NO309900B1 - (2-morfolinylmetyl)benzamid-derivater - Google Patents

(2-morfolinylmetyl)benzamid-derivater Download PDF

Info

Publication number: NO309900B1
Authority: NO; Norway
Prior art keywords: formula; pharmaceutically acceptable; amino; acid; alkyl
Prior art date: 1995-05-23

Application number

NO975342A

Other languages

English (en)

Norwegian (no)

Other versions

NO975342L (no

NO975342D0 (no

Inventor

Georges Henri Paul Van Daele

Frans Maria Alfons Van Keybus

Marc Gustaaf Celine Verdonck

Original Assignee

Janssen Pharmaceutica Nv

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.)

1995-05-23

Filing date

1997-11-21

Publication date

2001-04-17

1997-11-21 Application filed by Janssen Pharmaceutica Nv filed Critical Janssen Pharmaceutica Nv

1997-11-21 Publication of NO975342L publication Critical patent/NO975342L/no

1997-11-21 Publication of NO975342D0 publication Critical patent/NO975342D0/no

2001-04-17 Publication of NO309900B1 publication Critical patent/NO309900B1/no

Links

AXGXKFPDHUSMGJ-UHFFFAOYSA-N n-(morpholin-2-ylmethyl)benzamide Chemical class C=1C=CC=CC=1C(=O)NCC1CNCCO1 AXGXKFPDHUSMGJ-UHFFFAOYSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 49
150000003839 salts Chemical class 0.000 claims description 24
239000002253 acid Substances 0.000 claims description 16
238000002360 preparation method Methods 0.000 claims description 15
125000000217 alkyl group Chemical group 0.000 claims description 7
239000002585 base Substances 0.000 claims description 7
230000030136 gastric emptying Effects 0.000 claims description 7
239000004480 active ingredient Substances 0.000 claims description 6
239000003937 drug carrier Substances 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 5
125000001424 substituent group Chemical group 0.000 claims description 5
239000012458 free base Substances 0.000 claims description 4
229910052736 halogen Inorganic materials 0.000 claims description 4
150000002367 halogens Chemical class 0.000 claims description 4
125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
239000003513 alkali Substances 0.000 claims description 3
238000006243 chemical reaction Methods 0.000 claims description 3
239000003814 drug Substances 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 3
125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims description 2
HMMSZYGIHITKIH-UHFFFAOYSA-N 4-amino-5-chloro-2-methoxy-n-[[4-(4-oxo-4-pyrrolidin-1-ylbutyl)morpholin-2-yl]methyl]benzamide Chemical compound COC1=CC(N)=C(Cl)C=C1C(=O)NCC1OCCN(CCCC(=O)N2CCCC2)C1 HMMSZYGIHITKIH-UHFFFAOYSA-N 0.000 claims description 2
KWNXCTQGVJOVCT-UHFFFAOYSA-N 4-amino-5-chloro-n-[[4-[4-(diethylamino)-4-oxobutyl]morpholin-2-yl]methyl]-2-methoxybenzamide Chemical compound C1N(CCCC(=O)N(CC)CC)CCOC1CNC(=O)C1=CC(Cl)=C(N)C=C1OC KWNXCTQGVJOVCT-UHFFFAOYSA-N 0.000 claims description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
230000009466 transformation Effects 0.000 claims description 2
125000000815 N-oxide group Chemical group 0.000 claims 2
125000000524 functional group Chemical group 0.000 claims 1
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
239000000243 solution Substances 0.000 description 19
-1 1-piperazinyl Chemical group 0.000 description 17
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
239000000203 mixture Substances 0.000 description 14
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
150000001204 N-oxides Chemical group 0.000 description 10
238000000034 method Methods 0.000 description 8
239000003826 tablet Substances 0.000 description 8
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
241000700159 Rattus Species 0.000 description 6
210000002784 stomach Anatomy 0.000 description 6
239000000725 suspension Substances 0.000 description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
150000007513 acids Chemical class 0.000 description 5
230000005176 gastrointestinal motility Effects 0.000 description 5
239000002904 solvent Substances 0.000 description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-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
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
125000004432 carbon atom Chemical group C* 0.000 description 4
239000000543 intermediate Substances 0.000 description 4
235000012054 meals Nutrition 0.000 description 4
LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 4
150000003254 radicals Chemical class 0.000 description 4
230000004936 stimulating effect Effects 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
