FI65260C - Foerfarande foer framstaellning av terapeutiskt anvaendbara 3-1h-tetrazol-5-yl)-4h-pyrimido(2,1-b)benzotiazolderivat - Google Patents

Foerfarande foer framstaellning av terapeutiskt anvaendbara 3-1h-tetrazol-5-yl)-4h-pyrimido(2,1-b)benzotiazolderivat Download PDF

Info

Publication number: FI65260C
Authority: FI; Finland
Prior art keywords: formula; compound; pyrimido; tetrazol; give
Prior art date: 1978-05-05

Application number

FI791411A

Other languages

English (en)

Finnish (fi)

Other versions

FI791411A7 (fi

FI65260B (fi

Inventor

Robert R Covington

Jr Davis L Temple

Joseph P Yevich

Original Assignee

Bristol Myers Co

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.)

1978-05-05

Filing date

1979-05-02

Publication date

1984-04-10

1979-05-02 Application filed by Bristol Myers Co filed Critical Bristol Myers Co

1979-11-06 Publication of FI791411A7 publication Critical patent/FI791411A7/fi

1983-12-30 Application granted granted Critical

1983-12-30 Publication of FI65260B publication Critical patent/FI65260B/fi

1984-04-10 Publication of FI65260C publication Critical patent/FI65260C/fi

Links

230000001225 therapeutic effect Effects 0.000 title 2
150000001875 compounds Chemical class 0.000 claims description 96
-1 1H-tetrazol-5-yl Chemical group 0.000 claims description 22
239000000203 mixture Substances 0.000 claims description 12
150000003839 salts Chemical class 0.000 claims description 12
238000006243 chemical reaction Methods 0.000 claims description 11
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 10
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 claims description 10
238000000034 method Methods 0.000 claims description 10
229910052760 oxygen Inorganic materials 0.000 claims description 10
229910052717 sulfur Inorganic materials 0.000 claims description 8
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
239000001301 oxygen Substances 0.000 claims description 7
238000002360 preparation method Methods 0.000 claims description 7
OEICGMPRFOJHKO-UHFFFAOYSA-N 2-(ethoxymethylidene)propanedinitrile Chemical compound CCOC=C(C#N)C#N OEICGMPRFOJHKO-UHFFFAOYSA-N 0.000 claims description 5
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
239000002253 acid Substances 0.000 claims description 5
235000019270 ammonium chloride Nutrition 0.000 claims description 5
239000011593 sulfur Substances 0.000 claims description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
241001061127 Thione Species 0.000 claims description 3
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 3
150000003857 carboxamides Chemical class 0.000 claims description 3
150000002576 ketones Chemical class 0.000 claims description 3
CYEBJEDOHLIWNP-UHFFFAOYSA-N methanethioamide Chemical compound NC=S CYEBJEDOHLIWNP-UHFFFAOYSA-N 0.000 claims description 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
238000007363 ring formation reaction Methods 0.000 claims description 3
KGIWPGKKIFFMKP-UHFFFAOYSA-N 2-(ethoxymethylidene)-3-hydroxybutanedinitrile Chemical compound CCOC=C(C#N)C(O)C#N KGIWPGKKIFFMKP-UHFFFAOYSA-N 0.000 claims description 2
NOUQVXVFTQJPAL-UHFFFAOYSA-N C1C(=CN=C2N1C3=CC=CC=C3S2)C4=NNN=N4 Chemical class C1C(=CN=C2N1C3=CC=CC=C3S2)C4=NNN=N4 NOUQVXVFTQJPAL-UHFFFAOYSA-N 0.000 claims description 2
239000003086 colorant Substances 0.000 claims 2
229910000951 Aluminide Inorganic materials 0.000 claims 1
239000003990 capacitor Substances 0.000 claims 1
238000009472 formulation Methods 0.000 claims 1
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 28
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 25
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239000000047 product Substances 0.000 description 15
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239000001257 hydrogen Substances 0.000 description 14
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238000004458 analytical method Methods 0.000 description 10
238000002329 infrared spectrum Methods 0.000 description 10
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238000002474 experimental method Methods 0.000 description 5
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BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 3
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239000002184 metal Substances 0.000 description 3
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 3
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 2
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MKARNSWMMBGSHX-UHFFFAOYSA-N 3,5-dimethylaniline Chemical compound CC1=CC(C)=CC(N)=C1 MKARNSWMMBGSHX-UHFFFAOYSA-N 0.000 description 2
ZJEIYGPBIUDZKQ-UHFFFAOYSA-N 3-(2h-tetrazol-5-yl)pyrimido[2,1-b][1,3]benzothiazol-4-one Chemical compound C=1N=C2SC3=CC=CC=C3N2C(=O)C=1C1=NN=NN1 ZJEIYGPBIUDZKQ-UHFFFAOYSA-N 0.000 description 2
AKPWHGBCJISNKZ-UHFFFAOYSA-N 5,7-dimethyl-1,3-benzothiazol-2-amine Chemical compound CC1=CC(C)=C2SC(N)=NC2=C1 AKPWHGBCJISNKZ-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
