AP914A - Substituted diamino-1,3,5-triazine derivatives. - Google Patents

Substituted diamino-1,3,5-triazine derivatives. Download PDF

Info

Publication number: AP914A
Authority: AP; ARIPO
Prior art keywords: formula; amino; compound; independently selected; aminocarbonyl
Prior art date: 1996-10-01

Application number

APAP/P/1997/001109A

Other languages

English (en)

Other versions

AP9701109A0 (en

Inventor

Michael Joseph Kukla

Donald William Ludovici

Paul Adriaan Jan Janssen

Henri Emiel Lodewijk Moereels

Jan Heeres

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.)

1996-10-01

Filing date

1997-09-29

Publication date

2000-12-18

1997-09-29 Application filed by Janssen Pharmaceutica Nv filed Critical Janssen Pharmaceutica Nv

1997-10-31 Publication of AP9701109A0 publication Critical patent/AP9701109A0/xx

2000-12-18 Application granted granted Critical

2000-12-18 Publication of AP914A publication Critical patent/AP914A/en

Links

VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical class NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 title description 3
150000001875 compounds Chemical class 0.000 claims abstract description 142
-1 nitro, amino Chemical group 0.000 claims abstract description 137
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 47
239000001257 hydrogen Substances 0.000 claims abstract description 40
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 40
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 28
125000004953 trihalomethyl group Chemical group 0.000 claims abstract description 23
150000002431 hydrogen Chemical group 0.000 claims abstract description 22
150000003839 salts Chemical class 0.000 claims abstract description 22
239000002253 acid Substances 0.000 claims abstract description 21
241000725303 Human immunodeficiency virus Species 0.000 claims abstract description 19
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 16
238000002360 preparation method Methods 0.000 claims abstract description 14
239000003814 drug Substances 0.000 claims abstract description 12
238000011282 treatment Methods 0.000 claims abstract description 12
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 11
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 8
238000004519 manufacturing process Methods 0.000 claims abstract description 6
125000002757 morpholinyl group Chemical group 0.000 claims abstract description 6
125000003386 piperidinyl group Chemical group 0.000 claims abstract description 6
125000000719 pyrrolidinyl group Chemical group 0.000 claims abstract description 6
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims abstract description 5
208000015181 infectious disease Diseases 0.000 claims abstract description 5
125000001475 halogen functional group Chemical group 0.000 claims abstract 14
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 41
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 39
125000001424 substituent group Chemical group 0.000 claims description 32
239000012442 inert solvent Substances 0.000 claims description 17
125000001041 indolyl group Chemical group 0.000 claims description 16
238000000034 method Methods 0.000 claims description 16
238000006243 chemical reaction Methods 0.000 claims description 12
230000000798 anti-retroviral effect Effects 0.000 claims description 9
239000002585 base Substances 0.000 claims description 9
239000008194 pharmaceutical composition Substances 0.000 claims description 8
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
239000004480 active ingredient Substances 0.000 claims description 6
239000003937 drug carrier Substances 0.000 claims description 6
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
125000001544 thienyl group Chemical group 0.000 claims description 5
125000006239 protecting group Chemical group 0.000 claims description 4
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 3
230000036436 anti-hiv Effects 0.000 claims description 3
YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 claims description 2
239000003513 alkali Substances 0.000 claims description 2
150000001412 amines Chemical class 0.000 claims description 2
238000010511 deprotection reaction Methods 0.000 claims description 2
230000009466 transformation Effects 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 8
239000012458 free base Substances 0.000 claims 1
GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims 1
239000000203 mixture Substances 0.000 abstract description 32
125000004356 hydroxy functional group Chemical group O* 0.000 abstract description 14
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract description 2
125000000753 cycloalkyl group Chemical group 0.000 abstract 1
239000000543 intermediate Substances 0.000 description 51
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 36
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 35
ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 29
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RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
125000005843 halogen group Chemical group 0.000 description 19
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BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 18
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125000004432 carbon atom Chemical group C* 0.000 description 11
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 11
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229910000027 potassium carbonate Inorganic materials 0.000 description 9
150000003254 radicals Chemical class 0.000 description 9
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YBAZINRZQSAIAY-UHFFFAOYSA-N 4-aminobenzonitrile Chemical compound NC1=CC=C(C#N)C=C1 YBAZINRZQSAIAY-UHFFFAOYSA-N 0.000 description 5
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NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
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ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 4
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JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-diisopropylethylamine Substances CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
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229940079593 drug Drugs 0.000 description 4
239000003480 eluent Substances 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
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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 3
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VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
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239000002775 capsule Substances 0.000 description 3
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VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 3
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HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 3
241001430294 unidentified retrovirus Species 0.000 description 3
HBOMLICNUCNMMY-XLPZGREQSA-N zidovudine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](N=[N+]=[N-])C1 HBOMLICNUCNMMY-XLPZGREQSA-N 0.000 description 3
FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 description 2
JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 2
OXTFFPWHLJQPEE-UHFFFAOYSA-N 2-(2,6-dichlorophenyl)ethanimidamide Chemical compound NC(=N)CC1=C(Cl)C=CC=C1Cl OXTFFPWHLJQPEE-UHFFFAOYSA-N 0.000 description 2
NAFOOGOADMAIJN-UHFFFAOYSA-N 2-anilino-2-phenylacetamide Chemical compound C=1C=CC=CC=1C(C(=O)N)NC1=CC=CC=C1 NAFOOGOADMAIJN-UHFFFAOYSA-N 0.000 description 2
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125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
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125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 2
SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 2
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Classifications

