CA1057292A - 2-amino thiazoles - Google Patents

2-amino thiazoles

Info

Publication number: CA1057292A
Authority: CA; Canada
Prior art keywords: formula; derivative; atom; piperazino; cycloalkyl
Prior art date: 1973-05-16
Legal status (The legal status 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 status listed.): Expired

Application number

CA199,994A

Other languages

English (en)

French (fr)

Other versions

CA199994S (en

Inventor

Albert R. J. Castaigne

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Centre dEtudes pour lIndustrie Pharmaceutique

Original Assignee

Centre dEtudes pour lIndustrie Pharmaceutique

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.)

1973-05-16

Filing date

1974-05-15

Publication date

1979-06-26

1974-05-15 Application filed by Centre dEtudes pour lIndustrie Pharmaceutique filed Critical Centre dEtudes pour lIndustrie Pharmaceutique

1979-06-26 Application granted granted Critical

1979-06-26 Publication of CA1057292A publication Critical patent/CA1057292A/fr

Status Expired legal-status Critical Current

Links

150000003557 thiazoles Chemical class 0.000 title 1
-1 morpholino, methyl Chemical class 0.000 claims abstract description 30
238000000034 method Methods 0.000 claims abstract description 19
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 12
125000000217 alkyl group Chemical group 0.000 claims abstract description 10
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 10
229910052799 carbon Inorganic materials 0.000 claims abstract description 9
125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 9
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 8
239000001257 hydrogen Substances 0.000 claims abstract description 8
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
239000000126 substance Substances 0.000 claims abstract description 5
RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical class NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 claims abstract description 4
125000003342 alkenyl group Chemical group 0.000 claims abstract description 4
125000003118 aryl group Chemical group 0.000 claims abstract description 4
229910052717 sulfur Inorganic materials 0.000 claims abstract description 4
125000004434 sulfur atom Chemical group 0.000 claims abstract description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 3
125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 3
239000002904 solvent Substances 0.000 claims description 10
238000010438 heat treatment Methods 0.000 claims description 8
238000002360 preparation method Methods 0.000 claims description 8
239000002253 acid Substances 0.000 claims description 7
238000010992 reflux Methods 0.000 claims description 7
150000001412 amines Chemical class 0.000 claims description 6
150000002540 isothiocyanates Chemical class 0.000 claims description 6
239000002244 precipitate Substances 0.000 claims description 6
238000006243 chemical reaction Methods 0.000 claims description 5
125000005677 ethinylene group Chemical group [*:2]C#C[*:1] 0.000 claims description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
125000004429 atom Chemical group 0.000 claims description 4
150000001875 compounds Chemical class 0.000 claims description 4
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 4
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 3
229920006395 saturated elastomer Polymers 0.000 claims description 3
150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
238000009835 boiling Methods 0.000 claims description 2
238000001704 evaporation Methods 0.000 claims description 2
230000008020 evaporation Effects 0.000 claims description 2
PBMIETCUUSQZCG-UHFFFAOYSA-N n'-cyclohexylmethanediimine Chemical compound N=C=NC1CCCCC1 PBMIETCUUSQZCG-UHFFFAOYSA-N 0.000 claims description 2
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 description 2
238000011084 recovery Methods 0.000 claims description 2
238000000926 separation method Methods 0.000 claims description 2
125000004435 hydrogen atom Chemical class [H]* 0.000 claims 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims 1
238000006317 isomerization reaction Methods 0.000 claims 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
230000001052 transient effect Effects 0.000 claims 1
230000003110 anti-inflammatory effect Effects 0.000 abstract description 5
150000002431 hydrogen Chemical class 0.000 abstract description 3
230000003627 anti-cholesterol Effects 0.000 abstract 1
CBDKQYKMCICBOF-UHFFFAOYSA-N thiazoline Chemical compound C1CN=CS1 CBDKQYKMCICBOF-UHFFFAOYSA-N 0.000 description 33
HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 32
238000002844 melting Methods 0.000 description 30
230000008018 melting Effects 0.000 description 30
239000000243 solution Substances 0.000 description 24
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 18
239000000203 mixture Substances 0.000 description 16
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
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 15
235000012000 cholesterol Nutrition 0.000 description 13
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
239000013078 crystal Substances 0.000 description 6
239000006196 drop Substances 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
241000700159 Rattus Species 0.000 description 5
239000000047 product Substances 0.000 description 5
241001465754 Metazoa Species 0.000 description 4
206010030113 Oedema Diseases 0.000 description 4
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 4
239000003814 drug Substances 0.000 description 4
230000002757 inflammatory effect Effects 0.000 description 4
239000003826 tablet Substances 0.000 description 4
229920002261 Corn starch Polymers 0.000 description 3
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
108010058846 Ovalbumin Proteins 0.000 description 3
239000008280 blood Substances 0.000 description 3
210000004369 blood Anatomy 0.000 description 3
238000001816 cooling Methods 0.000 description 3
239000008120 corn starch Substances 0.000 description 3
230000007423 decrease Effects 0.000 description 3
XNMQEEKYCVKGBD-UHFFFAOYSA-N dimethylacetylene Natural products CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 description 3
230000000694 effects Effects 0.000 description 3
125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 description 3
150000002632 lipids Chemical class 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
229940092253 ovalbumin Drugs 0.000 description 3
239000003208 petroleum Substances 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
206010061218 Inflammation Diseases 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
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 2
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
229960000583 acetic acid Drugs 0.000 description 2
230000001154 acute effect Effects 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
239000002775 capsule Substances 0.000 description 2
DXHPZXWIPWDXHJ-UHFFFAOYSA-N carbon monosulfide Chemical compound [S+]#[C-] DXHPZXWIPWDXHJ-UHFFFAOYSA-N 0.000 description 2
239000000679 carrageenan Substances 0.000 description 2
235000010418 carrageenan Nutrition 0.000 description 2
229920001525 carrageenan Polymers 0.000 description 2
229940113118 carrageenan Drugs 0.000 description 2
239000012043 crude product Substances 0.000 description 2
PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
238000009472 formulation Methods 0.000 description 2
230000004927 fusion Effects 0.000 description 2
230000004054 inflammatory process Effects 0.000 description 2
238000010253 intravenous injection Methods 0.000 description 2
150000002500 ions Chemical class 0.000 description 2
239000008101 lactose Substances 0.000 description 2
231100000053 low toxicity Toxicity 0.000 description 2
239000011777 magnesium Substances 0.000 description 2
229910052749 magnesium Inorganic materials 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
239000000546 pharmaceutical excipient Substances 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000000829 suppository Substances 0.000 description 2
239000006188 syrup Substances 0.000 description 2
235000020357 syrup Nutrition 0.000 description 2
230000002110 toxicologic effect Effects 0.000 description 2
231100000027 toxicology Toxicity 0.000 description 2
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 2
ZYVPOPWDOQZIQC-UHFFFAOYSA-N 1,3-thiazole;dihydrochloride Chemical compound Cl.Cl.C1=CSC=N1 ZYVPOPWDOQZIQC-UHFFFAOYSA-N 0.000 description 1
VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 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
125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 1
244000215068 Acacia senegal Species 0.000 description 1
HSFWRNGVRCDJHI-UHFFFAOYSA-N Acetylene Chemical compound C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
241000153246 Anteros Species 0.000 description 1
COXVTLYNGOIATD-HVMBLDELSA-N CC1=C(C=CC(=C1)C1=CC(C)=C(C=C1)\N=N\C1=C(O)C2=C(N)C(=CC(=C2C=C1)S(O)(=O)=O)S(O)(=O)=O)\N=N\C1=CC=C2C(=CC(=C(N)C2=C1O)S(O)(=O)=O)S(O)(=O)=O Chemical compound CC1=C(C=CC(=C1)C1=CC(C)=C(C=C1)\N=N\C1=C(O)C2=C(N)C(=CC(=C2C=C1)S(O)(=O)=O)S(O)(=O)=O)\N=N\C1=CC=C2C(=CC(=C(N)C2=C1O)S(O)(=O)=O)S(O)(=O)=O COXVTLYNGOIATD-HVMBLDELSA-N 0.000 description 1
