JP2014512331A5 - - Google Patents
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- Publication number
- JP2014512331A5 JP2014512331A5 JP2013545050A JP2013545050A JP2014512331A5 JP 2014512331 A5 JP2014512331 A5 JP 2014512331A5 JP 2013545050 A JP2013545050 A JP 2013545050A JP 2013545050 A JP2013545050 A JP 2013545050A JP 2014512331 A5 JP2014512331 A5 JP 2014512331A5
- Authority
- JP
- Japan
- Prior art keywords
- ingenol
- carboxylate
- alkyl
- methyl
- pharmaceutically acceptable
- Prior art date
- 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.)
- Granted
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- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 41
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 39
- 229910003827 NRaRb Inorganic materials 0.000 claims description 38
- 125000001072 heteroaryl group Chemical group 0.000 claims description 38
- 125000003118 aryl group Chemical group 0.000 claims description 35
- 150000001875 compounds Chemical class 0.000 claims description 25
- 150000003839 salts Chemical class 0.000 claims description 24
- 239000012453 solvate Substances 0.000 claims description 24
- 229910052736 halogen Inorganic materials 0.000 claims description 23
- -1 cyano, hydroxy Chemical group 0.000 claims description 21
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 20
- 125000001424 substituent group Chemical group 0.000 claims description 20
- 150000002367 halogens Chemical class 0.000 claims description 18
- 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 15
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- 125000004366 heterocycloalkenyl group Chemical group 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 8
- 125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims description 8
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- VEBVPUXQAPLADL-UHFFFAOYSA-N Ingenol Natural products C1=C(CO)C(O)C2(O)C(O)C(C)=CC32C(C)CC2C(C)(C)C2C1C3=O VEBVPUXQAPLADL-UHFFFAOYSA-N 0.000 claims 105
- VEBVPUXQAPLADL-POYOOMFHSA-N ingenol Chemical compound C1=C(CO)[C@@H](O)[C@]2(O)[C@@H](O)C(C)=C[C@]32[C@H](C)C[C@H]2C(C)(C)[C@H]2[C@H]1C3=O VEBVPUXQAPLADL-POYOOMFHSA-N 0.000 claims 105
- 239000003814 drug Substances 0.000 claims 5
- 125000005843 halogen group Chemical group 0.000 claims 5
- 206010004146 Basal cell carcinoma Diseases 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 206010041823 squamous cell carcinoma Diseases 0.000 claims 4
- VVICVFRJARFOHY-UHFFFAOYSA-N 2-(trifluoromethyl)pyrrolidine-1-carboxylic acid Chemical compound OC(=O)N1CCCC1C(F)(F)F VVICVFRJARFOHY-UHFFFAOYSA-N 0.000 claims 3