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- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4196—1,2,4-Triazoles
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/04—Immunostimulants
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- 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
- C07D251/14—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 hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/16—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 hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom
- C07D251/18—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 hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom with nitrogen atoms directly attached to the two other ring carbon atoms, e.g. guanamines
- 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
- C07D251/48—Two nitrogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom 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
- C07D307/32—Oxygen atoms
- C07D307/33—Oxygen atoms in position 2, the oxygen atom being in its keto or unsubstituted enol form
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Medicinal Chemistry (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Pharmacology & Pharmacy (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
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Immunology (AREA)
Oncology (AREA)
Communicable Diseases (AREA)
Tropical Medicine & Parasitology (AREA)
AIDS & HIV (AREA)
Molecular Biology (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Epidemiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)

APAP/P/1997/001109A 1996-10-01 1997-09-29 Substituted diamino-1,3,5-triazine derivatives. AP914A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US2726096P	1996-10-01	1996-10-01

Publications (2)

Publication Number	Publication Date
AP9701109A0 AP9701109A0 (en)	1997-10-31
AP914A true AP914A (en)	2000-12-18

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APAP/P/1997/001109A AP914A (en)	1996-10-01	1997-09-29	Substituted diamino-1,3,5-triazine derivatives.

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EP (1)	EP0834507B1 (id)
JP (1)	JP4127882B2 (id)
KR (1)	KR100478846B1 (id)
CN (1)	CN1083438C (id)
AP (1)	AP914A (id)
AR (1)	AR008864A1 (id)
AT (1)	ATE267179T1 (id)
AU (1)	AU740809B2 (id)
BR (1)	BR9704937A (id)
CA (1)	CA2216486A1 (id)
CZ (1)	CZ297333B6 (id)
DE (1)	DE69729153T2 (id)
DK (1)	DK0834507T3 (id)
EE (1)	EE03826B1 (id)
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HR (1)	HRP970526B1 (id)
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ID (1)	ID19599A (id)
IL (1)	IL121849A (id)
MY (1)	MY123803A (id)
NO (1)	NO311614B1 (id)
NZ (1)	NZ328854A (id)
OA (1)	OA10620A (id)
PL (1)	PL190155B1 (id)
PT (1)	PT834507E (id)
RU (1)	RU2186774C2 (id)
SG (1)	SG53075A1 (id)
SI (1)	SI0834507T1 (id)
SK (1)	SK285241B6 (id)
TR (1)	TR199701070A2 (id)
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ZA (1)	ZA978766B (id)

