NO780576L - Analogifremgangsmaate for fremstilling av farmakologisk aktive triazinderivater - Google Patents

Analogifremgangsmaate for fremstilling av farmakologisk aktive triazinderivater

Info

Publication number: NO780576L
Authority: NO; Norway
Prior art keywords: radical; formula; isopropyl; alkyl; triazine
Prior art date: 1977-02-21

Application number

NO780576A

Other languages

English (en)

Norwegian (no)

Inventor

Edward Douglas Brown

Walter Hepworth

Ian Trevor Kay

Original Assignee

Ici Ltd

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.)

1977-02-21

Filing date

1978-02-20

Publication date

1978-08-22

1978-02-20 Application filed by Ici Ltd filed Critical Ici Ltd

1978-08-22 Publication of NO780576L publication Critical patent/NO780576L/no

Links

238000000034 method Methods 0.000 title claims description 22
238000002360 preparation method Methods 0.000 title claims description 15
150000003918 triazines Chemical class 0.000 title 1
-1 alkoxy radical Chemical class 0.000 claims description 68
150000001875 compounds Chemical class 0.000 claims description 59
150000003839 salts Chemical class 0.000 claims description 21
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical group [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 14
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
229910052799 carbon Inorganic materials 0.000 claims description 10
239000003795 chemical substances by application Substances 0.000 claims description 9
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
150000003254 radicals Chemical class 0.000 claims description 7
239000002253 acid Substances 0.000 claims description 6
125000003118 aryl group Chemical group 0.000 claims description 6
125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 claims description 6
238000006243 chemical reaction Methods 0.000 claims description 5
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 5
125000001424 substituent group Chemical group 0.000 claims description 5
HNUALPPJLMYHDK-UHFFFAOYSA-N C[CH]C Chemical group C[CH]C HNUALPPJLMYHDK-UHFFFAOYSA-N 0.000 claims description 3
125000005843 halogen group Chemical group 0.000 claims description 3
125000000896 monocarboxylic acid group Chemical group 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 2
239000000463 material Substances 0.000 claims 1
239000004480 active ingredient Substances 0.000 description 29
239000002585 base Substances 0.000 description 17
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
230000003110 anti-inflammatory effect Effects 0.000 description 11
239000000203 mixture Substances 0.000 description 10
102000004005 Prostaglandin-endoperoxide synthases Human genes 0.000 description 9
108090000459 Prostaglandin-endoperoxide synthases Proteins 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
230000001225 therapeutic effect Effects 0.000 description 8
239000003085 diluting agent Substances 0.000 description 7
239000007858 starting material Substances 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
230000000202 analgesic effect Effects 0.000 description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
239000007787 solid Substances 0.000 description 6
229920002261 Corn starch Polymers 0.000 description 5
239000008120 corn starch Substances 0.000 description 5
229940099112 cornstarch Drugs 0.000 description 5
239000000243 solution Substances 0.000 description 5
239000002904 solvent Substances 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical compound [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 description 4
YUDRVAHLXDBKSR-UHFFFAOYSA-N [CH]1CCCCC1 Chemical compound [CH]1CCCCC1 YUDRVAHLXDBKSR-UHFFFAOYSA-N 0.000 description 4
125000000217 alkyl group Chemical group 0.000 description 4
150000001412 amines Chemical class 0.000 description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
125000004432 carbon atom Chemical group C* 0.000 description 4
CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 4
235000019359 magnesium stearate Nutrition 0.000 description 4
239000000546 pharmaceutical excipient Substances 0.000 description 4
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
239000000725 suspension Substances 0.000 description 4
239000006188 syrup Substances 0.000 description 4
235000020357 syrup Nutrition 0.000 description 4
GEWRKGDRYZIFNP-UHFFFAOYSA-N 1h-1,3,5-triazine-2,4-dione Chemical class OC1=NC=NC(O)=N1 GEWRKGDRYZIFNP-UHFFFAOYSA-N 0.000 description 3
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
229910052783 alkali metal Inorganic materials 0.000 description 3
150000008064 anhydrides Chemical class 0.000 description 3
239000011575 calcium Substances 0.000 description 3
229910052791 calcium Inorganic materials 0.000 description 3
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
239000008187 granular material Substances 0.000 description 3
239000003112 inhibitor Substances 0.000 description 3
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
239000008101 lactose Substances 0.000 description 3
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
229940124531 pharmaceutical excipient Drugs 0.000 description 3
239000000825 pharmaceutical preparation Substances 0.000 description 3
OSFBJERFMQCEQY-UHFFFAOYSA-N propylidene Chemical compound [CH]CC OSFBJERFMQCEQY-UHFFFAOYSA-N 0.000 description 3
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 3
LJXPWUAAAAXJBX-UHFFFAOYSA-N 2-methylallyl radical Chemical compound [CH2]C(C)=C LJXPWUAAAAXJBX-UHFFFAOYSA-N 0.000 description 2
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 2
GKCVIYUQKOYNEK-UHFFFAOYSA-N 6-(cyclopropylamino)-3-propan-2-yl-1,3,5-triazinane-2,4-dione Chemical compound N1C(=O)N(C(C)C)C(=O)NC1NC1CC1 GKCVIYUQKOYNEK-UHFFFAOYSA-N 0.000 description 2
GYUMXYINZOCWFH-UHFFFAOYSA-N 6-methylsulfanyl-3-propan-2-yl-1,3,5-triazinane-2,4-dione Chemical compound CSC1NC(=O)N(C(C)C)C(=O)N1 GYUMXYINZOCWFH-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
208000006820 Arthralgia Diseases 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
229920000168 Microcrystalline cellulose Polymers 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