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206010002198 Anaphylactic reaction Diseases 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
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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 2
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STBKQYGBBYNKNI-UHFFFAOYSA-N 3-(2H-tetrazol-5-yl)-10H-pyrimido[1,2-a]benzimidazol-4-one Chemical compound C=1N=C2NC3=CC=CC=C3N2C(=O)C=1C1=NN=NN1 STBKQYGBBYNKNI-UHFFFAOYSA-N 0.000 description 1
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XRWSZZJLZRKHHD-WVWIJVSJSA-N asunaprevir Chemical compound O=C([C@@H]1C[C@H](CN1C(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)(C)C)OC1=NC=C(C2=CC=C(Cl)C=C21)OC)N[C@]1(C(=O)NS(=O)(=O)C2CC2)C[C@H]1C=C XRWSZZJLZRKHHD-WVWIJVSJSA-N 0.000 description 1
208000010216 atopic IgE responsiveness Diseases 0.000 description 1
229910052788 barium Inorganic materials 0.000 description 1
DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 1
210000004204 blood vessel Anatomy 0.000 description 1
239000001045 blue dye Substances 0.000 description 1
230000003182 bronchodilatating effect Effects 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
229940125961 compound 24 Drugs 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
238000004821 distillation Methods 0.000 description 1
231100000673 dose–response relationship Toxicity 0.000 description 1
238000010828 elution Methods 0.000 description 1
229960003699 evans blue Drugs 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000012065 filter cake Substances 0.000 description 1
238000005187 foaming Methods 0.000 description 1
235000020932 food allergy Nutrition 0.000 description 1
WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
238000003304 gavage Methods 0.000 description 1
125000005842 heteroatom Chemical group 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
239000005457 ice water Substances 0.000 description 1
102000018358 immunoglobulin Human genes 0.000 description 1
230000001939 inductive effect Effects 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
238000010253 intravenous injection Methods 0.000 description 1
239000007788 liquid Substances 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
CUONGYYJJVDODC-UHFFFAOYSA-N malononitrile Chemical compound N#CCC#N CUONGYYJJVDODC-UHFFFAOYSA-N 0.000 description 1
239000000463 material Substances 0.000 description 1
230000001404 mediated effect Effects 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
125000000896 monocarboxylic acid group Chemical group 0.000 description 1
150000004682 monohydrates Chemical class 0.000 description 1
210000004400 mucous membrane Anatomy 0.000 description 1
239000002858 neurotransmitter agent Substances 0.000 description 1
125000002560 nitrile group Chemical group 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
239000003495 polar organic solvent Substances 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
230000002265 prevention Effects 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
238000011321 prophylaxis Methods 0.000 description 1
239000012264 purified product Substances 0.000 description 1
150000003242 quaternary ammonium salts Chemical class 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
210000002345 respiratory system Anatomy 0.000 description 1
230000004044 response Effects 0.000 description 1
229940076279 serotonin Drugs 0.000 description 1
210000002966 serum Anatomy 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
230000003595 spectral effect Effects 0.000 description 1
238000010183 spectrum analysis Methods 0.000 description 1
238000012453 sprague-dawley rat model Methods 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
238000006277 sulfonation reaction Methods 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
229940066769 systemic antihistamines substituted alkylamines Drugs 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
150000003536 tetrazoles Chemical group 0.000 description 1
229960000278 theophylline Drugs 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
238000012795 verification Methods 0.000 description 1
150000003751 zinc Chemical class 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- 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
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D235/30—Nitrogen atoms not forming part of a nitro radical
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D249/14—Nitrogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/38—Nitrogen atoms
- C07D277/42—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D277/82—Nitrogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Pulmonology (AREA)
Engineering & Computer Science (AREA)
Veterinary Medicine (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Immunology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Thiazole And Isothizaole Compounds (AREA)