Families Citing this family (40)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NO311614B1 (no)	1996-10-01	2001-12-17	Janssen Pharmaceutica Nv	Substituerte diamino-1,3,5-triazinderivater
CN1207290C (zh)	1998-11-10	2005-06-22	詹森药业有限公司	2,4－二取代三嗪衍生物
ID28376A (id)	1998-11-10	2001-05-17	Janssen Pharmaceutica Nv	Pirimidina yang menghambat replikasi hiv
DE19945982A1 (de)	1999-09-24	2001-03-29	Knoll Ag	Geschwindigkeitsbestimmte Partikel
TR200200763T2 (tr)	1999-09-24	2003-09-22	Janssen Pharmaceutica N.V.	Antiviral bileşimler
CA2396693A1 (en) *	1999-12-28	2001-07-05	Stephen T. Wrobleski	Cytokine, especially tnf-alpha, inhibitors
US6906067B2 (en)	1999-12-28	2005-06-14	Bristol-Myers Squibb Company	N-heterocyclic inhibitors of TNF-α expression
US7034019B2 (en)	2000-05-08	2006-04-25	Janssen Pharmaceutica N.V.	Prodrugs of HIV replication inhibiting pyrimidines
CA2406562C (en)	2000-05-08	2009-09-15	Janssen Pharmaceutica N.V.	Hiv replication inhibiting pyrimidines and triazines
JP2004525109A (ja)	2001-02-15	2004-08-19	キング・ファーマシューティカルズ・インコーポレイティッド	安定化された甲状腺ホルモン医薬組成物、及びその製法
HUP0401712A3 (en) *	2001-06-26	2009-06-29	Bristol Myers Squibb Co	N-heterocyclic inhibitors of tnf-alpha and pharmaceutical compositions containing them
US6958211B2 (en)	2001-08-08	2005-10-25	Tibotech Bvba	Methods of assessing HIV integrase inhibitor therapy
US7101569B2 (en)	2001-08-14	2006-09-05	Franz G Andrew	Methods of administering levothyroxine pharmaceutical compositions
IL161662A0 (en)	2001-11-01	2004-09-27	Janssen Pharmaceutica Nv	Heteroaryl amines as glycogen synthase kinase 3 beta inhibitors (gsk3 inhibitors)
AU2002363174B2 (en)	2001-11-01	2008-09-25	Janssen Pharmaceutica N.V.	Amide derivatives as glycogen synthase kinase 3-beta inhibitors
CN100349887C (zh)	2002-05-16	2007-11-21	西托维亚公司	取代的4－芳基－4h－吡咯并[2,3－h]色烯和类似物及其药物组合物和用途
US7476741B2 (en) *	2002-05-16	2009-01-13	Cytovia, Inc.	Substituted 4H-chromens, 2H-chromenes, chromans and analogs as activators of caspases and inducers of apoptosis and the use thereof
AU2002350719A1 (en)	2002-11-29	2004-06-23	Janssen Pharmaceutica N.V.	Pharmaceutical compositions comprising a basic respectively acidic drug compound, a surfactant and a physiologically tolerable water-soluble acid respectively base
CN102503903A (zh)	2003-02-07	2012-06-20	詹森药业有限公司	抑制hiv的1,2,4-三嗪
CL2004000303A1 (es)	2003-02-20	2005-04-08	Tibotec Pharm Ltd	Compuestos derivados de pirimidinas y triazinas; proceso de preparacion; composicion farmaceutica; y su uso para inhibir la replicacion del vih.
WO2005003103A2 (en) *	2003-06-30	2005-01-13	Astrazeneca Ab	2, 4, 6-tri-substituted 6-membered heterocycles and their use in the treatment of neurodegenerative diseases
AU2005271161B2 (en)	2004-08-10	2011-05-12	Janssen Pharmaceutica N.V.	HIV inhibiting 1,2,4-triazin-6-one derivatives
EP1786787A4 (en) *	2004-09-03	2009-07-22	Prometic Biosciences Inc	2,4,6-TRIAMINO-S-TRIAZINE COMPOUNDS RELATED TO THE TAIL (Fc) PART OF IMMUNOGLOBULINS AND THEIR USE
ATE520672T1 (de)	2004-09-30	2011-09-15	Tibotec Pharm Ltd	Hiv-hemmende 5-carbo- oder heterozyklisch substituierte pyrimidine
ATE542802T1 (de)	2004-09-30	2012-02-15	Tibotec Pharm Ltd	Hiv-inhibierende 5-substituierte pyrimidine
US8575342B2 (en)	2004-09-30	2013-11-05	Tibotech Pharmaceuticals Ltd.	HIV inhibiting 5-heterocyclyl pyrimidines
BRPI0517272A (pt)	2004-10-29	2008-10-07	Tibotec Pharm Ltd	derivados de pirimidina bicìclicos de inibição de hiv
EA015890B1 (ru)	2005-06-14	2011-12-30	Тайджен Байотекнолоджи Ко. Лтд.	Производные пиримидина
US8193206B2 (en)	2005-06-14	2012-06-05	Taigen Biotechnology Co., Ltd.	Pyrimidine compounds
AU2007233737B2 (en)	2006-03-30	2012-11-29	Janssen Sciences Ireland Uc	HIV inhibiting 5-amido substituted pyrimidines
US8318736B2 (en)	2006-12-29	2012-11-27	Janssen R&D Ireland	HIV inhibiting 5,6-substituted pyrimidines
US9006243B2 (en)	2006-12-29	2015-04-14	Janssen R&D Ireland	HIV inhibiting 6-substituted pyrimidines
WO2008131547A1 (en)	2007-04-30	2008-11-06	Prometic Biosciences Inc.	'triazine derivatives, compositions containing such derivatives, and methods of treatment of cancer and autoimmune diseases using such derivatives'
AU2008355098B2 (en) *	2008-04-21	2012-11-15	Gpcr Therapeutics, Inc	Heterocyclic compounds
WO2010056847A2 (en)	2008-11-13	2010-05-20	Taigen Biotechnology Co., Ltd.	Lyophilization formulation
US9058223B2 (en) *	2011-04-22	2015-06-16	Microsoft Technology Licensing Llc	Parallel entropy encoding on GPU
JP6479667B2 (ja) *	2012-10-24	2019-03-06	ビーエーエスエフソシエタス・ヨーロピアＢａｓｆＳｅ	除草性アジン
US10941122B2 (en) *	2014-04-11	2021-03-09	Basf Se	Diaminotriazine derivatives as herbicides
WO2016059647A2 (en) *	2014-10-13	2016-04-21	SHRI CHHATRAPTI SHIVAJI COLLEGE Maharashtra, India)	Triaminotriazine picolinonitrile derivatives as potent reverse transcriptase inhibitor of hiv-1
CN105837525B (zh) *	2016-03-25	2019-05-28	浙江工业大学	2,4-二胺-1,3,5-三嗪类化合物及其制备方法与应用

