NO313699B1 - Nye heterocykliske forbindelser, deres fremstilling, farmasöytiske preparater inneholdende forbindelsene samtmellomprodukter til bruk ved fremstillingen - Google Patents

Nye heterocykliske forbindelser, deres fremstilling, farmasöytiske preparater inneholdende forbindelsene samtmellomprodukter til bruk ved fremstillingen Download PDF

Info

Publication number: NO313699B1
Authority: NO; Norway
Prior art keywords: compound; formula; oxo; dihydro; group
Prior art date: 1996-12-31

Application number

NO19986055A

Other languages

English (en)

Norwegian (no)

Other versions

NO986055L (no

NO986055D0 (no

Inventor

Vidya Bhushan Lohray

Braj Bhushan Lohray

Rao Bheema Paraselli

Ranga Madhavan Gurram

Rajagopalan Ramanujam

Ranjan Chakrabarti

Sarma K S Pakala

Original Assignee

Reddy Cheminor Inc

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.)

1996-12-31

Filing date

1998-12-22

Publication date

2002-11-18

1996-12-31 Priority claimed from US08/777,627 external-priority patent/US5885997A/en

1998-12-22 Application filed by Reddy Cheminor Inc filed Critical Reddy Cheminor Inc

1998-12-22 Publication of NO986055L publication Critical patent/NO986055L/no

1998-12-22 Publication of NO986055D0 publication Critical patent/NO986055D0/no

2002-11-18 Publication of NO313699B1 publication Critical patent/NO313699B1/no

Links

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238000002360 preparation method Methods 0.000 title claims description 88
239000008194 pharmaceutical composition Substances 0.000 title abstract 2
239000000543 intermediate Substances 0.000 title description 10
150000002391 heterocyclic compounds Chemical class 0.000 title 1
150000003839 salts Chemical class 0.000 claims abstract description 87
239000012453 solvate Substances 0.000 claims abstract description 29
238000000034 method Methods 0.000 claims description 123
238000006243 chemical reaction Methods 0.000 claims description 119
229910052739 hydrogen Inorganic materials 0.000 claims description 71
239000001257 hydrogen Substances 0.000 claims description 71
125000004433 nitrogen atom Chemical group N* 0.000 claims description 66
229910052757 nitrogen Inorganic materials 0.000 claims description 64
125000000217 alkyl group Chemical group 0.000 claims description 57
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 52
-1 halocarbonyl isocyanate Chemical class 0.000 claims description 44
239000002253 acid Substances 0.000 claims description 43
238000004519 manufacturing process Methods 0.000 claims description 43
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 41
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 39
ZOBPZXTWZATXDG-UHFFFAOYSA-N 1,3-thiazolidine-2,4-dione Chemical compound O=C1CSC(=O)N1 ZOBPZXTWZATXDG-UHFFFAOYSA-N 0.000 claims description 32
229910052717 sulfur Inorganic materials 0.000 claims description 30
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 28
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 25
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125000004429 atom Chemical group 0.000 claims description 14
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125000001544 thienyl group Chemical group 0.000 claims description 14
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 14
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239000003085 diluting agent Substances 0.000 claims description 8
125000005647 linker group Chemical group 0.000 claims description 8
125000004957 naphthylene group Chemical group 0.000 claims description 8
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238000007796 conventional method Methods 0.000 claims description 6
