventor

Juerg Zimmermann

Original Assignee

Novartis Ag

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.)

1993-10-01

Filing date

1995-05-29

Publication date

2003-11-14

1995-05-29 Application filed by Novartis Ag filed Critical Novartis Ag

1995-05-29 Publication of FI952607A7 publication Critical patent/FI952607A7/fi

1995-05-29 Publication of FI952607A0 publication Critical patent/FI952607A0/fi

2003-11-14 Application granted granted Critical

2003-11-14 Publication of FI112227B publication Critical patent/FI112227B/fi

Links

238000000034 method Methods 0.000 title claims description 63
230000008569 process Effects 0.000 title claims description 19
150000003222 pyridines Chemical class 0.000 title description 2
-1 amidino, carboxyl Chemical group 0.000 claims description 153
150000001875 compounds Chemical class 0.000 claims description 103
125000000217 alkyl group Chemical group 0.000 claims description 50
150000003839 salts Chemical class 0.000 claims description 49
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 31
238000006243 chemical reaction Methods 0.000 claims description 29
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 28
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 27
125000006239 protecting group Chemical group 0.000 claims description 26
125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 20
125000000524 functional group Chemical group 0.000 claims description 18
125000003282 alkyl amino group Chemical group 0.000 claims description 16
150000001412 amines Chemical class 0.000 claims description 15
238000002360 preparation method Methods 0.000 claims description 13
229910052736 halogen Inorganic materials 0.000 claims description 12
150000002367 halogens Chemical class 0.000 claims description 12
229910052739 hydrogen Inorganic materials 0.000 claims description 12
239000001257 hydrogen Substances 0.000 claims description 12
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 11
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 11
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 11
125000002883 imidazolyl group Chemical group 0.000 claims description 11
125000003545 alkoxy group Chemical group 0.000 claims description 10
125000001424 substituent group Chemical group 0.000 claims description 10
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 8
125000005236 alkanoylamino group Chemical group 0.000 claims description 7
238000010511 deprotection reaction Methods 0.000 claims description 7
125000002757 morpholinyl group Chemical group 0.000 claims description 7
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 6
125000001309 chloro group Chemical group Cl* 0.000 claims description 6
125000004193 piperazinyl group Chemical group 0.000 claims description 6
125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 claims description 5
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 5
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
125000004949 alkyl amino carbonyl amino group Chemical group 0.000 claims description 4
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 4
LJXQPZWIHJMPQQ-UHFFFAOYSA-N pyrimidin-2-amine Chemical compound NC1=NC=CC=N1 LJXQPZWIHJMPQQ-UHFFFAOYSA-N 0.000 claims description 4
150000004046 2-(N-anilino)pyrimidines Chemical class 0.000 claims description 2
IYJWFLHRBPXJIW-UHFFFAOYSA-N 2-[[4-[2-(3-chloroanilino)pyrimidin-4-yl]pyridin-2-yl]amino]ethanol Chemical compound C1=NC(NCCO)=CC(C=2N=C(NC=3C=C(Cl)C=CC=3)N=CC=2)=C1 IYJWFLHRBPXJIW-UHFFFAOYSA-N 0.000 claims description 2
FCJYHLXUOSWLSB-UHFFFAOYSA-N 3-[[4-[2-(2,5-dichloroanilino)pyrimidin-4-yl]pyridin-2-yl]amino]propan-1-ol Chemical compound C1=NC(NCCCO)=CC(C=2N=C(NC=3C(=CC=C(Cl)C=3)Cl)N=CC=2)=C1 FCJYHLXUOSWLSB-UHFFFAOYSA-N 0.000 claims description 2
QLZMZSUHSDFUET-UHFFFAOYSA-N 3-[[4-[2-(3-hydroxypropylamino)pyridin-4-yl]pyrimidin-2-yl]amino]benzoic acid Chemical compound C1=NC(NCCCO)=CC(C=2N=C(NC=3C=C(C=CC=3)C(O)=O)N=CC=2)=C1 QLZMZSUHSDFUET-UHFFFAOYSA-N 0.000 claims description 2
MWIMWDUYANAUGI-UHFFFAOYSA-N 3-[[4-[2-[3-(trifluoromethyl)anilino]pyrimidin-4-yl]pyridin-2-yl]amino]propan-1-ol Chemical compound C1=NC(NCCCO)=CC(C=2N=C(NC=3C=C(C=CC=3)C(F)(F)F)N=CC=2)=C1 MWIMWDUYANAUGI-UHFFFAOYSA-N 0.000 claims description 2