Citations (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2309663A (en) *		1943-01-26		Process fok preparing substituted
WO1995010506A1 (en) *	1993-10-12	1995-04-20	The Du Pont Merck Pharmaceutical Company	1n-alkyl-n-arylpyrimidinamines and derivatives thereof

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE226474C (id)
US2817814A (en)	1953-08-13	1957-12-24	Gen Electric	Corona detection probe
GB771327A (en)	1953-10-26	1957-03-27	Monsanto Chemicals	Production of heat hardenable melamine-formaldehyde condensation products
US2817614A (en) *	1953-10-26	1957-12-24	Monsanto Chemicals	Internally plasticized melamine resins and laminates made therewith
JPS4927592B1 (id) *	1970-05-13	1974-07-18
GB1390235A (en)	1971-08-07	1975-04-09	Kakenyaku Kako Kk	2-amino-4,6substituted-s triazines and methods for their preparation
DE3724379A1 (de) *	1987-07-23	1989-02-02	Bayer Ag	Verfahren zur herstellung feinteiliger magnetischer hexaferritpigmente
EP0411153B1 (en) *	1989-02-20	1996-09-11	Idemitsu Kosan Company Limited	Triazine derivative and herbicide containing the same as active ingredient
CA2123402A1 (en) *	1991-11-12	1993-05-27	Jotham W. Coe	Triazine derivatives for enhancing antitumor activity
US5516775A (en)	1992-08-31	1996-05-14	Ciba-Geigy Corporation	Further use of pyrimidine derivatives
NO311614B1 (no) *	1996-10-01	2001-12-17	Janssen Pharmaceutica Nv	Substituerte diamino-1,3,5-triazinderivater