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NRFACSVINOXODO-UHFFFAOYSA-N 5-[[4-[2-(2-ethyl-4-methyl-6-oxopyrimidin-1-yl)ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound CCC1=NC(C)=CC(=O)N1CCOC(C=C1)=CC=C1CC1C(=O)NC(=O)S1 NRFACSVINOXODO-UHFFFAOYSA-N 0.000 claims description 5
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BOBBACCHXQYJKT-UHFFFAOYSA-N 5-[[4-[2-(4-methyl-6-oxo-2-propylpyrimidin-1-yl)ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound CCCC1=NC(C)=CC(=O)N1CCOC(C=C1)=CC=C1CC1C(=O)NC(=O)S1 BOBBACCHXQYJKT-UHFFFAOYSA-N 0.000 claims description 5
150000001340 alkali metals Chemical class 0.000 claims description 5
230000015572 biosynthetic process Effects 0.000 claims description 5
229910052794 bromium Inorganic materials 0.000 claims description 5
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150000004820 halides Chemical class 0.000 claims description 5
239000013067 intermediate product Substances 0.000 claims description 5
229910052740 iodine Inorganic materials 0.000 claims description 5
GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 claims description 5
DBIIUZLQJNMMAK-UHFFFAOYSA-N 5-[[4-[(3-ethyl-4-oxoquinazolin-2-yl)methoxy]phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound N=1C2=CC=CC=C2C(=O)N(CC)C=1COC(C=C1)=CC=C1C=C1SC(=O)NC1=O DBIIUZLQJNMMAK-UHFFFAOYSA-N 0.000 claims description 4
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HEYWBWFMBWKADZ-UHFFFAOYSA-N 5-[[4-[2-(2-ethyl-4-methyl-6-oxopyrimidin-1-yl)ethoxy]phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound CCC1=NC(C)=CC(=O)N1CCOC(C=C1)=CC=C1C=C1C(=O)NC(=O)S1 HEYWBWFMBWKADZ-UHFFFAOYSA-N 0.000 claims description 4
VWTQBQLWUFQMAB-UHFFFAOYSA-N 5-[[4-[2-(2-ethyl-4-oxoquinazolin-3-yl)ethoxy]phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound CCC1=NC2=CC=CC=C2C(=O)N1CCOC(C=C1)=CC=C1C=C1SC(=O)NC1=O VWTQBQLWUFQMAB-UHFFFAOYSA-N 0.000 claims description 4
MCYUZEPDNRVSHG-UHFFFAOYSA-N 5-[[4-[2-(2-ethyl-6-oxo-4-phenylpyrimidin-1-yl)ethoxy]phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound CCC1=NC(C=2C=CC=CC=2)=CC(=O)N1CCOC(C=C1)=CC=C1C=C1SC(=O)NC1=O MCYUZEPDNRVSHG-UHFFFAOYSA-N 0.000 claims description 4
PSLUKBHFUUVUEF-UHFFFAOYSA-N 5-[[4-[2-(2-methyl-4-oxoquinazolin-3-yl)ethoxy]phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound CC1=NC2=CC=CC=C2C(=O)N1CCOC(C=C1)=CC=C1C=C1SC(=O)NC1=O PSLUKBHFUUVUEF-UHFFFAOYSA-N 0.000 claims description 4
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
125000004122 cyclic group Chemical group 0.000 claims description 4
239000003937 drug carrier Substances 0.000 claims description 4
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
239000000843 powder Substances 0.000 claims description 4
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
VYSFIYSQGRJGGM-UHFFFAOYSA-N 2-[[4-[2-(2-ethyl-4-methyl-6-oxopyrimidin-1-yl)ethoxy]phenyl]methyl]-1,2,4-oxadiazolidine-3,5-dione Chemical compound CCC1=NC(C)=CC(=O)N1CCOC(C=C1)=CC=C1CN1C(=O)NC(=O)O1 VYSFIYSQGRJGGM-UHFFFAOYSA-N 0.000 claims description 3
KSUNFZGWXMXICO-UHFFFAOYSA-N 5-[[3-methoxy-4-[(3-methyl-4-oxoquinazolin-2-yl)methoxy]phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C=1C=C(OCC=2N(C(=O)C3=CC=CC=C3N=2)C)C(OC)=CC=1C=C1SC(=O)NC1=O KSUNFZGWXMXICO-UHFFFAOYSA-N 0.000 claims description 3
GBDHAXNKCAKKAX-UHFFFAOYSA-N 5-[[4-[2-(2,4-dimethyl-6-oxopyrimidin-1-yl)ethoxy]phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound CC1=NC(C)=CC(=O)N1CCOC(C=C1)=CC=C1C=C1C(=O)NC(=O)S1 GBDHAXNKCAKKAX-UHFFFAOYSA-N 0.000 claims description 3
LHFRUPDIUXHDDO-UHFFFAOYSA-N 5-[[4-[2-(2-butyl-4-methyl-6-oxopyrimidin-1-yl)ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound CCCCC1=NC(C)=CC(=O)N1CCOC(C=C1)=CC=C1CC1C(=O)NC(=O)S1 LHFRUPDIUXHDDO-UHFFFAOYSA-N 0.000 claims description 3