FI791411A 1978-05-05 1979-05-02 Foerfarande foer framstaellning av terapeutiskt anvaendbara 3-1h-tetrazol-5-yl)-4h-pyrimido(2,1-b)benzotiazolderivat FI65260C (fi)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US05/903,265 US4223031A (en)	1978-05-05	1978-05-05	Azolopyrimidinones
US90326578		1978-05-05

Publications (3)

Publication Number	Publication Date
FI791411A7 FI791411A7 (fi)	1979-11-06
FI65260B FI65260B (fi)	1983-12-30
FI65260C true FI65260C (fi)	1984-04-10

Family

ID=25417203

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
FI791411A FI65260C (fi)	1978-05-05	1979-05-02	Foerfarande foer framstaellning av terapeutiskt anvaendbara 3-1h-tetrazol-5-yl)-4h-pyrimido(2,1-b)benzotiazolderivat

Country Status (18)

Country	Link
US (1)	US4223031A (da)
JP (1)	JPS54145696A (da)
AU (1)	AU528715B2 (da)
BE (1)	BE876059A (da)
CA (1)	CA1109870A (da)
CH (2)	CH641460A5 (da)
DE (1)	DE2918085A1 (da)
DK (1)	DK185079A (da)
FI (1)	FI65260C (da)
FR (1)	FR2424924A1 (da)
GB (1)	GB2020654B (da)
GR (1)	GR72717B (da)
IE (1)	IE47976B1 (da)
LU (1)	LU81231A1 (da)
NL (1)	NL7903535A (da)
SE (2)	SE445642B (da)
YU (1)	YU103679A (da)
ZA (1)	ZA792130B (da)

Families Citing this family (22)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4491587A (en) *	1978-05-05	1985-01-01	Mead Johnson & Company	Tetrazole derivatives
US4297355A (en) *	1979-11-15	1981-10-27	Schering Corporation	(1H,3H,5H)-(1)-Benzopyrano-(2,3-d)-pyrimidine-4-one-2-thiones and their use as anti-allergy agents
DK151811C (da) *	1979-11-23	1988-06-06	Pfizer	Analogifremgangsmaade til fremstilling af n-(5-tetrazolyl)-1-oxo-1h-thiazolooe3,2-aaa-pyrimidin-2-carboxamider eller farmaceutisk acceptable kationsalte deraf samt 1-oxo-1h-thiazolooe3,2-aaapyrimidin-2-carboxylsyrer til anvendelse som udgangsmaterialer ved fremgangsmaaden
US4414388A (en) *	1979-11-23	1983-11-08	Pfizer Inc.	1-Oxo-1H-thiazolo[3,2-a]pyrimidine-2-carboxamides
JPS57165318A (en) *	1981-04-03	1982-10-12	Mochida Pharmaceut Co Ltd	Remedy for asthma
US4510143A (en) *	1982-02-17	1985-04-09	Roussel Uclaf	Antiallergic pyrimido[1,2-a]quinoxalin-2-carboxylic acid derivatives
IL69417A (en) *	1982-08-27	1987-12-20	Roussel Uclaf	2-acyl imidazo(1,2-a)pyrimidines,their preparation and pharmaceutical compositions containing them
US4474953A (en) *	1982-09-09	1984-10-02	Riker Laboratories, Inc.	Process and intermediates for the preparation of 3(1H-tetrazol-5-yl)-4H-pyrido[1,2-a]pyrimidin-4-ones
US4476130A (en) *	1982-09-09	1984-10-09	Riker Laboratories, Inc.	3-(1H-Tetrazol-5-yl)-4H-pyrimido[2,1-b]benzoxazol-4-one compounds exhibiting anti-allergic activity
US4507477A (en) *	1982-09-09	1985-03-26	Riker Laboratories, Inc.	Process for tetrazolyl-pyrimidinone derivatives
GB8300728D0 (en) *	1983-01-12	1983-02-16	Erba Farmitalia	Substituted carboxy-thiazolo / 3 2 - a / pyrimidine derivatives
GB8334210D0 (en) *	1983-12-22	1984-02-01	Roussel Lab Ltd	Imidazo(1 2-c)pyrimidines
US4762840A (en) *	1984-02-13	1988-08-09	Roussel Uclaf	Pyrimido[2,1-b]benzothiazoles having antiallergic activity
JPS60226887A (ja) *	1984-04-25	1985-11-12	Dai Ichi Seiyaku Co Ltd	トリアゾロピリミジン誘導体
GB8422918D0 (en) *	1984-09-11	1984-10-17	May & Baker Ltd	Compositions of matter
GB8422916D0 (en) *	1984-09-11	1984-10-17	May & Baker Ltd	Compositions of matter
US4727104A (en) *	1985-01-29	1988-02-23	Ciba-Geigy Corporation	Novel triazole derivatives and the use thereof for stabilizing organic polymers
IL78017A (en) *	1986-03-03	1989-06-30	Yissum Res Dev Co	Sustained release tablets of theophylline
JPS6357522A (ja) *	1986-08-28	1988-03-12	Mect Corp	ピリミド〔２，１−ｄ〕ベンゾチアゾ−ル誘導体からなる血小板凝集抑制剤
IL85207A (en) *	1987-02-06	1992-06-21	Daiichi Seiyaku Co	6-substituted thiazolo-(and 1,3,4-thiadiazolo-)(3,2-a)-(1,2,3)triazolo(4,5-d)pyrimidin-9(1h)-ones and their preparation
US8349846B2 (en) *	2008-01-11	2013-01-08	Glenmark Pharmaceuticals, S.A.	Fused pyrimidine derivatives as TRPV3 modulators
US8119647B2 (en) *	2008-04-23	2012-02-21	Glenmark Pharmaceuticals S.A.	Fused pyrimidineone compounds as TRPV3 modulators