VYWXFVHUENMQKZ-UHFFFAOYSA-N 4-[[4-[2-(3-chloroanilino)pyrimidin-4-yl]pyridin-2-yl]amino]butan-1-ol Chemical compound C1=NC(NCCCCO)=CC(C=2N=C(NC=3C=C(Cl)C=CC=3)N=CC=2)=C1 VYWXFVHUENMQKZ-UHFFFAOYSA-N 0.000 claims description 2
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
RXPRBIRPAMMIPD-UHFFFAOYSA-N 5-[[4-[2-(3-chloroanilino)pyrimidin-4-yl]pyridin-2-yl]amino]pentan-1-ol Chemical compound C1=NC(NCCCCCO)=CC(C=2N=C(NC=3C=C(Cl)C=CC=3)N=CC=2)=C1 RXPRBIRPAMMIPD-UHFFFAOYSA-N 0.000 claims description 2
OGZKVNUWPYUXNL-UHFFFAOYSA-N n'-[4-[2-(3-chloroanilino)pyrimidin-4-yl]pyridin-2-yl]ethane-1,2-diamine Chemical compound C1=NC(NCCN)=CC(C=2N=C(NC=3C=C(Cl)C=CC=3)N=CC=2)=C1 OGZKVNUWPYUXNL-UHFFFAOYSA-N 0.000 claims description 2
DGUMNVQVABBBNL-UHFFFAOYSA-N n-(3-chlorophenyl)-4-(2-morpholin-4-ylpyridin-4-yl)pyrimidin-2-amine Chemical compound ClC1=CC=CC(NC=2N=C(C=CN=2)C=2C=C(N=CC=2)N2CCOCC2)=C1 DGUMNVQVABBBNL-UHFFFAOYSA-N 0.000 claims description 2
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims description 2
150000003254 radicals Chemical class 0.000 claims description 2
QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims 2
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
YZANBTIYOPQXRX-UHFFFAOYSA-N 2-[3-[[4-[2-(3-chloroanilino)pyrimidin-4-yl]pyridin-2-yl]amino]propylamino]ethanol Chemical compound C1=NC(NCCCNCCO)=CC(C=2N=C(NC=3C=C(Cl)C=CC=3)N=CC=2)=C1 YZANBTIYOPQXRX-UHFFFAOYSA-N 0.000 claims 1
KQLNJATZVWYARK-UHFFFAOYSA-N 3-[[4-[2-(3-methylanilino)pyrimidin-4-yl]pyridin-2-yl]amino]propan-1-ol Chemical compound CC1=CC=CC(NC=2N=C(C=CN=2)C=2C=C(NCCCO)N=CC=2)=C1 KQLNJATZVWYARK-UHFFFAOYSA-N 0.000 claims 1
LTLSHWQFIXMNKZ-UHFFFAOYSA-N 3-[[4-[2-(5-chloro-2-methylanilino)pyrimidin-4-yl]pyridin-2-yl]amino]propan-1-ol Chemical compound CC1=CC=C(Cl)C=C1NC1=NC=CC(C=2C=C(NCCCO)N=CC=2)=N1 LTLSHWQFIXMNKZ-UHFFFAOYSA-N 0.000 claims 1
DVRQQLBDGKUABY-UHFFFAOYSA-N 4-[2-(3-chloroanilino)pyrimidin-4-yl]-n-(2-hydroxyethyl)pyridine-2-carboxamide Chemical compound C1=NC(C(=O)NCCO)=CC(C=2N=C(NC=3C=C(Cl)C=CC=3)N=CC=2)=C1 DVRQQLBDGKUABY-UHFFFAOYSA-N 0.000 claims 1
ZNAKRVXQYWLLNH-UHFFFAOYSA-N 4-[2-(3-chloroanilino)pyrimidin-4-yl]-n-(3-hydroxypropyl)pyridine-2-carboxamide Chemical compound C1=NC(C(=O)NCCCO)=CC(C=2N=C(NC=3C=C(Cl)C=CC=3)N=CC=2)=C1 ZNAKRVXQYWLLNH-UHFFFAOYSA-N 0.000 claims 1
125000001246 bromo group Chemical group Br* 0.000 claims 1
BUZRUIZTMOKRPB-UHFFFAOYSA-N carboxycarbamic acid Chemical compound OC(=O)NC(O)=O BUZRUIZTMOKRPB-UHFFFAOYSA-N 0.000 claims 1
125000002346 iodo group Chemical group I* 0.000 claims 1
BXGUKULQABJWEB-UHFFFAOYSA-N n-(2-aminoethyl)-4-[2-(3-chloroanilino)pyrimidin-4-yl]pyridine-2-carboxamide Chemical compound C1=NC(C(=O)NCCN)=CC(C=2N=C(NC=3C=C(Cl)C=CC=3)N=CC=2)=C1 BXGUKULQABJWEB-UHFFFAOYSA-N 0.000 claims 1
IPWNDJWJXCLYIL-UHFFFAOYSA-N n-(3-chlorophenyl)-4-[2-[2-(1h-imidazol-5-yl)ethylamino]pyridin-4-yl]pyrimidin-2-amine Chemical compound ClC1=CC=CC(NC=2N=C(C=CN=2)C=2C=C(NCCC=3N=CNC=3)N=CC=2)=C1 IPWNDJWJXCLYIL-UHFFFAOYSA-N 0.000 claims 1
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239000002253 acid Substances 0.000 description 51
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 48
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238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 29
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239000007858 starting material Substances 0.000 description 24
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RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
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239000004480 active ingredient Substances 0.000 description 14
150000008064 anhydrides Chemical class 0.000 description 14
238000005160 1H NMR spectroscopy Methods 0.000 description 12
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125000003277 amino group Chemical group 0.000 description 12
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238000003556 assay Methods 0.000 description 6
150000002431 hydrogen Chemical class 0.000 description 6
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ZNZJJSYHZBXQSM-UHFFFAOYSA-N propane-2,2-diamine Chemical compound CC(C)(N)N ZNZJJSYHZBXQSM-UHFFFAOYSA-N 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
229950008679 protamine sulfate Drugs 0.000 description 1
108010008359 protein kinase C lambda Proteins 0.000 description 1
