IL96168A - History of 4-amidino as novel and 4-amidino pirano (C-3,2), preparation and pharmaceutical preparations containing them - Google Patents

History of 4-amidino as novel and 4-amidino pirano (C-3,2), preparation and pharmaceutical preparations containing them

Info

Publication number: IL96168A
Authority: IL; Israel
Prior art keywords: group; formula; compound; nitro; chroman
Prior art date: 1989-11-06

Application number

IL9616890A

Other languages

English (en)

Hebrew (he)

Other versions

IL96168A0 (en

Original Assignee

Sanofi Sa

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1989-11-06

Filing date

1990-10-30

Publication date

1995-03-15

1989-11-06 Priority claimed from FR8914518A external-priority patent/FR2654103B1/fr

1990-10-30 Application filed by Sanofi Sa filed Critical Sanofi Sa

1991-07-18 Publication of IL96168A0 publication Critical patent/IL96168A0/xx

1995-03-15 Publication of IL96168A publication Critical patent/IL96168A/en

Links

238000002360 preparation method Methods 0.000 title claims description 9
239000008194 pharmaceutical composition Substances 0.000 title claims description 7
RPOUKRIBZKUEQN-UHFFFAOYSA-N 2h-pyrano[3,2-c]pyridine-4-carboximidamide Chemical class C1=NC=C2C(C(=N)N)=CCOC2=C1 RPOUKRIBZKUEQN-UHFFFAOYSA-N 0.000 title description 2
FBAXQQAIEXHLEJ-UHFFFAOYSA-N 3,4-dihydro-2h-chromene-4-carboximidamide Chemical compound C1=CC=C2C(C(=N)N)CCOC2=C1 FBAXQQAIEXHLEJ-UHFFFAOYSA-N 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims description 45
229910052739 hydrogen Inorganic materials 0.000 claims description 22
150000002118 epoxides Chemical class 0.000 claims description 18
238000000034 method Methods 0.000 claims description 15
239000001257 hydrogen Substances 0.000 claims description 13
239000004480 active ingredient Substances 0.000 claims description 12
125000000217 alkyl group Chemical group 0.000 claims description 12
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 9
229910052736 halogen Inorganic materials 0.000 claims description 8
150000002367 halogens Chemical class 0.000 claims description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
-1 cyano, nitro, acetyl Chemical group 0.000 claims description 7
125000004093 cyano group Chemical group *C#N 0.000 claims description 6
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 6
ZOHLDHMGABPLCB-UHFFFAOYSA-N [1-(2,2-dimethyl-6-nitrochromen-4-yl)pyridin-2-ylidene]cyanamide Chemical compound C=1C(C)(C)OC2=CC=C([N+]([O-])=O)C=C2C=1N1C=CC=CC1=NC#N ZOHLDHMGABPLCB-UHFFFAOYSA-N 0.000 claims description 5
125000000623 heterocyclic group Chemical group 0.000 claims description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
229910052757 nitrogen Inorganic materials 0.000 claims description 5
125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 claims description 5
125000000815 N-oxide group Chemical group 0.000 claims description 3
125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
125000001476 phosphono group Chemical group [H]OP(*)(=O)O[H] 0.000 claims description 3
125000001424 substituent group Chemical group 0.000 claims description 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
KPUWVRGBWJFGEO-UHFFFAOYSA-N [1-(6-cyano-2,2-dimethylchromen-4-yl)pyridin-2-ylidene]cyanamide Chemical compound C=1C(C)(C)OC2=CC=C(C#N)C=C2C=1N1C=CC=CC1=NC#N KPUWVRGBWJFGEO-UHFFFAOYSA-N 0.000 claims description 2
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 2
125000003545 alkoxy group Chemical group 0.000 claims description 2
125000003277 amino group Chemical group 0.000 claims description 2
229910052799 carbon Inorganic materials 0.000 claims description 2
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims 1
239000000047 product Substances 0.000 description 18
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
239000000203 mixture Substances 0.000 description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
238000011282 treatment Methods 0.000 description 8
VZWXIQHBIQLMPN-UHFFFAOYSA-N chromane Chemical compound C1=CC=C2CCCOC2=C1 VZWXIQHBIQLMPN-UHFFFAOYSA-N 0.000 description 7
239000011541 reaction mixture Substances 0.000 description 7