JNMCTUBKLMLHPF-UHFFFAOYSA-N 5-[[4-[2-(4-methyl-6-oxo-2-propylpyrimidin-1-yl)ethoxy]phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound CCCC1=NC(C)=CC(=O)N1CCOC(C=C1)=CC=C1C=C1C(=O)NC(=O)S1 JNMCTUBKLMLHPF-UHFFFAOYSA-N 0.000 claims description 3
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150000002367 halogens Chemical class 0.000 claims description 3
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YBBMJYQHECYWLV-UHFFFAOYSA-N 2-[[4-[2-(4-methyl-6-oxo-2-propylpyrimidin-1-yl)ethoxy]phenyl]methyl]-1,2,4-oxadiazolidine-3,5-dione Chemical compound CCCC1=NC(C)=CC(=O)N1CCOC(C=C1)=CC=C1CN1C(=O)NC(=O)O1 YBBMJYQHECYWLV-UHFFFAOYSA-N 0.000 claims description 2
KWGUQECPNYYCKH-UHFFFAOYSA-N 5-[[4-[(3-methyl-4-oxoquinazolin-2-yl)methoxy]phenyl]methyl]-1,3-oxazolidine-2,4-dione Chemical compound N=1C2=CC=CC=C2C(=O)N(C)C=1COC(C=C1)=CC=C1CC1OC(=O)NC1=O KWGUQECPNYYCKH-UHFFFAOYSA-N 0.000 claims description 2
ULNWXTXHCKLBFK-UHFFFAOYSA-N 5-[[4-[2-(2,4-dimethyl-6-oxopyrimidin-1-yl)ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound CC1=NC(C)=CC(=O)N1CCOC(C=C1)=CC=C1CC1C(=O)NC(=O)S1 ULNWXTXHCKLBFK-UHFFFAOYSA-N 0.000 claims description 2
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AFYJUBLKCNPZRO-UHFFFAOYSA-N 5-[[4-[2-(2-ethyl-6,7-dimethoxy-4-oxoquinazolin-3-yl)ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound CCC1=NC2=CC(OC)=C(OC)C=C2C(=O)N1CCOC(C=C1)=CC=C1CC1SC(=O)NC1=O AFYJUBLKCNPZRO-UHFFFAOYSA-N 0.000 claims description 2
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150000002431 hydrogen Chemical class 0.000 claims 16
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125000004183 alkoxy alkyl group Chemical group 0.000 claims 1
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BJIAKEZFCFUZRE-UHFFFAOYSA-N calcium;5-[[4-[(3-methyl-4-oxoquinazolin-2-yl)methoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound [Ca].N=1C2=CC=CC=C2C(=O)N(C)C=1COC(C=C1)=CC=C1CC1SC(=O)NC1=O BJIAKEZFCFUZRE-UHFFFAOYSA-N 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
239000001768 carboxy methyl cellulose Substances 0.000 description 1
235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
239000008112 carboxymethyl-cellulose Substances 0.000 description 1
231100000259 cardiotoxicity Toxicity 0.000 description 1
230000007681 cardiovascular toxicity Effects 0.000 description 1
210000004027 cell Anatomy 0.000 description 1
210000000170 cell membrane Anatomy 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
239000002026 chloroform extract Substances 0.000 description 1
150000001860 citric acid derivatives Chemical class 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
229910000431 copper oxide Inorganic materials 0.000 description 1
LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 1
WZHCOOQXZCIUNC-UHFFFAOYSA-N cyclandelate Chemical compound C1C(C)(C)CC(C)CC1OC(=O)C(O)C1=CC=CC=C1 WZHCOOQXZCIUNC-UHFFFAOYSA-N 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
230000007812 deficiency Effects 0.000 description 1
230000002950 deficient Effects 0.000 description 1
HUMNYLRZRPPJDN-RAMDWTOOSA-N deuterio(phenyl)methanone Chemical compound [2H]C(=O)C1=CC=CC=C1 HUMNYLRZRPPJDN-RAMDWTOOSA-N 0.000 description 1
125000004188 dichlorophenyl group Chemical group 0.000 description 1
235000021004 dietary regimen Nutrition 0.000 description 1
238000000113 differential scanning calorimetry Methods 0.000 description 1
125000004185 ester group Chemical group 0.000 description 1
QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 1
SBQJZHNPSUHSAO-UHFFFAOYSA-N ethyl 2-[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy]acetate Chemical compound C1=CC(OCC(=O)OCC)=CC=C1CC1C(=O)NC(=O)S1 SBQJZHNPSUHSAO-UHFFFAOYSA-N 0.000 description 1