108010050991 protein kinase C zeta Proteins 0.000 description 1
150000003217 pyrazoles Chemical class 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
YDVHAJGGRNBAER-UHFFFAOYSA-N pyrimidin-2-amine;hydrochloride Chemical compound Cl.NC1=NC=CC=N1 YDVHAJGGRNBAER-UHFFFAOYSA-N 0.000 description 1
108091008598 receptor tyrosine kinases Proteins 0.000 description 1
102000027426 receptor tyrosine kinases Human genes 0.000 description 1
230000002829 reductive effect Effects 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
230000010076 replication Effects 0.000 description 1
229940100486 rice starch Drugs 0.000 description 1
125000006413 ring segment Chemical group 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
238000010517 secondary reaction Methods 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
238000013207 serial dilution Methods 0.000 description 1
235000004400 serine Nutrition 0.000 description 1
229960001153 serine Drugs 0.000 description 1
229940083542 sodium Drugs 0.000 description 1
235000011127 sodium aluminium sulphate Nutrition 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
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
RZWQDAUIUBVCDD-UHFFFAOYSA-M sodium;benzenethiolate Chemical compound [Na+].[S-]C1=CC=CC=C1 RZWQDAUIUBVCDD-UHFFFAOYSA-M 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
241000894007 species Species 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
150000003458 sulfonic acid derivatives Chemical class 0.000 description 1
OBTWBSRJZRCYQV-UHFFFAOYSA-N sulfuryl difluoride Chemical compound FS(F)(=O)=O OBTWBSRJZRCYQV-UHFFFAOYSA-N 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
125000003396 thiol group Chemical group [H]S* 0.000 description 1
235000008521 threonine Nutrition 0.000 description 1
229960002898 threonine Drugs 0.000 description 1
210000001519 tissue Anatomy 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
238000005809 transesterification reaction Methods 0.000 description 1
238000012546 transfer Methods 0.000 description 1
238000002054 transplantation Methods 0.000 description 1
ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 1
LEIMLDGFXIOXMT-UHFFFAOYSA-N trimethylsilyl cyanide Chemical compound C[Si](C)(C)C#N LEIMLDGFXIOXMT-UHFFFAOYSA-N 0.000 description 1
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
229960004799 tryptophan Drugs 0.000 description 1
102000003390 tumor necrosis factor Human genes 0.000 description 1
235000002374 tyrosine Nutrition 0.000 description 1
OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
229960004441 tyrosine Drugs 0.000 description 1
201000005112 urinary bladder cancer Diseases 0.000 description 1
235000014393 valine Nutrition 0.000 description 1
229960004295 valine Drugs 0.000 description 1
239000004474 valine Substances 0.000 description 1
230000029812 viral genome replication Effects 0.000 description 1
230000003612 virological effect Effects 0.000 description 1
238000005406 washing Methods 0.000 description 1
230000003442 weekly effect Effects 0.000 description 1
238000009736 wetting Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
239000002023 wood Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/28—Compounds containing heavy metals
- A61K31/305—Mercury compounds
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
- 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
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
- 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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- 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
- 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
- A61P37/02—Immunomodulators
- 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
- A61P37/02—Immunomodulators
- A61P37/04—Immunostimulants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Immunology (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Dermatology (AREA)
Vascular Medicine (AREA)
Rheumatology (AREA)
Communicable Diseases (AREA)
Hospice & Palliative Care (AREA)
Pain & Pain Management (AREA)
Oncology (AREA)
Psychiatry (AREA)
Urology & Nephrology (AREA)
Epidemiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Pyridine Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Medicinal Preparation (AREA)