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 6
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
238000010992 reflux Methods 0.000 description 5
229910000104 sodium hydride Inorganic materials 0.000 description 5
239000012312 sodium hydride Substances 0.000 description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
230000003276 anti-hypertensive effect Effects 0.000 description 4
150000002391 heterocyclic compounds Chemical class 0.000 description 4
150000002431 hydrogen Chemical class 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
FBUHFQUZAYMTOM-UHFFFAOYSA-N pyridin-2-ylcyanamide Chemical compound N#CNC1=CC=CC=N1 FBUHFQUZAYMTOM-UHFFFAOYSA-N 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
201000010099 disease Diseases 0.000 description 3
208000035475 disorder Diseases 0.000 description 3
239000003937 drug carrier Substances 0.000 description 3
230000000694 effects Effects 0.000 description 3
239000000284 extract Substances 0.000 description 3
239000000377 silicon dioxide Substances 0.000 description 3
230000000699 topical effect Effects 0.000 description 3
ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 2
SZNUGFYSIGMIBG-UHFFFAOYSA-N 2h-pyrano[3,2-c]pyridine Chemical class C1=NC=C2C=CCOC2=C1 SZNUGFYSIGMIBG-UHFFFAOYSA-N 0.000 description 2
SEBPXHSZHLFWRL-UHFFFAOYSA-N 3,4-dihydro-2,2,5,7,8-pentamethyl-2h-1-benzopyran-6-ol Chemical compound O1C(C)(C)CCC2=C1C(C)=C(C)C(O)=C2C SEBPXHSZHLFWRL-UHFFFAOYSA-N 0.000 description 2
WADSJYLPJPTMLN-UHFFFAOYSA-N 3-(cycloundecen-1-yl)-1,2-diazacycloundec-2-ene Chemical compound C1CCCCCCCCC=C1C1=NNCCCCCCCC1 WADSJYLPJPTMLN-UHFFFAOYSA-N 0.000 description 2
XEEPCXIOIGPEPA-UHFFFAOYSA-N 6-nitro-3,4-dihydro-2h-chromene Chemical compound O1CCCC2=CC([N+](=O)[O-])=CC=C21 XEEPCXIOIGPEPA-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
UDQBQKJYYYDDQD-SJORKVTESA-N C(#N)N=C1N(C=CC=C1)[C@H]1[C@@H](C(OC2=CC=C(C=C12)C#N)(C)C)O Chemical compound C(#N)N=C1N(C=CC=C1)[C@H]1[C@@H](C(OC2=CC=C(C=C12)C#N)(C)C)O UDQBQKJYYYDDQD-SJORKVTESA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
230000003288 anthiarrhythmic effect Effects 0.000 description 2
NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 2
239000002270 dispersing agent Substances 0.000 description 2
235000003599 food sweetener Nutrition 0.000 description 2
239000008187 granular material Substances 0.000 description 2
239000012442 inert solvent Substances 0.000 description 2
239000002198 insoluble material Substances 0.000 description 2
238000007918 intramuscular administration Methods 0.000 description 2
238000001990 intravenous administration Methods 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 2
239000000546 pharmaceutical excipient Substances 0.000 description 2
239000000843 powder Substances 0.000 description 2
QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 2
150000003222 pyridines Chemical class 0.000 description 2
210000000329 smooth muscle myocyte Anatomy 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
239000002904 solvent Substances 0.000 description 2
238000007920 subcutaneous administration Methods 0.000 description 2
239000003765 sweetening agent Substances 0.000 description 2
239000000080 wetting agent Substances 0.000 description 2
PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
VHNMRDQNCQBMEM-CVEARBPZSA-N (3S,4R)-2,2-dimethyl-4-(2-methyliminopyridin-1-yl)-6-nitro-3,4-dihydrochromen-3-ol Chemical compound CN=C1C=CC=CN1[C@@H]1C2=CC([N+]([O-])=O)=CC=C2OC(C)(C)[C@H]1O VHNMRDQNCQBMEM-CVEARBPZSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
HVEQAXBABGOAQI-UHFFFAOYSA-N 2,2-dimethyl-3,4-dihydrochromen-3-ol Chemical compound C1=CC=C2CC(O)C(C)(C)OC2=C1 HVEQAXBABGOAQI-UHFFFAOYSA-N 0.000 description 1
VSLNFOJWTXTUMK-UHFFFAOYSA-N 2,2-dimethyl-6-nitro-1a,7b-dihydrooxireno[2,3-c]chromene Chemical compound CC1(C)OC2=CC=C([N+]([O-])=O)C=C2C2C1O2 VSLNFOJWTXTUMK-UHFFFAOYSA-N 0.000 description 1
HBLDKCGIBIGVPC-UHFFFAOYSA-N 3,4-dihydro-2h-chromen-3-ol Chemical class C1=CC=C2CC(O)COC2=C1 HBLDKCGIBIGVPC-UHFFFAOYSA-N 0.000 description 1