238000007126 N-alkylation reaction Methods 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
230000009286 beneficial effect Effects 0.000 description 3
239000002775 capsule Substances 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
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239000007788 liquid Substances 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
239000000843 powder Substances 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
CUJPFPXNDSIBPG-UHFFFAOYSA-N 1,3-propanediyl Chemical group [CH2]C[CH2] CUJPFPXNDSIBPG-UHFFFAOYSA-N 0.000 description 2
OMIVCRYZSXDGAB-UHFFFAOYSA-N 1,4-butanediyl Chemical group [CH2]CC[CH2] OMIVCRYZSXDGAB-UHFFFAOYSA-N 0.000 description 2
QKWAMNZOEPKQBV-UHFFFAOYSA-N 2-(morpholin-2-ylmethyl)benzamide Chemical class NC(=O)C1=CC=CC=C1CC1OCCNC1 QKWAMNZOEPKQBV-UHFFFAOYSA-N 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
208000016285 Movement disease Diseases 0.000 description 2
BELBBZDIHDAJOR-UHFFFAOYSA-N Phenolsulfonephthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2S(=O)(=O)O1 BELBBZDIHDAJOR-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
229920002472 Starch Polymers 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
230000008033 biological extinction Effects 0.000 description 2
230000037396 body weight Effects 0.000 description 2
238000009835 boiling Methods 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
201000006549 dyspepsia Diseases 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000000284 extract Substances 0.000 description 2
239000008103 glucose Substances 0.000 description 2
235000011187 glycerol Nutrition 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
238000002347 injection Methods 0.000 description 2
239000007924 injection Substances 0.000 description 2
230000000968 intestinal effect Effects 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 2
125000004433 nitrogen atom Chemical group N* 0.000 description 2
231100000252 nontoxic Toxicity 0.000 description 2
230000003000 nontoxic effect Effects 0.000 description 2
150000007530 organic bases Chemical class 0.000 description 2
150000002978 peroxides Chemical class 0.000 description 2
239000008194 pharmaceutical composition Substances 0.000 description 2
229960003531 phenolsulfonphthalein Drugs 0.000 description 2
239000006187 pill Substances 0.000 description 2
239000001267 polyvinylpyrrolidone Substances 0.000 description 2
229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
XXQBEVHPUKOQEO-UHFFFAOYSA-N potassium superoxide Chemical compound [K+].[K+].[O-][O-] XXQBEVHPUKOQEO-UHFFFAOYSA-N 0.000 description 2
235000010232 propyl p-hydroxybenzoate Nutrition 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
229960003415 propylparaben Drugs 0.000 description 2
230000000862 serotonergic effect Effects 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
239000007787 solid Substances 0.000 description 2
235000019698 starch Nutrition 0.000 description 2
239000008215 water for injection Substances 0.000 description 2
XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 1
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
VQMPTVQCADWACQ-UHFFFAOYSA-N 3-methylpentan-3-amine Chemical compound CCC(C)(N)CC VQMPTVQCADWACQ-UHFFFAOYSA-N 0.000 description 1
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
IMGMDZSNZZJYQC-UHFFFAOYSA-N 4-amino-5-chloro-2-methoxy-n-(morpholin-2-ylmethyl)benzamide Chemical compound COC1=CC(N)=C(Cl)C=C1C(=O)NCC1OCCNC1 IMGMDZSNZZJYQC-UHFFFAOYSA-N 0.000 description 1
DGRPEAXNACKOJS-UHFFFAOYSA-N 4-amino-5-chloro-n-[[4-[4-(diethylamino)-4-oxobutyl]morpholin-2-yl]methyl]-2-methoxybenzamide;hydrochloride Chemical compound Cl.C1N(CCCC(=O)N(CC)CC)CCOC1CNC(=O)C1=CC(Cl)=C(N)C=C1OC DGRPEAXNACKOJS-UHFFFAOYSA-N 0.000 description 1
HHBZYNJHOOGYPZ-UHFFFAOYSA-N 4-chloro-n,n-diethylbutanamide Chemical compound CCN(CC)C(=O)CCCCl HHBZYNJHOOGYPZ-UHFFFAOYSA-N 0.000 description 1
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108091005479 5-HT2 receptors Proteins 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
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 description 1
239000005995 Aluminium silicate Substances 0.000 description 1
239000004475 Arginine Substances 0.000 description 1
COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
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ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
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DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