- 206010028980 Neoplasm Diseases 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- GLIUZQUNUNICGS-XUBYYPQFSA-N 3b100vj4zw Chemical compound CCC1=NOC(CC)=C1C(=O)O[C@@H]1[C@@]2(O)[C@H](O)C(CO)=C[C@H](C3=O)[C@H](C4(C)C)[C@H]4C[C@@H](C)[C@]23C=C1C GLIUZQUNUNICGS-XUBYYPQFSA-N 0.000 claims 2
- 206010051999 Anogenital dysplasia Diseases 0.000 claims 2
- 206010059313 Anogenital warts Diseases 0.000 claims 2
- 206010008263 Cervical dysplasia Diseases 0.000 claims 2
- 208000000907 Condylomata Acuminata Diseases 0.000 claims 2
- 208000009608 Papillomavirus Infections Diseases 0.000 claims 2
- 206010054932 Vulvar dysplasia Diseases 0.000 claims 2
- 208000018777 Vulvar intraepithelial neoplasia Diseases 0.000 claims 2
- 208000000260 Warts Diseases 0.000 claims 2
- 208000009621 actinic keratosis Diseases 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 208000007951 cervical intraepithelial neoplasia Diseases 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 239000002537 cosmetic Substances 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 206010020718 hyperplasia Diseases 0.000 claims 2
- 230000003902 lesion Effects 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 208000017520 skin disease Diseases 0.000 claims 2
- 201000010153 skin papilloma Diseases 0.000 claims 2
- 125000000335 thiazolyl group Chemical group 0.000 claims 2
- 125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 claims 1
- MIKOZAZRIJWWRE-UHFFFAOYSA-N 1,2,4-trimethylpyrrole-3-carboxylic acid Chemical compound CC1=CN(C)C(C)=C1C(O)=O MIKOZAZRIJWWRE-UHFFFAOYSA-N 0.000 claims 1
- JTEBLTWGSAXWEE-UHFFFAOYSA-N 1,2,5-trimethylpyrrole-3-carboxylic acid Chemical compound CC1=CC(C(O)=O)=C(C)N1C JTEBLTWGSAXWEE-UHFFFAOYSA-N 0.000 claims 1
- VPYXATIIMHQAPR-UHFFFAOYSA-N 1,2-benzoxazole-3-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=NOC2=C1 VPYXATIIMHQAPR-UHFFFAOYSA-N 0.000 claims 1
- XYRXQPDMBJNYIU-UHFFFAOYSA-N 1,2-dimethylindole-3-carboxylic acid Chemical compound C1=CC=C2N(C)C(C)=C(C(O)=O)C2=C1 XYRXQPDMBJNYIU-UHFFFAOYSA-N 0.000 claims 1
- NOIOGQJFLIPRBI-UHFFFAOYSA-N 1,3,5-trimethylpyrazole-4-carboxylic acid Chemical compound CC1=NN(C)C(C)=C1C(O)=O NOIOGQJFLIPRBI-UHFFFAOYSA-N 0.000 claims 1
- UUYNZCLYPLJBTG-UHFFFAOYSA-N 1,3,5-trimethylpyrrole-2-carboxylic acid Chemical compound CC=1C=C(C)N(C)C=1C(O)=O UUYNZCLYPLJBTG-UHFFFAOYSA-N 0.000 claims 1
- ZPPXWZDJDIOJFP-UHFFFAOYSA-N 1,3-dihydroisoindole-2-carboxylic acid Chemical compound C1=CC=C2CN(C(=O)O)CC2=C1 ZPPXWZDJDIOJFP-UHFFFAOYSA-N 0.000 claims 1
- GUAVXCSZSKSTBL-UHFFFAOYSA-N 1,3-dimethylindole-2-carboxylic acid Chemical compound C1=CC=C2C(C)=C(C(O)=O)N(C)C2=C1 GUAVXCSZSKSTBL-UHFFFAOYSA-N 0.000 claims 1
- SIZRIGSBZPWTOL-UHFFFAOYSA-N 1,3-dimethylpyrrole-2-carboxylic acid Chemical compound CC=1C=CN(C)C=1C(O)=O SIZRIGSBZPWTOL-UHFFFAOYSA-N 0.000 claims 1