YRFXIJHNLSPNPJ-UHFFFAOYSA-N 6-nitro-2,7b-dihydro-1ah-oxireno[2,3-c]chromene Chemical compound O1CC2OC2C2=CC([N+](=O)[O-])=CC=C21 YRFXIJHNLSPNPJ-UHFFFAOYSA-N 0.000 description 1
244000215068 Acacia senegal Species 0.000 description 1
201000004384 Alopecia Diseases 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
206010002383 Angina Pectoris Diseases 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
QKWQPMIRGNJEQS-WBVHZDCISA-N C(#N)N=C1N(C=CC=C1)[C@H]1[C@@H](C(OC2=CC=C(C=C12)C(C(F)(F)F)=O)(C)C)O Chemical compound C(#N)N=C1N(C=CC=C1)[C@H]1[C@@H](C(OC2=CC=C(C=C12)C(C(F)(F)F)=O)(C)C)O QKWQPMIRGNJEQS-WBVHZDCISA-N 0.000 description 1
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208000018152 Cerebral disease Diseases 0.000 description 1
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
208000020401 Depressive disease Diseases 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
239000004593 Epoxy Substances 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
208000010412 Glaucoma Diseases 0.000 description 1
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206010019280 Heart failures Diseases 0.000 description 1
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206010021639 Incontinence Diseases 0.000 description 1
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BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
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206010036600 Premature labour Diseases 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
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MRYGLUMYEDIRAR-UHFFFAOYSA-N [1-(2,2-dimethylpyrano[3,2-c]pyridin-4-yl)pyridin-2-ylidene]cyanamide Chemical compound C=1C(C)(C)OC2=CC=NC=C2C=1N1C=CC=CC1=NC#N MRYGLUMYEDIRAR-UHFFFAOYSA-N 0.000 description 1
UXHPCIPZPOXRNL-CABCVRRESA-N [1-[(3S,4R)-3-hydroxy-2,2-dimethyl-3,4-dihydropyrano[3,2-c]pyridin-4-yl]pyridin-2-ylidene]cyanamide Chemical compound C(#N)N=C1N(C=CC=C1)[C@H]1[C@@H](C(OC2=C1C=NC=C2)(C)C)O UXHPCIPZPOXRNL-CABCVRRESA-N 0.000 description 1
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OCKXNPVQLZWMBH-KGLIPLIRSA-N [1-[(3S,4R)-3-hydroxy-2,2-dimethyl-6-nitro-3,4-dihydrochromen-4-yl]pyrimidin-2-ylidene]cyanamide Chemical compound C(#N)N=C1N(C=CC=N1)[C@H]1[C@@H](C(OC2=CC=C(C=C12)[N+](=O)[O-])(C)C)O OCKXNPVQLZWMBH-KGLIPLIRSA-N 0.000 description 1
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230000002107 myocardial effect Effects 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
239000002674 ointment Substances 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
230000001575 pathological effect Effects 0.000 description 1
230000010287 polarization Effects 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
210000003240 portal vein Anatomy 0.000 description 1
230000000069 prophylactic effect Effects 0.000 description 1
238000011321 prophylaxis Methods 0.000 description 1
235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
229960003415 propylparaben Drugs 0.000 description 1
DRYYOLGDWVJUCL-UHFFFAOYSA-N pyrimidin-2-ylcyanamide Chemical compound N#CNC1=NC=CC=N1 DRYYOLGDWVJUCL-UHFFFAOYSA-N 0.000 description 1
150000003230 pyrimidines Chemical class 0.000 description 1
125000001453 quaternary ammonium group Chemical group 0.000 description 1
230000002336 repolarization Effects 0.000 description 1
230000000241 respiratory effect Effects 0.000 description 1
238000007142 ring opening reaction Methods 0.000 description 1
JBYXPOFIGCOSSB-UQGDGPGGSA-N rumenic acid Chemical compound CCCCCC\C=C/C=C/CCCCCCCC(O)=O JBYXPOFIGCOSSB-UQGDGPGGSA-N 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
239000007901 soft capsule Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000008247 solid mixture Substances 0.000 description 1
239000012265 solid product Substances 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
230000002459 sustained effect Effects 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
231100000397 ulcer Toxicity 0.000 description 1
230000002485 urinary effect Effects 0.000 description 1
229940124549 vasodilator Drugs 0.000 description 1
239000003071 vasodilator agent Substances 0.000 description 1
238000009736 wetting Methods 0.000 description 1

