LU87114A1 - Nouveaux derives oxy-5 du tetrahydrofurane,un procede pour leur preparation et compositions therapeutiques en contenant - Google Patents

Nouveaux derives oxy-5 du tetrahydrofurane,un procede pour leur preparation et compositions therapeutiques en contenant Download PDF

Info

Publication number: LU87114A1
Authority: LU; Luxembourg
Prior art keywords: compound; alkyl; amino; preparation; des
Prior art date: 1987-01-27

Application number

LU87114A

Other languages

English (en)

French (fr)

Inventor

Jean-Jacques Godfroid

Francoise Heymans

Pierre Braquet

Original Assignee

Scras

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.)

1987-01-27

Filing date

1988-01-26

Publication date

1988-05-03

1988-01-26 Application filed by Scras filed Critical Scras

1988-05-03 Publication of LU87114A1 publication Critical patent/LU87114A1/fr

Links

239000000203 mixture Substances 0.000 title claims description 20
238000002360 preparation method Methods 0.000 title claims description 14
238000000034 method Methods 0.000 title claims description 8
230000008569 process Effects 0.000 title claims description 6
230000001225 therapeutic effect Effects 0.000 title claims description 6
OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical class C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims description 46
125000004432 carbon atom Chemical group C* 0.000 claims description 9
125000000217 alkyl group Chemical group 0.000 claims description 8
239000002904 solvent Substances 0.000 claims description 8
125000004429 atom Chemical group 0.000 claims description 7
150000001413 amino acids Chemical class 0.000 claims description 6
229910052757 nitrogen Inorganic materials 0.000 claims description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 4
108090000765 processed proteins & peptides Proteins 0.000 claims description 4
125000003277 amino group Chemical group 0.000 claims description 3
125000000623 heterocyclic group Chemical group 0.000 claims description 3
125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
229910052717 sulfur Inorganic materials 0.000 claims description 3
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
239000004480 active ingredient Substances 0.000 claims description 2
150000001351 alkyl iodides Chemical class 0.000 claims description 2
150000001408 amides Chemical class 0.000 claims description 2
150000001450 anions Chemical class 0.000 claims description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
RWSXRVCMGQZWBV-WDSKDSINSA-N glutathione Chemical compound OC(=O)[C@@H](N)CCC(=O)N[C@@H](CS)C(=O)NCC(O)=O RWSXRVCMGQZWBV-WDSKDSINSA-N 0.000 claims description 2
125000004430 oxygen atom Chemical group O* 0.000 claims description 2
239000002243 precursor Substances 0.000 claims description 2
239000011593 sulfur Substances 0.000 claims description 2
239000002253 acid Substances 0.000 claims 1
239000003085 diluting agent Substances 0.000 claims 1
239000000546 pharmaceutical excipient Substances 0.000 claims 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 29
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 20
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 15
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 15
125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 description 14
HVAUUPRFYPCOCA-AREMUKBSSA-N 2-O-acetyl-1-O-hexadecyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCCOC[C@@H](OC(C)=O)COP([O-])(=O)OCC[N+](C)(C)C HVAUUPRFYPCOCA-AREMUKBSSA-N 0.000 description 13
WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 13
108010003541 Platelet Activating Factor Proteins 0.000 description 12
101150041968 CDC13 gene Proteins 0.000 description 11
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239000007787 solid Substances 0.000 description 10
-1 trifluoro-methylethio group Chemical group 0.000 description 10
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
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238000004587 chromatography analysis Methods 0.000 description 6
238000001704 evaporation Methods 0.000 description 6
230000008020 evaporation Effects 0.000 description 6
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 6
230000008018 melting Effects 0.000 description 6
238000002844 melting Methods 0.000 description 6
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
241000283973 Oryctolagus cuniculus Species 0.000 description 5
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230000008602 contraction Effects 0.000 description 5
239000003480 eluent Substances 0.000 description 5
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
239000003921 oil Substances 0.000 description 5
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
239000000741 silica gel Substances 0.000 description 5
229910002027 silica gel Inorganic materials 0.000 description 5
MYNRDUPGBPOWQT-IDTAVKCVSA-N (2r,3r,4s,5r)-2-(6-aminopurin-9-yl)-5-[[3-hydrazinylpropyl(methyl)amino]methyl]oxolane-3,4-diol Chemical compound O[C@@H]1[C@H](O)[C@@H](CN(CCCNN)C)O[C@H]1N1C2=NC=NC(N)=C2N=C1 MYNRDUPGBPOWQT-IDTAVKCVSA-N 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