- DYGGJXVTZCRGTE-UHFFFAOYSA-N 1,5-dimethyl-3-phenylpyrazole-4-carboxylic acid Chemical compound CN1C(C)=C(C(O)=O)C(C=2C=CC=CC=2)=N1 DYGGJXVTZCRGTE-UHFFFAOYSA-N 0.000 claims 1
- NDJXNNQYGYBVNQ-UHFFFAOYSA-N 1,5-dimethylpyrrole-2-carboxylic acid Chemical compound CC1=CC=C(C(O)=O)N1C NDJXNNQYGYBVNQ-UHFFFAOYSA-N 0.000 claims 1
- VPQDTFDJFQLUQA-UHFFFAOYSA-N 1-(2-methoxyethyl)-2,4-dimethylpyrrole-3-carboxylic acid Chemical compound COCCN1C=C(C)C(C(O)=O)=C1C VPQDTFDJFQLUQA-UHFFFAOYSA-N 0.000 claims 1
- OWECYPGUAPISSL-UHFFFAOYSA-N 1-(cyclopropylmethyl)-2,4-dimethylpyrrole-3-carboxylic acid Chemical compound CC1=C(C(O)=O)C(C)=CN1CC1CC1 OWECYPGUAPISSL-UHFFFAOYSA-N 0.000 claims 1
- QBQWUFSHKRRJPB-UHFFFAOYSA-N 1-benzyl-3,5-dimethylpyrazole-4-carboxylic acid Chemical compound CC1=C(C(O)=O)C(C)=NN1CC1=CC=CC=C1 QBQWUFSHKRRJPB-UHFFFAOYSA-N 0.000 claims 1
- VOOZJPFNBFNPEK-UHFFFAOYSA-N 1-cyclopropyl-2,5-dimethylpyrrole-3-carboxylic acid Chemical compound CC1=CC(C(O)=O)=C(C)N1C1CC1 VOOZJPFNBFNPEK-UHFFFAOYSA-N 0.000 claims 1
- VDFAGHFIPYSSIU-UHFFFAOYSA-N 1-cyclopropylpyrrole-2-carboxylic acid Chemical compound OC(=O)C1=CC=CN1C1CC1 VDFAGHFIPYSSIU-UHFFFAOYSA-N 0.000 claims 1
- CDCPECFYUDCGAB-UHFFFAOYSA-N 1-ethyl-2,4-dimethylpyrrole-3-carboxylic acid Chemical compound CCN1C=C(C)C(C(O)=O)=C1C CDCPECFYUDCGAB-UHFFFAOYSA-N 0.000 claims 1
- JRMRPWSXOZSUAM-UHFFFAOYSA-N 1-ethyl-3,5-dimethylpyrrole-2-carboxylic acid Chemical compound CCN1C(C)=CC(C)=C1C(O)=O JRMRPWSXOZSUAM-UHFFFAOYSA-N 0.000 claims 1
- ZPUSQIWNVXTSPW-UHFFFAOYSA-N 1-methyl-3-phenylindole-2-carboxylic acid Chemical compound C12=CC=CC=C2N(C)C(C(O)=O)=C1C1=CC=CC=C1 ZPUSQIWNVXTSPW-UHFFFAOYSA-N 0.000 claims 1
- OVVDFORZEGKEJM-UHFFFAOYSA-M 1-methylindazole-3-carboxylate Chemical compound C1=CC=C2N(C)N=C(C([O-])=O)C2=C1 OVVDFORZEGKEJM-UHFFFAOYSA-M 0.000 claims 1
- HVRCLXXJIQTXHC-UHFFFAOYSA-M 1-methylindole-3-carboxylate Chemical compound C1=CC=C2N(C)C=C(C([O-])=O)C2=C1 HVRCLXXJIQTXHC-UHFFFAOYSA-M 0.000 claims 1
- ILAOVOOZLVGAJF-UHFFFAOYSA-N 1-methylpyrrole-2-carboxylic acid Chemical compound CN1C=CC=C1C(O)=O ILAOVOOZLVGAJF-UHFFFAOYSA-N 0.000 claims 1
- UORJTRNJVITXTP-UHFFFAOYSA-N 1-tert-butyl-3,5-dimethylpyrazole-4-carboxylic acid Chemical compound CC1=NN(C(C)(C)C)C(C)=C1C(O)=O UORJTRNJVITXTP-UHFFFAOYSA-N 0.000 claims 1
- IPDOBVFESNNYEE-UHFFFAOYSA-M 1h-indole-7-carboxylate Chemical compound [O-]C(=O)C1=CC=CC2=C1NC=C2 IPDOBVFESNNYEE-UHFFFAOYSA-M 0.000 claims 1
- SYWUPYPWAYRZDQ-UHFFFAOYSA-N 2,3-dihydro-1,4-benzoxazine-4-carboxylic acid Chemical compound C1=CC=C2N(C(=O)O)CCOC2=C1 SYWUPYPWAYRZDQ-UHFFFAOYSA-N 0.000 claims 1