Classifications

- 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
- C07D405/04—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 directly linked by a ring-member-to-ring-member bond
- 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
- A61P9/06—Antiarrhythmics
- 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
- A61P9/12—Antihypertensives
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Cardiology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Heart & Thoracic Surgery (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Plural Heterocyclic Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Pyridine Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

IL9616890A 1989-11-06 1990-10-30 History of 4-amidino as novel and 4-amidino pirano (C-3,2), preparation and pharmaceutical preparations containing them IL96168A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR8914518A FR2654103B1 (fr)	1989-11-06	1989-11-06	Derives d'amidino-4 chromanne, procede d'obtention et compositions pharmaceutiques les contenant.
FR909001258A FR2657872B2 (fr)	1989-11-06	1990-02-02	Derive d'amidino-4 chromanne, procede d'obtention et compositions pharmaceutiques le contenant.

Publications (2)

Publication Number	Publication Date
IL96168A0 IL96168A0 (en)	1991-07-18
IL96168A true IL96168A (en)	1995-03-15

Family

ID=26227645

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL9616890A IL96168A (en)	1989-11-06	1990-10-30	History of 4-amidino as novel and 4-amidino pirano (C-3,2), preparation and pharmaceutical preparations containing them

Country Status (21)

Country	Link
US (2)	US5116849A (de)
EP (1)	EP0427606B1 (de)
JP (1)	JPH07103117B2 (de)
KR (1)	KR910009708A (de)
AR (1)	AR248021A1 (de)
AT (1)	ATE118004T1 (de)
AU (1)	AU635080B2 (de)
CA (1)	CA2029278A1 (de)
DE (1)	DE69016592T2 (de)
DK (1)	DK0427606T3 (de)
ES (1)	ES2070292T3 (de)
FI (1)	FI95249C (de)
FR (1)	FR2657872B2 (de)
GR (1)	GR3015684T3 (de)
HU (2)	HU215111B (de)
IE (1)	IE66726B1 (de)
IL (1)	IL96168A (de)
MX (1)	MX9203616A (de)
NO (1)	NO176517C (de)
NZ (1)	NZ235944A (de)
PT (1)	PT95791A (de)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5387587A (en) *	1986-12-23	1995-02-07	Merck Patent Gesellschaft Mit Beschrankter Haftung	Chroman derivatives
US5284838A (en) *	1987-06-23	1994-02-08	Elf Sanofi	Use of 2,2-dimethylchroman-3-ol derivatives in the treatment of asthma
FR2657872B2 (fr) *	1989-11-06	1992-06-12	Sanofi Sa	Derive d'amidino-4 chromanne, procede d'obtention et compositions pharmaceutiques le contenant.
EP0655448B1 (de) *	1992-08-17	2000-04-12	Chugai Seiyaku Kabushiki Kaisha	Benzopyran und benzoxazin-derivate
US5500442A (en) *	1994-06-10	1996-03-19	American Home Products Corporation	Cyclobut-3-ene-1,2-dione derivatives as smooth muscle relaxants
US5470861A (en) *	1994-08-04	1995-11-28	Hoffmann-La Roche Inc.	Method of promoting hair growth
GB2397054B (en) *	2003-01-07	2006-02-15	Jensen	A collection bin for a laundry