229910052801 chlorine Inorganic materials 0.000 description 4
229960001340 histamine Drugs 0.000 description 4
230000005764 inhibitory process Effects 0.000 description 4
VNYSSYRCGWBHLG-AMOLWHMGSA-N leukotriene B4 Chemical compound CCCCC\C=C/C[C@@H](O)\C=C\C=C\C=C/[C@@H](O)CCCC(O)=O VNYSSYRCGWBHLG-AMOLWHMGSA-N 0.000 description 4
YEESKJGWJFYOOK-IJHYULJSSA-N leukotriene D4 Chemical compound CCCCC\C=C/C\C=C/C=C/C=C/[C@H]([C@@H](O)CCCC(O)=O)SC[C@H](N)C(=O)NCC(O)=O YEESKJGWJFYOOK-IJHYULJSSA-N 0.000 description 4
239000003208 petroleum Substances 0.000 description 4
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 4
UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 3
230000009471 action Effects 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
125000001309 chloro group Chemical group Cl* 0.000 description 3
229960002887 deanol Drugs 0.000 description 3
230000000694 effects Effects 0.000 description 3
239000002158 endotoxin Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 3
238000004809 thin layer chromatography Methods 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
LDLCZOVUSADOIV-UHFFFAOYSA-N 2-bromoethanol Chemical compound OCCBr LDLCZOVUSADOIV-UHFFFAOYSA-N 0.000 description 2
PFCMQIWQXUAYPK-UHFFFAOYSA-N 2-hexyloxolane Chemical compound CCCCCCC1CCCO1 PFCMQIWQXUAYPK-UHFFFAOYSA-N 0.000 description 2
MVQVNTPHUGQQHK-UHFFFAOYSA-N 3-pyridinemethanol Chemical compound OCC1=CC=CN=C1 MVQVNTPHUGQQHK-UHFFFAOYSA-N 0.000 description 2
JVZRCNQLWOELDU-UHFFFAOYSA-N 4-Phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=NC=C1 JVZRCNQLWOELDU-UHFFFAOYSA-N 0.000 description 2
JNTPTNNCGDAGEJ-UHFFFAOYSA-N 6-chlorohexan-1-ol Chemical compound OCCCCCCCl JNTPTNNCGDAGEJ-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
241000283977 Oryctolagus Species 0.000 description 2
102100034937 Poly(A) RNA polymerase, mitochondrial Human genes 0.000 description 2
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
125000002947 alkylene group Chemical group 0.000 description 2
150000001414 amino alcohols Chemical class 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
GDCXBZMWKSBSJG-UHFFFAOYSA-N azane;4-methylbenzenesulfonic acid Chemical compound [NH4+].CC1=CC=C(S([O-])(=O)=O)C=C1 GDCXBZMWKSBSJG-UHFFFAOYSA-N 0.000 description 2
230000005540 biological transmission Effects 0.000 description 2
239000008280 blood Substances 0.000 description 2
210000004369 blood Anatomy 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
125000000753 cycloalkyl group Chemical group 0.000 description 2
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
YOMFVLRTMZWACQ-UHFFFAOYSA-N ethyltrimethylammonium Chemical compound CC[N+](C)(C)C YOMFVLRTMZWACQ-UHFFFAOYSA-N 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
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125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
238000010253 intravenous injection Methods 0.000 description 2
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
210000004072 lung Anatomy 0.000 description 2
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KYLWPCMAKMOTED-UHFFFAOYSA-N 1-chlorohexan-2-ol Chemical compound CCCCC(O)CCl KYLWPCMAKMOTED-UHFFFAOYSA-N 0.000 description 1
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IEROJUSCUBGJEB-UHFFFAOYSA-M 1-hexylquinolin-1-ium;chloride Chemical compound [Cl-].C1=CC=C2[N+](CCCCCC)=CC=CC2=C1 IEROJUSCUBGJEB-UHFFFAOYSA-M 0.000 description 1
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BCAARMUWIRURQS-UHFFFAOYSA-N dicalcium;oxocalcium;silicate Chemical compound [Ca+2].[Ca+2].[Ca]=O.[O-][Si]([O-])([O-])[O-] BCAARMUWIRURQS-UHFFFAOYSA-N 0.000 description 1
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125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
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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 description 1
238000012360 testing method Methods 0.000 description 1
150000007984 tetrahydrofuranes Chemical class 0.000 description 1
NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
DSNBHJFQCNUKMA-SCKDECHMSA-N thromboxane A2 Chemical compound OC(=O)CCC\C=C/C[C@@H]1[C@@H](/C=C/[C@@H](O)CCCCC)O[C@@H]2O[C@H]1C2 DSNBHJFQCNUKMA-SCKDECHMSA-N 0.000 description 1
231100000027 toxicology Toxicity 0.000 description 1
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A41—WEARING APPAREL
- A41B—SHIRTS; UNDERWEAR; BABY LINEN; HANDKERCHIEFS
- A41B11/00—Hosiery; Panti-hose
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- 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
- 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
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/18—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no 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
- C07D307/20—Oxygen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/94—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom spiro-condensed with carbocyclic rings or ring systems, e.g. griseofulvins
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