- TYHYESDUJZRBKS-UHFFFAOYSA-N 2,3-dihydroindole-1-carboxylic acid Chemical compound C1=CC=C2N(C(=O)O)CCC2=C1 TYHYESDUJZRBKS-UHFFFAOYSA-N 0.000 claims 1
- BAZBYDHOWMSZBD-UHFFFAOYSA-N 2,4,5-trimethylfuran-3-carboxylic acid Chemical compound CC=1OC(C)=C(C(O)=O)C=1C BAZBYDHOWMSZBD-UHFFFAOYSA-N 0.000 claims 1
- MQGBARXPCXAFRZ-UHFFFAOYSA-N 2,4-dimethyl-1,3-thiazole-5-carboxylic acid Chemical compound CC1=NC(C)=C(C(O)=O)S1 MQGBARXPCXAFRZ-UHFFFAOYSA-N 0.000 claims 1
- XBPJVSRTTKVMEN-UHFFFAOYSA-M 2,4-dimethyl-1h-pyrrole-3-carboxylate Chemical compound CC1=CNC(C)=C1C([O-])=O XBPJVSRTTKVMEN-UHFFFAOYSA-M 0.000 claims 1
- LHGRUGVXZLHYKE-UHFFFAOYSA-N 2,5-dimethyl-1,3-oxazole-4-carboxylic acid Chemical compound CC1=NC(C(O)=O)=C(C)O1 LHGRUGVXZLHYKE-UHFFFAOYSA-N 0.000 claims 1
- JBGWUKMKNIMSOU-UHFFFAOYSA-N 2-chloro-5-propan-2-yl-1,3-thiazole-4-carboxylic acid Chemical compound CC(C)C=1SC(Cl)=NC=1C(O)=O JBGWUKMKNIMSOU-UHFFFAOYSA-N 0.000 claims 1
- NNMGTKSNBXYSER-UHFFFAOYSA-N 2-methoxy-4-methyl-1,3-thiazole-5-carboxylic acid Chemical compound COC1=NC(C)=C(C(O)=O)S1 NNMGTKSNBXYSER-UHFFFAOYSA-N 0.000 claims 1
- JPFHYMMFZMXFMY-UHFFFAOYSA-M 2-methyl-4,5,6,7-tetrahydroindazole-3-carboxylate Chemical compound C1CCCC2=C(C([O-])=O)N(C)N=C21 JPFHYMMFZMXFMY-UHFFFAOYSA-M 0.000 claims 1
- GOEZJIAQSROMFY-UHFFFAOYSA-N 2-methyl-4-(2-methylphenyl)pyrazole-3-carboxylic acid Chemical compound CC1=CC=CC=C1C1=C(C(O)=O)N(C)N=C1 GOEZJIAQSROMFY-UHFFFAOYSA-N 0.000 claims 1
- BNJPPGUQUVZCBA-UHFFFAOYSA-N 2-methyl-4-phenylpyrazole-3-carboxylic acid Chemical compound CN1N=CC(C=2C=CC=CC=2)=C1C(O)=O BNJPPGUQUVZCBA-UHFFFAOYSA-N 0.000 claims 1
- FBIUGCLQMKPURJ-UHFFFAOYSA-M 2-methylimidazo[1,2-a]pyridine-3-carboxylate Chemical compound C1=CC=CN2C(C([O-])=O)=C(C)N=C21 FBIUGCLQMKPURJ-UHFFFAOYSA-M 0.000 claims 1
- ABRISPFTOZIXMP-UHFFFAOYSA-N 2-methylindazole-3-carboxylic acid Chemical compound C1=CC=CC2=C(C(O)=O)N(C)N=C21 ABRISPFTOZIXMP-UHFFFAOYSA-N 0.000 claims 1
- FLYDUXCFCARXHI-UHFFFAOYSA-N 2-phenylpyrazole-3-carboxylic acid Chemical compound OC(=O)C1=CC=NN1C1=CC=CC=C1 FLYDUXCFCARXHI-UHFFFAOYSA-N 0.000 claims 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
- JZPMLZWJUMATOQ-UHFFFAOYSA-N 2-tert-butyl-5-methylpyrazole-3-carboxylic acid Chemical compound CC=1C=C(C(O)=O)N(C(C)(C)C)N=1 JZPMLZWJUMATOQ-UHFFFAOYSA-N 0.000 claims 1
- FVTWJYOGVFLUNJ-UHFFFAOYSA-N 3,3-dimethyl-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid Chemical compound CC(C)(C)OC(=O)N1CCC(C)(C)C1C(O)=O FVTWJYOGVFLUNJ-UHFFFAOYSA-N 0.000 claims 1
- YIEADNILIRHBHR-UHFFFAOYSA-N 3,3-dimethylpiperidine-1-carboxylic acid Chemical compound CC1(C)CCCN(C(O)=O)C1 YIEADNILIRHBHR-UHFFFAOYSA-N 0.000 claims 1