SIPISKJLCRICKM-UHFFFAOYSA-N ethyl 2-[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methylidene]cyclohexa-1,5-dien-1-yl]oxyacetate Chemical compound C1=CC(OCC(=O)OCC)=CCC1=CC1C(=O)NC(=O)S1 SIPISKJLCRICKM-UHFFFAOYSA-N 0.000 description 1
FAIKJEMHIIBNJW-UHFFFAOYSA-N ethyl 2-bromo-3-[4-[2-(2-ethyl-4-methyl-6-oxopyrimidin-1-yl)ethoxy]phenyl]propanoate Chemical compound C1=CC(CC(Br)C(=O)OCC)=CC=C1OCCN1C(=O)C=C(C)N=C1CC FAIKJEMHIIBNJW-UHFFFAOYSA-N 0.000 description 1
WCEJEOVQQGSLGL-UHFFFAOYSA-N ethyl 2-bromo-3-[4-[2-(2-methyl-4-oxoquinazolin-3-yl)ethoxy]phenyl]propanoate Chemical compound C1=CC(CC(Br)C(=O)OCC)=CC=C1OCCN1C(=O)C2=CC=CC=C2N=C1C WCEJEOVQQGSLGL-UHFFFAOYSA-N 0.000 description 1
FCZCIXQGZOUIDN-UHFFFAOYSA-N ethyl 2-diethoxyphosphinothioyloxyacetate Chemical compound CCOC(=O)COP(=S)(OCC)OCC FCZCIXQGZOUIDN-UHFFFAOYSA-N 0.000 description 1
MUPMYWGIHXQXOA-UHFFFAOYSA-N ethyl 3-[4-[2-(2-ethyl-4-methyl-6-oxopyrimidin-1-yl)ethoxy]phenyl]-2-hydroxypropanoate Chemical compound C1=CC(CC(O)C(=O)OCC)=CC=C1OCCN1C(=O)C=C(C)N=C1CC MUPMYWGIHXQXOA-UHFFFAOYSA-N 0.000 description 1
VMVZGGPZNHFGKS-UHFFFAOYSA-N ethyl n-(oxomethylidene)carbamate Chemical compound CCOC(=O)N=C=O VMVZGGPZNHFGKS-UHFFFAOYSA-N 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000000945 filler Substances 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
239000011737 fluorine Chemical group 0.000 description 1
229910052731 fluorine Chemical group 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 description 1
125000002541 furyl group Chemical group 0.000 description 1
238000003304 gavage Methods 0.000 description 1
230000002068 genetic effect Effects 0.000 description 1
229940116332 glucose oxidase Drugs 0.000 description 1
235000019420 glucose oxidase Nutrition 0.000 description 1
230000006377 glucose transport Effects 0.000 description 1
150000002315 glycerophosphates Chemical class 0.000 description 1
229940096919 glycogen Drugs 0.000 description 1
150000002366 halogen compounds Chemical class 0.000 description 1
230000020169 heat generation Effects 0.000 description 1
231100000304 hepatotoxicity Toxicity 0.000 description 1
125000005842 heteroatom Chemical group 0.000 description 1
150000004677 hydrates Chemical class 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
150000002430 hydrocarbons Chemical group 0.000 description 1
229960001330 hydroxycarbamide Drugs 0.000 description 1
230000003345 hyperglycaemic effect Effects 0.000 description 1
230000035879 hyperinsulinaemia Effects 0.000 description 1
230000000910 hyperinsulinemic effect Effects 0.000 description 1
230000001771 impaired effect Effects 0.000 description 1
239000012535 impurity Substances 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
239000011630 iodine Substances 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
230000007794 irritation Effects 0.000 description 1
238000010667 large scale reaction Methods 0.000 description 1
239000008141 laxative Substances 0.000 description 1
229940125722 laxative agent Drugs 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
210000004185 liver Anatomy 0.000 description 1
230000007056 liver toxicity Effects 0.000 description 1
VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
239000000347 magnesium hydroxide Substances 0.000 description 1
229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
150000002688 maleic acid derivatives Chemical class 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate group Chemical class CS(=O)(=O)[O-] AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 description 1
UCFFGYASXIPWPD-UHFFFAOYSA-N methyl hypochlorite Chemical group COCl UCFFGYASXIPWPD-UHFFFAOYSA-N 0.000 description 1
230000000813 microbial effect Effects 0.000 description 1
239000002808 molecular sieve Substances 0.000 description 1