Landscapes

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

LU87114A 1987-01-27 1988-01-26 Nouveaux derives oxy-5 du tetrahydrofurane,un procede pour leur preparation et compositions therapeutiques en contenant LU87114A1 (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB8701727		1987-01-27
GB878701727A GB8701727D0 (en)	1987-01-27	1987-01-27	Tetrahydrofuran derivatives

Publications (1)

Publication Number	Publication Date
LU87114A1 true LU87114A1 (fr)	1988-05-03

Family

ID=10611264

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
LU87114A LU87114A1 (fr)	1987-01-27	1988-01-26	Nouveaux derives oxy-5 du tetrahydrofurane,un procede pour leur preparation et compositions therapeutiques en contenant

Country Status (31)

Country	Link
US (1)	US4888337A (es)
JP (1)	JPS63192767A (es)
KR (1)	KR900004696B1 (es)
AR (1)	AR243888A1 (es)
AT (1)	AT397800B (es)
AU (1)	AU610787B2 (es)
BE (1)	BE1000694A3 (es)
CA (1)	CA1329205C (es)
CH (1)	CH678426A5 (es)
DE (1)	DE3802362A1 (es)
DK (1)	DK36588A (es)
ES (1)	ES2005504A6 (es)
FI (1)	FI93727C (es)
FR (2)	FR2611139B1 (es)
GB (2)	GB8701727D0 (es)
HK (1)	HK17993A (es)
IE (1)	IE61326B1 (es)
IN (1)	IN169175B (es)
IT (1)	IT1221779B (es)
LU (1)	LU87114A1 (es)
MA (1)	MA21167A1 (es)
MY (1)	MY102310A (es)
NL (1)	NL192520C (es)
NO (1)	NO173332C (es)
NZ (1)	NZ223156A (es)
OA (1)	OA08709A (es)
PT (1)	PT86641B (es)
SE (1)	SE467974B (es)
SG (1)	SG125992G (es)
TN (1)	TNSN88003A1 (es)
ZA (1)	ZA8878B (es)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB8712694D0 (en) *	1987-05-29	1987-07-01	Scras	Tetrahydrofurans etc
GB8712693D0 (en) *	1987-05-29	1987-07-01	Scras	Tetrahydrofurans etc
ES2013834A6 (es) *	1989-01-30	1990-06-01	Uriach & Cia Sa J	Procedimiento para la obtencion de derivados 4-sustituidos de 2-alcoxitetrahidrofurano.
GB9009469D0 (en) *	1990-04-27	1990-06-20	British Bio Technology	Compounds
GB9104746D0 (en) *	1991-03-06	1991-04-17	British Bio Technology	Compounds
GB9114337D0 (en) *	1991-07-03	1991-08-21	British Bio Technology	Compounds
GB9122308D0 (en) *	1991-10-21	1991-12-04	British Bio Technology	Compounds
ES2062943B1 (es) *	1993-03-23	1995-11-16	Uriach & Cia Sa J	Nuevos derivados de la (2-metil-3-piridil) cianometilpiperazinas.
KR100863572B1 (ko)	2007-05-04	2008-10-15	충남대학교산학협력단	신규 페로몬 성 냄새 물질 및 이를 함유하는 돼지의 발정유도용 조성물
US20120226002A1 (en)	2011-03-04	2012-09-06	Gelest Technologies, Inc.	Silicon compounds derived from furfuryl alcohols and methods of preparation

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2185220A (en) *	1938-08-17	1940-01-02	Smith Kline French Lab	Medicinal agent
CH625784A5 (en) *	1976-09-17	1981-10-15	Ciba Geigy Ag	Microbicides