- ZLUUPCCXIKTEBG-UHFFFAOYSA-N 3,4-dihydro-2h-quinoline-1-carboxylic acid Chemical compound C1=CC=C2N(C(=O)O)CCCC2=C1 ZLUUPCCXIKTEBG-UHFFFAOYSA-N 0.000 claims 1
- KTRDIIZBYGBKTO-UHFFFAOYSA-N 3,4-dihydro-2h-quinoxaline-1-carboxylic acid Chemical compound C1=CC=C2N(C(=O)O)CCNC2=C1 KTRDIIZBYGBKTO-UHFFFAOYSA-N 0.000 claims 1
- IJEUISLJVBUNRE-UHFFFAOYSA-N 3,5-dimethyl-1,2-oxazole-4-carboxylic acid Chemical compound CC1=NOC(C)=C1C(O)=O IJEUISLJVBUNRE-UHFFFAOYSA-N 0.000 claims 1
- QFUYZERHMQJGCA-UHFFFAOYSA-N 3,5-dimethyl-1,2-thiazole-4-carboxylic acid Chemical compound CC1=NSC(C)=C1C(O)=O QFUYZERHMQJGCA-UHFFFAOYSA-N 0.000 claims 1
- LPYTYYLNGJGJGW-UHFFFAOYSA-N 3,5-dimethyl-1-phenylpyrazole-4-carboxylic acid Chemical compound CC1=C(C(O)=O)C(C)=NN1C1=CC=CC=C1 LPYTYYLNGJGJGW-UHFFFAOYSA-N 0.000 claims 1
- YLPYLNUXWGDQAG-UHFFFAOYSA-N 3,5-dimethyl-1-propan-2-ylpyrazole-4-carboxylic acid Chemical compound CC(C)N1N=C(C)C(C(O)=O)=C1C YLPYLNUXWGDQAG-UHFFFAOYSA-N 0.000 claims 1
- REIPZLFZMOQHJT-UHFFFAOYSA-N 3-(2-chloro-6-fluorophenyl)-5-methyl-1,2-oxazole-4-carboxylic acid Chemical compound OC(=O)C1=C(C)ON=C1C1=C(F)C=CC=C1Cl REIPZLFZMOQHJT-UHFFFAOYSA-N 0.000 claims 1
- KOQSJBSGCNLIJY-UHFFFAOYSA-N 3-(2-methoxyphenyl)-5-methyl-1,2-oxazole-4-carboxylic acid Chemical compound COC1=CC=CC=C1C1=NOC(C)=C1C(O)=O KOQSJBSGCNLIJY-UHFFFAOYSA-N 0.000 claims 1
- UXANYOUSBMHKBA-UHFFFAOYSA-N 3-azabicyclo[3.2.2]nonane-3-carboxylic acid Chemical compound C1N(C(=O)O)CC2CCC1CC2 UXANYOUSBMHKBA-UHFFFAOYSA-N 0.000 claims 1
- KBDIRPOTVAODSA-UHFFFAOYSA-M 3-bromopyridine-2-carboxylate Chemical compound [O-]C(=O)C1=NC=CC=C1Br KBDIRPOTVAODSA-UHFFFAOYSA-M 0.000 claims 1
- RSWFHHWVFZWIMV-UHFFFAOYSA-N 3-ethyl-5-methyl-1,2-oxazole-4-carboxylic acid Chemical compound CCC1=NOC(C)=C1C(O)=O RSWFHHWVFZWIMV-UHFFFAOYSA-N 0.000 claims 1
- YIVHOQIKHMTVRG-UHFFFAOYSA-N 3-methyl-1h-pyrrole-2-carboxylic acid Chemical compound CC=1C=CNC=1C(O)=O YIVHOQIKHMTVRG-UHFFFAOYSA-N 0.000 claims 1
- JDUCBQRNGOSNDG-UHFFFAOYSA-N 3-methyl-2,3-dihydro-1,4-benzoxazine-4-carboxylic acid Chemical compound CC1COC2=CC=CC=C2N1C(=O)O JDUCBQRNGOSNDG-UHFFFAOYSA-N 0.000 claims 1
- RLAVEODUCXLMQJ-UHFFFAOYSA-N 3-methyl-2-oxo-1-oxaspiro[4.5]dec-3-ene-4-carboxylic acid Chemical compound O1C(=O)C(C)=C(C(O)=O)C11CCCCC1 RLAVEODUCXLMQJ-UHFFFAOYSA-N 0.000 claims 1
- IFLKEBSJTZGCJG-UHFFFAOYSA-M 3-methylthiophene-2-carboxylate Chemical compound CC=1C=CSC=1C([O-])=O IFLKEBSJTZGCJG-UHFFFAOYSA-M 0.000 claims 1
- HHTIPFPDSPKHSV-UHFFFAOYSA-N 3-oxo-2,4-dihydroquinoxaline-1-carboxylic acid Chemical compound O=C1CN(C2=CC=CC=C2N1)C(=O)O HHTIPFPDSPKHSV-UHFFFAOYSA-N 0.000 claims 1
- FSVMTMFHLLEQAS-UHFFFAOYSA-N 3-phenylimidazole-4-carboxylic acid Chemical compound OC(=O)C1=CN=CN1C1=CC=CC=C1 FSVMTMFHLLEQAS-UHFFFAOYSA-N 0.000 claims 1