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WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
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238000000227 grinding Methods 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
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 1
XGIHQYAWBCFNPY-AZOCGYLKSA-N hydrabamine Chemical class C([C@@H]12)CC3=CC(C(C)C)=CC=C3[C@@]2(C)CCC[C@@]1(C)CNCCNC[C@@]1(C)[C@@H]2CCC3=CC(C(C)C)=CC=C3[C@@]2(C)CCC1 XGIHQYAWBCFNPY-AZOCGYLKSA-N 0.000 description 1
150000004677 hydrates Chemical class 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
239000008172 hydrogenated vegetable oil Substances 0.000 description 1
230000001771 impaired effect Effects 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
229940102223 injectable solution Drugs 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
230000008991 intestinal motility Effects 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
239000011630 iodine Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
239000008101 lactose Substances 0.000 description 1
238000002350 laparotomy Methods 0.000 description 1
210000002429 large intestine Anatomy 0.000 description 1
RRHJHSBDJDZUGL-UHFFFAOYSA-N lidamidine Chemical compound CN=C(N)NC(=O)NC1=C(C)C=CC=C1C RRHJHSBDJDZUGL-UHFFFAOYSA-N 0.000 description 1
229960005045 lidamidine Drugs 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 1
229940126601 medicinal product Drugs 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
TTWJBBZEZQICBI-UHFFFAOYSA-N metoclopramide Chemical compound CCN(CC)CCNC(=O)C1=CC(Cl)=C(N)C=C1OC TTWJBBZEZQICBI-UHFFFAOYSA-N 0.000 description 1
229960004503 metoclopramide Drugs 0.000 description 1
235000019813 microcrystalline cellulose Nutrition 0.000 description 1
239000008108 microcrystalline cellulose Substances 0.000 description 1
229940016286 microcrystalline cellulose Drugs 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
150000002780 morpholines Chemical class 0.000 description 1
125000002757 morpholinyl group Chemical group 0.000 description 1
230000004899 motility Effects 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
239000003921 oil Substances 0.000 description 1
235000019198 oils Nutrition 0.000 description 1
239000006186 oral dosage form Substances 0.000 description 1
229940100688 oral solution Drugs 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000001451 organic peroxides Chemical class 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
235000019371 penicillin G benzathine Nutrition 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
230000008855 peristalsis Effects 0.000 description 1
150000004965 peroxy acids Chemical class 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
239000001294 propane Substances 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000008213 purified water Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
102000005962 receptors Human genes 0.000 description 1
108020003175 receptors Proteins 0.000 description 1
JZWFDVDETGFGFC-UHFFFAOYSA-N salacetamide Chemical group CC(=O)NC(=O)C1=CC=CC=C1O JZWFDVDETGFGFC-UHFFFAOYSA-N 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
229930195734 saturated hydrocarbon Natural products 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
210000000813 small intestine Anatomy 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
PFUVRDFDKPNGAV-UHFFFAOYSA-N sodium peroxide Chemical compound [Na+].[Na+].[O-][O-] PFUVRDFDKPNGAV-UHFFFAOYSA-N 0.000 description 1
ILJOYZVVZZFIKA-UHFFFAOYSA-M sodium;1,1-dioxo-1,2-benzothiazol-3-olate;hydrate Chemical compound O.[Na+].C1=CC=C2C(=O)[N-]S(=O)(=O)C2=C1 ILJOYZVVZZFIKA-UHFFFAOYSA-M 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
239000007921 spray Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000008223 sterile water Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
238000007910 systemic administration Methods 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
238000002627 tracheal intubation Methods 0.000 description 1
238000000844 transformation Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
- C07D265/30—1,4-Oxazines; Hydrogenated 1,4-oxazines not condensed with other rings
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Bioinformatics & Cheminformatics (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Engineering & Computer Science (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Epidemiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