US4289884A (en) *	1979-01-08	1981-09-15	Shell Oil Company	Herbicidal tetrahydrofuran derivatives
DE3413996A1 (de) *	1984-04-13	1985-10-24	Bayer Ag, 5090 Leverkusen	Tetrahydrofuran-2-ylmethylamine
GB8712694D0 (en) *	1987-05-29	1987-07-01	Scras	Tetrahydrofurans etc
GB8712693D0 (en) *	1987-05-29	1987-07-01	Scras	Tetrahydrofurans etc

1987
- 1987-01-27 GB GB878701727A patent/GB8701727D0/en active Pending
1988
- 1988-01-05 IN IN07/DEL/88A patent/IN169175B/en unknown
- 1988-01-06 ZA ZA8878A patent/ZA8878B/xx unknown
- 1988-01-11 NZ NZ223156A patent/NZ223156A/xx unknown
- 1988-01-11 MY MYPI88000021A patent/MY102310A/en unknown
- 1988-01-13 AR AR88309829A patent/AR243888A1/es active
- 1988-01-14 NL NL8800078A patent/NL192520C/nl not_active IP Right Cessation
- 1988-01-15 US US07/144,238 patent/US4888337A/en not_active Expired - Lifetime
- 1988-01-18 FI FI880190A patent/FI93727C/fi not_active IP Right Cessation
- 1988-01-20 SE SE8800171A patent/SE467974B/sv not_active IP Right Cessation
- 1988-01-21 CH CH202/88A patent/CH678426A5/fr not_active IP Right Cessation
- 1988-01-22 ES ES8800154A patent/ES2005504A6/es not_active Expired
- 1988-01-25 BE BE8800082A patent/BE1000694A3/fr active
- 1988-01-25 NO NO880294A patent/NO173332C/no not_active IP Right Cessation
- 1988-01-26 IE IE18888A patent/IE61326B1/en not_active IP Right Cessation
- 1988-01-26 TN TNTNSN88003A patent/TNSN88003A1/fr unknown
- 1988-01-26 CA CA000557392A patent/CA1329205C/en not_active Expired - Fee Related
- 1988-01-26 KR KR1019880000599A patent/KR900004696B1/ko not_active IP Right Cessation
- 1988-01-26 DK DK036588A patent/DK36588A/da not_active Application Discontinuation
- 1988-01-26 GB GB8801652A patent/GB2200634B/en not_active Expired - Fee Related
- 1988-01-26 LU LU87114A patent/LU87114A1/fr unknown
- 1988-01-26 MA MA21404A patent/MA21167A1/fr unknown
- 1988-01-27 DE DE3802362A patent/DE3802362A1/de active Granted
- 1988-01-27 OA OA59270A patent/OA08709A/xx unknown
- 1988-01-27 JP JP63014781A patent/JPS63192767A/ja active Pending
- 1988-01-27 IT IT19222/88A patent/IT1221779B/it active
- 1988-01-27 AU AU10760/88A patent/AU610787B2/en not_active Ceased
- 1988-01-27 PT PT86641A patent/PT86641B/pt not_active IP Right Cessation
- 1988-01-27 FR FR888800908A patent/FR2611139B1/fr not_active Expired
- 1988-01-27 AT AT0016688A patent/AT397800B/de not_active IP Right Cessation
- 1988-01-27 FR FR888800909A patent/FR2609988B1/fr not_active Expired
1992
- 1992-12-10 SG SG1259/92A patent/SG125992G/en unknown
1993
- 1993-03-04 HK HK179/93A patent/HK17993A/xx not_active IP Right Cessation