- KWWGBNRBZMJKPA-UHFFFAOYSA-N 3-phenylthiophene-2-carboxylic acid Chemical compound S1C=CC(C=2C=CC=CC=2)=C1C(=O)O KWWGBNRBZMJKPA-UHFFFAOYSA-N 0.000 claims 1
- WGNBQRMKJSODLB-UHFFFAOYSA-N 3-phenyltriazole-4-carboxylic acid Chemical compound OC(=O)C1=CN=NN1C1=CC=CC=C1 WGNBQRMKJSODLB-UHFFFAOYSA-N 0.000 claims 1
- UKBDFVBVJCUFQV-UHFFFAOYSA-N 3-tert-butyl-5-methyl-1,2-oxazole-4-carboxylic acid Chemical compound CC=1ON=C(C(C)(C)C)C=1C(O)=O UKBDFVBVJCUFQV-UHFFFAOYSA-N 0.000 claims 1
- KLPASEZGNSBTBD-UHFFFAOYSA-N 4,5-dimethyl-1,2-oxazole-3-carboxylic acid Chemical compound CC=1ON=C(C(O)=O)C=1C KLPASEZGNSBTBD-UHFFFAOYSA-N 0.000 claims 1
- BAWHTKAHVSSEGC-UHFFFAOYSA-N 4-(4-methoxyphenyl)-2-methylpyrazole-3-carboxylic acid Chemical compound C1=CC(OC)=CC=C1C1=C(C(O)=O)N(C)N=C1 BAWHTKAHVSSEGC-UHFFFAOYSA-N 0.000 claims 1
- LEEPGDCCHVRYHK-UHFFFAOYSA-M 4-bromo-1-methylpyrazole-3-carboxylate Chemical compound CN1C=C(Br)C(C([O-])=O)=N1 LEEPGDCCHVRYHK-UHFFFAOYSA-M 0.000 claims 1
- QBZXHFRMFOYDSR-UHFFFAOYSA-N 4-bromo-2-ethylpyrazole-3-carboxylic acid Chemical compound CCN1N=CC(Br)=C1C(O)=O QBZXHFRMFOYDSR-UHFFFAOYSA-N 0.000 claims 1
- YXIJCAVZGBGUKM-UHFFFAOYSA-N 4-bromo-2-methylpyrazole-3-carboxylic acid Chemical compound CN1N=CC(Br)=C1C(O)=O YXIJCAVZGBGUKM-UHFFFAOYSA-N 0.000 claims 1
- BZFXEYAWDBWTSY-UHFFFAOYSA-N 4-chloro-1-methylpyrazole-3-carboxylic acid Chemical compound CN1C=C(Cl)C(C(O)=O)=N1 BZFXEYAWDBWTSY-UHFFFAOYSA-N 0.000 claims 1
- BSCNPVBDEITWDU-UHFFFAOYSA-N 4-chloro-2,5-dimethylpyrazole-3-carboxylic acid Chemical compound CC1=NN(C)C(C(O)=O)=C1Cl BSCNPVBDEITWDU-UHFFFAOYSA-N 0.000 claims 1
- SOCMTMNWGCJGLA-UHFFFAOYSA-N 4-chloro-2-methylpyrazole-3-carboxylic acid Chemical compound CN1N=CC(Cl)=C1C(O)=O SOCMTMNWGCJGLA-UHFFFAOYSA-N 0.000 claims 1
- GAIAHHRZVGJYQW-UHFFFAOYSA-N 4-methyl-1,2,5-oxadiazole-3-carboxylic acid Chemical compound CC1=NON=C1C(O)=O GAIAHHRZVGJYQW-UHFFFAOYSA-N 0.000 claims 1
- YXYAHRAFINYJPL-UHFFFAOYSA-N 4-methyl-1h-pyrrole-2-carboxylic acid Chemical compound CC1=CNC(C(O)=O)=C1 YXYAHRAFINYJPL-UHFFFAOYSA-N 0.000 claims 1
- NVHAAIMFHOSMHD-UHFFFAOYSA-N 4-methyl-2-oxo-3h-1,3-thiazole-5-carboxylic acid Chemical compound CC=1NC(=O)SC=1C(O)=O NVHAAIMFHOSMHD-UHFFFAOYSA-N 0.000 claims 1
- HZZBITVSVYFOND-UHFFFAOYSA-N 5-bromopyrimidine-4-carboxylic acid Chemical compound OC(=O)C1=NC=NC=C1Br HZZBITVSVYFOND-UHFFFAOYSA-N 0.000 claims 1
- DZFFAHLKOQEHBW-UHFFFAOYSA-N 5-ethyl-3-propan-2-yl-1,2-oxazole-4-carboxylic acid Chemical compound CCC=1ON=C(C(C)C)C=1C(O)=O DZFFAHLKOQEHBW-UHFFFAOYSA-N 0.000 claims 1
- XTIWMXFCHBNILL-UHFFFAOYSA-N 5-iodo-3-methyl-1,2-thiazole-4-carboxylic acid Chemical compound CC1=NSC(I)=C1C(O)=O XTIWMXFCHBNILL-UHFFFAOYSA-N 0.000 claims 1