241000700159 Rattus Species 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
NVFHNPHLUPYMCH-UHFFFAOYSA-N [CH2]COCC Chemical compound [CH2]COCC NVFHNPHLUPYMCH-UHFFFAOYSA-N 0.000 description 2
230000010933 acylation Effects 0.000 description 2
238000005917 acylation reaction Methods 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
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WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
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OROGSEYTTFOCAN-DNJOTXNNSA-N codeine Chemical compound C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC OROGSEYTTFOCAN-DNJOTXNNSA-N 0.000 description 2
239000003086 colorant Substances 0.000 description 2
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
230000000694 effects Effects 0.000 description 2
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150000002367 halogens Chemical group 0.000 description 2
238000000338 in vitro Methods 0.000 description 2
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BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 2
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235000019813 microcrystalline cellulose Nutrition 0.000 description 2
229940016286 microcrystalline cellulose Drugs 0.000 description 2
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
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125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 2
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VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
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WHTVZRBIWZFKQO-AWEZNQCLSA-N (S)-chloroquine Chemical compound ClC1=CC=C2C(N[C@@H](C)CCCN(CC)CC)=CC=NC2=C1 WHTVZRBIWZFKQO-AWEZNQCLSA-N 0.000 description 1
JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical class C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
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NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
KTOQRRDVVIDEAA-UHFFFAOYSA-N 2-methylpropane Chemical compound [CH2]C(C)C KTOQRRDVVIDEAA-UHFFFAOYSA-N 0.000 description 1
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OROGSEYTTFOCAN-UHFFFAOYSA-N hydrocodone Natural products C1C(N(CCC234)C)C2C=CC(O)C3OC2=C4C1=CC=C2OC OROGSEYTTFOCAN-UHFFFAOYSA-N 0.000 description 1
229960001680 ibuprofen Drugs 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
239000003701 inert diluent Substances 0.000 description 1
208000027866 inflammatory disease Diseases 0.000 description 1
230000004054 inflammatory process Effects 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
239000007928 intraperitoneal injection Substances 0.000 description 1
150000002561 ketenes Chemical class 0.000 description 1
DKYWVDODHFEZIM-UHFFFAOYSA-N ketoprofen Chemical compound OC(=O)C(C)C1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 DKYWVDODHFEZIM-UHFFFAOYSA-N 0.000 description 1
229960000991 ketoprofen Drugs 0.000 description 1
239000007788 liquid Substances 0.000 description 1
230000005923 long-lasting effect Effects 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
159000000003 magnesium salts Chemical class 0.000 description 1
208000007106 menorrhagia Diseases 0.000 description 1
238000004452 microanalysis Methods 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
238000002156 mixing Methods 0.000 description 1
USJMGSDXAXHGLS-UHFFFAOYSA-N n-(4,6-dioxo-5-propan-2-yl-1,3,5-triazinan-2-yl)-n-pentan-3-ylacetamide Chemical compound CCC(CC)N(C(C)=O)C1NC(=O)N(C(C)C)C(=O)N1 USJMGSDXAXHGLS-UHFFFAOYSA-N 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
229960002009 naproxen Drugs 0.000 description 1
CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical compound C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 description 1
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
231100000344 non-irritating Toxicity 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
229940094443 oxytocics prostaglandins Drugs 0.000 description 1
229960005489 paracetamol Drugs 0.000 description 1
229960001639 penicillamine Drugs 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
229960002895 phenylbutazone Drugs 0.000 description 1
VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
OIGNJSKKLXVSLS-VWUMJDOOSA-N prednisolone Chemical compound O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OIGNJSKKLXVSLS-VWUMJDOOSA-N 0.000 description 1
229960005205 prednisolone Drugs 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
230000002335 preservative effect Effects 0.000 description 1
DBABZHXKTCFAPX-UHFFFAOYSA-N probenecid Chemical compound CCCN(CCC)S(=O)(=O)C1=CC=C(C(O)=O)C=C1 DBABZHXKTCFAPX-UHFFFAOYSA-N 0.000 description 1
229960003081 probenecid Drugs 0.000 description 1
150000003180 prostaglandins Chemical class 0.000 description 1
238000000746 purification Methods 0.000 description 1
230000008707 rearrangement Effects 0.000 description 1
210000000664 rectum Anatomy 0.000 description 1
238000010992 reflux Methods 0.000 description 1
210000001625 seminal vesicle Anatomy 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
150000003431 steroids Chemical class 0.000 description 1
229910052682 stishovite Inorganic materials 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
229910052905 tridymite Inorganic materials 0.000 description 1
229940116269 uric acid Drugs 0.000 description 1
210000001215 vagina Anatomy 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
201000010653 vesiculitis Diseases 0.000 description 1
239000000341 volatile oil Substances 0.000 description 1
238000005303 weighing Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/40—Nitrogen atoms
- C07D251/42—One nitrogen atom
- C07D251/46—One nitrogen atom with oxygen or sulfur atoms attached to the two other ring carbon atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Public Health (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Veterinary Medicine (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Pain & Pain Management (AREA)
Rheumatology (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