Also Published As

Publication number	Publication date
BE1000694A3 (fr)	1989-03-14
PT86641A (pt)	1988-02-01
GB2200634B (en)	1990-09-12
IT1221779B (it)	1990-07-12
FR2611139A1 (fr)	1988-08-26
NO880294L (no)	1988-07-28
FI93727B (fi)	1995-02-15
FR2609988B1 (fr)	1989-12-22
DE3802362A1 (de)	1988-08-04
NO173332C (no)	1993-12-01
US4888337A (en)	1989-12-19
NL192520C (nl)	1997-09-02
ES2005504A6 (es)	1989-03-01
AU1076088A (en)	1988-07-28
SG125992G (en)	1993-02-19
CH678426A5 (es)	1991-09-13
FR2611139B1 (fr)	1989-12-22
PT86641B (pt)	1992-01-31
AR243888A1 (es)	1993-09-30
NZ223156A (en)	1989-08-29
NL8800078A (nl)	1988-08-16
AT397800B (de)	1994-06-27
TNSN88003A1 (fr)	1990-07-10
IE61326B1 (en)	1994-11-02
GB2200634A (en)	1988-08-10
SE8800171D0 (sv)	1988-01-20
GB8801652D0 (en)	1988-02-24
SE8800171L (sv)	1988-07-28
OA08709A (fr)	1989-03-31
DK36588A (da)	1988-07-28
SE467974B (sv)	1992-10-12
IE880188L (en)	1988-07-27
KR900004696B1 (ko)	1990-07-02
NL192520B (nl)	1997-05-01
IT8819222A0 (it)	1988-01-27
MY102310A (en)	1992-05-28
MA21167A1 (fr)	1988-10-01
ATA16688A (de)	1993-11-15
AU610787B2 (en)	1991-05-23
FR2609988A1 (fr)	1988-07-29
HK17993A (en)	1993-03-12
NO880294D0 (no)	1988-01-25
CA1329205C (en)	1994-05-03
FI880190A (fi)	1988-07-28
DK36588D0 (da)	1988-01-26
ZA8878B (en)	1988-08-31
GB8701727D0 (en)	1987-03-04
FI93727C (fi)	1995-05-26
NO173332B (no)	1993-08-23
FI880190A0 (fi)	1988-01-18
JPS63192767A (ja)	1988-08-10
IN169175B (es)	1991-09-14
KR880009010A (ko)	1988-09-13