230000035772 mutation Effects 0.000 description 1
CUBQECXWDYGAMO-UHFFFAOYSA-N n-[1-[2-(4-formylphenoxy)ethyl]-2-oxopyrimidin-4-yl]acetamide Chemical compound O=C1N=C(NC(=O)C)C=CN1CCOC1=CC=C(C=O)C=C1 CUBQECXWDYGAMO-UHFFFAOYSA-N 0.000 description 1
150000002823 nitrates Chemical class 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
235000018343 nutrient deficiency Nutrition 0.000 description 1
235000016709 nutrition Nutrition 0.000 description 1
230000035764 nutrition Effects 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
125000004043 oxo group Chemical group O=* 0.000 description 1
IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
210000000496 pancreas Anatomy 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
230000007310 pathophysiology Effects 0.000 description 1
239000000312 peanut oil Substances 0.000 description 1
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical class OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
150000004965 peroxy acids Chemical class 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
IPNPIHIZVLFAFP-UHFFFAOYSA-N phosphorus tribromide Chemical compound BrP(Br)Br IPNPIHIZVLFAFP-UHFFFAOYSA-N 0.000 description 1
RAIYODFGMLZUDF-UHFFFAOYSA-N piperidin-1-ium;acetate Chemical compound CC([O-])=O.C1CC[NH2+]CC1 RAIYODFGMLZUDF-UHFFFAOYSA-N 0.000 description 1
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
229910052700 potassium Chemical class 0.000 description 1
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
229910000105 potassium hydride Inorganic materials 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
230000000750 progressive effect Effects 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
230000000069 prophylactic effect Effects 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000000376 reactant Substances 0.000 description 1
102000005962 receptors Human genes 0.000 description 1
108020003175 receptors Proteins 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000011160 research Methods 0.000 description 1
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
150000003873 salicylate salts Chemical class 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
230000019491 signal transduction Effects 0.000 description 1
238000010583 slow cooling Methods 0.000 description 1
238000010512 small scale reaction Methods 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
235000000891 standard diet Nutrition 0.000 description 1
230000000638 stimulation Effects 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000000758 substrate Substances 0.000 description 1
150000003890 succinate salts Chemical class 0.000 description 1
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
150000003892 tartrate salts Chemical class 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
125000004149 thio group Chemical class *S* 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
235000012141 vanillin Nutrition 0.000 description 1
FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
239000003981 vehicle Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/34—One oxygen atom
- C07D239/36—One oxygen atom as doubly bound oxygen atom or as unsubstituted hydroxy radical
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/86—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
- C07D239/88—Oxygen 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
- C07D277/34—Oxygen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Diabetes (AREA)
Pharmacology & Pharmacy (AREA)
General Health & Medical Sciences (AREA)
Hematology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Obesity (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Emergency Medicine (AREA)
Endocrinology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