NO780576A 1977-02-21 1978-02-20 Analogifremgangsmaate for fremstilling av farmakologisk aktive triazinderivater NO780576L (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB7183/77A GB1599518A (en)	1977-02-21	1977-02-21	1,3,5-triazine-2,6-diones and pharmaceutical compositions thereof

Publications (1)

Publication Number	Publication Date
NO780576L true NO780576L (no)	1978-08-22

Family

ID=9828208

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO780576A NO780576L (no)	1977-02-21	1978-02-20	Analogifremgangsmaate for fremstilling av farmakologisk aktive triazinderivater

Country Status (32)

Country	Link
US (1)	US4156002A (da)
JP (1)	JPS53105487A (da)
AR (1)	AR220120A1 (da)
AT (1)	AT358592B (da)
AU (1)	AU519803B2 (da)
BE (1)	BE864124A (da)
CA (1)	CA1117867A (da)
CH (1)	CH637646A5 (da)
CS (2)	CS208463B2 (da)
DD (1)	DD134091A5 (da)
DE (1)	DE2807381A1 (da)
DK (1)	DK67978A (da)
ES (3)	ES467170A1 (da)
FI (1)	FI64152C (da)
FR (1)	FR2381034A1 (da)
GB (1)	GB1599518A (da)
GR (1)	GR62157B (da)
HU (2)	HU182653B (da)
IE (1)	IE46650B1 (da)
IL (1)	IL54026A (da)
IT (1)	IT1158652B (da)
LU (1)	LU79092A1 (da)
MW (1)	MW478A1 (da)
NL (1)	NL7801921A (da)
NO (1)	NO780576L (da)
NZ (1)	NZ186406A (da)
PL (2)	PL107871B1 (da)
PT (1)	PT67668B (da)
SE (1)	SE440775B (da)
SU (2)	SU890976A3 (da)
ZA (1)	ZA78671B (da)
ZM (1)	ZM1878A1 (da)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2962124D1 (en) *	1978-05-26	1982-03-25	Ici Plc	Analgesic 6-acylaminotetrahydro-1,3,5-triazine-2,4-dione derivatives, pharmaceutical compositions thereof, and process for their manufacture
GB8629567D0 (en) *	1986-12-10	1987-01-21	Boots Co Plc	Therapeutic agents
US6348216B1 (en) *	1996-06-10	2002-02-19	Knoll Pharmaceutical Company	Ibuprofen and narcotic analgesic compositions
US6361794B1 (en)	1996-06-12	2002-03-26	Basf Corporation	Method of making ibuprofen and narcotic analgesic composition
SG173647A1 (en) *	2009-02-13	2011-10-28	Shionogi & Co	Novel triazine derivative and pharmaceutical composition containing same
US9718790B2 (en)	2010-08-10	2017-08-01	Shionogi & Co., Ltd.	Triazine derivative and pharmaceutical composition having an analgesic activity comprising the same
WO2012020742A1 (ja)	2010-08-10	2012-02-16	塩野義製薬株式会社	新規複素環誘導体およびそれらを含有する医薬組成物
JP6124351B2 (ja)	2012-02-09	2017-05-10	塩野義製薬株式会社	複素環および炭素環誘導体
TWI637949B (zh)	2013-06-14	2018-10-11	塩野義製藥股份有限公司	胺基三衍生物及含有其等之醫藥組合物
TW202302541A (zh) *	2021-03-17	2023-01-16	美商翰森生物有限責任公司	含氮雜環酮、其製備方法和醫藥用途