1997
- 1997-09-22 NO NO19974368A patent/NO311614B1/no unknown
- 1997-09-23 SG SG1997003520A patent/SG53075A1/en unknown
- 1997-09-23 CZ CZ0299397A patent/CZ297333B6/cs not_active IP Right Cessation
- 1997-09-24 AT AT97202917T patent/ATE267179T1/de not_active IP Right Cessation
- 1997-09-24 SI SI9730663T patent/SI0834507T1/xx unknown
- 1997-09-24 PT PT97202917T patent/PT834507E/pt unknown
- 1997-09-24 EP EP97202917A patent/EP0834507B1/en not_active Expired - Lifetime
- 1997-09-24 DE DE69729153T patent/DE69729153T2/de not_active Expired - Fee Related
- 1997-09-24 ES ES97202917T patent/ES2221679T3/es not_active Expired - Lifetime
- 1997-09-24 DK DK97202917T patent/DK0834507T3/da active
- 1997-09-25 CA CA002216486A patent/CA2216486A1/en not_active Abandoned
- 1997-09-26 EE EE9700253A patent/EE03826B1/xx not_active IP Right Cessation
- 1997-09-26 AU AU39266/97A patent/AU740809B2/en not_active Ceased
- 1997-09-26 NZ NZ328854A patent/NZ328854A/xx unknown
- 1997-09-26 US US08/938,602 patent/US6380194B1/en not_active Expired - Fee Related
- 1997-09-29 ID IDP973312A patent/ID19599A/id unknown
- 1997-09-29 MY MYPI97004540A patent/MY123803A/en unknown
- 1997-09-29 AP APAP/P/1997/001109A patent/AP914A/en active
- 1997-09-29 KR KR1019970049662A patent/KR100478846B1/ko not_active Expired - Fee Related
- 1997-09-29 SK SK1319-97A patent/SK285241B6/sk unknown
- 1997-09-29 IL IL12184997A patent/IL121849A/xx not_active IP Right Cessation
- 1997-09-29 JP JP27938797A patent/JP4127882B2/ja not_active Expired - Fee Related
- 1997-09-30 HU HU9701596A patent/HU225270B1/hu not_active IP Right Cessation
- 1997-09-30 AR ARP970104503A patent/AR008864A1/es active IP Right Grant
- 1997-09-30 TW TW086114172A patent/TW411335B/zh not_active IP Right Cessation
- 1997-09-30 BR BR9704937-9A patent/BR9704937A/pt not_active Application Discontinuation
- 1997-09-30 RU RU97116200/04A patent/RU2186774C2/ru not_active IP Right Cessation
- 1997-09-30 TR TR97/01070A patent/TR199701070A2/xx unknown
- 1997-09-30 ZA ZA978766A patent/ZA978766B/xx unknown
- 1997-09-30 PL PL97322369A patent/PL190155B1/pl not_active IP Right Cessation
- 1997-09-30 CN CN97121454A patent/CN1083438C/zh not_active Expired - Fee Related
- 1997-09-30 HR HR970526A patent/HRP970526B1/xx not_active IP Right Cessation
- 1997-10-01 OA OA70094A patent/OA10620A/en unknown
2001
- 2001-11-15 US US10/002,456 patent/US6858609B2/en not_active Expired - Fee Related
2003
- 2003-03-26 US US10/397,760 patent/US6962916B2/en not_active Expired - Fee Related
2005
- 2005-08-12 US US11/203,325 patent/US7449575B2/en not_active Expired - Fee Related