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Publication number	Priority date	Publication date	Assignee	Title
GB1070243A (en) *	1964-07-15	1967-06-01	Smith Kline French Lab	S-triazolopyrimidones, their preparation and compositions containing them
CH491944A (de) *	1966-11-29	1970-06-15	Ciba Geigy	Verfahren zur Herstellung von benzheterocyclischen Verbindungen
IE33549B1 (en) *	1968-09-13	1974-08-07	Ici Ltd	S-triazolo (1,5-a) pyrimidine derivatives
US3888983A (en) *	1970-08-14	1975-06-10	Seperic	Derivatives of thiazolino-pyrimidin-6-ones, in inducing analgesia
US3907799A (en) *	1971-08-16	1975-09-23	Icn Pharmaceuticals	Xanthine oxidase inhibitors
US4033961A (en) *	1975-10-07	1977-07-05	Warner-Lambert Company	Pyrido[2-1-b]quinazolin-ones and their methods of preparation
DE2557425C2 (de) *	1975-12-19	1987-03-19	C.H. Boehringer Sohn, 6507 Ingelheim	11-Oxo-11-H-pyrido[2,1-b]-chinazolin-2-carbonsäure und ihre Salze, Verfahren zu ihrer Herstellung und Arzneimittel
US4041163A (en) *	1976-03-29	1977-08-09	Pfizer Inc.	N-(5-Tetrazolyl)-4-oxo-4H-pyrimido(2,1-b)benzothiazole-3-carboxamide antiallergy agents
US4072679A (en) *	1976-06-15	1978-02-07	E. R. Squibb & Sons, Inc.	1,4- AND 4,10-DIHYDRO-4-OXO-PYRIMIDO (1,2-A)-benzimidazole-3-carboxylic acids, esters and amides
US4122274A (en) *	1977-05-25	1978-10-24	Bristol-Myers Company	3-Tetrazolo-5,6,7,8-substituted-pyrido[1,2-a]pyrimidin-4-ones

1978
- 1978-05-05 US US05/903,265 patent/US4223031A/en not_active Expired - Lifetime
1979
- 1979-05-01 GB GB7915178A patent/GB2020654B/en not_active Expired
- 1979-05-02 AU AU46667/79A patent/AU528715B2/en not_active Ceased
- 1979-05-02 FI FI791411A patent/FI65260C/fi not_active IP Right Cessation
- 1979-05-03 YU YU01036/79A patent/YU103679A/xx unknown
- 1979-05-03 ZA ZA792130A patent/ZA792130B/xx unknown
- 1979-05-04 GR GR59006A patent/GR72717B/el unknown
- 1979-05-04 FR FR7911351A patent/FR2424924A1/fr active Granted
- 1979-05-04 DK DK185079A patent/DK185079A/da not_active Application Discontinuation
- 1979-05-04 DE DE19792918085 patent/DE2918085A1/de not_active Withdrawn
- 1979-05-04 JP JP5414279A patent/JPS54145696A/ja active Pending
- 1979-05-04 SE SE7903927A patent/SE445642B/sv unknown
- 1979-05-04 CA CA326,912A patent/CA1109870A/en not_active Expired
- 1979-05-04 NL NL7903535A patent/NL7903535A/xx not_active Application Discontinuation
- 1979-05-04 BE BE0/195011A patent/BE876059A/xx not_active IP Right Cessation
- 1979-05-07 CH CH426779A patent/CH641460A5/de not_active IP Right Cessation
- 1979-05-07 LU LU81231A patent/LU81231A1/xx unknown
- 1979-05-07 CH CH597/84A patent/CH651300A5/de not_active IP Right Cessation
- 1979-08-08 IE IE912/79A patent/IE47976B1/en unknown
1984
- 1984-08-20 SE SE8404151A patent/SE8404151D0/xx not_active Application Discontinuation