NO19986055A 1996-12-31 1998-12-22 Nye heterocykliske forbindelser, deres fremstilling, farmasöytiske preparater inneholdende forbindelsene samtmellomprodukter til bruk ved fremstillingen NO313699B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US08/777,627 US5885997A (en)	1996-07-01	1996-12-31	Heterocyclic compounds, process for their preparation and pharmaceutical compositions containing them and their use in the treatment of diabetes and related diseases
PCT/US1997/011522 WO1997041097A2 (en)	1996-12-31	1997-06-30	Novel heterocyclic compounds process for their preparation and pharmaceutical compositions containing them and their use in the treatment of diabetes and related diseases

Publications (3)

Publication Number	Publication Date
NO986055L NO986055L (no)	1998-12-22
NO986055D0 NO986055D0 (no)	1998-12-22
NO313699B1 true NO313699B1 (no)	2002-11-18

Family

ID=25110787

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO19986055A NO313699B1 (no)	1996-12-31	1998-12-22	Nye heterocykliske forbindelser, deres fremstilling, farmasöytiske preparater inneholdende forbindelsene samtmellomprodukter til bruk ved fremstillingen

Country Status (15)

Country	Link
EP (1)	EP0958296B1 (de)
JP (1)	JP4339402B2 (de)
CN (1)	CN1190434C (de)
AT (1)	ATE246190T1 (de)
DE (1)	DE69723869T2 (de)
DK (1)	DK0958296T3 (de)
ES (1)	ES2199366T3 (de)
HU (1)	HUP0301101A3 (de)
IL (2)	IL142649A (de)
NO (1)	NO313699B1 (de)
PL (1)	PL192664B1 (de)
PT (1)	PT958296E (de)
RU (1)	RU2200161C2 (de)
UA (1)	UA64713C2 (de)
WO (1)	WO1997041097A2 (de)

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Publication number	Priority date	Publication date	Assignee	Title
USRE39266E1 (en) *	1996-07-01	2006-09-05	Dr. Reddy's Laboratories, Limited	Heterocyclic compounds, process for their preparation and pharmaceutical compositions containing them and their use in the treatment of diabetes and related diseases
AU744518B2 (en)	1996-07-01	2002-02-28	Dr. Reddy's Laboratories Limited	Novel heterocyclic compounds process for their preparation and pharmaceutical compositions containing them and their use in the treatment of diabetes and related diseases
US6313113B1 (en)	1997-04-15	2001-11-06	Reddy-Cheminor, Inc.	Heterocyclic compounds having antidiabetic, hypolipidemic and antihypertensive properties, process for their preparation and pharmaceutical compositions containing them
CA2307068C (en)	1997-10-27	2007-04-10	Dr. Reddy's Laboratories Limited	Bicyclic compounds, process for their preparation and pharmaceutical compositions containing them
BR9812772A (pt)	1997-10-27	2000-10-10	Reddy Research Foundation	"compostos tricìclicos inéditos e o seu emprego na medicina;processo para a sua preparação e composições farmacêuticas contendo os mesmos"
US6265401B1 (en)	1997-10-27	2001-07-24	Reddy-Cheminor, Inc.	Bicyclic compounds and their use in medicine, process for their preparation and pharmaceutical compositions containing them
US6444816B1 (en)	1997-10-27	2002-09-03	Dr. Reddy's Research Foundation	Fused 7-oxo-pyrimidinyl compounds, preparation, composition and use thereof
US6440961B1 (en)	1997-10-27	2002-08-27	Dr. Reddy's Research Foundation	Tricyclic compounds and their use in medicine: process for their preparation and pharmaceutical compositions containing them
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1997
- 1997-06-30 WO PCT/US1997/011522 patent/WO1997041097A2/en not_active Ceased
- 1997-06-30 DK DK97934041T patent/DK0958296T3/da active
- 1997-06-30 DE DE69723869T patent/DE69723869T2/de not_active Expired - Lifetime
- 1997-06-30 AT AT97934041T patent/ATE246190T1/de active
- 1997-06-30 EP EP97934041A patent/EP0958296B1/de not_active Expired - Lifetime
- 1997-06-30 CN CNB971957789A patent/CN1190434C/zh not_active Expired - Lifetime
- 1997-06-30 UA UA98126783A patent/UA64713C2/uk unknown
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- 1997-06-30 RU RU98123195/04A patent/RU2200161C2/ru active
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RU2200161C2 (ru)	2003-03-10
IL142649A (en)	2004-12-15
DE69723869D1 (de)	2003-09-04
JP4339402B2 (ja)	2009-10-07
DK0958296T3 (da)	2003-08-18
WO1997041097A2 (en)	1997-11-06
UA64713C2 (uk)	2004-03-15
IL142649A0 (en)	2002-03-10
HUP0301101A2 (hu)	2003-12-29
DE69723869T2 (de)	2004-04-22
IL127296A0 (en)	1999-09-22
EP0958296A1 (de)	1999-11-24
HK1026204A1 (en)	2000-12-08
HUP0301101A3 (en)	2009-03-30
PL342608A1 (en)	2001-06-18
IL127296A (en)	2003-01-12
ES2199366T3 (es)	2004-02-16
ATE246190T1 (de)	2003-08-15
PT958296E (pt)	2003-11-28
PL192664B1 (pl)	2006-11-30
EP0958296B1 (de)	2003-07-30
CN1275982A (zh)	2000-12-06
NO986055L (no)	1998-12-22
NO986055D0 (no)	1998-12-22
JP2002515874A (ja)	2002-05-28
CN1190434C (zh)	2005-02-23