NO975342A 1995-05-23 1997-11-21 (2-morfolinylmetyl)benzamid-derivater NO309900B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
EP95201350		1995-05-23
PCT/EP1996/002141 WO1996037486A1 (fr)	1995-05-23	1996-05-15	Derives de (2-morpholinylmethyl)benzamide

Publications (3)

Publication Number	Publication Date
NO975342L NO975342L (no)	1997-11-21
NO975342D0 NO975342D0 (no)	1997-11-21
NO309900B1 true NO309900B1 (no)	2001-04-17

Family

ID=8220318

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO975342A NO309900B1 (no)	1995-05-23	1997-11-21	(2-morfolinylmetyl)benzamid-derivater

Country Status (18)

Country	Link
US (1)	US6100262A (fr)
EP (1)	EP0827500B1 (fr)
JP (1)	JPH11505815A (fr)
KR (1)	KR100446099B1 (fr)
AT (1)	ATE208766T1 (fr)
AU (1)	AU710037B2 (fr)
CA (1)	CA2220140C (fr)
DE (1)	DE69617001T2 (fr)
DK (1)	DK0827500T3 (fr)
ES (1)	ES2167563T3 (fr)
IL (1)	IL118379A (fr)
MY (1)	MY117938A (fr)
NO (1)	NO309900B1 (fr)
NZ (1)	NZ309065A (fr)
PT (1)	PT827500E (fr)
TW (1)	TW505639B (fr)
WO (1)	WO1996037486A1 (fr)
ZA (1)	ZA964100B (fr)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IL155093A0 (en)	2000-09-29	2003-10-31	Glaxo Group Ltd	Morpholin-acetamide derivatives for the treatment on inflammatory diseases
UA77515C2 (en) *	2002-04-04	2006-12-15		Diazabicyclo alkane derivatives possessing neuroldnin-nk1 receptor antagonistic activity
TWI423967B (zh) *	2008-02-21	2014-01-21	Dainippon Sumitomo Pharma Co	醯胺衍生物及含有其之醫藥組合物
MD3762368T2 (ro)	2018-03-08	2022-07-31	Incyte Corp	Compuși diol aminopirazină ca inhibitori ai PI3K-Y
US11046658B2 (en)	2018-07-02	2021-06-29	Incyte Corporation	Aminopyrazine derivatives as PI3K-γ inhibitors
CN110938068B (zh) *	2019-11-06	2022-12-23	广东东阳光药业有限公司	N-(吗啉-2-基甲基)酰胺衍生物及其用途

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CZ284687B6 (cs) *	1986-04-30	1999-02-17	Dainippon Pharmaceutical Co., Ltd.	Substituovaný benzamidový derivát, způsob jeho výroby a farmaceutický prostředek na jeho bázi
EP0774460A1 (fr) *	1994-03-30	1997-05-21	Yoshitomi Pharmaceutical Industries, Ltd.	Compose d'acide benzo que et son utilisation comme medicament

1996
- 1996-05-15 ES ES96916121T patent/ES2167563T3/es not_active Expired - Lifetime
- 1996-05-15 KR KR1019970707669A patent/KR100446099B1/ko not_active Expired - Fee Related
- 1996-05-15 EP EP96916121A patent/EP0827500B1/fr not_active Expired - Lifetime
- 1996-05-15 WO PCT/EP1996/002141 patent/WO1996037486A1/fr not_active Ceased
- 1996-05-15 AT AT96916121T patent/ATE208766T1/de not_active IP Right Cessation
- 1996-05-15 NZ NZ309065A patent/NZ309065A/xx unknown
- 1996-05-15 JP JP8535361A patent/JPH11505815A/ja active Pending
- 1996-05-15 DK DK96916121T patent/DK0827500T3/da active
- 1996-05-15 DE DE69617001T patent/DE69617001T2/de not_active Expired - Lifetime
- 1996-05-15 PT PT96916121T patent/PT827500E/pt unknown
- 1996-05-15 CA CA002220140A patent/CA2220140C/fr not_active Expired - Lifetime
- 1996-05-15 AU AU58992/96A patent/AU710037B2/en not_active Ceased
- 1996-05-21 MY MYPI96001904A patent/MY117938A/en unknown
- 1996-05-22 IL IL11837996A patent/IL118379A/xx not_active IP Right Cessation
- 1996-05-22 ZA ZA9604100A patent/ZA964100B/xx unknown
- 1996-06-04 TW TW085106627A patent/TW505639B/zh active
1997
- 1997-11-21 NO NO975342A patent/NO309900B1/no unknown
1999
- 1999-09-22 US US09/401,729 patent/US6100262A/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
ZA964100B (en)	1997-11-24
NO975342L (no)	1997-11-21
DK0827500T3 (da)	2002-02-25
IL118379A (en)	1999-12-31
WO1996037486A1 (fr)	1996-11-28
TW505639B (en)	2002-10-11
NZ309065A (en)	1999-06-29
MY117938A (en)	2004-08-30
KR100446099B1 (ko)	2004-11-10
NO975342D0 (no)	1997-11-21
ATE208766T1 (de)	2001-11-15
AU5899296A (en)	1996-12-11
DE69617001T2 (de)	2002-07-11
PT827500E (pt)	2002-04-29
CA2220140A1 (fr)	1996-11-28
CA2220140C (fr)	2008-02-12
DE69617001D1 (de)	2001-12-20
EP0827500A1 (fr)	1998-03-11
IL118379A0 (en)	1996-09-12
EP0827500B1 (fr)	2001-11-14
US6100262A (en)	2000-08-08
AU710037B2 (en)	1999-09-09
JPH11505815A (ja)	1999-05-25
KR19990008144A (ko)	1999-01-25
ES2167563T3 (es)	2002-05-16