Also Published As

Publication number	Publication date
SE8404151L (sv)	1984-08-20
NL7903535A (nl)	1979-11-07
FR2424924B1 (da)	1983-01-14
CH651300A5 (de)	1985-09-13
GB2020654A (en)	1979-11-21
IE790912L (en)	1979-11-05
AU528715B2 (en)	1983-05-12
GB2020654B (en)	1982-08-04
BE876059A (fr)	1979-11-05
FR2424924A1 (fr)	1979-11-30
SE7903927L (sv)	1979-11-06
ZA792130B (en)	1980-06-25
AU4666779A (en)	1979-11-22
SE8404151D0 (sv)	1984-08-20
CA1109870A (en)	1981-09-29
DE2918085A1 (de)	1979-11-15
FI791411A7 (fi)	1979-11-06
DK185079A (da)	1979-11-06
CH641460A5 (de)	1984-02-29
SE445642B (sv)	1986-07-07
JPS54145696A (en)	1979-11-14
US4223031A (en)	1980-09-16
YU103679A (en)	1983-02-28
GR72717B (da)	1983-12-01
LU81231A1 (fr)	1979-12-06
IE47976B1 (en)	1984-08-08
FI65260B (fi)	1983-12-30

Legal Events

Date	Code	Title	Description
1996-01-11	FD	Application lapsed
2004-08-31	MM	Patent lapsed	Owner name: BRISTOL-MYERS CO

Publication	Publication Date	Title
FI65260B (fi)	1983-12-30	Foerfarande foer framstaellning av terapeutiskt anvaendbara 3-1h-tetrazol-5-yl)-4h-pyrimido(2,1-b)benzotiazolderivat
AU613503B2 (en)	1991-08-01	2-phenyl-purin-6-one derivatives for use as bronchodilators and vasodilators
FI64594B (fi)	1983-08-31	Foerfarande foer framstaellning av antiallergiska 3-(1h-tetrazol-5-yl)-4-pyrido(1,2-a)pyrimidin-4-onderivat
AU640289B2 (en)	1993-08-19	New oxazolopyridine derivatives, processes for preparing these and pharmaceutical compositions containing them
KR940000828B1 (ko)	1994-02-02	항혈전성 강심제 이미다조 퀴놀린의 제조방법
HU188852B (en)	1986-05-28	Process for producing thiazolidine derivatives active against gastric ulcer and intestinal ulcer
CH653684A5 (fr)	1986-01-15	Derives de carbostyrile, procede pour leur preparation et compositions les contenant.
FI69833C (fi)	1986-05-26	Foerfarande foer framstaellning av terapeutiskt anvaendbara sustituerade heterocykliska bensamider
JP5199079B2 (ja)	2013-05-15	アンドロゲン受容体モジュレーター化合物および方法
BRPI0610337A2 (pt)	2010-06-15	derivados de fenilacetileno tendo afinidade com o receptor mglur5
JPH0655728B2 (ja)	1994-07-27	ヒスタミン誘導体及びその製造方法並びに該誘導体を含有する医薬
JPH0146514B2 (da)	1989-10-09
JPH02268172A (ja)	1990-11-01	新規なベンズオキサゾリノン誘導体
US20250313576A1 (en)	2025-10-09	Compound for photooxygenation catalyst and medicinal composition containing same
FI64598C (fi)	1983-12-12	Foerfarande foer framstaellning av terapeutiskt anvaendbara imdazo(1,2-a)-purin-9-onderivat
US3740413A (en)	1973-06-19	2-benzimidazolecarboxamides
EP0400799A1 (en)	1990-12-05	Phenylpyrimidone derivatives
FI77658C (fi)	1989-04-10	Foerfarande foer framstaellning av analgetiskt verkande salt av n-(3-trifluormetylfenyl)-n'-propargylpiperazin.
US3899583A (en)	1975-08-12	Method of using 6-substituted amino phenyl-2,3,5,6-tetrahydro-{8 2,1-B{9 thiazoles
US5179089A (en)	1993-01-12	Isoquinoline compounds, compositions and use
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