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2309663A (en) *		1943-01-26		Process fok preparing substituted
WO1995010506A1 (en) *	1993-10-12	1995-04-20	The Du Pont Merck Pharmaceutical Company	1n-alkyl-n-arylpyrimidinamines and derivatives thereof

Also Published As

Publication number	Publication date
DE69729153T2 (de)	2005-01-27
NO974368D0 (no)	1997-09-22
RU2186774C2 (ru)	2002-08-10
MY123803A (en)	2006-06-30
CZ297333B6 (cs)	2006-11-15
ATE267179T1 (de)	2004-06-15
US20020147181A1 (en)	2002-10-10
CZ299397A3 (cs)	1998-11-11
TW411335B (en)	2000-11-11
IL121849A0 (en)	1998-02-22
US6858609B2 (en)	2005-02-22
EE9700253A (et)	1998-04-15
CN1083438C (zh)	2002-04-24
IL121849A (en)	2001-08-26
HU9701596D0 (en)	1997-11-28
SI0834507T1 (en)	2004-10-31
HK1009676A1 (en)	1999-06-04
US6962916B2 (en)	2005-11-08
NO311614B1 (no)	2001-12-17
US20060189614A1 (en)	2006-08-24
US7449575B2 (en)	2008-11-11
EE03826B1 (et)	2002-08-15
US6380194B1 (en)	2002-04-30
ZA978766B (en)	1999-03-30
JPH10114759A (ja)	1998-05-06
AU740809B2 (en)	2001-11-15
JP4127882B2 (ja)	2008-07-30
PL190155B1 (pl)	2005-11-30
AR008864A1 (es)	2000-02-23
DE69729153D1 (de)	2004-06-24
CA2216486A1 (en)	1998-04-01
AU3926697A (en)	1998-04-09
AP9701109A0 (en)	1997-10-31
MX9707511A (es)	1998-06-30
HUP9701596A3 (en)	2000-04-28
HU225270B1 (en)	2006-08-28
CN1180698A (zh)	1998-05-06
ID19599A (id)	1998-07-23
HRP970526A2 (en)	1998-10-31
HUP9701596A2 (hu)	1999-06-28
NZ328854A (en)	2000-10-27
SG53075A1 (en)	1998-09-28
HRP970526B1 (en)	2002-10-31
BR9704937A (pt)	2000-06-06
OA10620A (en)	2002-09-03
TR199701070A2 (xx)	1998-04-21
KR19980032428A (ko)	1998-07-25
EP0834507A1 (en)	1998-04-08
NO974368L (no)	1998-04-02
PL322369A1 (en)	1998-04-14
SK131997A3 (en)	1999-06-11
EP0834507B1 (en)	2004-05-19
SK285241B6 (sk)	2006-09-07
ES2221679T3 (es)	2005-01-01
KR100478846B1 (ko)	2006-06-13
PT834507E (pt)	2004-10-29
DK0834507T3 (da)	2004-09-06
US20030199473A1 (en)	2003-10-23

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EP0834507B1 (en)	2004-05-19	Substituted diamino-1,3,5-triazine derivatives
US20060049177A1 (en)	2006-03-09	Induction heating cooker
CA2406562C (en)	2009-09-15	Hiv replication inhibiting pyrimidines and triazines
EP1066269B1 (en)	2005-05-11	Trisubstituted 1,3,5-triazine derivatives for treatment of hiv infections
US20010011094A1 (en)	2001-08-02	HIV inhibiting pyrimidine derivatives
JP2002509920A (ja)	2002-04-02	Ｈｉｖを阻害するピリミジン誘導体
EP0945442A1 (en)	1999-09-29	Trisubstituted pyrimidine derivatives
HK1009676B (en)	2004-10-29	Substituted diamino-1,3,5-triazine derivatives
MXPA97007511A (en)	1998-10-30	Derivatives of diamino-1,3,5-triazina substituted, its preparation, compositions that contain them and the use of the mis
MXPA00009436A (en)	2001-07-09	Trisubstituted 1,3,5-triazine derivatives for treatment of hiv infections
HK1032394B (en)	2005-10-21	Trisubstituted 1,3,5-triazine derivatives for treatment of hiv infections