FI952607A 1993-10-01 1995-05-29 Menetelmä farmakologisesti aktiivisten pyridiinijohdannaisten valmistamiseksi FI112227B (fi)

Applications Claiming Priority (6)

Application Number	Priority Date	Filing Date	Title
CH296993		1993-10-01
CH296993		1993-10-01
CH228194		1994-07-18
CH228194		1994-07-18
PCT/EP1994/003151 WO1995009853A1 (en)	1993-10-01	1994-09-21	Pharmacologically active pyridine derivatives and processes for the preparation thereof
EP9403151		1994-09-21

Publications (3)

Publication Number	Publication Date
FI952607A7 FI952607A7 (fi)	1995-05-29
FI952607A0 FI952607A0 (fi)	1995-05-29
FI112227B true FI112227B (fi)	2003-11-14

Family

ID=25690002

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
FI952607A FI112227B (fi)	1993-10-01	1995-05-29	Menetelmä farmakologisesti aktiivisten pyridiinijohdannaisten valmistamiseksi

Country Status (21)

Country	Link
US (1)	US5728708A (de)
EP (1)	EP0672041B1 (de)
JP (1)	JP2983636B2 (de)
KR (1)	KR100330553B1 (de)
CN (1)	CN1047776C (de)
AT (1)	ATE208772T1 (de)
AU (1)	AU691834B2 (de)
CA (1)	CA2148928C (de)
CZ (1)	CZ290681B6 (de)
DE (1)	DE69429078T2 (de)
DK (1)	DK0672041T3 (de)
ES (1)	ES2167377T3 (de)
FI (1)	FI112227B (de)
HU (1)	HU228172B1 (de)
IL (1)	IL111077A (de)
NO (1)	NO308794B1 (de)
NZ (1)	NZ273617A (de)
PL (1)	PL179417B1 (de)
PT (1)	PT672041E (de)
RU (1)	RU2135491C1 (de)
WO (1)	WO1995009853A1 (de)