241001440267 Cyclodes Species 0.000 description 1
206010018092 Generalised oedema Diseases 0.000 description 1
229920000084 Gum arabic Polymers 0.000 description 1
240000006240 Linum usitatissimum Species 0.000 description 1
235000004431 Linum usitatissimum Nutrition 0.000 description 1
206010024769 Local reaction Diseases 0.000 description 1
206010048961 Localised oedema Diseases 0.000 description 1
229920000168 Microcrystalline cellulose Polymers 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
102100026933 Myelin-associated neurite-outgrowth inhibitor Human genes 0.000 description 1
208000037656 Respiratory Sounds Diseases 0.000 description 1
229920001800 Shellac Polymers 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
241000906446 Theraps Species 0.000 description 1
239000000205 acacia gum Substances 0.000 description 1
235000010489 acacia gum Nutrition 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
150000001346 alkyl aryl ethers Chemical class 0.000 description 1
239000003529 anticholesteremic agent Substances 0.000 description 1
230000003143 atherosclerotic effect Effects 0.000 description 1
230000037396 body weight Effects 0.000 description 1
210000000988 bone and bone Anatomy 0.000 description 1
IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
239000004203 carnauba wax Substances 0.000 description 1
235000013869 carnauba wax Nutrition 0.000 description 1
150000001768 cations Chemical class 0.000 description 1
235000013339 cereals Nutrition 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
230000001684 chronic effect Effects 0.000 description 1
125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
208000035475 disorder Diseases 0.000 description 1
230000002497 edematous effect Effects 0.000 description 1
125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 description 1
229960003699 evans blue Drugs 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
210000000548 hind-foot Anatomy 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
230000000260 hypercholesteremic effect Effects 0.000 description 1
239000005457 ice water Substances 0.000 description 1
229940102223 injectable solution Drugs 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
239000007928 intraperitoneal injection Substances 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000000644 isotonic solution Substances 0.000 description 1
150000003893 lactate salts Chemical class 0.000 description 1
239000007788 liquid Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
229910052753 mercury Inorganic materials 0.000 description 1
230000004060 metabolic process Effects 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
235000010981 methylcellulose Nutrition 0.000 description 1
229940016286 microcrystalline cellulose Drugs 0.000 description 1
235000019813 microcrystalline cellulose Nutrition 0.000 description 1
239000008108 microcrystalline cellulose Substances 0.000 description 1
238000002156 mixing Methods 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
201000008482 osteoarthritis Diseases 0.000 description 1
150000003891 oxalate salts Chemical class 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
230000002093 peripheral effect Effects 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
239000012071 phase Substances 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
230000000793 phophlogistic effect Effects 0.000 description 1
125000000719 pyrrolidinyl group Chemical group 0.000 description 1
206010037833 rales Diseases 0.000 description 1
239000000376 reactant Substances 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
210000002966 serum Anatomy 0.000 description 1
239000004208 shellac Substances 0.000 description 1
229940113147 shellac Drugs 0.000 description 1
235000013874 shellac Nutrition 0.000 description 1
ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
AZLXCBPKSXFMET-UHFFFAOYSA-M sodium 4-[(4-sulfophenyl)diazenyl]naphthalen-1-olate Chemical compound [Na+].C12=CC=CC=C2C(O)=CC=C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 AZLXCBPKSXFMET-UHFFFAOYSA-M 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
238000001356 surgical procedure Methods 0.000 description 1
208000011580 syndromic disease Diseases 0.000 description 1
150000003892 tartrate salts Chemical class 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
230000002792 vascular Effects 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1