Publication	Publication Date	Title
FR2665444A1 (fr)	1992-02-07	Derives d'amino-benzofuranne, benzothiophene ou indole, leur procede de preparation ainsi que les compositions les contenant.
EP0116494B1 (fr)	1988-01-27	Dérivés de la pyridazine ayant une action psychotrope, procédé d'obtention, intermédiaires et médicaments en contenant
EP0022118A1 (fr)	1981-01-07	Nouveaux dérivés de sulfonyl-aniline, leur procédé de préparation et leur application en thérapeutique
LU87114A1 (fr)	1988-05-03	Nouveaux derives oxy-5 du tetrahydrofurane,un procede pour leur preparation et compositions therapeutiques en contenant
EP0037778A1 (fr)	1981-10-14	Benzodioxanne 1,4 méthoxy-2 propanolamines, leur préparation et leur application en tant que médicaments
CH646687A5 (fr)	1984-12-14	Derives de l'acide cyclohexane carboxylique.
LU83293A1 (fr)	1981-12-02	Amines antihypertensives,leur procede de preparation et compositions antihypertensives en contenant
EP0110755A1 (fr)	1984-06-13	Dérivés de la pipéridinedione protecteurs du myocarde présentant une activité antiarythmique, leur procédé de préparation et les médicaments qui contiennent lesdits dérivés
FR2637596A1 (fr)	1990-04-13	Methyl-4 ((aryl-4 piperazinyl-1)-2 ethyl)-5 thiazole et ses derives, leur procede de preparation et les medicaments en contenant
LU87719A1 (fr)	1990-07-24	Derives di-substitues des n,n'-ditrimethoxybenzoyl piperazines,un procede pour leur preparation et compositions therapeutiques en contenant
EP1001944B1 (fr)	2003-10-01	Derives de pyrazine, leur preparation et les medicaments les contenant
LU87230A1 (fr)	1988-12-13	Nouveaux methoxy-5 alcoyl ammonium tetrahydrofuranes et tetrahydrothiophenes,un procede pour leur preparation et compositions therapeutiques en contenant
EP0362006A1 (fr)	1990-04-04	Dérivés de quinoléine, leurs procédés de préparation et les médicaments les contenant
LU87604A1 (fr)	1990-02-07	Nouveaux derives de la carbonyl-2 n,n'-di-(trimethoxybenzoyle)piperazine,un procede pour leur preparation et compositions therapeutiques en contenant
CA1089867A (fr)	1980-11-18	Derives du benzofuranne
EP0275762B1 (fr)	1993-11-18	Dérivés de l'indole carboxamide ainsi que leurs sels, procédé et intermédiaires de préparation, application à titre de médicaments de ces dérivés et compositions les renfermant
EP0233801B1 (fr)	1990-05-23	Nouveaux amides substitués, leur préparation et les compositions pharmaceutiques qui les contiennent
FR2650592A1 (es)	1991-02-08
EP0347305B1 (fr)	1993-05-12	[(Aryl-4-pipérazinyl-1)-2 éthoxy]-3 p-cymène, les dérivés ortho, méta, para monosubstitués ou disubstitués sur le noyau phényle dudit produit, le procédé de préparation desdits dérivés, et les médicaments contenant lesdits composés comme principe actif
EP0026168B1 (fr)	1983-03-16	Nouveaux dérivés de décahydroquinoléinol, leur procédé de préparation ainsi que leurs applications en thérapeutique
FR2539414A1 (fr)	1984-07-20	Derives de la pyrimidine, leur procede de preparation et les medicaments ayant une activite sur le systeme nerveux central qui en contiennent
LU83827A1 (fr)	1982-05-07	Nouveaux composes heterocycliques azotes anti-inflammatoires et immunoregulateurs et composition pharmaceutique les contenant
CH625249A5 (en)	1981-09-15	Process for the preparation of imidazothiazole derivatives
EP0031266A1 (fr)	1981-07-01	Nouveaux dérivés de l'amino-1 propanol-2, leur procédé de préparation et leur application thérapeutique
EP0323303B1 (fr)	1992-08-12	Dérivés de nicotinoyl-pipérazine, procédé de préparation et utilisation en thérapeutique