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EP0958296B1 (de)	2003-07-30	Heterozyklische verbindungen, verfahren zu ihrer herstellung, pharmazeutische zusammensetzungen die diese enthalten und ihre anwendung in der behandlung von diabetis und verwandten krankheiten
US5885997A (en)	1999-03-23	Heterocyclic compounds, process for their preparation and pharmaceutical compositions containing them and their use in the treatment of diabetes and related diseases
EP0971917B1 (de)	2002-02-06	Thiazolidinedione- und oxazolidinedione-derivate mit antidiabetischen, hypolipidämischen und anti hypertensiven eigenschaften
EP0222576B1 (de)	1992-03-18	Heterocyclische Oxophthalazinylessigsäure
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JP7399122B2 (ja)	2023-12-15	ウレア構造を有する縮合環化合物
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US7034151B2 (en)	2006-04-25	Process for preparing pyrrolotriazine kinase inhibitors
US6159966A (en)	2000-12-12	Azolidinediones useful for the treatment of diabetes, dyslipidemia and hypertension: process for their preparation and pharmaceutical compositions containing them
US6573268B1 (en)	2003-06-03	Heterocyclic compounds, process for their preparation and pharmaceutical compositions containing them and their use in the treatment of diabetes and related diseases
USRE39266E1 (en)	2006-09-05	Heterocyclic compounds, process for their preparation and pharmaceutical compositions containing them and their use in the treatment of diabetes and related diseases
EP1036075B1 (de)	2004-06-23	Substituierte thiazolidinedione und oxazolidinedione mit antidiabetischen,hypolipidämischen und antihypertensiven eigenschaften
EP0382199A1 (de)	1990-08-16	Oxazol-Verbindungen und ihre Verwendung
US6372750B2 (en)	2002-04-16	Heterocyclic compounds, process for their preparation and pharmaceutical compounds containing them and their use in the treatment of diabetes and related diseases
HK1026204B (en)	2005-01-21	Heterocyclic compounds process for their preparation and pharmaceutical compositions containing them and their use in the treatment of diabetes and related diseases
MXPA98010782A (es)	2000-11-01	Compuestos heterociclicos novedosos, proceso parasu preparacion y composiciones farmaceuticas que los contienen, y su uso en el tratamiento de diabetes y enfermedades relacionadas