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
SE347973B (da) *	1965-07-21	1972-08-21	Takeda Chemical Industries Ltd
US4035365A (en) *	1973-11-01	1977-07-12	Imperial Chemical Industries Limited	Triazinediones
GB1543037A (en) *	1975-02-05	1979-03-28	Ici Ltd	Selective herbicidal triazine-diones
JPS5623425B2 (da) *	1973-11-09	1981-05-30

1977
- 1977-02-21 GB GB7183/77A patent/GB1599518A/en not_active Expired
1978
- 1978-02-02 IE IE217/78A patent/IE46650B1/en unknown
- 1978-02-03 ZA ZA00780671A patent/ZA78671B/xx unknown
- 1978-02-07 NZ NZ186406A patent/NZ186406A/en unknown
- 1978-02-07 CA CA000296415A patent/CA1117867A/en not_active Expired
- 1978-02-08 AU AU33112/78A patent/AU519803B2/en not_active Expired
- 1978-02-09 ZM ZM18/78A patent/ZM1878A1/xx unknown
- 1978-02-12 IL IL54026A patent/IL54026A/xx unknown
- 1978-02-13 US US05/877,391 patent/US4156002A/en not_active Expired - Lifetime
- 1978-02-15 DK DK67978A patent/DK67978A/da not_active Application Discontinuation
- 1978-02-15 HU HU78IE836A patent/HU182653B/hu unknown
- 1978-02-15 HU HU78IE826A patent/HU176980B/hu unknown
- 1978-02-15 PL PL1978204641A patent/PL107871B1/pl unknown
- 1978-02-15 PL PL1978211162A patent/PL109995B1/pl unknown
- 1978-02-16 PT PT67668A patent/PT67668B/pt unknown
- 1978-02-16 GR GR55469A patent/GR62157B/el unknown
- 1978-02-17 CS CS781045A patent/CS208463B2/cs unknown
- 1978-02-17 FI FI780529A patent/FI64152C/fi not_active IP Right Cessation
- 1978-02-20 FR FR7804760A patent/FR2381034A1/fr active Granted
- 1978-02-20 NO NO780576A patent/NO780576L/no unknown
- 1978-02-20 BE BE185309A patent/BE864124A/xx not_active IP Right Cessation
- 1978-02-20 SU SU782587045A patent/SU890976A3/ru active
- 1978-02-20 LU LU79092A patent/LU79092A1/xx unknown
- 1978-02-20 SE SE7801930A patent/SE440775B/sv not_active IP Right Cessation
- 1978-02-21 DE DE19782807381 patent/DE2807381A1/de not_active Ceased
- 1978-02-21 JP JP1898978A patent/JPS53105487A/ja active Pending
- 1978-02-21 DD DD78203776A patent/DD134091A5/xx unknown
- 1978-02-21 AT AT127178A patent/AT358592B/de not_active IP Right Cessation
- 1978-02-21 NL NL7801921A patent/NL7801921A/xx not_active Application Discontinuation
- 1978-02-21 AR AR271164A patent/AR220120A1/es active
- 1978-02-21 MW MW4/78A patent/MW478A1/xx unknown
- 1978-02-21 CH CH186378A patent/CH637646A5/de not_active IP Right Cessation
- 1978-02-21 ES ES467170A patent/ES467170A1/es not_active Expired
- 1978-02-21 IT IT20500/78A patent/IT1158652B/it active
- 1978-12-28 ES ES476427A patent/ES476427A1/es not_active Expired
- 1978-12-28 ES ES476428A patent/ES476428A1/es not_active Expired
1979
- 1979-02-13 SU SU792723300A patent/SU867303A3/ru active
1980
- 1980-05-22 CS CS803610A patent/CS208464B2/cs unknown