Publication	Publication Date	Title
EP0300272B1 (fr)	1992-09-16	Oxazolidinones
DE69128231T2 (de)	1998-06-18	Heterozyklische Alkylamine, Verfahren zu ihrer Herstellung und pharmazeutische Zusammensetzungen die sie enthalten
NO179789B (no)	1996-09-09	Arylacetamider
NO164349B (no)	1990-06-18	Analogifremgangsmaate for fremstilling av terapeutisk aktive n-(piperidinyl-alkyl)-karboksamider og deres salter.
US4604389A (en)	1986-08-05	Benzazepine derivatives
NO172392B (no)	1993-04-05	Analogifremgangsmaate for fremstilling av 1h,3h-(1,2-c)-pyrrolo-7-tiazolkarboksamider
NO146359B (no)	1982-06-07	Analogifremgangsmaate ved fremstilling av terapeutisk aktive cyproheptadinderivater
US4420485A (en)	1983-12-13	1'-[3-(1,2-Benzisoxazol-3-yl) proply]spiro[benzofuran-2(3H),3' or 4'-piperidines or 3'-pyrrolidines]
US4540691A (en)	1985-09-10	Dopamine agonists and use thereof
EP0164633A2 (fr)	1985-12-18	Dérivés de l'indole
NO169960B (no)	1992-05-18	Analogifremgangsmaate for fremstilling av terapeutisk aktive, substituerte 1h-imidazoler og deres ikke-toksiske, farmasoeytisk akseptable syreaddisjonssalter
US6100262A (en)	2000-08-08	(2-morpholinylmethyl) benzamide derivatives
NO309425B1 (no)	2001-01-29	Prokinetiske oksadiazoler
EP0091511B1 (fr)	1988-05-11	Pipérazines et -pipéridines-1-(3-(6-fluoro-1,2-benzisoxazol-3-yl)propyl)-4-(substituées), procédé de leur préparation, compositions pharmaceutiques les contenant et leur application comme médicaments
NZ202045A (en)	1986-03-14	Benzisoxazole derivatives and pharmaceutical compositions
EP0389425B1 (fr)	1995-04-26	Benzothiopyranylamines
CA2603866C (fr)	2011-05-31	Modulateurs des androgenes
EP0180794B1 (fr)	1989-05-31	Dérivés de la pyridine
IE55377B1 (en)	1990-08-29	1,5-diphenylpyrazolin-3-one compounds,method for preparing them,and pharmaceutical compositions containing these compounds
DK153843B (da)	1988-09-12	Analogifremgangsmaade til fremstilling af 5-substituerede 10,11-dihydro-5h-dibenzooea,daacyclohepten-5,10-iminer eller salte deraf
SK77494A3 (en)	1995-07-11	Piperidines and piperazines
WO2001014332A1 (fr)	2001-03-01	Alcools de piperidine
US4044010A (en)	1977-08-23	Dibenzo[b,f] thiepins bearing piperazinyl substitution
NO177962B (no)	1995-09-18	Analogifremgangsmåte for fremstilling av terapeutisk aktive 1-oxa-2-oxo-8-azaspiro[4,5Ådecan-derivater
EP0237908B1 (fr)	1990-08-29	Dérivés de la pyridine