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JP2001526230A (ja)	1997-12-19	2001-12-18	スミスクライン・ビーチャム・コーポレイション	ヘテロアリール置換イミダゾール化合物、その医薬組成物および使用
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EP1140083A4 (de)	1999-01-08	2004-01-02	Smithkline Beecham Corp	Neue verbindungen
GB9905075D0 (en)	1999-03-06	1999-04-28	Zeneca Ltd	Chemical compounds
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1994
- 1994-09-21 DE DE69429078T patent/DE69429078T2/de not_active Expired - Lifetime
- 1994-09-21 EP EP94927635A patent/EP0672041B1/de not_active Expired - Lifetime
- 1994-09-21 PL PL94309225A patent/PL179417B1/pl unknown
- 1994-09-21 AU AU76977/94A patent/AU691834B2/en not_active Expired
- 1994-09-21 US US08/446,743 patent/US5728708A/en not_active Expired - Lifetime
- 1994-09-21 WO PCT/EP1994/003151 patent/WO1995009853A1/en not_active Ceased
- 1994-09-21 HU HU9501953A patent/HU228172B1/hu unknown
- 1994-09-21 AT AT94927635T patent/ATE208772T1/de active
- 1994-09-21 KR KR1019950702202A patent/KR100330553B1/ko not_active Expired - Lifetime
- 1994-09-21 ES ES94927635T patent/ES2167377T3/es not_active Expired - Lifetime
- 1994-09-21 CZ CZ19951722A patent/CZ290681B6/cs not_active IP Right Cessation
- 1994-09-21 JP JP7510578A patent/JP2983636B2/ja not_active Expired - Lifetime
- 1994-09-21 PT PT94927635T patent/PT672041E/pt unknown
- 1994-09-21 CN CN94190753A patent/CN1047776C/zh not_active Expired - Lifetime
- 1994-09-21 CA CA002148928A patent/CA2148928C/en not_active Expired - Lifetime
- 1994-09-21 RU RU95112504A patent/RU2135491C1/ru active
- 1994-09-21 NZ NZ273617A patent/NZ273617A/en not_active IP Right Cessation
- 1994-09-21 DK DK94927635T patent/DK0672041T3/da active
- 1994-09-29 IL IL11107794A patent/IL111077A/xx not_active IP Right Cessation
1995
- 1995-05-29 FI FI952607A patent/FI112227B/fi not_active IP Right Cessation
- 1995-05-30 NO NO952132A patent/NO308794B1/no not_active IP Right Cessation

Also Published As

Publication number	Publication date
PT672041E (pt)	2002-04-29
CZ290681B6 (cs)	2002-09-11
CA2148928A1 (en)	1995-04-13
NO952132D0 (no)	1995-05-30
EP0672041B1 (de)	2001-11-14
AU7697794A (en)	1995-05-01
HUT72609A (en)	1996-05-28
ES2167377T3 (es)	2002-05-16
FI952607A7 (fi)	1995-05-29
HU228172B1 (en)	2013-01-28
IL111077A (en)	1999-10-28
PL179417B1 (en)	2000-09-29
DE69429078D1 (de)	2001-12-20
NO952132L (no)	1995-05-30
NO308794B1 (no)	2000-10-30
RU2135491C1 (ru)	1999-08-27
AU691834B2 (en)	1998-05-28
FI952607A0 (fi)	1995-05-29
US5728708A (en)	1998-03-17
DK0672041T3 (da)	2002-02-25
ATE208772T1 (de)	2001-11-15
CZ172295A3 (en)	1996-03-13
IL111077A0 (en)	1994-11-28
DE69429078T2 (de)	2002-07-11
HU9501953D0 (en)	1995-09-28
CN1115982A (zh)	1996-01-31
KR950704296A (ko)	1995-11-17
PL309225A1 (en)	1995-10-02
EP0672041A1 (de)	1995-09-20
JPH08504215A (ja)	1996-05-07
JP2983636B2 (ja)	1999-11-29
CA2148928C (en)	2005-10-18
NZ273617A (en)	1996-11-26
KR100330553B1 (ko)	2002-11-27
CN1047776C (zh)	1999-12-29
WO1995009853A1 (en)	1995-04-13

Legal Events

Date	Code	Title	Description
1997-08-08	GB	Transfer or assigment of application	Owner name: NOVARTIS AG
2014-11-03	MA	Patent expired

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