Also Published As

Publication number	Publication date
DD134091A5 (de)	1979-02-07
CS208464B2 (en)	1981-09-15
PL109995B1 (en)	1980-06-30
MW478A1 (en)	1980-02-13
PT67668A (en)	1978-03-01
DE2807381A1 (de)	1978-08-24
ES476428A1 (es)	1979-05-01
SE7801930L (sv)	1978-08-22
ES467170A1 (es)	1979-08-16
IT1158652B (it)	1987-02-25
BE864124A (fr)	1978-08-21
FR2381034B1 (da)	1980-09-19
NL7801921A (nl)	1978-08-23
AU519803B2 (en)	1981-12-24
FI64152B (fi)	1983-06-30
NZ186406A (en)	1984-08-24
ES476427A1 (es)	1979-04-16
CA1117867A (en)	1982-02-09
HU182653B (en)	1984-02-28
PL204641A1 (pl)	1978-12-04
GR62157B (en)	1979-03-01
AT358592B (de)	1980-09-25
PL107871B1 (pl)	1980-03-31
SE440775B (sv)	1985-08-19
IE780217L (en)	1978-08-21
ZA78671B (en)	1978-12-27
ATA127178A (de)	1980-02-15
IL54026A (en)	1983-06-15
JPS53105487A (en)	1978-09-13
IE46650B1 (en)	1983-08-10
HU176980B (hu)	1981-06-28
AU3311278A (en)	1979-08-16
CS208463B2 (en)	1981-09-15
GB1599518A (en)	1981-10-07
LU79092A1 (fr)	1979-05-25
ZM1878A1 (en)	1981-06-22
SU867303A3 (ru)	1981-09-23
US4156002A (en)	1979-05-22
CH637646A5 (de)	1983-08-15
FI780529A7 (fi)	1978-08-22
DK67978A (da)	1978-08-22
SU890976A3 (ru)	1981-12-15
FI64152C (fi)	1983-10-10
AR220120A1 (es)	1980-10-15
PT67668B (en)	1979-09-20
IT7820500A0 (it)	1978-02-21
FR2381034A1 (fr)	1978-09-15

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JPS5814435B2 (ja)	1983-03-18	プロスタグランジン「きつ」抗剤としての４↓−ピロン誘導体
JPH01106839A (ja)	1989-04-24	アルカジエン誘導体類、それらの製造、およびそれらを含有している薬学的組成物
CN115322077B (zh)	2024-03-15	一类烷基酚类化合物及其制备方法
JP3694774B2 (ja)	2005-09-14	フェニルカルボン酸誘導体
JPS6341460A (ja)	1988-02-22	新規なジヒドロピリジン誘導体
JPH02169571A (ja)	1990-06-29	置換アリルアミン誘導体
JPS58188868A (ja)	1983-11-04	オレフイン系ベンズイミダゾ−ル類
IE883598L (en)	1989-06-02	Acyl derivatives of hydroxy pyrimidines
BE897208A (fr)	1984-01-04	Composes de carbostyryle
US5578596A (en)	1996-11-26	2-alkoxy-5,6,7,8-tetrahydroquinoxaline derivatives, and production method and use thereof
US4612317A (en)	1986-09-16	Tetrahydro-β-carboline dithioic acid derivatives and treatment of liver diseases
US3657271A (en)	1972-04-18	1 3-dimethyl-5-methylamino-8-phenylpyrazolo(4 3-e)(1 4)diazepine
NO174928B (no)	1994-04-25	Analogifremgangsmåte for fremstilling av terapeutisk aktive enoletere av 6-klor-4-hydroksy-2-metyl-N-(2-pyridyl)-2H-tieno(2,3-e)-1,2-tiazin-3-karboksylsyreamid-1,1-dioksyd
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