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0205292B1 (de) *	1985-06-08	1991-11-06	Beecham Group Plc	Pyrano[3,2-c]pyridinderivate, Verfahren und Zwischenprodukte zu ihrer Herstellung und diese enthaltende pharmazeutische Zubereitungen
IL86798A (en) *	1987-06-23	1992-12-01	Sanofi Sa	2,2-dimethylchroman-3-ol derivatives, their preparation and pharmaceutical compositions containing them
FR2621587B1 (fr) *	1987-10-12	1990-02-09	Sanofi Sa	Derives du dimethyl-2,2 chromene, procede pour leur preparation et composition pharmaceutiques les contenant
GB8800199D0 (en) *	1988-01-06	1988-02-10	Beecham Group Plc	Pharmaceutical preparation
US5021432A (en) *	1988-04-26	1991-06-04	Yoshitomi Pharmaceutical Industries, Ltd.	Benzopyran compound and its pharmaceutical use
US4988723A (en) *	1988-06-02	1991-01-29	Fujisawa Pharmaceutical Co., Ltd.	Benzopyran derivatives and their use as anti-hypertensives
DE3823533A1 (de) *	1988-07-12	1990-02-08	Beiersdorf Ag	Substituierte 4-heterocyclyl-2h-benzo(b)pyrane, verfahren und 4-hydroxy-3-brom-, 3,4-oxiranyl-3,4-dehydro-2h-benzo(b)pyrane als zwischenprodukte zu ihrer herstellung, sowie sie enthaltende pharmazeutsche praeparate
CA2015296C (en) *	1989-05-31	2001-08-07	Karnail Atwal	Pyranyl cyanoguanidine derivatives
JP2906349B2 (ja) *	1989-11-01	1999-06-21	住友重機械工業株式会社	光ディスク基板の製造方法
FR2657872B2 (fr) *	1989-11-06	1992-06-12	Sanofi Sa	Derive d'amidino-4 chromanne, procede d'obtention et compositions pharmaceutiques le contenant.
US5061813A (en) *	1990-04-02	1991-10-29	E. R. Squibb & Sons, Inc.	Substituted cyanoimino benzopyranes

1990
- 1990-02-02 FR FR909001258A patent/FR2657872B2/fr not_active Expired - Lifetime
- 1990-10-30 IL IL9616890A patent/IL96168A/en not_active IP Right Cessation
- 1990-10-31 US US07/606,864 patent/US5116849A/en not_active Expired - Fee Related
- 1990-10-31 AU AU65644/90A patent/AU635080B2/en not_active Ceased
- 1990-11-02 FI FI905445A patent/FI95249C/fi not_active IP Right Cessation
- 1990-11-02 HU HU907000A patent/HU215111B/hu not_active IP Right Cessation
- 1990-11-02 NZ NZ235944A patent/NZ235944A/en unknown
- 1990-11-05 CA CA002029278A patent/CA2029278A1/en not_active Abandoned
- 1990-11-05 AR AR90318294A patent/AR248021A1/es active
- 1990-11-05 NO NO904805A patent/NO176517C/no unknown
- 1990-11-05 PT PT95791A patent/PT95791A/pt not_active Application Discontinuation
- 1990-11-05 IE IE397590A patent/IE66726B1/en not_active IP Right Cessation
- 1990-11-06 AT AT90403124T patent/ATE118004T1/de not_active IP Right Cessation
- 1990-11-06 EP EP90403124A patent/EP0427606B1/de not_active Expired - Lifetime
- 1990-11-06 KR KR1019900017898A patent/KR910009708A/ko not_active Withdrawn
- 1990-11-06 JP JP2300930A patent/JPH07103117B2/ja not_active Expired - Lifetime
- 1990-11-06 ES ES90403124T patent/ES2070292T3/es not_active Expired - Lifetime
- 1990-11-06 DE DE69016592T patent/DE69016592T2/de not_active Expired - Fee Related
- 1990-11-06 DK DK90403124.2T patent/DK0427606T3/da active
1992
- 1992-03-12 US US07/850,993 patent/US5225415A/en not_active Expired - Fee Related
- 1992-06-26 MX MX9203616A patent/MX9203616A/es not_active Application Discontinuation
1995
- 1995-04-04 GR GR950400831T patent/GR3015684T3/el unknown
- 1995-06-28 HU HU95P/P00486P patent/HU211234A9/hu unknown