Classifications

- 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
- C07D277/38—Nitrogen atoms
- C07D277/42—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
- 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
- C07D277/08—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D277/12—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D277/18—Nitrogen 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
- C07D277/38—Nitrogen atoms
- C07D277/40—Unsubstituted amino or imino radicals

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Thiazole And Isothizaole Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA199,994A 1973-05-16 1974-05-15 2-amino thiazoles Expired CA1057292A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FR7317698A FR2247234B1 (de)	1973-05-16	1973-05-16

Publications (1)

Publication Number	Publication Date
CA1057292A true CA1057292A (fr)	1979-06-26

Family

ID=9119403

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA199,994A Expired CA1057292A (fr)	1973-05-16	1974-05-15	2-amino thiazoles

Country Status (19)

Country	Link
JP (1)	JPS5030888A (de)
AT (1)	AT334894B (de)
BE (1)	BE814579A (de)
CA (1)	CA1057292A (de)
CH (1)	CH595364A5 (de)
DD (1)	DD112268A5 (de)
DE (1)	DE2423403A1 (de)
ES (1)	ES426206A1 (de)
FR (1)	FR2247234B1 (de)
GB (1)	GB1456257A (de)
HU (1)	HU169176B (de)
IL (1)	IL44845A (de)
NL (1)	NL7406490A (de)
PL (1)	PL91265B1 (de)
RO (1)	RO66055A (de)
SE (1)	SE429653B (de)
SU (1)	SU535906A3 (de)
YU (1)	YU36712B (de)
ZA (1)	ZA743048B (de)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4018786A (en) *	1974-08-06	1977-04-19	Centre D'etudes Pour L'industrie Pharmaceutique	2-Aminothiazolines and a process for preparation thereof
GB2550950B (en) *	2016-06-02	2021-03-10	Dixon Barnaby	Puppet

1973
- 1973-05-16 RO RO7378803A patent/RO66055A/ro unknown
- 1973-05-16 FR FR7317698A patent/FR2247234B1/fr not_active Expired
1974
- 1974-05-05 SU SU742027407A patent/SU535906A3/ru active
- 1974-05-06 BE BE143945A patent/BE814579A/xx not_active IP Right Cessation
- 1974-05-11 ES ES426206A patent/ES426206A1/es not_active Expired
- 1974-05-13 ZA ZA00743048A patent/ZA743048B/xx unknown
- 1974-05-14 DD DD178502A patent/DD112268A5/xx unknown
- 1974-05-14 DE DE2423403A patent/DE2423403A1/de not_active Withdrawn
- 1974-05-15 NL NL7406490A patent/NL7406490A/xx not_active Application Discontinuation
- 1974-05-15 CA CA199,994A patent/CA1057292A/fr not_active Expired
- 1974-05-15 SE SE7406478A patent/SE429653B/xx unknown
- 1974-05-15 CH CH665274A patent/CH595364A5/xx not_active IP Right Cessation
- 1974-05-15 GB GB2161474A patent/GB1456257A/en not_active Expired
- 1974-05-15 AT AT403574A patent/AT334894B/de not_active IP Right Cessation
- 1974-05-15 HU HUCE999A patent/HU169176B/hu unknown
- 1974-05-15 YU YU1332/74A patent/YU36712B/xx unknown
- 1974-05-16 JP JP49053961A patent/JPS5030888A/ja active Pending
- 1974-05-16 PL PL1974171105A patent/PL91265B1/pl unknown
- 1974-05-16 IL IL44845A patent/IL44845A/en unknown

Also Published As

Publication number	Publication date
FR2247234A1 (de)	1975-05-09
YU36712B (en)	1984-08-31
SE429653B (sv)	1983-09-19
CH595364A5 (de)	1978-02-15
RO66055A (ro)	1981-07-30
IL44845A (en)	1977-06-30
DE2423403A1 (de)	1974-12-05
PL91265B1 (de)	1977-02-28
HU169176B (de)	1976-10-28
GB1456257A (en)	1976-11-24
ZA743048B (en)	1975-05-28
YU133274A (en)	1982-06-18
DD112268A5 (de)	1975-04-05
AT334894B (de)	1977-02-10
SU535906A3 (ru)	1976-11-15
AU6889574A (en)	1975-11-20
NL7406490A (de)	1974-11-19
ATA403574A (de)	1976-06-15
BE814579A (fr)	1974-09-02
FR2247234B1 (de)	1977-01-21
ES426206A1 (es)	1976-07-01
JPS5030888A (de)	1975-03-27
IL44845A0 (en)	1974-07-31

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EP0173585B1 (de)	1988-08-24	Arzneimittel auf Basis von Piperidinderivaten, Piperidinderivate und Verfahren zu ihrer Herstellung
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