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- YIJZWIPPIODAAK-UHFFFAOYSA-N 5-methoxy-1,3-dimethylindole-2-carboxylic acid Chemical compound COC1=CC=C2N(C)C(C(O)=O)=C(C)C2=C1 YIJZWIPPIODAAK-UHFFFAOYSA-N 0.000 claims 1
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| CA2909207C (en) | 2013-04-19 | 2021-11-02 | Incyte Corporation | Bicyclic heterocycles as fgfr inhibitors |
| JP5877251B2 (ja) | 2013-09-26 | 2016-03-02 | 三井化学株式会社 | アイウェア材料、アイウェアフレームおよびアイウェア |
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| WO2016191836A1 (pt) * | 2015-06-03 | 2016-12-08 | Amazônia Fitomedicamentos Ltda. | Método de preparação de ingenol-3-dodecanoato, método de preparação de 3-etinil-3-hidroxi-4.7.7-trimetilbiciclo[4.1.0]heptano-2-carbaldeído e método de preparação de 2,2-dimetil-4-etinil-5-trifenilfosforanilideno-1,3-dioxano |
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| WO2018209062A1 (en) | 2017-05-12 | 2018-11-15 | The Board Of Trustees Of The Lealand Stanford Junior University | Prodrug derivatives of protein kinase c modulators |
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| WO2006116897A1 (fr) * | 2005-04-30 | 2006-11-09 | Nihon University | Diterpenes provenant de euphorbia kansui et leur utilisation |
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2011
- 2011-12-22 WO PCT/DK2011/000154 patent/WO2012083953A1/en not_active Ceased
- 2011-12-22 EP EP11808566.1A patent/EP2655323B1/en not_active Not-in-force
- 2011-12-22 MY MYPI2013002354A patent/MY160501A/en unknown
- 2011-12-22 KR KR1020137019271A patent/KR20140010372A/ko not_active Ceased
- 2011-12-22 TW TW100148201A patent/TWI548616B/zh active
- 2011-12-22 NZ NZ612446A patent/NZ612446A/en not_active IP Right Cessation
- 2011-12-22 MX MX2013006995A patent/MX339823B/es active IP Right Grant
- 2011-12-22 SG SG10201510566UA patent/SG10201510566UA/en unknown
- 2011-12-22 AU AU2011348637A patent/AU2011348637B2/en not_active Ceased
- 2011-12-22 NZ NZ710133A patent/NZ710133A/en not_active IP Right Cessation
- 2011-12-22 JP JP2013545050A patent/JP5845283B2/ja not_active Expired - Fee Related
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- 2011-12-22 CN CN201180068162.3A patent/CN103402977B/zh not_active Expired - Fee Related
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- 2011-12-22 ES ES11808566.1T patent/ES2659739T3/es active Active
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2013
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2015
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- 2015-10-09 JP JP2015201428A patent/JP6111308B2/ja not_active Expired - Fee Related
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