Also Published As

Publication number	Publication date
ATE118004T1 (de)	1995-02-15
JPH03169878A (ja)	1991-07-23
ES2070292T3 (es)	1995-06-01
NO904805L (no)	1991-05-07
FR2657872A2 (fr)	1991-08-09
HU907000D0 (en)	1991-05-28
FI95249B (fi)	1995-09-29
NO904805D0 (no)	1990-11-05
HU215111B (hu)	1998-12-28
AU635080B2 (en)	1993-03-11
US5225415A (en)	1993-07-06
NO176517C (no)	1995-04-19
EP0427606A1 (de)	1991-05-15
AR248021A1 (es)	1995-05-31
US5116849A (en)	1992-05-26
NZ235944A (en)	1992-02-25
PT95791A (pt)	1991-09-13
IL96168A0 (en)	1991-07-18
HUT59395A (en)	1992-05-28
IE66726B1 (en)	1996-01-24
EP0427606B1 (de)	1995-02-01
GR3015684T3 (en)	1995-07-31
NO176517B (no)	1995-01-09
AU6564490A (en)	1991-05-09
DE69016592D1 (de)	1995-03-16
JPH07103117B2 (ja)	1995-11-08
IE903975A1 (en)	1991-05-08
KR910009708A (ko)	1991-06-28
HU211234A9 (en)	1995-11-28
CA2029278A1 (en)	1991-05-27
DK0427606T3 (da)	1995-06-06
FI95249C (fi)	1996-01-10
FR2657872B2 (fr)	1992-06-12
DE69016592T2 (de)	1995-08-03
MX9203616A (es)	1992-07-01
FI905445A0 (fi)	1990-11-02

Legal Events

Date	Code	Title
1997-01-10	KB	Patent renewed
2001-06-14	RH	Patent void
2001-07-24	MM9K	Patent not in force due to non-payment of renewal fees

Publication	Publication Date	Title
US5151442A (en)	1992-09-29	Chroman derivative active on the central nervous system, their method of preparation and pharmaceutical compositions in which they are present
PL141134B1 (en)	1987-06-30	Method of manufacture of novel benzopyranes
TW200918528A (en)	2009-05-01	DNA-PK inhibitors
JPH01319481A (ja)	1989-12-25	クロマン誘導体
US4999371A (en)	1991-03-12	Substituted 3,4-dihydro-2H-benzopyrans, processes for their preparation, their use and pharmaceutical products based on these compounds
US5112839A (en)	1992-05-12	Chroman derivatives
US5143924A (en)	1992-09-01	Oxodihydropyridyl chroman derivatives
US5116849A (en)	1992-05-26	4-amidino chroman and 4-amidino pyrano (3,2-c) pyridine derivatives, a process for their preparation and pharmaceutical compositions containing them
JPH0320275A (ja)	1991-01-29	クロマン誘導体
EP0411912B1 (de)	1995-04-19	Cumarinderivate, ihre Herstellung und ihre Verwendung zur Behandlung von zerebrovaskulären Störungen
AU628395B2 (en)	1992-09-17	Chroman derivatives
EP2880023A1 (de)	2015-06-10	Griseofulvinderivate
JPH02172973A (ja)	1990-07-04	テトラリン誘導体
JP2000508299A (ja)	2000-07-04	抗ウイルス作用を有する置換キノリン誘導体
KR101027977B1 (ko)	2011-04-13	퀴놀린 유도체
KR20040013126A (ko)	2004-02-11	녹내장 및 근시 치료용 벤조 [ｇ] 퀴놀린 유도체
WO1994017075A1 (en)	1994-08-04	Diazepin derivatives and antiviral compositions
US5550129A (en)	1996-08-27	Benzopyranones, processes for their preparation and their use
US5185345A (en)	1993-02-09	4-amidino pyrano (3,2-c) pyridine derivatives, and pharmaceutical compositions containing them
US4868315A (en)	1989-09-19	Novel aryloxycycloalkanolaminoalkylene aryl ketones
AU625697B2 (en)	1992-07-16	Benzoxazine derivatives
HUP0202485A2 (hu)	2003-04-28	Új benzo[b]pirano[3,2-h]akridin-7-on-származékok, eljárás azok előállítására és a vegyületeket tartalmazó gyógyszerkészítmények
US5171857A (en)	1992-12-15	Antihypertensive benzopyran derivatives
US5252597A (en)	1993-10-12	Antihypertensive benzopyran derivatives
EP1191027A1 (de)	2002-03-27	Kondensierte Ringderivate von Indol als M4 selektive Aza-anthracen Muscarin-Rezeptor Antagonisten